TITLE: Transition Metal Complexes of Dimethyl Sulfoxide:

The Preparation of Cu(DMSO)2Cl2

CHE 323

LAB 8

JOEL MARUMO

201204901

27 OCTOBER 2014

TITLE: Transition Metal Complexes of Dimethyl Sulfoxide: The Preparation

of
Cu(DMSO)2Cl2
AIM: To prepare the metal complexes of dimethyl sulphoxide and to determine the method of
bonding in the complex by using infrared spectroscopy
ABSTRACT:

In order to determine through which atom (sulpur or oxygen), dimethyl

sulphoxide (DMSO) has bonded to the metal center, copper (II) chloride was reacted with
DMSO to form dimethyl sulphoxide copper (II) chloride and the product of the reaction weighed
to determine the percentage yield and then its melting point taken to determine its purity before
its infrared spectrum was obtained and the absorption frequency of the S-O band was
determined. The infrared results indicated that the DMSO formed a coordinate bond to copper
(II) through the oxygen atom as the IR spectrum for the complex was 2985.89 cm -1 while that of
DMSO was 2995.41 cm-1. The percentage yield was determined to be 68.0 % and the melting
point was found to be 123-125 C.
INTRODUCTION
Dimethyl sulphoxide (CH3SOCH3) is structurally similar to acetone, with a sulfur replacing the
carbonyl carbon. The normal absorption of the S=O bond occurs at 1050 cm -1. This is lower than
the C=O frequency, since the SO bond has a larger reduced mass than the CO bond resulting in
the frequency shift. Metals can bond to DMSO either through its oxygen or its sulfur. If the
bonding is to the sulfur, the metal donates electrons from its orbitals (the t2g) into an empty
orbital on the DMSO ligand, thereby increasing the S-O bond order. Thus, if the metal is bonded
to the DMSO at the sulfur, the frequency of the absorption increases. If the bonding is to the
oxygen of the DMSO, the metal forms a bond with one of the lone pairs on the oxygen, and
thereby withdraws electron density from the oxygen. This favors the second resonance form
since the oxygen will "seek" to gain electrons to compensate for the electrons donated to the
metal. The net effect is that the S=O bond order declines and the S=O absorption appears at
lower frequency. The sulfur center in DMSO is nucleophilic toward soft electrophiles and the
oxygen is nucleophilic toward hard electrophiles and related to its ability to dissolve many salts,
DMSO is a common ligand in coordination chemistry. In its deuterated form (DMSO-d6), it is a
1

useful solvent for NMR spectroscopy, again due to its ability to dissolve a wide range of
analytes, the simplicity of its own simple spectrum, and its suitability for high-temperature NMR
spectroscopic studies.
EXPERIMENTAL SECTION
PROCEDURE
0.2957 g of copper (II) chloride was placed in a 25 mL Erlenmeyer flask and 2 mL of ethanol
was added. The mixture was stirred until all the copper chloride had dissolved and 0.5 mL
dimethyl sulphoxide added slowly. The product was then collected by suction filtration, washed
with cold ethanol, air dried, weighed, its melting point determined and its infrared spectrum
obtained.
OBSERVATION AND RESULTS
Mass of CuCl2 + weighing Boat = 1.2063 g
Mass of Boat

= 0.910 g

Mass of CuCl2

= 0.2957 g

Volume of DMSO

= 0.50 mL

Product: a light green precipitate was formed

Mass of petri dish + filter paper

31.5309 g

Mass of petri dish + filter dish + CuCl2.2(CH3SOCH3) =

31.9657 g

Mass of CuCl2.2(CH3SOCH3)

0.4348 g

Reaction Equation

CuCl2 + 2CH3SOCH3

CuCl2.2(CH3SOCH3)

DIAGRAM OF THE CuCl2.2(CH3SOCH3)

CALCULATION OF PERCENTAGE YIELD

Moles CuCl2 = Mass/ molar mass

0.2957g / 134.452 g/mol

= 0.0021993 moles

Mass DMSO : = Density x Volume

= 1.1004 g cm3 x 0.5 cm3
=

0.5502 g

Moles DMSO = Mass / molar mass

0.5502 g / 78.13 g mol1

= 0.007042 moles

Therefore CuCl2 is a limiting reactant

Ratio of moles = 1: 1
3

No of moles CuCl2.2(CH3SOCH3) = 0.0021993 moles

Theoretical mass CuCl2.2(CH3SOCH3) = moles molar mass
= 0.0021993 moles 290.736 g /mol
= 0.6394 g
% yield = actual mass / theoretical mass x 100 %
= 0.4348 g / 0.6394 g x 100 %
= 68.0 %

DISCUSSION
CuCl2.2(CH3SOCH3) was synthesized to find out if the DMSO would bind to each metal by
either the oxygen or the sulfur atoms. This information was found out by taking both the melting
point as well as IR spectra. From literature review, the main peak to look at while looking at free
DMSO, is at 1050cm-1. From the experiment the main peak of free DMSO was determined to be
2995.41 cm-1 .When looking at the IR spectrum of CuCl2.2(CH3SOCH3) it was found that the
peak had downshifted shifted to 2985.89 cm-1 for the product. This decrease in S=O stretching
frequency suggest that the DMSO ligand has bonded through oxygen because if the bonding of
the metal is to the oxygen of the DMSO, the metal forms a bond with one of the lone pairs on the
oxygen , (HOMO ), and thereby withdraws electron density from the oxygen. Since the oxygen
will "seek" to regain electrons to compensate for the electrons donated to the metal, the net effect
is that the S=O bond order declines and the S=O absorption appears at a lower frequency as in
the case of our experiment. The melting points of CuCl 2.2(CH3SOCH3) , which was 123-125 C,
and comparing it to that of literature, which was 120-123 C, it was found out that it was close
but not exact therefore there might still might have been some impurities left in the product.
Some product was lost in the transfer from one container to another, and incomplete reactions or
side reactions were accountable for the low yield, which was determined and found out to be
68.0 %.
CONCLUSION

CuCl2.2(CH3SOCH3) was synthesized and it was found that the copper (II) metal complexes with
the DMSO through the oxygen atom from the IR spectra. The percentage yield was determined
and found out to be 68.0 % and the melting point was found out to be 123-125 C.

REFERENCES
1. Armarego, W. L. F&Chai, C. L (2009). Purification of laboratory chemicals (6 ed.).
New York: Butterworth-Heinemann. pp 78.
2. Greenwood, N. N &Earnshaw, A. (1997). Chemistry of the Elements, 2nd ed. Oxford,
UK: Butterworth-Heinemann. pp 673
3. Lee J.D. (1996). Concise Inorganic Chemistry, 5th edition, London: Blackkwell
Science. pp. 713
4. Masterson, W. L., & Hurley, C. N. (2004). Chemistry: Principles and Reactions, 5th
Ed. Thomson Learning, Inc. pp 498.
5. Reynolds, W. R. "Dimethyl Sulfoxide in Inorganic Chemistry", Progress in Inorganic
Chemistry, S. J. Lippard, Ed., Interscience: New York, 1970, volume 12, 1.