Scribd Logo
Upload

Welcome to Scribd!

  • 22 views

    Quick Guide to Molecular Orbitals: Fukui, K.; Ynoezawa, T.; Shingu, H. J. Chem. Phys. π

    Uploaded by

    Richard Zhu
    The document provides a quick guide to molecular orbitals and frontier molecular orbital theory. It explains that organic reactions occur between the highest occupied molecular orbital (HOMO) of the nucleophile and the lowest unoccupied molecular orbital (LUMO) of the electrophile. Good nucleophiles have high energy HOMOs and want to donate electrons, while good electrophiles have low energy LUMOs and want to accept electrons. Orbital interactions lead to stabilization when filled orbitals interact with empty orbitals of similar size and energy. The document then provides guidelines for predicting the HOMO and LUMO of simple molecules based on the presence of lone pairs, empty orbitals, or the weakest sigma bond.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd

    Quick Guide to Molecular Orbitals: Fukui, K.; Ynoezawa, T.; Shingu, H. J. Chem. Phys. π

    Uploaded by

    Richard Zhu
    22 views2 pages
    The document provides a quick guide to molecular orbitals and frontier molecular orbital theory. It explains that organic reactions occur between the highest occupied molecular orbital (HOMO) of the nucleophile and the lowest unoccupied molecular orbital (LUMO) of the electrophile. Good nucleophiles have high energy HOMOs and want to donate electrons, while good electrophiles have low energy LUMOs and want to accept electrons. Orbital interactions lead to stabilization when filled orbitals interact with empty orbitals of similar size and energy. The document then provides guidelines for predicting the HOMO and LUMO of simple molecules based on the presence of lone pairs, empty orbitals, or the weakest sigma bond.

    Original Description:

    d

    Original Title

    Molecular Orbital Handout

    Copyright

    © © All Rights Reserved

    Available Formats

    PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    The document provides a quick guide to molecular orbitals and frontier molecular orbital theory. It explains that organic reactions occur between the highest occupied molecular orbital (HOMO) of the nucleophile and the lowest unoccupied molecular orbital (LUMO) of the electrophile. Good nucleophiles have high energy HOMOs and want to donate electrons, while good electrophiles have low energy LUMOs and want to accept electrons. Orbital interactions lead to stabilization when filled orbitals interact with empty orbitals of similar size and energy. The document then provides guidelines for predicting the HOMO and LUMO of simple molecules based on the presence of lone pairs, empty orbitals, or the weakest sigma bond.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    22 views2 pages

    Quick Guide to Molecular Orbitals: Fukui, K.; Ynoezawa, T.; Shingu, H. J. Chem. Phys. π

    Uploaded by

    Richard Zhu
    The document provides a quick guide to molecular orbitals and frontier molecular orbital theory. It explains that organic reactions occur between the highest occupied molecular orbital (HOMO) of the nucleophile and the lowest unoccupied molecular orbital (LUMO) of the electrophile. Good nucleophiles have high energy HOMOs and want to donate electrons, while good electrophiles have low energy LUMOs and want to accept electrons. Orbital interactions lead to stabilization when filled orbitals interact with empty orbitals of similar size and energy. The document then provides guidelines for predicting the HOMO and LUMO of simple molecules based on the presence of lone pairs, empty orbitals, or the weakest sigma bond.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 2

    Quick Guide to Molecular Orbitals

    Frontier Molecular Orbital (FMO) Theory: organic reactions will


    occur between the highest occupied molecular orbital (HOMO) of
    the nucleophile and the lowest unoccupied molecular orbital (LUMO)
    of the electrophile.


    Fukui, K.;Ynoezawa, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722.


    in molecules with -bonds, the LUMO is usually the * orbital, and


    the HOMO is usually the orbital (unless there are lone pairs)

    C C

    H 2C

    CH2

    good nucleophiles have high energy HOMOs and want to give


    up electrons

    c-c (LUMO)

    Cp

    Cp

    good electrophiles have low energy LUMOs and want to gain


    electrons

    c-c

    (HOMO)

    C C

    molecules are stabilized when filled orbitals interact with


    empty orbitals

    the electrons involved


    in the bonds
    are not shown

    orbitals of similar energies and sizes have better overlap,


    which leads to greater stabilization and stronger bonding
    interactions

    Guidelines for predicting the HOMO and LUMO of simple molecules:

    C O

    H 2C O

    c-o (LUMO)

    if there is a lone pair, the lone pair is usually the HOMO



    NH3 :

    H3C

    Cp

    (CH3)2CO :

    CH3

    if there is an atom with an empty orbital (i.e. without a filled


    octet), the empty orbital is usually the LUMO

    BCl3 :

    Cl

    Cl
    Cl

    (HOMO)

    no

    c-o
    C O

    the electrons involved


    in the bonds
    are not shown

    Op

    Quick Guide to Molecular Orbitals


    in electrophiles with -bonds, the LUMO is usually the * orbital
    of the weakest covalent bond

    in an amide, we need to combine three p orbitals



    O
    H

    NH 2
    O

    CH3-Cl
    C

    combine 3 p orbitals

    Cl

    c-c (LUMO)

    Clsp3

    c-c
    Cl

    in organometallic nucleophiles with -bonds, the HOMO is the


    orbital of the carbon-metal bond

    CH 3-Li

    Li

    C-Li (LUMO)

    Li s
    Csp3
    (HOMO)

    Li

    C-Li
    C

    Op

    n (HOMO)

    Cp
    Np

    Csp3

    (two for nitrogen


    because of the lone pair,
    also showing here the
    nonbonding electrons
    on oxygen)

    (LUMO)

    no
    (HOMO)

    You might also like