Zihan - Yin CH315 - Ruthenium Experiment - 2024

Preparation of a -arene ruthenium complex
Preparation of a -arene ruthenium

complex
Student name: Zihan.Yin
Lab Group: 1
Date: 23/10/2024
When completing this pro-forma, remember to make use of the supporting information on
the CH315 Myplace page:
The 3rd Year Laboratory Manual

Guides on: experimental protocols, yield calculations and spectral analysis
Documents detailing experimental techniques
In order to assign the NMR spectra correctly, you will need to label the structures provided.
To do this, install ChemDraw on your computer and double click each structure and you will
open ChemDraw with the structure in. Make your changes in ChemDraw, then close
ChemDraw and the changes will be saved in this MSWord template.
Also, you may ask for help, or discuss sections of this pro-forma by emailing the Inorganic
course organiser: [email protected]
Please remember to convert your completed pro-forma to pdf before uploading to the
relevant Myplace assignment.
Mark break-down by section:

Product /8
Experimental Protocol /2
% Yield Calculation /2
Characterisation (IR) /1
NMR Spectroscopy /6
Theory /1
Total /20
1
Reaction schemes and yield calculations
Synthesis of [(6-p-cymene)Ru(PPh3)Cl2]
Complete the following table, using the values recorded in your laboratory note book and
the information in the experimental instructions.
Table 1. Quantities of chemicals used in the synthesis of [(6-p-cymene)Ru(PPh3)Cl2]
compound molar mass / g mol-1 mass / g moles / mmol
[(6-p-cymene)RuCl2]2 612.36 0.100 0.163
triphenylphosphine 262.29 0.0960 0.366
Which is the limiting reagent?

[(6-p-cymene)RuCl2]2
Calculate your yield of [(6-p-cymene)Ru(PPh3)Cl2], showing your working below:
Ratio of stoichiometry of [(6-p-cymene)RuCl2]2:[(6-p-cymene)Ru(PPh3)Cl2]=1:2

%yield=actual moles of product/theoretical moles of product x100%
=(1/2 x mass of the [(6-p-cymene)Ru(PPh3)Cl2]/molar mass of the [(6-p-
cymene)Ru(PPh3)Cl2])/(mass of the [(6-p-cymene)RuCl2]2/molar mass of the [(6-p-
cymene)RuCl2]2)x100%
=(1/2 x 0.179 g/568.36 g/mol)/(0.1 g/612.36 g/mol)
=96.43 %
2
Experimental
Write a concise, scientific account of your experimental procedure for the synthesis of
[(6-p-cymene)Ru(PPh3)Cl2].
6
[(η -p-cymene)RuCl2]2 (0.100 g,0.163 mmol)was dissolved in chloroform (10
mL) Triphenylphosphine (0.0960 g,0.366 mmol)was added to the solution.The
solution was stirred,heated (to 80 °C)and refluxed (1 hour).The mixture
was cooled to room temperature and dried in vacuo.The sticky solid residues
obtained were washed with diethyl ether (5 mL).The product was dissolved in
dichloromethane (2 mL).The diethyl ether (12-15 mL)was added,forming to
layers.The solution was air dried (overnight),giving a dark crystals and
brown solvent.The solvent was carefully removed and diethyl ether was added
to cover the crystals.The crystals was scraped and isolated by
6
filtration.The crystals were dried by air,giving [(η -p-cymene)Ru(PPh3)Cl2]
(0.179 g,0.315 mmol,96.43 %) as dark powders.
Characterisation by ATR-IR
Assign the IR spectrum of your product. Report all strong/isolated absorption wavenumber
values and indicate those that are a result of key functional groups.
3
ATR-IR, � / cm–1 ([(6-p-cymene)Ru(PPh3)Cl2]):3051~2871,1437(C=C),1091(C-P),744,696.
ATR-IR Spectrum
Insert an image of your recorded ATR-IR spectrum for the reaction product on this page.
4
NMR Spectroscopy Interpretation

Interpret both the 1H and 13C NMR spectra of ([(6-p-cymene)Ru(PPh3)Cl2]). Ensure that you
calculate both the 1H-1H and 13C-31P coupling constants. The NMR spectra for [(6-p-
cymene)Ru(PPh3)Cl2] are available on the Myplace site for CH315.
1
H NMR (500.1 MHz, CDCl3):  7.844~7.260(15H in the PPh3),5.19(2H,d,J=6.0
Hz,A/B),4.99(2H,d,J=5.0 Hz,A/B),2.85(1H,s,J=6.9 Hz,C),1.86(3H,s,D),1.10(6H,d,J=7.0 Hz,E)
5
C {1H} NMR (126 MHz, CDCl3):  =134.41(d,J=8.8 Hz,a/d),133.91(d,J=46.5

13
Hz,b),130.27(c),128.01(d,J= 10.1 Hz,a/d),111.14(d,J=3.8

e/f),96.06(e/f),89.15(d,J=2.52,g/h),87.23(d,J=6.3,g/h),30.31(i),21.94(j),17.8(k).
6
Theory
What is the electron count of [(6-p-cymene)Ru(PPh3)Cl2]? (Show your working!)
Ru is 4d75s1.The available valence electrons are 7+1=8.
The Ru atom is next to a aromatic ring, two Cl atoms and one PPh3.
The electron count=the available valence electrons of Ru+ the number of electrons
corresponding to the aromatic ring + the number of electrons corresponding to 2 chlorine
atoms+the number of electrons corresponding to the PPh3 =8+6 + 2 x 1+2 = 18
The electron count is 18.

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Preparation of a -arene ruthenium complex

Preparation of a -arene ruthenium

The 3rd Year Laboratory Manual

Mark break-down by section:

Reaction schemes and yield calculations

Table 1. Quantities of chemicals used in the synthesis of [(6-p-cymene)Ru(PPh3)Cl2]

compound molar mass / g mol-1 mass / g moles / mmol

[(6-p-cymene)RuCl2]2 612.36 0.100 0.163

triphenylphosphine 262.29 0.0960 0.366

Which is the limiting reagent?

Calculate your yield of [(6-p-cymene)Ru(PPh3)Cl2], showing your working below:

Ratio of stoichiometry of [(6-p-cymene)RuCl2]2:[(6-p-cymene)Ru(PPh3)Cl2]=1:2

ATR-IR, � / cm–1 ([(6-p-cymene)Ru(PPh3)Cl2]):3051~2871,1437(C=C),1091(C-P),744,696.

NMR Spectroscopy Interpretation

C {1H} NMR (126 MHz, CDCl3):  =134.41(d,J=8.8 Hz,a/d),133.91(d,J=46.5

Hz,b),130.27(c),128.01(d,J= 10.1 Hz,a/d),111.14(d,J=3.8

What is the electron count of [(6-p-cymene)Ru(PPh3)Cl2]? (Show your working!)

Ru is 4d75s1.The available valence electrons are 7+1=8.

The electron count is 18.

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