Ie0c03003 Si 001

DFT studies on thermal and oxidative degradation
of monoethanolamine
Christopher. Parks* a, Ehsan. Alborzi a, Muhammad Akram a,
Mohammed. Pourkashanian, a
a
Department of Mechanical Engineering, The University of Sheffield, Sheffield, S3 7RD,UK
E-mail: [email protected], [email protected], [email protected]
Electronic Supplementary Information (ESI)
Contents:
1. Raw DFT Data

2. Comparative data with M06 functional and Def2-TZVP basis set
3. Comparative data using SMD solvent model in place of PCM model.
All calculations were performed as described in the main text of the paper unless stated otherwise.
1.1 CO2.......................................................................................................................................... 4
1.2 MEA ........................................................................................................................................ 5
1.3 MEACO2 ................................................................................................................................. 6
1.4 MEACO2_MEA_H_transfer_product ..................................................................................... 7
1.5 MEACO2_MEA_H_transfer_TS3 ............................................................................................ 9
1.6 MEA_CO2 ............................................................................................................................. 11
1.7 MEA_protonated.................................................................................................................. 12
1.8 OH......................................................................................................................................... 13
1.9 AEHEIA .................................................................................................................................. 14
1.10 AEHEIA_formation_TS........................................................................................................ 16
1.11 HEEDA ................................................................................................................................. 18
1.12 HEEDACO2 .......................................................................................................................... 19
1.13 HEEDACO2_intermediate................................................................................................... 21
1.14 HEEDA_CO2 ........................................................................................................................ 23
1.15 HEEDA_OXD_H_transfer_product ..................................................................................... 25
1.16 HEEDA_OXD_TS.................................................................................................................. 27
1.17 HEIA ..................................................................................................................................... 29
1.18 HEIA_Formation_TS ............................................................................................................ 31
1.19 MEA_CO2_Ring_formation_TS ........................................................................................... 33
1.20 OZD...................................................................................................................................... 35
1.21 OZD_MEA ............................................................................................................................ 36
1.22 OZD_MEA_H2O ................................................................................................................... 38
1.23 OZD_MEA_TS ...................................................................................................................... 40
1.24 Pre_AEHEIA_1 ...................................................................................................................... 42
1.25 AEHEIA_1_3_H_transfer_TS ............................................................................................... 44
1.26 Pre_AEHEIA_2 ..................................................................................................................... 46
1.27 Isocyanate ............................................................................................................................ 48
1.28 Isocyanate_MEA................................................................................................................. 49
1.29 Isocyanate_MEA_BHEU_formation_TS ............................................................................. 51
1.30 Isocyanate_formation_TS ................................................................................................... 53
1.31 Isocyanate_H2O ................................................................................................................. 54
1.32 Isocyanate_H2O_H2O ........................................................................................................ 55
1.33 BHEOX_intermediate ......................................................................................................... 57
1.34 BHEOX_intermediate_2_TS ............................................................................................... 59
1.35 BHEOX_intermediate_3 ..................................................................................................... 61
1.36 BHEOX_intermediate_4 ..................................................................................................... 63
1.37 BHEOX_intermediate_4_TS ............................................................................................... 64
1.38 BHEOX-intermediate_2 ...................................................................................................... 66
1.39 BHEOX-intermediate_5 ...................................................................................................... 68
1.40 BHEOX-intermediate1 ........................................................................................................ 70
1.41 Ethanoic_acid ..................................................................................................................... 72
1.42 Formic_acid .......................................................................................................................... 73
1.43 HHEA_intermediate ............................................................................................................ 74
1.44 HEA_intermediate_2 ........................................................................................................... 76
1.45 HEA_intermediate_2_TS ..................................................................................................... 78
1.46 HHEA_intermediate ........................................................................................................... 80
1.47 HEA_intermediate_2 .......................................................................................................... 81
1.50 HEA_intermediate_4_TS .................................................................................................... 87
1.52 HEA_intermediate1 ............................................................................................................ 89
1.53 HEF_intermediate .............................................................................................................. 90
1.54 HEF_intermediate_2 .......................................................................................................... 91
1.57 HEF_intermediate_4_TS ..................................................................................................... 94
1.59 HEF_intermediate1 ............................................................................................................ 96
1.60 HHEA_intermediate ........................................................................................................... 97
1.61 HHEA_intermediate_2 ....................................................................................................... 99
1.62 HHEA_intermediate_2_TS................................................................................................ 101
1.63 HHEA_intermediate_3 ..................................................................................................... 103
1.65 HHEA_intermediate_4_TS................................................................................................ 107
1.67 HHEA_intermediate1 ....................................................................................................... 110
1.68 2-hydroxy-Ethanoic_acid.................................................................................................. 112
1.69 2-R-Ethanoic_acid ............................................................................................................. 113
1.1 CO2
Setup: B3LYP, cc-pVTZ

Formula: CO2
Charge: 0
Energy: -188.648955 a.u
Gibbs: -188.672929 a.u
Multiplicity: 1
Dipole: 0.0000
Setup: B3LYP, def2TZVP

Formula: CO2
Charge: 0
Energy: -188.658395 a.u
Gibbs: -188.68236 a.u
Multiplicity: 1
Dipole: 0.0000
Setup: M06, def2TZVP

Formula: CO2
Charge: 0
Energy: -188.572538 a.u
Gibbs: -188.596460 a.u
Multiplicity: 1
Dipole: 0.0000
C, 8.516283, -9.094919, 12.235643

O, 8.894158, -9.097775, 11.138637
O, 8.138407, -9.092064, 13.332652
1.2 MEA
Formula: C2H7NO
Charge: 0
Energy: -210.381663 a.u
Gibbs: -210.414974 a.u
Multiplicity: 1
Dipole: 1.4511

Formula: C2H7NO
Charge: 0
Energy: -210.387652 a.u
Gibbs: -210.420959 a.u
Multiplicity: 1
Dipole: 1.4890

Formula: C2H7NO
Charge: 0
Energy: -210.238802 a.u
Gibbs: -210.272082 a.u
Multiplicity: 1
Dipole: 1.4489
C, 1.959249, 1.737827, -0.201285

H, 1.307446, 2.043799, 0.626299
H, 2.965761, 1.589188, 0.203248
C, 1.994251, 2.831224, -1.254383
H, 2.677115, 2.527085, -2.049857
H, 0.995373, 2.915847, -1.701165
O, 1.467581, 0.548478, -0.821826
H, 1.438756, -0.149605, -0.160959
H, 2.629464, 4.770353, -1.391844
H, 1.790471, 4.467935, -0.043255
N, 2.491519, 4.079199, -0.664548
1.3 MEACO2
Formula: C3H7NO3
Charge: 0
Energy: -399.034587 a.u
Gibbs: -399.082374 a.u
Multiplicity: 1
Dipole: 3.7059

Formula: C3H7NO3
Charge: 0
Energy: -399.029133 a.u
Gibbs: -399.069635 a.u
Multiplicity: 1
Dipole: 11.2394

Formula: C3H7NO3
Charge: 0
Energy: -398.788083 a.u
Gibbs: -398.828061 a.u
Multiplicity: 1
Dipole: 11.0668
C, 10.144442, -5.063696, 11.701820

H, 11.137201, -5.133379, 12.162377
H, 9.504950, -4.477224, 12.372378
C, 9.561427, -6.460622, 11.535121
H, 8.580954, -6.382552, 11.061650
H, 10.195281, -7.031542, 10.854039
O, 10.220311, -4.460951, 10.408197
H, 10.588241, -3.577271, 10.503222
C, 8.325462, -9.735440, 12.162550
O, 8.290930, -9.460999, 11.034862
O, 8.326730, -10.086019, 13.269554
H, 8.820770, -6.715722, 13.431686
H, 10.318036, -7.317621, 13.239149
N, 9.419637, -7.212068, 12.781606
1.4 MEACO2_MEA_H_transfer_product
Formula: C5H14N2O4
Charge: 0
Energy: -609.438551 a.u
Gibbs: -609.494921 a.u
Multiplicity: 1
Dipole: 8.9290

Formula: C5H14N2O4
Charge: 0
Energy: -609.463613 a.u
Gibbs: -609.520051 a.u
Multiplicity: 1
Dipole: 9.9221

Formula: C5H14N2O4
Charge: 0
Energy: -609.068343 a.u
Gibbs: -609.125326 a.u
Multiplicity: 1
Dipole: 10.1952
C, -1.012817, 0.839954, -0.062520

H, -0.775630, 1.496801, 0.781178
H, -1.435531, -0.086936, 0.342398
C, 0.261027, 0.534433, -0.835333
H, 0.005258, -0.066327, -1.716189
H, 0.699147, 1.464555, -1.190206
O, -1.926236, 1.463232, -0.967198
H, -2.747020, 1.640026, -0.498141
C, 2.676305, 0.108511, -0.147683
O, 3.027393, 1.159376, -0.755142
O, 3.435038, -0.742163, 0.375644
H, 1.044317, -1.087133, 0.241794
N, 1.233888, -0.123117, 0.015663
C, 6.697579, -0.185120, -0.437999
H, 6.729918, -0.354451, 0.646199
H, 7.655421, -0.518121, -0.842071
C, 6.590302, 1.307766, -0.712691
H, 7.484497, 1.823288, -0.366025
H, 6.464718, 1.487362, -1.777998
O, 5.677665, -0.937964, -1.053207
H, 4.856298, -0.876813, -0.504751
H, 5.396901, 2.921896, -0.141904
H, 4.442640, 1.533887, -0.382019
H, 5.447635, 1.733404, 0.980465
N, 5.407877, 1.911549, -0.021520
1.5 MEACO2_MEA_H_transfer_TS3
Formula: C5H14N2O4
Charge: 0
Energy: -609.393415 a.u
Gibbs: -609.450711 a.u
Multiplicity: 1
Dipole: 8.5475

Formula: C5H14N2O4
Charge: 0
Energy: -609.438882 a.u
Gibbs: -609.497637 a.u
Multiplicity: 1
Dipole: 14.2952

Formula: C5H14N2O4
Charge: 0
Energy: -398.752276 a.u
Gibbs: -398.792886 a.u
Multiplicity: 1
Dipole: 5.9231
C, -1.591711, 1.133363, -0.466689

H, -1.243394, 0.947465, -1.492453
H, -1.974694, 2.153383, -0.410736
C, -0.426569, 0.989576, 0.500054
H, -0.753980, 1.275008, 1.497040
H, -0.111660, -0.056106, 0.526518
O, -2.575751, 0.172770, -0.085604
H, -3.411368, 0.410274, -0.495824
C, 0.598080, 3.342766, 0.354654
O, -0.432200, 3.726677, 0.895534
O, 1.636582, 3.926600, -0.016219
H, 1.009344, 1.682276, -0.816629
H, 1.962922, 1.671367, 0.860804
N, 0.724975, 1.826682, 0.147801
C, 5.500242, 1.650937, 0.923370
H, 5.664545, 1.591877, 2.006900
H, 5.593312, 2.701438, 0.624793
C, 4.106185, 1.149535, 0.586976
H, 3.931076, 1.241812, -0.483674
H, 4.012047, 0.098684, 0.856162
O, 6.405925, 0.820346, 0.214298
H, 7.300186, 1.150749, 0.338656
H, 3.064409, 2.909225, 1.027176
H, 3.104652, 1.821895, 2.291979
N, 3.051795, 1.913858, 1.282390
1.6 MEA_CO2
Formula: C3H7NO3
Charge: 0
Energy: -399.034587 a.u
Gibbs: -399.082374 a.u
Multiplicity: 1
Dipole: 3.7059

Formula: C3H7NO3
Charge: 0
Energy: -399.048889 a.u
Gibbs: -399.096968 a.u
Multiplicity: 1
Dipole: 3.7935

Formula: C3H7NO3
Charge: 0
Energy: -398.812962 a.u
Gibbs: -398.859505 a.u
Multiplicity: 1
Dipole: 3.6982
C, 10.144442, -5.063696, 11.701820

H, 11.137201, -5.133379, 12.162377
H, 9.504950, -4.477224, 12.372379
C, 9.561427, -6.460622, 11.535121
H, 8.580954, -6.382552, 11.061650
H, 10.195281, -7.031542, 10.854039
O, 10.220311, -4.460951, 10.408197
H, 10.588241, -3.577271, 10.503222
C, 8.325462, -9.735440, 12.162550
O, 8.290930, -9.460999, 11.034862
O, 8.326730, -10.086019, 13.269554
H, 8.820770, -6.715722, 13.431686
H, 10.318036, -7.317621, 13.239149
N, 9.419637, -7.212068, 12.781606
1.7 MEA_protonated
Formula: C2H8NO(1+)
Charge: 1
Energy: -210.820937 a.u
Gibbs: -210.854505 a.u
Multiplicity: 1
Dipole: 7.9208

Formula: C2H8NO(1+)
Charge: 0
Energy: -210.824501 a.u
Gibbs: -210.858066 a.u
Multiplicity: 1
Dipole: 8.0024

Formula: C2H8NO(1+)
Charge: 0
Energy: -210.671102 a.u
Gibbs: -210.705754 a.u
Multiplicity: 1
Dipole: 7.8736
C, 1.952758, 1.725063, -0.179795

H, 1.272791, 2.044599, 0.617057
H, 2.945908, 1.576495, 0.257482
C, 2.016681, 2.785972, -1.264449
H, 2.704607, 2.494771, -2.052775
H, 1.034514, 2.965357, -1.691785
O, 1.485728, 0.554305, -0.828676
H, 1.423116, -0.153123, -0.179197
H, 3.441762, 4.004482, -0.304997
H, 2.549614, 4.806263, -1.429503
H, 1.889281, 4.441443, 0.031328
N, 2.505656, 4.091043, -0.703362
1.8 OH
Formula: HO(1-)
Charge: -1
Energy: -75.91617 a.u
Gibbs: -75.934783 a.u
Multiplicity: 1
Dipole: 1.7356

Formula: HO(1-)
Charge: -1
Energy: -75.935646 a.u
Gibbs: -75.955203a.u
Multiplicity: 1
Dipole: 1.9515

Formula: HO(1-)
Charge: -1
Energy: -75.891492 a.u
Gibbs: -75.911040 a.u
Multiplicity: 1
Dipole: 1.9279
O, 10.167980, -4.491072, 10.539476

H, 10.599973, -3.649477, 10.729001
1.9 AEHEIA
Formula: C7H15N3O2
Charge: 0
Energy: -590.494215 a.u
Gibbs: -590.548784 a.u
Multiplicity: 1
Dipole: 5.6047

Formula: C7H15N3O2
Charge: 0
Energy: -590.515421 a.u
Gibbs: -590.570570 a.u
Multiplicity: 1
Dipole: 5.9675

Formula: C7H15N3O2
Charge: 0
Energy: -590.103727 a.u
Gibbs: -590.159323 a.u
Multiplicity: 1
Dipole: 5.6432
C, -3.343175, 0.699169, -0.029438

C, -5.507119, 0.731327, 1.143365
H, -5.590563, 1.016548, 2.195578
H, -5.346813, -0.344461, 1.095605
N, -4.359717, 1.386001, 0.551979
C, -6.798714, 1.086361, 0.419002
H, -6.736210, 0.746431, -0.619785
H, -6.938416, 2.172399, 0.412025
O, -7.858017, 0.436924, 1.118186
H, -8.688837, 0.651634, 0.683649
C, 0.123435, 1.910529, -0.909525
H, 0.425221, 1.452026, 0.040737
H, 0.094991, 2.990000, -0.748087
O, -3.314278, -0.478263, -0.340759
C, -3.968561, 2.745790, 0.906240
H, -3.683280, 2.792961, 1.962006
H, -4.778020, 3.451306, 0.733362
C, -1.275100, 1.411061, -1.262784
H, -1.602310, 1.887226, -2.196940
H, -1.247879, 0.334345, -1.433766
N, 1.042275, 1.643393, -2.021224
H, 1.943753, 2.064957, -1.832082
H, 1.211920, 0.645800, -2.092415
C, -2.770716, 2.992968, -0.013121
H, -2.047116, 3.671383, 0.434085
H, -3.095555, 3.415372, -0.972866
N, -2.223195, 1.654167, -0.193796
1.10 AEHEIA_formation_TS
Formula: C7H17N3O3
Charge: 0
Energy: -666.877646 a.u
Gibbs: -666.934686 a.u
Multiplicity: 1
Dipole: 9.2808

Formula: C7H17N3O3
Charge: 0
Energy: a.u
Gibbs: a.u
Multiplicity: 1
Dipole:

Formula: C7H17N3O3
Charge: 0
Energy: -666.438842 a.u
Gibbs: -666.496739 a.u
Multiplicity: 1
Dipole: 9.4748
C, -0.511017, -1.007435, 0.256719

C, -2.884264, -1.655103, -0.480973
H, -2.595067, -1.960963, -1.486082
H, -3.023200, -0.576834, -0.475451
C, -4.169071, -2.351777, -0.043361
H, -4.422866, -2.046833, 0.972651
H, -4.044226, -3.437988, -0.044737
O, -5.255614, -1.956184, -0.869325
H, -5.168979, -2.391743, -1.723835
C, 2.927229, -2.057462, -0.557297
H, 2.580540, -2.094863, -1.597643
H, 3.010555, -3.088633, -0.210055
O, -0.666509, -0.826515, 2.264006
C, -1.222886, -3.340420, 0.421655
H, -1.350599, -3.741774, -0.580567
H, -1.751037, -3.963814, 1.135834
C, 1.888495, -1.312707, 0.275086
H, 2.180624, -1.314799, 1.330734
H, 1.837489, -0.274175, -0.050879
N, 4.235798, -1.418116, -0.385354
H, 4.951411, -1.970188, -0.842563
H, 4.240355, -0.516554, -0.850198
C, 0.254369, -3.151521, 0.751096
H, 0.855265, -3.949902, 0.324606
H, 0.422187, -3.103783, 1.830425
N, 0.553804, -1.872714, 0.125081
O, -0.640099, 0.099447, -0.222872
N, -1.764600, -1.953010, 0.434865
H, -1.934111, -1.642570, 1.419368
H, -0.736427, 0.131742, 2.303779
1.11 HEEDA
Formula: C4H12N2O
Charge: 0
Energy: -344.329012 a.u
Gibbs: -344.372749 a.u
Multiplicity: 1
Dipole: 3.2567

Formula: C4H12N2O
Charge: 0
Energy: -344.336446 a.u
Gibbs: -344.381080 a.u
Multiplicity: 1
Dipole: 3.3937

Formula: C4H12N2O
Charge: 0
Energy: -344.081110 a.u
Gibbs: -344.125719 a.u
Multiplicity: 1
Dipole: 3.3217
C, -3.996264, 1.674543, -0.063449

H, -4.266983, 1.889705, 0.975159
H, -2.905849, 1.565153, -0.110197
C, -4.436072, 2.825423, -0.950535
H, -4.222515, 2.567386, -1.999410
H, -5.519557, 2.939804, -0.867078
O, -4.644623, 0.492097, -0.534894
H, -4.380069, -0.243431, 0.025470
N, -3.804452, 4.070610, -0.529176
H, -2.797780, 3.972156, -0.609976
C, -4.228458, 5.226041, -1.314577
H, -5.308041, 5.347419, -1.198479
H, -4.041003, 5.091226, -2.393249
C, -3.532041, 6.495210, -0.841844
H, -2.444251, 6.338833, -0.875535
H, -3.794064, 6.673344, 0.202563
N, -3.977221, 7.647215, -1.636255
H, -3.567070, 8.496738, -1.266344
H, -3.626485, 7.562960, -2.584443
1.12 HEEDACO2
Formula: C5H12N2O3
Charge: 0
Energy: -532.965593 a.u
Gibbs: -533.016575 a.u
Multiplicity: 1
Dipole: 8.7997

Formula: C5H12N2O3
Charge: 0
Energy: -532.983456 a.u
Gibbs: -533.034264 a.u
Multiplicity: 1
Dipole: 8.9726

Formula: C5H12N2O3
Charge: 0
Energy: -532.636106 a.u
Gibbs: -532.686125 a.u
Multiplicity: 1
Dipole: 8.6363
C, -3.848726, 1.596583, -0.017462

H, -3.964433, 1.715494, 1.063152
H, -2.782451, 1.470904, -0.234728
C, -4.392030, 2.814685, -0.746516
H, -4.301968, 2.677879, -1.821401
H, -5.431116, 2.989564, -0.484768
O, -4.611228, 0.499626, -0.503036
H, -4.346169, -0.292069, -0.024674
N, -3.636552, 4.060850, -0.380165
H, -2.649731, 3.908893, -0.591652
C, -4.109194, 5.237848, -1.196547
H, -5.146151, 5.407908, -0.924727
H, -4.050649, 4.942300, -2.242248
C, -3.264501, 6.478341, -0.934673
H, -2.204201, 6.239502, -1.086321
H, -3.380314, 6.784774, 0.104929
N, -3.760080, 7.556146, -1.790847
H, -3.365116, 8.439499, -1.493334
H, -3.451205, 7.414683, -2.745974
C, -3.699058, 4.336543, 1.062397
O, -2.587792, 4.298576, 1.600604
O, -4.837305, 4.554204, 1.480328
1.13 HEEDACO2_intermediate
Formula: C5H12N2O3
Charge: 0
Energy: -532.981792 a.u
Gibbs: -533.040187 a.u
Multiplicity: 1
Dipole: 1.8928

Formula: C5H12N2O3
Charge: 0
Energy: -532.998482 a.u
Gibbs: -533.057311 a.u
Multiplicity: 1
Dipole: 1.8997

Formula: C5H12N2O3
Charge: 0
Energy: -532.656221 a.u
Gibbs: -532.713629 a.u
Multiplicity: 1
Dipole: 1.9086
C, -1.470345, 0.789751, -1.032476

H, -1.527186, -0.285084, -1.228069
H, -1.663308, 1.295217, -1.993277
C, -0.058648, 1.137773, -0.561830
H, -0.005310, 2.204374, -0.328335
H, 0.149020, 0.606096, 0.368353
C, 3.456487, 1.556281, -0.326901
O, 2.895911, 2.002587, 0.586786
H, 0.849731, 1.325513, -2.391268
N, 1.005372, 0.832035, -1.519374
O, 4.091831, 1.132807, -1.201775
C, -4.800849, 1.122670, 0.711594
H, -4.736594, 2.187365, 0.967208
H, -4.530292, 0.547437, 1.602805
C, -3.829455, 0.803907, -0.410761
H, -3.886592, -0.264519, -0.632560
H, -4.149327, 1.336069, -1.319920
N, -2.462365, 1.122081, -0.013984
H, -2.401087, 2.114366, 0.189564
H, 1.003442, -0.156199, -1.746043
O, -6.113420, 0.789294, 0.256880
H, -6.737839, 0.985716, 0.961559
1.14 HEEDA_CO2
Formula: C5H12N2O3
Charge: 0
Energy: -532.982813 a.u
Gibbs: -533.039824 a.u
Multiplicity: 1
Dipole: 3.4509

Formula: C5H12N2O3
Charge: 0
Energy: -532.999707 a.u
Gibbs: -533.056700 a.u
Multiplicity: 1
Dipole: 3.5546

Formula: C5H12N2O3
Charge: 0
Energy: -532.658692 a.u
Gibbs: -532.712736 a.u
Multiplicity: 1
Dipole: 3.5084
C, -3.766207, 1.593905, -0.294292

H, -3.584328, 1.744026, 0.774773
H, -2.795899, 1.429514, -0.778383
C, -4.432487, 2.826049, -0.879824
H, -4.686930, 2.626461, -1.931457
H, -5.371129, 3.004849, -0.350879
O, -4.638785, 0.485682, -0.515964
H, -4.236100, -0.299559, -0.133428
N, -3.583059, 3.999241, -0.715042
H, -2.698232, 3.843493, -1.185624
C, -4.188246, 5.227253, -1.221345
H, -5.110667, 5.409454, -0.665900
H, -4.467468, 5.145685, -2.284475
C, -3.253913, 6.416074, -1.038778
H, -2.288370, 6.188181, -1.512524
H, -3.056758, 6.555705, 0.025591
N, -3.881558, 7.638189, -1.555567
H, -3.289042, 8.436421, -1.359715
H, -3.948466, 7.586080, -2.566439
C, -3.512950, 4.420911, 2.066915
O, -2.355591, 4.405025, 2.158922
O, -4.673786, 4.450093, 2.055773
1.15 HEEDA_OXD_H_transfer_product
Formula: C7H17N3O3
Charge: 0
Energy: -666.930304 a.u
Gibbs: -666.995807 a.u
Multiplicity: 1
Dipole: 4.2617

Formula: C7H17N3O3
Charge: 0
Energy: -666.948486 a.u
Gibbs: -667.017768 a.u
Multiplicity: 1
Dipole: 4.3256

Formula: C7H17N3O3
Charge: 0
Energy: -666.499613 a.u
Gibbs: -666.566481 a.u
Multiplicity: 1
Dipole: 4.2577
C, -3.338623, 0.918750, -1.085330

H, -2.978036, 0.083165, -0.478040
H, -3.460120, 0.532121, -2.111103
C, -2.282365, 2.023158, -1.091805
H, -2.649733, 2.875363, -1.669513
H, -2.134470, 2.381020, -0.071350
C, 0.727579, 3.868566, -1.444260
O, 1.683009, 3.247974, -1.668829
H, -1.085017, 1.309345, -2.596261
N, -0.982650, 1.633238, -1.640964
O, -0.176600, 4.559088, -1.212115
C, -6.914166, 0.921917, 0.147085
H, -7.235910, 1.816119, -0.412615
H, -6.701330, 1.251404, 1.166514
C, -5.637043, 0.372520, -0.473422
H, -5.280382, -0.465686, 0.129588
H, -5.862883, -0.033302, -1.473976
N, -4.594037, 1.392598, -0.510969
H, -4.926067, 2.181900, -1.055632
H, -0.595787, 0.856933, -1.115937
N, -7.952610, -0.102845, 0.198683
H, -8.137206, -0.429445, -0.744102
C, -9.199780, 0.371907, 0.787379
H, -9.642648, 1.215829, 0.236202
H, -8.992617, 0.728273, 1.799324
C, -10.217236, -0.752160, 0.863968
H, -10.415726, -1.142953, -0.141464
H, -9.812042, -1.570621, 1.467429
O, -11.408682, -0.219306, 1.444601
H, -12.058513, -0.925686, 1.506225
1.16 HEEDA_OXD_TS
Formula: C7H17N3O3
Charge: 0
Energy: -666.881865 a.u
Gibbs: -666.942685 a.u
Multiplicity: 1
Dipole: 15.2934

Formula: C7H17N3O3
Charge: 0
Energy: -666.963467 a.u
Gibbs: -666.902372 a.u
Multiplicity: 1
Dipole: 15.4061

Formula: C7H17N3O3
Charge: 0
Energy: -666.442253 a.u
Gibbs: -666.503172 a.u
Multiplicity: 1
Dipole: 15.0875
C, -2.628563, 0.696444, -0.116929

H, -3.008288, 0.052617, 0.651049
H, -2.732791, 0.387583, -1.141325
C, -1.845544, 1.950106, 0.213218
H, -2.288709, 2.817833, -0.272531
H, -1.875977, 2.117852, 1.295234
C, -0.011616, 0.466567, -0.183325
O, -0.958696, -0.392900, -0.018530
H, 0.167732, 2.508831, -0.126350
N, -0.495946, 1.768302, -0.285930
O, 1.197764, 0.222845, -0.281315
C, -6.924353, 1.093005, -0.392697
H, -6.976133, 1.756316, -1.270485
H, -7.137909, 1.710879, 0.483162
C, -5.513754, 0.524453, -0.272655
H, -5.442128, -0.092124, 0.622860
H, -5.290666, -0.113972, -1.129105
N, -4.469138, 1.555782, -0.203333
H, -4.489833, 2.157420, -1.020445
H, -4.591089, 2.146535, 0.613147
N, -7.900704, 0.011547, -0.439360
H, -7.718784, -0.561796, -1.256570
C, -9.281558, 0.482684, -0.487629
H, -9.493034, 1.105188, -1.369906
H, -9.467092, 1.103109, 0.392152
C, -10.244946, -0.690580, -0.470904
H, -10.053033, -1.341498, -1.332496
H, -10.085429, -1.280622, 0.437178
O, -11.570130, -0.160798, -0.520721
H, -12.191360, -0.894968, -0.508350
1.17 HEIA
Formula: C5H9NO3
Charge: 0
Energy: -476.429205 a.u
Gibbs: -476.473704 a.u
Multiplicity: 1
Dipole: 7.5778

Formula: C5H9NO3
Charge: 0
Energy: -476.445840 a.u
Gibbs: -476.490287 a.u
Multiplicity: 1
Dipole: 7.7377

Formula: C5H9NO3
Charge: 0
Energy: -476.144590 a.u
Gibbs: -476.189240 a.u
Multiplicity: 1
Dipole: 7.1614
C, -1.315555, 5.825191, 1.483916

C, 0.016938, 6.139128, 2.170302
C, -1.226030, 8.064169, 2.109627
H, -1.176143, 5.310360, 0.535727
H, -1.982370, 5.228565, 2.112581
H, 0.843530, 6.168287, 1.461389
H, 0.254879, 5.464759, 2.986868
N, -1.847155, 7.167327, 1.301778
O, -0.158538, 7.470724, 2.712976
O, -1.521772, 9.223366, 2.311833
C, -3.119311, 7.432241, 0.664320
H, -3.841550, 6.667753, 0.961430
H, -3.480380, 8.395799, 1.018702
C, -3.001576, 7.455922, -0.853827
H, -2.320147, 8.259069, -1.152426
H, -2.586712, 6.508292, -1.212820
O, -4.315246, 7.667857, -1.364026
H, -4.273960, 7.673396, -2.324982
1.18 HEIA_Formation_TS
Formula: C5H12N2O3
Charge: 0
Energy: -532.924822 a.u
Gibbs: -532.971378 a.u
Multiplicity: 1
Dipole: 8.3006

Formula: C5H12N2O3
Charge: 0
Energy: -532.942317 a.u
Gibbs: -532.989015 a.u
Multiplicity: 1
Dipole: 8.6594

Formula: C5H12N2O3
Charge: 0
Energy: -532.589279 a.u
Gibbs: -532.636288 a.u
Multiplicity: 1
Dipole: 8.4621
C, -0.315739, 1.146642, 0.071421

C, 2.117824, 0.465795, 0.552183
H, 1.883381, -0.155206, 1.416854
H, 2.184549, 1.500593, 0.879808
C, 3.432289, 0.035457, -0.091808
H, 3.630631, 0.654994, -0.967260
H, 3.381595, -1.005215, -0.423308
O, 4.516779, 0.239399, 0.803780
H, 4.485718, -0.438385, 1.487301
O, -0.177730, 1.951963, -1.798971
C, 0.538562, -0.972803, -0.813446
H, 0.699664, -1.651502, 0.020842
H, 1.096239, -1.316657, -1.678716
C, -0.953507, -0.782918, -1.084981
H, -1.503947, -1.708195, -0.938408
H, -1.124296, -0.405033, -2.094106
N, -1.308531, 0.205008, -0.076093
O, -0.251866, 2.057950, 0.865273
N, 0.993344, 0.383979, -0.399257
H, 1.099194, 1.002069, -1.243902
H, -0.116255, 2.875985, -1.538873
H, -2.243756, 0.581350, -0.092622
1.19 MEA_CO2_Ring_formation_TS
Formula: C5H14N2O4
Charge: 0
Energy: -609.375575 a.u
Gibbs: -609.432866 a.u
Multiplicity: 1
Dipole: 16.9188

Formula: C5H14N2O4
Charge: 0
Energy: -609.395669 a.u
Gibbs: -609.453063 a.u
Multiplicity: 1
Dipole: 17.1599

Formula:
Charge: 0
Energy: a.u
Gibbs: a.u
Multiplicity: 1
Dipole:
C, 0.934440, -0.192568, -0.023130

H, 1.455991, 0.251575, -0.878363
H, 1.154104, -1.258880, -0.016494
C, 1.441139, 0.446247, 1.249473
H, 2.078740, 1.307157, 1.220778
H, 0.944566, 0.226677, 2.177142
N, -0.502151, -0.009824, -0.082933
H, -0.982653, -0.434533, -0.860116
C, -0.948408, 1.265465, 0.291067
O, -2.085250, 1.645254, -0.030956
O, -0.085928, 1.903830, 0.990742
H, 2.608323, -1.532050, 1.848646
O, 2.902961, -0.632155, 1.658366
C, 5.149529, 1.675107, 0.233003
H, 4.539609, 1.630922, 1.141252
H, 4.512142, 2.029856, -0.585726
C, 5.684592, 0.291692, -0.094099
H, 6.360617, 0.361533, -0.949333
H, 6.255226, -0.084270, 0.754506
O, 6.276633, 2.527030, 0.413452
H, 5.961394, 3.407769, 0.637773
H, 4.923724, -1.579656, -0.488545
H, 3.561960, -0.677023, 0.836919
H, 4.088674, -0.389088, -1.206937
N, 4.567780, -0.640479, -0.347735
1.20 OZD
Formula: C3H5NO2
Charge: 0
Energy: -322.590256 a.u
Gibbs: -322.623839 a.u
Multiplicity: 1
Dipole: 6.8510

Formula: C3H5NO2
Charge: 0
Energy: -322.602419 a.u
Gibbs: -322.635983 a.u
Multiplicity: 1
Dipole: 7.0451

Formula: C3H5NO2
Charge: 0
Energy: -322.404114 a.u
Gibbs: -322.438649 a.u
Multiplicity: 1
Dipole: 6.7281
C, -1.440154, 5.730298, 1.889827

C, -0.007951, 6.081514, 2.312499
C, -0.964859, 7.959363, 1.409642
H, -1.481908, 4.812012, 1.309032
H, -2.110877, 5.641602, 2.746940
H, 0.732123, 5.649936, 1.639211
H, 0.222187, 5.810020, 3.337881
N, -1.753110, 6.900864, 1.083324
H, -2.674539, 7.076640, 0.720606
O, 0.060979, 7.524473, 2.193612
O, -1.086704, 9.119352, 1.082646
1.21 OZD_MEA
Formula: C5H12N2O3
Charge: 0
Energy: -532.977372 a.u
Gibbs: -533.032062 a.u
Multiplicity: 1
Dipole: 6.4415

Formula: C5H12N2O3
Charge: 0
Energy: -532.994456 a.u
Gibbs: a -533.048858 .u
Multiplicity: 1
Dipole: 6.8764

Formula: C5H12N2O3
Charge: 0
Energy: -532.648106 a.u
Gibbs: -532.701038 a.u
Multiplicity: 1
Dipole: 6.9237
C, 10.504567, -7.546756, 12.721673

H, 11.418181, -8.131689, 12.691994
H, 10.640150, -6.672019, 13.355130
C, 9.964350, -7.178862, 11.333534
H, 10.192381, -6.149992, 11.066871
H, 10.345218, -7.843274, 10.555962
C, 8.294425, -8.196086, 12.605710
O, 9.459899, -8.366710, 13.309972
H, 7.859758, -7.314487, 10.815786
N, 8.539742, -7.380210, 11.553770
O, 7.259283, -8.722111, 12.943161
C, 9.963653, -12.938018, 11.803066
H, 9.603094, -13.560107, 12.632307
H, 11.049727, -13.044553, 11.770734
C, 9.627175, -11.489137, 12.107003
H, 10.038207, -10.848980, 11.318139
H, 8.538362, -11.353885, 12.107458
O, 10.177226, -11.158706, 13.380459
H, 9.937321, -10.241572, 13.568569
N, 9.418816, -13.316055, 10.493793
H, 9.737862, -14.244587, 10.245075
H, 8.407868, -13.376999, 10.549032
1.22 OZD_MEA_H2O
Formula: C5H14N2O4
Charge: 0
Energy: -609.428541 a.u
Gibbs: -609.490056 a.u
Multiplicity: 1
Dipole: 8.6927

Formula: C5H14N2O4
Charge: 0
Energy: -609.447738 a.u
Gibbs: -609.510230 a.u
Multiplicity: 1
Dipole: 8.8742

Formula: C5H14N2O4
Charge: 0
Energy: -609.059067 a.u
Gibbs: -609.119745 a.u
Multiplicity: 1
Dipole: 8.7566
C, -2.728548, -1.186021, -0.449131

H, -3.247886, -1.848417, -1.137816
H, -3.155605, -0.184544, -0.526414
C, -2.764996, -1.704844, 0.994275
H, -2.913483, -2.783169, 1.038484
H, -3.496979, -1.187651, 1.605235
N, -1.292783, -1.179575, -0.681253
H, -0.879108, -0.775517, -1.503999
C, -0.595289, -1.151144, 0.485292
O, 0.588149, -0.947871, 0.649736
O, -1.443226, -1.410174, 1.517319
H, -3.918556, 1.422778, 1.539816
O, -4.706843, 0.909521, 1.740606
C, -6.460095, -1.852019, 0.139372
H, -5.932438, -1.614324, 1.067990
H, -5.723839, -2.226289, -0.582313
C, -7.121500, -0.598629, -0.406788
H, -7.704622, -0.864615, -1.294426
H, -7.816930, -0.213242, 0.339657
O, -7.487581, -2.816704, 0.360103
H, -7.086439, -3.610635, 0.726163
H, -6.559044, 1.302360, -0.937567
H, -5.153423, 0.778035, 0.869505
H, -5.530715, 0.165657, -1.460564
N, -6.108297, 0.434873, -0.671519
1.23 OZD_MEA_TS
Formula: C5H12N2O3
Charge: 0
Energy: -532.933919 a.u
Gibbs: -532.983953 a.u
Multiplicity: 1
Dipole: 17.3753

Formula: C5H12N2O3
Charge: 0
Energy: -532.951970 a.u
Gibbs: -533.002064 a.u
Multiplicity: 1
Dipole: 17.6218

Formula: C5H12N2O3
Charge: 0
Energy: -532.598441 a.u
Gibbs: -532.648500 a.u
Multiplicity: 1
Dipole: 17.3223
C, 10.441561, -7.419143, 12.509922

H, 10.882030, -8.337635, 12.176387
H, 10.539371, -7.151641, 13.546614
C, 9.572562, -6.579179, 11.598096
H, 9.946703, -5.558365, 11.544467
H, 9.599260, -7.001310, 10.587686
C, 7.844606, -7.763733, 12.749799
O, 8.849999, -8.525811, 13.015140
H, 7.524241, -6.052205, 11.665927
N, 8.236655, -6.562570, 12.162175
O, 6.654338, -7.998183, 12.994509
C, 14.671994, -6.602988, 12.521051
H, 14.674703, -5.587760, 12.933258
H, 14.875516, -6.532061, 11.446821
C, 13.311057, -7.245012, 12.744424
H, 13.315473, -8.257563, 12.341216
H, 13.109998, -7.314376, 13.813315
N, 12.209427, -6.504843, 12.117013
H, 12.151430, -5.555697, 12.471864
H, 12.327178, -6.449239, 11.110194
O, 15.629475, -7.429602, 13.176075
H, 16.502457, -7.044514, 13.052356
1.24 Pre_AEHEIA_1
Formula: C7H17N3O3
Charge: 0
Energy: -666.923961 a.u
Gibbs: -666.985782 a.u
Multiplicity: 1
Dipole: 8.2142

Formula: C7H17N3O3
Charge: 0
Energy: -666.943465 a.u
Gibbs: -667.004676 a.u
Multiplicity: 1
Dipole: 8.6933

Formula: C7H17N3O3
Charge: 0
Energy: -666.466979 a.u
Gibbs: -666.525151 a.u
Multiplicity: 1
Dipole: 10.0493
C, -1.557864, 1.431929, 0.295473

C, 1.449502, -2.908945, 0.164549
H, 1.511126, -3.138384, 1.240615
H, 2.073376, -2.029684, -0.009465
C, 2.019626, -4.079218, -0.626743
H, 2.040905, -3.828952, -1.687330
H, 1.379072, -4.961108, -0.506621
O, 3.365158, -4.372084, -0.254531
H, 3.365944, -4.691399, 0.653939
C, -4.621187, 1.291521, 0.804695
H, -4.026476, 2.211934, 0.776985
H, -4.698125, 0.991205, 1.851679
O, -1.151719, 1.781332, 1.378101
C, -0.498525, -1.466935, 0.414317
H, 0.161674, -0.609254, 0.273210
H, -0.591791, -1.619941, 1.500965
C, -3.910419, 0.197507, 0.018144
H, -4.471781, -0.734598, 0.089306
H, -3.830492, 0.472654, -1.033052
N, -5.976192, 1.452038, 0.271143
H, -6.509268, 2.068454, 0.872466
H, -5.937449, 1.909087, -0.633417
C, -1.867627, -1.166017, -0.180829
H, -2.515676, -2.041359, -0.104453
H, -1.773289, -0.899175, -1.231260
N, -2.527841, -0.027918, 0.501086
O, -1.531399, 1.721804, -0.875306
N, 0.088946, -2.609655, -0.271968
H, -0.494727, -3.425316, -0.119049
H, -2.533536, -0.185557, 1.506246
1.25 AEHEIA_1_3_H_transfer_TS
Formula: C7H17N3O3
Charge: 0
Energy: -666.876506 a.u
Gibbs: -666.936889 a.u
Multiplicity: 1
Dipole: 7.6043

Formula:
Charge: 0
Energy: -666.895892 a.u
Gibbs: -666.956123 a.u
Multiplicity: 1
Dipole: 7.8257

Formula: C7H17N3O3
Charge: 0
Energy: -666.445040 a.u
Gibbs: -666.505123 a.u
Multiplicity: 1
Dipole: 7.6213
C, -1.419780, 1.483922, -0.465556

H, -1.360509, 2.573964, -0.337125
H, -1.619425, 1.297647, -1.521191
C, -2.575236, 0.917902, 0.356851
H, -2.690379, -0.140496, 0.131978
H, -2.378360, 1.017497, 1.427175
N, -3.859570, 1.585967, 0.053212
H, -4.031878, 2.290215, -1.074624
C, -5.011462, 0.913110, 0.693046
H, -4.917516, 0.995182, 1.778677
H, -4.954605, -0.142471, 0.427626
C, -6.349343, 1.487026, 0.239594
H, -6.395809, 1.464045, -0.856346
H, -6.425365, 2.532892, 0.542023
N, -7.429577, 0.747214, 0.896272
H, -8.314661, 1.207907, 0.723222
H, -7.511375, -0.178287, 0.489923
C, -3.829100, 3.076306, 0.333391
O, -4.018960, 3.525691, -0.865417
O, -3.668620, 3.598842, 1.403173
N, -0.170990, 0.820552, -0.100554
H, 0.454380, 0.837690, -0.895721
C, 0.503927, 1.412670, 1.052460
H, 0.810178, 2.453998, 0.875247
H, -0.181844, 1.424049, 1.901103
C, 1.724590, 0.593631, 1.430748
H, 2.415380, 0.541492, 0.580462
H, 1.416734, -0.427860, 1.675473
O, 2.342232, 1.232977, 2.548258
H, 3.114109, 0.719294, 2.804013
1.26 Pre_AEHEIA_2
Formula: C7H17N3O3
Charge: 0
Energy: -666.926615 a.u
Gibbs: -666.987725 a.u
Multiplicity: 1
Dipole: 6.5986

Formula: C7H17N3O3
Charge: 0
Energy: -666.945760 a.u
Gibbs: -667.006681 a.u
Multiplicity: 1
Dipole: 6.7576

Formula: C7H17N3O3
Charge: 0
Energy: -666.494493 a.u
Gibbs: -666.554691 a.u
Multiplicity: 1
Dipole: 6.4210
C, -1.638031, 1.947381, -0.107592

C, 0.727988, -3.007649, 0.630190
H, 0.079574, -3.447300, 1.405223
H, 1.405547, -2.317336, 1.137320
C, 1.550037, -4.115140, -0.016508
H, 2.257359, -3.681554, -0.723367
H, 0.893687, -4.791850, -0.576607
O, 2.325744, -4.834550, 0.940539
H, 1.723531, -5.309099, 1.523144
C, -4.123883, 0.109872, 0.962642
H, -3.647323, 0.692876, 1.759782
H, -3.776407, -0.919255, 1.061666
O, -0.291298, 2.058109, -0.267002
C, -0.791689, -1.158120, 0.167942
H, -0.108322, -0.502679, 0.711972
H, -1.557088, -1.477512, 0.888131
C, -3.674934, 0.673756, -0.385441
H, -4.041560, 0.038856, -1.191090
H, -4.102585, 1.665057, -0.521304
N, -5.588834, 0.103682, 1.020010
H, -5.899922, -0.385171, 1.850820
H, -5.932937, 1.053604, 1.110248
C, -1.459283, -0.375888, -0.966833
H, -2.150599, -1.025335, -1.501737
H, -0.705748, -0.085906, -1.704422
N, -2.220642, 0.788730, -0.517710
O, -2.240089, 2.885180, 0.384121
N, -0.021762, -2.266933, -0.379981
H, -0.651728, -2.903511, -0.857246
H, 0.091144, 1.321652, -0.758014
1.27 Isocyanate
Formula: C3H5NO2
Charge: 0
Energy: -322.565066 a.u
Gibbs: -322.604221 a.u
Multiplicity: 1
Dipole: 3.5292

Formula: C3H5NO2
Charge: 0
Energy: -322.577098 a.u
Gibbs: -322.616214 a.u
Multiplicity: 1
Dipole: 3.6070

Formula: C3H5NO2
Charge: 0
Energy: -322.381443 a.u
Gibbs: -322.420656 a.u
Multiplicity: 1
Dipole: 3.6605
C, -0.028150, 0.455938, -0.203989

H, 0.176347, -0.575397, -0.494106
H, 0.714894, 0.757020, 0.535522
C, 0.074017, 1.356969, -1.423424
H, -0.669719, 1.056124, -2.167615
H, -0.128994, 2.392769, -1.134681
N, -1.353379, 0.550607, 0.366719
C, -2.003460, 0.116742, 1.267652
O, -2.740901, -0.238544, 2.112722
O, 1.405231, 1.204412, -1.922919
H, 1.504409, 1.765066, -2.698157
1.28 Isocyanate_MEA
Formula: C5H12N2O3
Charge: 0
Energy: -532.957023 a.u
Gibbs: -533.015122 a.u
Multiplicity: 1
Dipole: 4.8520

Formula: C5H12N2O3
Charge: 0
Energy: -532.973312 a.u
Gibbs: -533.032423 a.u
Multiplicity: 1
Dipole: 5.0166

Formula: C5H12N2O3
Charge: 0
Energy: -532.627701 a.u
Gibbs: -532.685346 a.u
Multiplicity: 1
Dipole: 4.7735
C, -1.055691, 0.468673, 0.279366

H, -1.986822, 0.086028, 0.692619
H, -0.233306, -0.099407, 0.714742
C, -1.061154, 0.288528, -1.233967
H, -1.899439, 0.832317, -1.674453
H, -0.130728, 0.679130, -1.655251
N, -0.939613, 1.863591, 0.633847
C, -0.151500, 2.759839, 0.595316
O, 0.528866, 3.718985, 0.618013
O, -1.184508, -1.116689, -1.475427
H, -1.227582, -1.271886, -2.424618
C, 2.479123, -1.247284, -1.268078
H, 1.718891, -0.856392, -1.948715
H, 2.576563, -0.525185, -0.454264
C, 1.992178, -2.577677, -0.691267
H, 1.879384, -3.304662, -1.506496
H, 2.743983, -2.972763, -0.004262
O, 0.785043, -2.449275, 0.053175
H, 0.096082, -2.100259, -0.538181
N, 3.751386, -1.322112, -1.991126
H, 4.475066, -1.681752, -1.377875
H, 3.675666, -1.986600, -2.753921
1.29 Isocyanate_MEA_BHEU_formation_TS
Formula: C5H12N2O3
Charge: 0
Energy: -532.911212 a.u
Gibbs: -532.963508 a.u
Multiplicity: 1
Dipole: 7.4040

Formula: C5H12N2O3
Charge: 0
Energy: -532.928325 a.u
Gibbs: -532.980621 a.u
Multiplicity: 1
Dipole: 7.6366

Formula: C5H12N2O3
Charge: 0
Energy: -532.580259 a.u
Gibbs: -532.632089 a.u
Multiplicity: 1
Dipole: 7.4309
C, 0.399745, 0.289675, 0.242921

H, 0.324128, -0.523873, 0.970101
H, 1.201481, 0.954616, 0.568268
C, 0.761173, -0.290294, -1.118386
H, -0.021798, -0.986621, -1.437095
H, 0.818357, 0.516764, -1.856320
N, -0.842689, 1.030580, 0.190311
C, -2.002541, 0.506864, 0.546069
O, -2.411528, -0.545940, 1.001137
O, 2.019378, -0.955756, -0.980618
H, 2.261095, -1.329706, -1.833238
C, -3.593345, 2.278012, 1.404074
H, -2.867440, 2.466795, 2.194930
H, -4.315181, 1.546295, 1.771393
C, -4.300614, 3.570276, 1.036701
H, -3.567756, 4.306417, 0.691090
H, -5.008073, 3.387769, 0.219735
O, -4.973701, 4.015988, 2.209740
H, -5.427950, 4.839417, 2.006843
N, -2.867514, 1.731506, 0.248579
H, -3.492551, 1.552956, -0.533931
H, -1.654532, 2.064764, -0.048568
1.30 Isocyanate_formation_TS
Formula: C3H7NO3
Charge: 0
Energy: -398.953718 a.u
Gibbs: -398.995821 a.u
Multiplicity: 1
Dipole: 4.5916

Formula: C3H7NO3
Charge: 0
Energy: -398.967651 a.u
Gibbs: -399.009799 a.u
Multiplicity: 1
Dipole: 4.7204

Formula: C3H7NO3
Charge: 0
Energy: -398.727671 a.u
Gibbs: -398.768808 a.u
Multiplicity: 1
Dipole: 4.7452
C, -0.320461, 0.665305, -1.168629

H, -0.564220, 1.377817, -1.959557
H, 0.301151, -0.117963, -1.603535
C, 0.462021, 1.371172, -0.070305
H, -0.143160, 2.181787, 0.348767
H, 0.685134, 0.662256, 0.733440
N, -1.530919, 0.058680, -0.636584
H, -2.235780, -0.843522, 0.040981
C, -2.708211, 0.550238, -0.834011
O, -3.383002, 1.395864, -1.319069
O, -3.432322, -0.738238, 0.007396
H, -3.806610, -0.412431, 0.838782
O, 1.659984, 1.873573, -0.668115
H, 2.178712, 2.312152, 0.013018
1.31 Isocyanate_H2O
Formula: C3H7NO3
Charge: 0
Energy: -399.011495 a.u
Gibbs: -399.059457 a.u
Multiplicity: 1
Dipole: 3.3206

Formula: C3H7NO3
Charge: 0
Energy: -399.026109 a.u
Gibbs: -399.074646 a.u
Multiplicity: 1
Dipole: 3.9522

Formula: C3H7NO3
Charge: 0
Energy: -398.787828 a.u
Gibbs: -398.836603 a.u
Multiplicity: 1
Dipole: 2.9882
C, -0.146078, 0.903546, 0.015627

H, 0.531655, 0.086349, 0.258331
H, 0.223097, 1.810162, 0.492452
C, -0.197848, 1.115761, -1.491070
H, -0.551035, 0.202638, -1.979946
H, -0.896496, 1.924944, -1.719593
N, -1.479582, 0.632599, 0.532274
C, -2.076124, -0.317962, 0.957766
O, -2.756548, -1.165615, 1.394288
O, 1.135547, 1.441104, -1.892457
H, 1.136200, 1.596743, -2.841747
O, -2.870157, 3.166798, -0.310910
H, -2.575628, 2.322903, 0.060926
H, -2.256192, 3.811660, 0.054877
1.32 Isocyanate_H2O_H2O
Formula: C3H9NO4
Charge: 0
Energy: -475.462917 a.u
Gibbs: -475.517923 a.u
Multiplicity: 1
Dipole: 3.7519
Formula: C3H9NO4
Charge: 0
Energy: -475.478962a.u
Gibbs: -475.534269a.u
Multiplicity: 1
Dipole: 4.2547
Formula: C3H9NO4
Charge: 0
Energy: -475.199019 a.u
Gibbs: -475.253683 a.u
Multiplicity: 1
Dipole: 4.4349
C, -1.625245, 1.128767, 0.055937

H, -0.868045, 0.454181, 0.450213
H, -1.888160, 1.850279, 0.828091
C, -1.079840, 1.861166, -1.163420
H, -0.797974, 1.134438, -1.932161
H, -1.858161, 2.510341, -1.574280
N, -2.795349, 0.350051, -0.289280
C, -3.920770, 0.542228, -0.637055
O, -5.043731, 0.594905, -0.989488
O, 0.047474, 2.607954, -0.712690
H, 0.414016, 3.088301, -1.461177
O, -4.271010, 3.282350, -2.426663
H, -4.182577, 3.400476, -1.464778
H, -4.753455, 2.453621, -2.510317
O, -3.878411, 3.406672, 0.373909
H, -3.317320, 4.129073, 0.676338
H, -4.673406, 3.461784, 0.915292
1.33 BHEOX_intermediate
Formula: C6H14N2O5
Charge: 0
Energy: -722.778048 a.u
Gibbs: -722.843382 a.u
Multiplicity: 1
Dipole: 5.9645

Formula: C6H14N2O5
Charge: 0
Energy: -722.815197 a.u
Gibbs: -722.880852 a.u
Multiplicity: 1
Dipole: 7.6302

Formula: C6H14N2O5
Charge: 0
Energy: -722.366002 a.u
Gibbs: -722.430954 a.u
Multiplicity: 1
Dipole: 7.4486
O, -3.568938, 1.360524, 0.058120

C, -6.219419, -0.783921, -0.588153
H, -5.602687, -0.215644, -1.285608
H, -6.320856, -1.791041, -0.996448
C, -7.596254, -0.140142, -0.509146
H, -7.496914, 0.883793, -0.127584
H, -8.224036, -0.700891, 0.195667
O, -8.153592, -0.153244, -1.820227
H, -9.013152, 0.276264, -1.798565
H, -6.024179, -1.419698, 1.363033
H, -5.381412, 0.063403, 1.082402
N, -5.511413, -0.862204, 0.690874
C, -2.464635, 1.117604, -0.367958
O, -1.545704, 2.049083, -0.627219
H, -1.933570, 2.910837, -0.411096
C, -1.942324, -0.300509, -0.698173
O, -0.877451, -0.463123, -1.271084
N, -2.777369, -1.266509, -0.289977
H, -3.678172, -1.038952, 0.145683
C, -2.489487, -2.666065, -0.539041
H, -2.996887, -3.262469, 0.218484
H, -1.417109, -2.835213, -0.454859
C, -2.957362, -3.101382, -1.923063
H, -4.028868, -2.894280, -2.028573
H, -2.419254, -2.523445, -2.680447
O, -2.685755, -4.495095, -2.033790
H, -2.868281, -4.775503, -2.934680
1.34 BHEOX_intermediate_2_TS
Formula: C6H14N2O5
Charge: 0
Energy: -722.731637 a.u
Gibbs: -722.791383 a.u
Multiplicity: 1
Dipole: 2.7565

Formula: C6H14N2O5
Charge: 0
Energy: -722.756215 a.u
Gibbs: -722.815797 a.u
Multiplicity: 1
Dipole: 2.8378

Formula: C6H14N2O5
Charge: 0
Energy: -722.307227 a.u
Gibbs: -722.366323 a.u
Multiplicity: 1
Dipole: 2.9099
O, 1.304468, 0.267834, -0.240536

C, -0.359736, 3.025939, -1.279897
H, 0.576864, 3.236698, -1.790312
H, -1.135640, 2.892484, -2.035412
C, -0.716424, 4.185911, -0.366392
H, 0.066017, 4.312766, 0.388845
H, -1.658246, 3.978246, 0.153797
O, -0.831287, 5.338073, -1.195789
H, -1.050810, 6.092689, -0.640802
H, -1.048299, 1.548666, 0.010586
H, 0.822183, 1.414027, 0.153786
N, -0.198661, 1.797190, -0.494650
C, 0.331121, 0.517658, -1.157002
O, 0.790758, 0.739798, -2.459767
H, 1.726683, 0.966774, -2.379283
C, -0.786248, -0.553331, -1.173460
O, -1.666204, -0.537388, -0.314907
N, -0.663474, -1.489555, -2.122618
H, 0.084663, -1.379353, -2.787423
C, -1.540341, -2.643800, -2.213636
H, -2.531883, -2.356592, -1.867624
H, -1.613844, -2.945399, -3.257226
C, -1.029517, -3.807320, -1.373411
H, -0.954952, -3.492121, -0.327884
H, -0.030185, -4.097455, -1.714557
O, -1.962387, -4.873484, -1.530781
H, -1.664169, -5.621657, -1.004755
1.35 BHEOX_intermediate_3
Formula: C6H14N2O5
Charge: 0
Energy: -722.778298 a.u
Gibbs: -722.841173 a.u
Multiplicity: 1
Dipole: 5.6553
Formula: C6H14N2O5
Charge: 0
Energy: -722.801044 a.u
Gibbs: -722.865086 a.u
Multiplicity: 1
Dipole: 2.9365
Formula: C6H14N2O5
Charge: 0
Energy: -722.347429 a.u
Gibbs: -722.411208 a.u
Multiplicity: 1
Dipole: 4.5047
O, 3.097779, -0.600507, -2.360419

C, -0.840016, 2.603406, -0.560661
H, -0.093228, 2.836311, 0.205448
H, -0.495858, 3.079497, -1.484687
C, -2.181259, 3.185398, -0.153403
H, -2.522660, 2.703621, 0.769234
H, -2.921900, 2.977053, -0.933041
O, -2.003321, 4.589782, 0.028998
H, -2.847225, 4.973137, 0.285474
H, 3.636330, -1.078769, -1.720778
H, 2.322475, -1.170404, -2.526266
N, -0.973931, 1.166272, -0.731836
C, 0.045060, 0.500189, -1.076052
O, 1.247048, 1.050557, -1.292084
H, 1.933957, 0.416133, -1.619150
C, -0.090878, -0.990859, -1.346847
O, 0.544034, -1.499122, -2.281051
N, -0.909183, -1.727514, -0.582355
H, -0.959201, -2.692302, -0.878201
C, -1.687105, -1.369076, 0.597711
H, -1.627129, -2.201479, 1.299048
H, -1.253992, -0.493864, 1.069496
C, -3.143723, -1.089150, 0.257106
H, -3.183550, -0.279627, -0.473814
H, -3.603955, -1.983275, -0.177305
O, -3.782722, -0.721886, 1.479853
H, -4.706182, -0.527150, 1.294208
1.36 BHEOX_intermediate_4
Formula: C6H14N2O5
Charge: 0
Energy: -722.689644 a.u
Gibbs: -722.750475 a.u
Multiplicity: 1
Dipole: 7.7201
O, 1.419091, 0.717664, -0.678971

C, -0.667751, 2.577039, -1.012878
H, 0.102268, 2.883390, -0.287996
H, -0.340319, 2.979839, -1.985998
C, -1.963623, 3.273753, -0.638759
H, -2.300184, 2.908434, 0.338303
H, -2.738486, 3.024984, -1.372535
O, -1.729044, 4.687195, -0.603199
H, -2.554879, 5.124746, -0.377147
H, 2.045085, 1.058337, -1.326378
H, 1.406025, -0.895483, 0.119506
N, -0.888628, 1.146819, -1.035081
C, 0.186948, 0.403585, -1.333247
O, 0.535874, 0.350323, -2.799492
H, 1.265040, -0.268875, -2.944845
C, -0.127491, -1.020980, -0.863914
O, 0.689260, -1.562688, 0.002248
N, -1.143538, -1.734614, -1.250491
H, -1.247027, -2.638114, -0.805580
C, -2.163364, -1.352041, -2.225920
H, -2.342659, -2.213338, -2.869061
H, -1.777277, -0.530278, -2.817055
C, -3.451448, -0.933182, -1.534000
H, -3.231833, -0.071090, -0.902434
H, -3.830547, -1.751502, -0.911767
O, -4.371386, -0.609554, -2.575411
H, -5.177745, -0.272270, -2.174057
1.37 BHEOX_intermediate_4_TS
Formula: C6H12N2O4
Charge: 0
Energy: -646.273915 a.u
Gibbs: -646.33166 a.u
Multiplicity: 1
Dipole: 5.1016

Formula: C6H12N2O4
Charge: 0
Energy: -646.295851 a.u
Gibbs: -646.352772 a.u
Multiplicity: 1
Dipole: 5.6037

Formula: C6H12N2O4
Charge: 0
Energy: -645.887813 a.u
Gibbs: -645.944367 a.u
Multiplicity: 1
Dipole: 5.7101
O, 1.447734, 0.472073, 1.588200

C, 0.343855, 2.494390, -1.078072
H, 0.592797, 3.553107, -1.000260
H, 0.896511, 2.081671, -1.923827
C, -1.153987, 2.352385, -1.319198
H, -1.702341, 2.734380, -0.451881
H, -1.403555, 1.292464, -1.438431
O, -1.458973, 3.094348, -2.496988
H, -2.403761, 3.026957, -2.665058
H, 0.878965, 1.651022, 1.492782
N, 0.737858, 1.834610, 0.149707
C, 1.292247, 0.678781, 0.315833
C, 1.781256, -0.278706, -0.746878
O, 2.645848, 0.104084, -1.527008
N, 1.217548, -1.495675, -0.766633
H, 1.580231, -2.119279, -1.473608
C, 0.189775, -2.006010, 0.131258
H, -0.492079, -2.627119, -0.448095
H, -0.388502, -1.177101, 0.534251
C, 0.782827, -2.818138, 1.274228
H, 1.377092, -3.644356, 0.869059
H, 1.440084, -2.174506, 1.865012
O, -0.315776, -3.297029, 2.045304
H, 0.028386, -3.794588, 2.793119
.
1.38 BHEOX-intermediate_2
Formula: C6H14N2O5
Charge: 0
Energy: -722.77291 a.u
Gibbs: -722.832829 a.u
Multiplicity: 1
Dipole: 8.1729

Formula: C6H14N2O5
Charge: 0
Energy: -722.796982 a.u
Gibbs: -722.856868 a.u
Multiplicity: 1
Dipole: 8.4363

Formula: C6H14N2O5
Charge: 0
Energy: -722.351318 a.u
Gibbs: -722.410463 a.u
Multiplicity: 1
Dipole: 8.2788
O, 1.400448, 0.975047, 0.413879

C, -0.043957, 2.741364, -1.382230
H, 0.878117, 3.039049, -0.887097
H, 0.191572, 2.546137, -2.433078
C, -1.049939, 3.874987, -1.293119
H, -1.230601, 4.120916, -0.241773
H, -2.004273, 3.562533, -1.733497
O, -0.501782, 4.985923, -2.001504
H, -1.129158, 5.713778, -1.958920
H, -1.358576, 1.177386, -1.221437
H, 0.985470, 1.424038, 1.160822
N, -0.575247, 1.556157, -0.701219
C, 0.372405, 0.506038, -0.449813
O, 1.000575, 0.043457, -1.603954
H, 1.143972, -0.907086, -1.461507
C, -0.315745, -0.707952, 0.244839
O, 0.093681, -1.842588, 0.008920
N, -1.280025, -0.403445, 1.120744
H, -1.573972, 0.560620, 1.161552
C, -1.990541, -1.403317, 1.899965
H, -2.302475, -0.954110, 2.841470
H, -1.307296, -2.221889, 2.118792
C, -3.205713, -1.941286, 1.155048
H, -2.881187, -2.389651, 0.210809
H, -3.890629, -1.118280, 0.924941
O, -3.818809, -2.905311, 2.006504
H, -4.589937, -3.264736, 1.557495
1.39 BHEOX-intermediate_5
Formula: C6H12N2O4
Charge: 0
Energy: -646.333819 a.u
Gibbs: -646.391647 a.u
Multiplicity: 1
Dipole: 4.5846

Formula: C6H12N2O4
Charge: 0
Energy: -646.355505 a.u
Gibbs: -646.412901 a.u
Multiplicity: 1
Dipole: 4.7760

Formula: C6H12N2O4
Charge: 0
Energy: -645.947773 a.u
Gibbs: -646.004045 a.u
Multiplicity: 1
Dipole: 4.4338
C, -0.494948, 2.777634, -1.253572

H, 0.566836, 3.028921, -1.343606
H, -0.949790, 2.987851, -2.226966
C, -1.134891, 3.655910, -0.194542
H, -0.669446, 3.455961, 0.776527
H, -2.199878, 3.413379, -0.113299
O, -0.940850, 5.012056, -0.593288
H, -1.342761, 5.584739, 0.066566
N, -0.662116, 1.376803, -0.897194
C, -0.212184, 0.496476, -1.680730
O, 0.422691, 0.734772, -2.840911
H, 0.637051, -0.143873, -3.210568
C, -0.351623, -0.986582, -1.385529
O, 0.098780, -1.791887, -2.203208
N, -0.955854, -1.292706, -0.236542
H, -1.289352, -0.514455, 0.312584
C, -1.199302, -2.655830, 0.197799
H, -0.404520, -3.290763, -0.189930
H, -1.164878, -2.687372, 1.285592
C, -2.546325, -3.174172, -0.291984
H, -3.348702, -2.533767, 0.089263
H, -2.571797, -3.138648, -1.385696
O, -2.672600, -4.509049, 0.189378
H, -3.513492, -4.865719, -0.112514
1.40 BHEOX-intermediate1
Formula: C6H14N2O5
Charge: 0
Energy: -722.755949 a.u
Gibbs: -722.814429 a.u
Multiplicity: 1
Dipole: 5.6030

Formula: C6H14N2O5
Charge: 0
Energy: -722.808110 a.u
Gibbs: -722.875038 a.u
Multiplicity: 1
Dipole: 6.0120

Formula: C6H14N2O5
Charge: 0
Energy: -722.360119 a.u
Gibbs: -722.425744 a.u
Multiplicity: 1
Dipole: 7.1103
O, 0.654812, -0.115252, -0.700935

C, 0.118452, 2.516074, -1.434844
H, 1.122267, 2.117401, -1.528480
H, -0.450284, 2.263067, -2.325645
C, 0.138009, 4.017529, -1.213027
H, 0.689581, 4.253540, -0.296234
H, -0.881844, 4.401678, -1.103155
O, 0.776346, 4.568122, -2.357851
H, 0.797834, 5.525657, -2.265727
H, -1.484146, 2.138888, -0.182693
H, -0.049825, 2.046169, 0.596643
N, -0.521005, 1.816003, -0.284775
C, -0.497630, 0.348782, -0.372051
O, -1.580443, 0.037487, -1.298766
H, -1.123512, -0.330183, -2.065387
C, -0.928348, -0.123673, 1.057407
O, -0.561880, 0.513583, 2.049049
N, -1.591557, -1.284947, 1.099313
H, -1.865289, -1.681060, 0.214980
C, -1.872717, -2.003281, 2.328701
H, -2.797217, -2.565366, 2.204641
H, -2.016305, -1.280365, 3.130196
C, -0.738236, -2.949693, 2.700047
H, -0.587844, -3.677818, 1.895935
H, 0.186639, -2.375853, 2.816831
O, -1.110509, -3.590520, 3.918047
H, -0.406981, -4.194730, 4.173763
1.41 Ethanoic_acid
Formula: C2H4O2
Charge: 0
Energy: -229.125201 a.u
Gibbs: -229.156867 a.u
Multiplicity: 1
Dipole: 2.1883

Formula: C2H4O2
Charge: 0
Energy: -229.133815 a.u
Gibbs: -229.165553 a.u
Multiplicity: 1
Dipole: 2.2391

Formula: C2H4O2
Charge: 0
Energy: -228.997699 a.u
Gibbs: -229.029478 a.u
Multiplicity: 1
Dipole: 2.2083
C, 0.645047, 0.600592, -0.127886

O, 1.852510, 0.657174, -0.127975
O, -0.132871, 1.703363, -0.127848
H, 0.446359, 2.480920, -0.127875
C, -0.175174, -0.655235, -0.127846
H, -0.819872, -0.672046, 0.750806
H, -0.820213, -0.671913, -1.006247
H, 0.476663, -1.522471, -0.128028
1.42 Formic_acid
Formula: CH2O2
Charge: 0
Energy: -189.811772 a.u
Gibbs: -189.839023 a.u
Multiplicity: 1
Dipole: 1.9528

Formula: CH2O2
Charge: 0
Energy: -189.820151 a.u
Gibbs: -189.847404 a.u
Multiplicity: 1
Dipole: 1.9868

Formula: CH2O2
Charge: 0
Energy: -189.719181 a.u
Gibbs: -189.746414 a.u
Multiplicity: 1
Dipole: 1.9664
C, 0.645457, 0.639335, -0.127881

O, 1.848173, 0.627255, -0.127895
H, 0.010378, -0.253546, -0.127855
O, -0.115939, 1.739345, -0.127894
H, 0.461001, 2.521044, -0.127919
1.43 HHEA_intermediate
Formula: C4H11NO4
Charge: 0
Energy: -514.745924 a.u
Gibbs: -514.799134 a.u
Multiplicity: 1
Dipole: 5.7895

Formula: C4H11NO4
Charge: 0
Energy: -439.523561 a.u
Gibbs: -439.576776 a.u
Multiplicity: 1
Dipole: 4.7221

Formula: C4H11NO4
Charge: 0
Energy: -439.238687 a.u
Gibbs: -439.292853 a.u
Multiplicity: 1
Dipole: 4.3740
O, -1.986764, 1.981519, -0.912543

C, -6.295042, 0.022867, -0.088238
H, -6.388489, -0.199948, 0.975321
H, -5.618406, 0.873095, -0.179741
C, -7.658442, 0.419654, -0.636851
H, -8.353542, -0.424300, -0.539301
H, -7.566519, 0.654368, -1.705331
O, -8.106338, 1.548728, 0.105166
H, -8.967458, 1.819706, -0.224888
H, -5.552405, -0.939319, -1.746309
H, -6.273778, -1.950818, -0.681108
N, -5.686375, -1.128821, -0.759443
C, -2.572594, 0.928477, -0.950541
O, -3.383504, 0.581908, -1.976494
H, -3.360425, 1.315854, -2.609296
C, -2.511772, -0.108997, 0.161855
H, -3.050990, 0.344152, 1.006830
H, -1.464834, -0.167493, 0.461021
O, -2.963764, -1.392981, -0.150565
H, -3.935398, -1.360363, -0.317110
1.44 HEA_intermediate_2
Formula: C4H11NO3
Charge: 0
Energy: -439.490784 a.u
Gibbs: -439.536208 a.u
Multiplicity: 1
Dipole: 3.7152

Formula: C4H11NO3
Charge: 0
Energy: -439.222077 a.u
Gibbs: -439.267114 a.u
Multiplicity: 1
Dipole: 3.8149

Formula:
Charge: 0
Energy: -439.504076 a.u
Gibbs: -439.549519 a.u
Multiplicity: 1
Dipole: 3.9234
O, 1.669241, 1.350536, 0.481057

C, -0.155191, 2.506077, -1.513040
H, 0.858007, 2.872871, -1.357477
H, -0.185907, 2.037696, -2.502201
C, -1.120787, 3.677296, -1.483729
H, -1.033562, 4.198257, -0.524690
H, -2.151445, 3.313498, -1.574254
O, -0.788159, 4.536931, -2.575035
H, -1.397435, 5.281084, -2.572462
H, -1.334542, 1.077876, -0.621278
H, 1.339089, 1.891562, 1.207783
N, -0.473486, 1.574018, -0.432131
C, 0.558599, 0.645272, -0.066453
O, 1.063113, -0.002593, -1.223708
H, 1.806114, -0.557951, -0.960237
C, 0.019810, -0.374851, 0.932259
H, -0.783609, -0.958032, 0.483420
H, 0.822714, -1.050352, 1.223320
H, -0.358480, 0.126083, 1.822245
1.45 HEA_intermediate_2_TS
Formula: C4H11NO3
Charge: 0
Energy: -439.449503 a.u
Gibbs: -439.494321 a.u
Multiplicity: 1
Dipole: 5.6655

Formula: C4H11NO3
Charge: 0
Energy: -439.463154 a.u
Gibbs: -439.507829 a.u
Multiplicity: 1
Dipole: 5.8415

Formula: C4H11NO3
Charge: 0
Energy: -439.178034 a.u
Gibbs: -439.222572 a.u
Multiplicity: 1
Dipole: 5.9283
O, 0.895541, 0.842915, 1.285733

C, -0.153023, 2.473850, -1.479008
H, 0.880786, 2.809847, -1.489857
H, -0.324685, 1.882805, -2.380540
C, -1.077468, 3.679322, -1.464537
H, -0.898890, 4.268906, -0.559346
H, -2.122957, 3.350698, -1.453188
O, -0.789805, 4.431296, -2.640165
H, -1.363059, 5.203772, -2.655878
H, -1.333435, 1.355802, -0.211681
H, 0.152111, 1.822420, 0.847174
N, -0.363817, 1.650205, -0.284226
C, 0.593129, 0.434857, 0.024084
O, 1.685459, 0.444536, -0.859157
H, 2.335268, 1.043591, -0.470133
C, -0.123067, -0.893087, -0.126063
H, 0.539850, -1.682233, 0.224652
H, -1.027416, -0.900898, 0.479980
H, -0.380310, -1.085304, -1.167152
Formula: C4H11NO4
Charge: 0
Energy: -514.745924 a.u
Gibbs: -514.799134 a.u
Multiplicity: 1
Dipole: 5.7895
O, -1.986764, 1.981519, -0.912543

C, -6.295042, 0.022867, -0.088238
H, -6.388489, -0.199948, 0.975321
H, -5.618406, 0.873095, -0.179741
C, -7.658442, 0.419654, -0.636851
H, -8.353542, -0.424300, -0.539301
H, -7.566519, 0.654368, -1.705331
O, -8.106338, 1.548728, 0.105166
H, -8.967458, 1.819706, -0.224888
H, -5.552405, -0.939319, -1.746309
H, -6.273778, -1.950818, -0.681108
N, -5.686375, -1.128821, -0.759443
C, -2.572594, 0.928477, -0.950541
O, -3.383504, 0.581908, -1.976494
H, -3.360425, 1.315854, -2.609296
C, -2.511772, -0.108997, 0.161855
H, -3.050990, 0.344152, 1.006830
H, -1.464834, -0.167493, 0.461021
O, -2.963764, -1.392981, -0.150565
H, -3.935398, -1.360363, -0.317110
Formula: C4H11NO3
Charge: 0
Energy: -439.490784 a.u
Gibbs: -439.536208 a.u
Multiplicity: 1
Dipole: 3.7152

Formula: C4H11NO3
Charge: 0
Energy: -439.222077 a.u
Gibbs: -439.267114 a.u
Multiplicity: 1
Dipole: 3.8149

Formula:
Charge: 0
Energy: -439.504076 a.u
Gibbs: -439.549519 a.u
Multiplicity: 1
Dipole: 3.9234
O, 1.669241, 1.350536, 0.481057

C, -0.155191, 2.506077, -1.513040
H, 0.858007, 2.872871, -1.357477
H, -0.185907, 2.037696, -2.502201
C, -1.120787, 3.677296, -1.483729
H, -1.033562, 4.198257, -0.524690
H, -2.151445, 3.313498, -1.574254
O, -0.788159, 4.536931, -2.575035
H, -1.397435, 5.281084, -2.572462
H, -1.334542, 1.077876, -0.621278
H, 1.339089, 1.891562, 1.207783
N, -0.473486, 1.574018, -0.432131
C, 0.558599, 0.645272, -0.066453
O, 1.063113, -0.002593, -1.223708
H, 1.806114, -0.557951, -0.960237
C, 0.019810, -0.374851, 0.932259
H, -0.783609, -0.958032, 0.483420
H, 0.822714, -1.050352, 1.223320
H, -0.358480, 0.126083, 1.822245
Formula: C4H11NO3
Charge: 0
Energy: -439.49509 a.u
Gibbs: -439.54597 a.u
Multiplicity: 1
Dipole: 5.1040
O, 2.756872, 1.416750, 0.067987

C, -0.387843, 2.688093, -1.030404
H, 0.510578, 2.678581, -0.406662
H, -0.083405, 3.061353, -2.013609
C, -1.403938, 3.638842, -0.425322
H, -1.700074, 3.275300, 0.564628
H, -2.300718, 3.668009, -1.053717
O, -0.789950, 4.925604, -0.341235
H, -1.421698, 5.539897, 0.043959
H, 2.239854, 1.172957, -0.712782
H, 2.326702, 0.946294, 0.789066
N, -0.971449, 1.355915, -1.129988
C, -0.305555, 0.432377, -1.670644
O, 0.965893, 0.659066, -2.149641
H, 1.313711, -0.133337, -2.576427
C, -0.815222, -0.965064, -1.832722
H, -0.818489, -1.248834, -2.887244
H, -0.168272, -1.667536, -1.303391
H, -1.823986, -1.041116, -1.439661
Formula: C4H11NO3
Charge: 0
Energy: -439.384574 a.u
Gibbs: -439.428837 a.u
Multiplicity: 1
Dipole: 7.2820

Formula: C4H11NO3
Charge: 0
Energy: -439.397906 a.u
Gibbs: -439.442137 a.u
Multiplicity: 1
Dipole: 7.4331

Formula: C4H11NO3
Charge: 0
Energy: -439.119286 a.u
Gibbs: -439.162663a.u
Multiplicity: 1
Dipole: 7.4133
O, 1.291860, 0.447134, -0.394356

C, -0.326636, 2.798691, -1.096103
H, 0.664857, 3.047899, -0.673197
H, -0.290378, 3.150538, -2.139445
C, -1.347592, 3.645940, -0.358142
H, -1.357382, 3.364057, 0.700958
H, -2.344629, 3.443657, -0.765318
O, -1.001655, 5.028120, -0.516307
H, -1.658245, 5.558091, -0.055264
H, 0.968033, 0.873789, 0.423589
H, 2.123431, 0.858660, -0.696407
N, -0.703719, 1.400429, -0.985396
C, 0.240219, 0.517731, -1.360776
O, 1.029991, 0.876946, -2.542259
H, 1.356475, 0.074713, -2.964902
C, -0.279317, -0.912527, -1.497226
H, -0.970427, -0.954607, -2.334791
H, 0.535696, -1.619449, -1.663038
H, -0.807573, -1.196659, -0.589432
1.50 HEA_intermediate_4_TS
Formula: C4H9NO2
Charge: 0
Energy: -363.005697 a.u
Gibbs: -363.048335 a.u
Multiplicity: 1
Dipole: 3.3092

Formula: C4H9NO2
Charge: 0
Energy: -363.016822 a.u
Gibbs: -363.059511 a.u
Multiplicity: 1
Dipole: 3.3600

Formula: C4H9NO2
Charge: 0
Energy: -362.773425 a.u
Gibbs: -362.815620 a.u
Multiplicity: 1
Dipole: 3.4322
O, 0.666933, 0.570332, 1.388275

C, 0.349299, 2.745354, -1.352239
H, 1.072943, 3.561059, -1.394182
H, 0.538789, 2.097673, -2.212055
C, -1.054639, 3.327522, -1.461513
H, -1.257302, 3.956573, -0.588381
H, -1.786803, 2.512844, -1.469261
O, -1.106086, 4.083073, -2.670106
H, -1.984134, 4.466904, -2.753761
H, 0.683949, 1.862636, 1.212578
N, 0.525450, 2.022866, -0.113393
C, 0.506414, 0.739838, 0.106439
C, 0.345952, -0.398119, -0.834099
H, 1.198522, -1.069177, -0.733946
H, -0.548504, -0.959257, -0.563700
H, 0.262711, -0.067998, -1.866071
Formula: C4H9NO2
Charge: 0
Energy: -363.047596 a.u
Gibbs: -363.08962 a.u
Multiplicity: 1
Dipole: 3.3024

Formula: C4H9NO2
Charge: 0
Energy: -363.058448 a.u
Gibbs: -363.100466 a.u
Multiplicity: 1
Dipole: 3.3803

Formula:
Charge: 0
Energy: -362.814197 a.u
Gibbs: -362.855885 a.u
Multiplicity: 1
Dipole: 3.3630
C, -0.370337, 2.777165, -1.136285

H, 0.618779, 2.963694, -0.704779
H, -0.320824, 3.103818, -2.180402
C, -1.401157, 3.613155, -0.400546
H, -1.442454, 3.302703, 0.649190
H, -2.390604, 3.443155, -0.838961
O, -1.012180, 4.982595, -0.519169
H, -1.656051, 5.523327, -0.052425
N, -0.730944, 1.368428, -1.040308
C, 0.018934, 0.518476, -1.599631
O, 1.140235, 0.903293, -2.278321
H, 1.595622, 0.135325, -2.642111
C, -0.253951, -0.953953, -1.565894
H, -0.365251, -1.342169, -2.580509
H, 0.579579, -1.483395, -1.099601
H, -1.161955, -1.153574, -1.005641
1.52 HEA_intermediate1
Formula: C4H11NO3
Charge: 0
Energy: -439.467264 a.u
Gibbs: -439.513833 a.u
Multiplicity: 1
Dipole: 9.3164

Formula: C4H11NO3
Charge: 0
Energy: -400.175576 a.u
Gibbs: -400.215979 a.u
Multiplicity: 1
Dipole: 9.7200

Formula: C4H11NO3
Charge: 0
Energy: -399.924642 a.u
Gibbs: -399.964981 a.u
Multiplicity: 1
Dipole: 9.5491
O, 1.892688, 0.972249, 0.103652

C, 0.058416, 2.483543, -1.414190
H, 1.105117, 2.757939, -1.337649
H, -0.085149, 1.848214, -2.282318
C, -0.834807, 3.708612, -1.483793
H, -0.692871, 4.329785, -0.592072
H, -1.888412, 3.411067, -1.523896
O, -0.449024, 4.403285, -2.662999
H, -1.001221, 5.186378, -2.751390
H, -1.211366, 1.314993, -0.278290
H, -0.223408, 2.267908, 0.613637
N, -0.253557, 1.660346, -0.205852
C, 0.676364, 0.550524, 0.048002
O, 0.398456, -0.358826, -1.081975
H, 1.191500, -0.277234, -1.624146
C, 0.145583, -0.186019, 1.297421
H, -0.876500, -0.549939, 1.175661
H, 0.800335, -1.036922, 1.466479
H, 0.193906, 0.469105, 2.168161
1.53 HEF_intermediate
Formula: C3H9NO3
Charge: 0
Energy: -400.196538 a.u
Gibbs: -400.245144 a.u
Multiplicity: 1
Dipole: 3.3970

Formula: C3H9NO3
Charge: 0
Energy: -400.209668 a.u
Gibbs: -400.258634 a.u
Multiplicity: 1
Dipole: 2.4047

Formula: C3H9NO3
Charge: 0
Energy: -399.959726 a.u
Gibbs: -400.007886 a.u
Multiplicity: 1
Dipole: 3.3107
O, 2.191151, 0.812719, 0.317617

C, -0.410355, 2.466641, -1.288534
H, 0.681117, 2.458451, -1.260284
H, -0.712657, 1.813599, -2.109707
C, -0.883323, 3.883983, -1.582195
H, -0.576453, 4.548182, -0.765320
H, -1.978382, 3.903246, -1.635905
O, -0.301749, 4.293451, -2.822014
H, -0.591739, 5.190041, -3.015025
H, -1.924130, 1.878672, -0.036004
H, -0.634588, 2.486045, 0.747906
N, -0.910854, 1.904421, -0.035033
C, 1.329233, -0.006090, 0.124572
H, 0.650821, -0.395535, 0.886568
O, 1.081131, -0.590060, -1.054854
H, 1.689037, -0.222143, -1.716522
1.54 HEF_intermediate_2
Formula: C3H9NO3
Charge: 0
Energy: -400.181923 a.u
Gibbs: -400.224701 a.u
Multiplicity: 1
Dipole: 3.6583

Formula: C3H9NO3
Charge: 0
Energy: -400.195371 a.u
Gibbs: -400.238139 a.u
Multiplicity: 1
Dipole: 3.8177

Formula: C3H9NO3
Charge: 0
Energy: -399.947659 a.u
Gibbs: -399.990193 a.u
Multiplicity: 1
Dipole: 3.6363
O, 1.639235, 1.341289, 0.517801

C, -0.154360, 2.525500, -1.537453
H, 0.856412, 2.894089, -1.368842
H, -0.176118, 2.070206, -2.532775
C, -1.124550, 3.692694, -1.500570
H, -1.045732, 4.202168, -0.534749
H, -2.152712, 3.325166, -1.602458
O, -0.788010, 4.566841, -2.578952
H, -1.401949, 5.307181, -2.573562
H, -1.329579, 1.070345, -0.668846
H, 1.282231, 1.832072, 1.267413
N, -0.476885, 1.577352, -0.470279
C, 0.557245, 0.665153, -0.099646
H, 0.123797, -0.066797, 0.591896
O, 1.095635, 0.008001, -1.227165
H, 1.793599, -0.585637, -0.926549
Formula: C3H9NO3
Charge: 0
Energy: -400.190182 a.u
Gibbs: -400.238445 a.u
Multiplicity: 1
Dipole: 5.8110

Formula: C3H9NO3
Charge: 0
Energy: -400.203208 a.u
Gibbs: -400.252134 a.u
Multiplicity: 1
Dipole: 5.8185

Formula: C3H9NO3
Charge: 0
Energy: -399.947659 a.u
Gibbs: -399.990193 a.u
Multiplicity: 1
Dipole: 3.6363
O, 2.502173, -1.078503, -0.952242

C, -0.663138, 3.238497, -1.019842
H, 0.115017, 3.634424, -0.358392
H, -0.274643, 3.321964, -2.040586
C, -1.910531, 4.092295, -0.889503
H, -2.293478, 4.026375, 0.134772
H, -2.686748, 3.710743, -1.561867
O, -1.554022, 5.435256, -1.221995
H, -2.337512, 5.986948, -1.140760
H, 3.221468, -1.118562, -0.312057
H, 2.882307, -1.389800, -1.781349
N, -0.983812, 1.854336, -0.688484
C, -0.048558, 1.005958, -0.747511
H, -0.244774, -0.037661, -0.508184
O, 1.219829, 1.285663, -1.093168
H, 1.754685, 0.457691, -1.063564
Formula: C3H9NO3
Charge: 0
Energy: -400.078365 a.u
Gibbs: -400.117382 a.u
Multiplicity: 1
Dipole: 7.3533

Formula: C3H9NO3
Charge: 0
Energy: -400.091915 a.u
Gibbs: -400.130905 a.u
Multiplicity: 1
Dipole: 7.4843

Formula: C3H9NO3
Charge: 0
Energy: -399.947659 a.u
Gibbs: -399.990193 a.u
Multiplicity: 1
Dipole: 3.6363
O, 1.325637, 0.438540, -0.429219

C, -0.312907, 2.804761, -1.110150
H, 0.660502, 3.051314, -0.648749
H, -0.244946, 3.173245, -2.145560
C, -1.365850, 3.630197, -0.393296
H, -1.406573, 3.332260, 0.660577
H, -2.346953, 3.423864, -0.835515
O, -1.028653, 5.017389, -0.520216
H, -1.701881, 5.534520, -0.068641
H, 1.003890, 0.802077, 0.418470
H, 2.153255, 0.878130, -0.703977
N, -0.681823, 1.398543, -1.037585
C, 0.277305, 0.539805, -1.396506
H, -0.087989, -0.486439, -1.478948
O, 1.074837, 0.855163, -2.578522
H, 1.380411, 0.032255, -2.976896
1.57 HEF_intermediate_4_TS
Formula: C3H7NO2
Charge: 0
Energy: -323.691103 a.u
Gibbs: -323.72969 a.u
Multiplicity: 1
Dipole: 3.0760

Formula: C3H7NO2
Charge: 0
Energy: -323.702026 a.u
Gibbs: -323.740606 a.u
Multiplicity: 1
Dipole: 3.1357

Formula: C3H7NO2
Charge: 0
Energy: -645.887813 a.u
Gibbs: -645.944367 a.u
Multiplicity: 1
Dipole: 5.7101
O, 0.264657, 0.380694, 1.201841

C, 0.264235, 2.806863, -1.348198
H, 1.082271, 3.528316, -1.304734
H, 0.413579, 2.188440, -2.236276
C, -1.051392, 3.564534, -1.470825
H, -1.218891, 4.153715, -0.563026
H, -1.875965, 2.850529, -1.568747
O, -0.947679, 4.400270, -2.621403
H, -1.770153, 4.889333, -2.719398
H, 0.288866, 1.698774, 1.170883
N, 0.284737, 1.988838, -0.154197
C, 0.257275, 0.701141, -0.052348
H, 0.236510, -0.030879, -0.854766
Formula: C3H7NO2
Charge: 0
Energy: -323.73678 a.u
Gibbs: -323.775684 a.u
Multiplicity: 1
Dipole: 2.6952

Formula: C3H7NO2
Charge: 0
Energy: -323.747609 a.u
Gibbs: -323.786425 a.u
Multiplicity: 1
Dipole: 2.7464

Formula: C3H7NO2
Charge: 0
Energy: -323.538198 a.u
Gibbs: -323.576928 a.u
Multiplicity: 1
Dipole: 2.7238
C, -0.369808, 2.801090, -1.159342

H, 0.646018, 3.050466, -0.836129
H, -0.443485, 3.092927, -2.211940
C, -1.366589, 3.604937, -0.345160
H, -1.284962, 3.326696, 0.711142
H, -2.383807, 3.369156, -0.676154
O, -1.066458, 4.987254, -0.540602
H, -1.690664, 5.510021, -0.028790
N, -0.639676, 1.376979, -0.989513
C, 0.093137, 0.553173, -1.596534
H, -0.073561, -0.516538, -1.497494
O, 1.124261, 0.912013, -2.403417
H, 1.549933, 0.125981, -2.766021
1.59 HEF_intermediate1
Formula: C3H9NO3
Charge: 0
Energy: -400.160781 a.u
Gibbs: -400.201076 a.u
Multiplicity: 1
Dipole: 9.4832

Formula: C3H9NO3
Charge: 0
Energy: -400.175576 a.u
Gibbs: -400.215979 a.u
Multiplicity: 1
Dipole: 9.7200

Formula: C3H9NO3
Charge: 0
Energy: -399.924642 a.u
Gibbs: -399.964981 a.u
Multiplicity: 1
Dipole: 9.5491
O, 1.864591, 0.965352, 0.175847

C, 0.049148, 2.492274, -1.400424
H, 1.096219, 2.764651, -1.319857
H, -0.089035, 1.845018, -2.260805
C, -0.835568, 3.721457, -1.498721
H, -0.702677, 4.353208, -0.613169
H, -1.890079, 3.429915, -1.551510
O, -0.427172, 4.397643, -2.681232
H, -0.978766, 5.178047, -2.793926
H, -1.232401, 1.336050, -0.251612
H, -0.244761, 2.295076, 0.635016
N, -0.275348, 1.685184, -0.182955
C, 0.647420, 0.572418, 0.083787
H, 0.194033, 0.077920, 0.972285
O, 0.364966, -0.368697, -1.004471
H, 1.157690, -0.319895, -1.552986
Formula: C4H11NO3
Charge: 0
Energy: -439.502262 a.u
Gibbs: -439.555185 a.u
Multiplicity: 1
Dipole: 3.8376

Formula: C4H11NO3
Charge: 0
Energy: -439.523561 a.u
Gibbs: -439.576776 a.u
Multiplicity: 1
Dipole: 4.7221

Formula: C4H11NO3
Charge: 0
Energy: -439.237743 a.u
Gibbs: -439.292853 a.u
Multiplicity: 1
Dipole: 4.8579
O, -3.438008, 3.248231, 0.257440

C, -0.132108, 4.488996, -1.021071
H, -0.634511, 3.959180, -0.210379
H, -0.589651, 4.145567, -1.949924
C, 1.341026, 4.102801, -1.024567
H, 1.803231, 4.411129, -0.077928
H, 1.856625, 4.633635, -1.835844
O, 1.419298, 2.690259, -1.202116
H, 2.341837, 2.422341, -1.172911
H, 0.060821, 6.447121, -1.614942
H, -0.016377, 6.267553, 0.002155
N, -0.389728, 5.922234, -0.874323
C, -3.504426, 3.868310, -0.775597
O, -3.254059, 3.295369, -1.978449
H, -3.006519, 2.373550, -1.810836
C, -3.812817, 5.328339, -0.904342
H, -2.856809, 5.856952, -0.965524
H, -4.381980, 5.533823, -1.808398
H, -4.350363, 5.664533, -0.022637
1.61 HHEA_intermediate_2
Formula: C4H11NO4
Charge: 0
Energy: -514.730044 a.u
Gibbs: -514.778225 a.u
Multiplicity: 1
Dipole: 5.7779

Formula: C4H11NO4
Charge: 0
Energy: -514.747159 a.u
Gibbs: -514.795432 a.u
Multiplicity: 1
Dipole: 5.9553

Formula: C4H11NO4
Charge: 0
Energy: -514.433916 a.u
Gibbs: -514.481543 a.u
Multiplicity: 1
Dipole: 5.9022
O, 1.718077, 1.402407, 0.481491

C, -0.110294, 2.541435, -1.468345
H, 0.860564, 2.980625, -1.246209
H, -0.041159, 2.070685, -2.454659
C, -1.157697, 3.639590, -1.510630
H, -1.177681, 4.162351, -0.548898
H, -2.150185, 3.203083, -1.675323
O, -0.808559, 4.523300, -2.576667
H, -1.468187, 5.221819, -2.621211
H, -1.268694, 1.062104, -0.652601
H, 1.387345, 1.985487, 1.175215
N, -0.437602, 1.585986, -0.407828
C, 0.608885, 0.677425, -0.036229
O, 1.098953, -0.036148, -1.146700
H, 1.576040, -0.797981, -0.787404
C, 0.071863, -0.307739, 1.014332
H, -0.846236, -0.763341, 0.638093
H, -0.155065, 0.236375, 1.934070
O, 1.077849, -1.294662, 1.237571
H, 0.651425, -2.136772, 1.416891
1.62 HHEA_intermediate_2_TS
Formula: C4H11NO4
Charge: 0
Energy: -514.682674 a.u
Gibbs: -514.730661 a.u
Multiplicity: 1
Dipole: 7.7961

Formula: C4H11NO4
Charge: 0
Energy: -514.699640 a.u
Gibbs: -514.748461 a.u
Multiplicity: 1
Dipole: 7.9755

Formula: C4H11NO4
Charge: 0
Energy: -514.382883 a.u
Gibbs: -514.431331 a.u
Multiplicity: 1
Dipole: 8.0227
O, 0.749392, 1.005197, 1.471656

C, -0.126068, 2.516231, -1.436908
H, 0.885947, 2.906679, -1.382977
H, -0.200424, 1.883725, -2.322190
C, -1.119904, 3.661363, -1.526708
H, -1.034243, 4.294311, -0.637482
H, -2.143070, 3.270041, -1.565921
O, -0.801451, 4.383598, -2.712190
H, -1.405403, 5.128748, -2.786982
H, -1.337178, 1.385890, -0.200998
H, 0.015072, 1.971303, 0.927589
N, -0.376700, 1.719944, -0.225982
C, 0.586905, 0.589693, 0.191172
O, 1.734930, 0.688256, -0.626765
H, 2.126285, -0.195826, -0.637999
C, -0.050857, -0.790552, -0.001658
H, -0.881884, -0.895840, 0.700107
H, -0.422439, -0.884246, -1.025005
O, 0.972542, -1.752221, 0.256657
H, 0.737355, -2.578912, -0.174528
Formula: C4H11NO4
Charge: 0
Energy: -514.735444 a.u
Gibbs: -514.788748 a.u
Multiplicity: 1
Dipole: 5.5522

Formula: C4H11NO4
Charge: 0
Energy: -514.752630 a.u
Gibbs: -514.806901 a.u
Multiplicity: 1
Dipole: 5.6672

Formula: C4H11NO4
Charge: 0
Energy: -514.433638 a.u
Gibbs: -514.488646 a.u
Multiplicity: 1
Dipole: 4.9940
O, 2.295312, -0.176597, 0.504050

C, -0.534969, 2.953603, -1.208928
H, 0.432502, 3.173489, -0.745456
H, -0.447033, 3.232186, -2.264158
C, -1.608085, 3.803280, -0.554065
H, -1.688046, 3.538261, 0.505760
H, -2.575466, 3.597488, -1.024921
O, -1.233321, 5.171276, -0.718471
H, -1.907558, 5.722970, -0.311186
H, 2.443179, 0.599341, -0.046212
H, 1.923699, -0.826736, -0.110379
N, -0.873136, 1.544079, -1.060991
C, -0.096545, 0.687516, -1.560884
O, 1.051462, 1.006254, -2.211421
H, 1.489668, 0.178558, -2.467703
C, -0.416057, -0.789255, -1.503598
H, -1.052399, -1.045724, -2.354021
H, -0.954340, -1.003002, -0.581394
O, 0.822013, -1.507351, -1.574793
H, 0.660127, -2.411803, -1.859477
Formula: C4H11NO4
Charge: 0
Energy: -514.628143 a.u
Gibbs: -514.675304 a.u
Multiplicity: 1
Dipole: 9.0242

Formula: C4H11NO4
Charge: 0
Energy: -514.645106 a.u
Gibbs: -514.691866a.u
Multiplicity: 1
Dipole: 9.0919

Formula: C4H11NO4
Charge: 0
Energy: -514.334149 a.u
Gibbs: -514.380137a.u
Multiplicity: 1
Dipole: 9.2238
O, 1.310081, 0.439270, -0.440440

C, -0.346465, 2.852283, -0.973955
H, 0.549469, 3.085072, -0.367388
H, -0.125349, 3.234051, -1.983551
C, -1.486045, 3.681295, -0.408631
H, -1.694926, 3.360401, 0.618150
H, -2.389006, 3.502566, -1.003448
O, -1.113756, 5.064908, -0.446998
H, -1.839325, 5.582969, -0.086985
H, 2.017041, 1.090935, -0.589806
H, 1.666146, -0.487702, -0.579541
N, -0.724521, 1.453692, -0.952985
C, 0.213241, 0.594550, -1.344725
O, 0.915949, 0.947372, -2.591614
H, 1.409782, 0.181782, -2.913271
C, -0.312653, -0.847294, -1.453016
H, -0.899836, -0.936476, -2.363544
H, -0.920782, -1.074627, -0.580636
O, 0.855255, -1.699616, -1.509819
H, 0.646705, -2.577598, -1.176043
1.65 HHEA_intermediate_4_TS
Formula: C4H9NO3
Charge: 0
Energy: -438.240392 a.u
Gibbs: -438.286357 a.u
Multiplicity: 1
Dipole: 3.7282

Formula: C4H9NO3
Charge: 0
Energy: -438.255307 a.u
Gibbs: -438.300689 a.u
Multiplicity: 1
Dipole: 3.8549

Formula: C4H9NO3
Charge: 0
Energy: -438.021778 a.u
Gibbs: -438.066256 a.u
Multiplicity: 1
Dipole: 3.1542
O, 0.362858, 0.314624, 1.354679

C, 0.401728, 2.753784, -1.180768
H, 1.058363, 3.605946, -1.000797
H, 0.799558, 2.210037, -2.041346
C, -0.993042, 3.270279, -1.513938
H, -1.400342, 3.802732, -0.648242
H, -1.654223, 2.425343, -1.734089
O, -0.861320, 4.133284, -2.641238
H, -1.731316, 4.475074, -2.868389
H, 0.339212, 1.614841, 1.322496
N, 0.388774, 1.917847, 0.000311
C, 0.405405, 0.623690, 0.091466
C, 0.425259, -0.428262, -0.976665
H, 1.037857, -0.093123, -1.812710
H, -0.602130, -0.534099, -1.347406
O, 0.954617, -1.658968, -0.522637
H, 0.580519, -1.838657, 0.348263
Formula: C4H9NO3
Charge: 0
Energy: -438.281342 a.u
Gibbs: -438.327027 a.u
Multiplicity: 1
Dipole: 4.8203

Formula: C4H9NO3
Charge: 0
Energy: -438.296282 a.u
Gibbs: -438.342041 a.u
Multiplicity: 1
Dipole: 4.9434

Formula: C4H9NO3
Charge: 0
Energy: -438.020574 a.u
Gibbs: -438.065716 a.u
Multiplicity: 1
Dipole: 4.9370
C, -0.367340, 2.779329, -1.120577

H, 0.597602, 2.916494, -0.621674
H, -0.241105, 3.136500, -2.147865
C, -1.415565, 3.625760, -0.422477
H, -1.533948, 3.282351, 0.610934
H, -2.379647, 3.504436, -0.928143
O, -0.974570, 4.983462, -0.468876
H, -1.631111, 5.532031, -0.029708
N, -0.778886, 1.381341, -1.095903
C, -0.027043, 0.526903, -1.632786
O, 1.150010, 0.871652, -2.230447
H, 1.600974, 0.097957, -2.590608
C, -0.331643, -0.949377, -1.678208
H, -0.340200, -1.254200, -2.732888
H, 0.503495, -1.475516, -1.197532
O, -1.560827, -1.230399, -1.043273
H, -1.708775, -2.179796, -1.099339
1.67 HHEA_intermediate1
Formula: C4H11NO4
Charge: 0
Energy: -514.701609 a.u
Gibbs: -514.751038 a.u
Multiplicity: 1
Dipole: 10.8483

Formula: C4H11NO4
Charge: 0
Energy: -514.779184 a.u
Gibbs: -514.831253 a.u
Multiplicity: 1
Dipole: 9.9520

Formula: C4H11NO4
Charge: 0
Energy: -514.460155 a.u
Gibbs: -514.511530 a.u
Multiplicity: 1
Dipole: 9.8107
O, 1.955693, 1.107523, 0.100458

C, 0.076463, 2.558251, -1.414805
H, 1.099829, 2.895494, -1.290240
H, 0.011278, 1.932362, -2.298374
C, -0.891043, 3.724677, -1.493755
H, -0.830348, 4.327065, -0.579896
H, -1.920176, 3.362061, -1.591651
O, -0.497414, 4.476142, -2.634676
H, -1.097699, 5.221850, -2.732266
H, -1.158625, 1.284887, -0.347018
H, -0.260324, 2.281430, 0.598303
N, -0.228891, 1.690276, -0.232998
C, 0.766786, 0.638353, 0.017972
O, 0.487854, -0.239219, -1.145440
H, 0.989179, -1.040262, -0.957764
C, 0.268800, -0.144602, 1.269970
H, -0.791827, -0.401965, 1.182930
H, 0.414106, 0.485129, 2.154590
O, 1.065337, -1.323792, 1.347667
H, 0.592292, -1.975045, 1.872938
1.68 2-hydroxy-Ethanoic_acid
Formula: C2H4O3
Charge: 0
Energy: -304.359668 a.u
Gibbs: -304.394017 a.u
Multiplicity: 1
Dipole: 3.9310

Formula: C2H4O3
Charge: 0
Energy: -304.372346 a.u
Gibbs: -304.406703 a.u
Multiplicity: 1
Dipole: 4.0677

Formula: C2H4O3
Charge: 0
Energy: -304.205004 a.u
Gibbs: -304.239167 a.u
Multiplicity: 1
Dipole: 3.9579
C, 0.664987, 0.587292, -0.127808

O, 1.867545, 0.652795, -0.128074
O, -0.142506, 1.664915, -0.127790
H, 0.411148, 2.460698, -0.127893
C, -0.160083, -0.678680, -0.127849
H, -0.809334, -0.646496, 0.753824
H, -0.809591, -0.646283, -1.009323
O, 0.700786, -1.796575, -0.128110
H, 0.155157, -2.589171, -0.128124
1.69 2-R-Ethanoic_acid
Formula: C4H7NO4
Charge: 0
Energy: -512.390657 a.u
Gibbs: -512.436906 a.u
Multiplicity: 1
Dipole: 3.3806

Formula: C4H7NO4
Charge: 0
Energy: -512.409514 a.u
Gibbs: -512.456856 a.u
Multiplicity: 1
Dipole: 3.6941

Formula: C4H7NO4
Charge: 0
Energy: -512.110130 a.u
Gibbs: -512.157003 a.u
Multiplicity: 1
Dipole: 3.5530
C, 0.789825, 0.157424, 0.180911

O, 1.872025, -0.020326, 0.682093
O, 0.085404, 1.286706, 0.263196
H, 0.589052, 1.929262, 0.789395
C, 0.090291, -0.869548, -0.723704
O, -0.217339, -0.535955, -1.860347
N, -0.090083, -2.097518, -0.214234
H, -0.490782, -2.761335, -0.861788
C, 0.240094, -2.578694, 1.120911
H, -0.558325, -3.242746, 1.450330
H, 0.276339, -1.744039, 1.816776
C, 1.568532, -3.322128, 1.145514
H, 1.536896, -4.154803, 0.434508
H, 2.366052, -2.638463, 0.843163
O, 1.751194, -3.786053, 2.480664
H, 2.591766, -4.251059, 2.530958
2. Alternative basis set and functional data
The following tables contain data for two additional computational setups
(B3LYP, def2-TZVP and M06, def2-TZVP) for all of the figures in the main
text.
Fig. 3
B3LYP, cc-pVTZ 0 22.9 -8.9 0 -14.3 -13.9 -27.2
B3LYP, def2-tzvp 0 23.6 -8.25 0 -12.8 - -29.4
M06, def2-tzvp 0 22.5 -10.2 0 -13.2 -12.1 -27.2
Fig. 4
B3LYP, cc-pVTZ 0 39.5 6.3
B3LYP, def2-tzvp 0 42.6 10.0
M06, def2-tzvp 0 44.0 6.4
Fig 5.
B3LYP, cc-pVTZ 0 -11.8 23.0 4.5
B3LYP, def2-tzvp 0 -10.4 24.8 6.1
M06, def2-tzvp 0 -10.3 27.1 6.1
Fig 6.
B3LYP, cc-pVTZ 0 -7.1 21.7 -23.6
B3LYP, def2-tzvp 0 -6.0 22.3 -23.0
M06, def2-tzvp 0 -5.9 24.5 -21.4
Fig 7
B3LYP, cc-pVTZ 0 -17.6 -14.7 -35.3
B3LYP, def2-tzvp 0 -15.8 -12.6 -33.3
M06, def2-tzvp 0 -14.1 - -31.0
Fig 8.
B3LYP, cc-pVTZ 0 27.3 7.9 9.2 -2.8 0.2
B3LYP, def2-tzvp 0 26.7 6.2 5.8 -2.5 -0.3
M06, def2-tzvp 0 31.2 9.4 8.4 -5.1 -3.5
Fig. 9
B3LYP, cc-pVTZ 0 -3.7 30.2 2.7 32.8 -6.7
B3LYP, def2-tzvp 0 -3.1 30.8 -0.2 33.0 -10.9
M06, def2-tzvp 0 -3.2 33.0 2.1 40.4 -4.1
Fig 11.
B3LYP, cc-pVTZ 0 -3.7 22.9 -7.5 -3.5 26.2 -5.2 25.5 -10.9
B3LYP, def2- 0 -2.6 22.9 -6.0 -2.8 26.9 -4.3 26.1 -13.9
tzvp
M06, def2-tzvp 0 -3.8 27.6 -8.3 - 25.8 -5.2 29.7 -13.8
Fig 12.
B3LYP, cc-pVTZ 0 -2.7 8.1 7.8 6.9 5.5 -4.9 -8.3 -13.4 -0.5
B3LYP, def2- 0 -2.2 8.2 8.1 7.3 5.5 -3.9 -7.6 -12.0 -0.2
tzvp
M06, def2-tzvp 0 -2.61 10.2 10.1 8.4 9.6 -4.0 -8.2 -12.0 0.3
Fig 13
B3LYP, cc-pVTZ 0 -13.4 -41.3 -125.0 -134.6 -86.2 -121.3
B3LYP, def2-tzvp 0 -12.0 -41.4 -123.8 -131.2 -75.1 -118.3
M06, def2-tzvp 0 -12.1 -43.6 -128.0 -133.8 -71.4 -117.9
Fig 16
B3LYP, cc-pVTZ 0 -2.5 19.9 33.1 6.6 1.5 8.9 37.6 -7.8
B3LYP, def2- 0 -1.8 19.6 33.5 7.2 2.3 8.6 37.2 -8.7
tzvp
M06, def2-tzvp 0 -1.7 20.3 33.9 5.9 3.3 9.1 37.5 -7.6
Fig 17
B3LYP, cc-pVTZ 0 50.2 -3.7 0 67.8 -3.4
B3LYP, def2-tzvp 0 49.1 -4.3 0 65.6 -4.5
M06, def2-tzvp 0 54.2 -5.7 0 70.1 -5.6
3. Alternative Solvent Model
The following table contains data comparison data to that in the main text
carried out using the SMD solvent model as opposed to PCM.
Activation energies / kcalmol-1

Reaction B3LYP, cc-pVTZ B3LYP, def2-tzvp M06, def2-tzvp M06, def2-tzvp
PCM solvent PCM solvent PCM solvent SMD Solvent
model model model model
Carbamate 0.4 1.1 1.3
formation (Fig3)
Carbamic acid 22.9 23.6 22.5 26.7
formation (Fig 3)
OZD formation 39.5 42.6 44.0 42.4
from Ion pair (Fig
4)
Isocyanate from 34.8 35.2 37.4 37.3
carbamic acid (Fig
5)
BHEU formation 28.8 28.3 30.4 28.7
(Fig 6)
HEEDA formation 27.3 26.7 31.2 29.7
(Fig 8)
HEIA formation 33.9 33.9 36.2 30.3
(Fig 9) 30.1 33.0 38.3 36.4
AHEIA formation 26.6 25.5 31.4 29.0
(Fig 11) 29.7 29.7 37.0
30.7 30.4 34.9 34.9
Radical formation 8.1 8.2 10.2 12.5
(Fig 12) 7.8 8.1 10.1 12.1
6.9 7.3 8.4 11.5
5.5 5.5 9.6 10.3
HEF formation (fig 35.6 35.3 35.6 35.7
16) 36.1 34.9 34.2 30.3
HEPO formation 50.2 49.1 54.2 50.8
(Fig 17) 67.8 65.6 70.1 64.5

Ie0c03003 Si 001

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DFT studies on thermal and oxidative degradation

Christopher. Parks* a, Ehsan. Alborzi a, Muhammad Akram a,

E-mail: [email protected], [email protected], [email protected]

Electronic Supplementary Information (ESI)

1. Raw DFT Data

Setup: B3LYP, cc-pVTZ

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, 8.516283, -9.094919, 12.235643

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, 1.959249, 1.737827, -0.201285

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, 10.144442, -5.063696, 11.701820

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -1.012817, 0.839954, -0.062520

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -1.591711, 1.133363, -0.466689

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, 10.144442, -5.063696, 11.701820

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, 1.952758, 1.725063, -0.179795

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

O, 10.167980, -4.491072, 10.539476

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -3.343175, 0.699169, -0.029438

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -0.511017, -1.007435, 0.256719

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -3.996264, 1.674543, -0.063449

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -3.848726, 1.596583, -0.017462

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -1.470345, 0.789751, -1.032476

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -3.766207, 1.593905, -0.294292

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -3.338623, 0.918750, -1.085330

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -2.628563, 0.696444, -0.116929

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP

C, -1.315555, 5.825191, 1.483916

Setup: B3LYP, def2TZVP

Setup: M06, def2TZVP