Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Deuterated DMSO: Difference between pages

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477002518

| ImageFile = DMSO deuterated structure.png

| ImageSize =

| ImageName = Wireframe of deuterated DMSO

| ImageFile2 = DMSO-d6.jpg

| PIN = [(²H₃)Methanesulfinyl](²H₃)methane

| OtherNames = Deuterated dimethyl sulfoxide, DMSO-d6

|Section1={{Chembox Identifiers

| Abbreviations = DMSO-d6

| InChI1 = 1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 2206-27-1

| PubChem = 75151

| PubChem_Comment = (anhydrate)

| ChemSpiderID = 67699

| ChemSpiderID_Comment = (anhydrate)

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 218-617-0

| RTECS = PV6210000

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3

| InChIKey = IAZDPXIOMUYVGZ-WFGJKAKNSA-N

| Beilstein = 1237248}}

|Section2={{Chembox Properties

| Density = 1.19 g/cm³ (20 °C)

| MeltingPtC = 20.2

| BoilingPt =

}}

'''Deuterated DMSO''', also known as '''dimethyl sulfoxide-d₆''', is an [[isotopologue]] of [[dimethyl sulfoxide]] (DMSO, (CH₃)₂S=O)) with chemical formula ((CD₃)₂S=O) in which the [[hydrogen]] atoms ("H") are replaced with their [[isotope]] [[deuterium]] ("D"). Deuterated DMSO is a common [[solvent]] used in [[NMR spectroscopy]].

==Production==

Deuterated DMSO is produced by heating DMSO in [[heavy water]] (D₂O) with a basic catalyst such as [[calcium oxide]]. The reaction does not give complete conversion to the d₆ product, and the [[water]] produced must be removed and replaced with D₂O several times to drive the [[Chemical equilibrium|equilibrium]] to the fully deuterated product.<ref>{{cite patent |country= DE|number= 1171422B|status= application|title= Process for the production of hexadeuterodimethyl sulfoxide|pubdate= 1964-06-04|fdate= 1962-10-25|pridate= 1962-10-25|invent1= Fruhstorfer, Wolfgang|invent2= Hampel, Bruno|assign1= E. Merck A.G.}}</ref>

==Use in NMR spectroscopy==

[[File:13CNMR Spectra of DMSO d6.gif|thumb|¹³C NMR Spectrum of DMSO-''d''₆]]

Pure deuterated DMSO shows no peaks in ¹H [[NMR spectroscopy]] and as a result is commonly used as an NMR solvent.<ref>{{Cite journal |last=Chandak |first=MS |last2=Nakamura |first2=T |last3=Takenaka |first3=T |last4=Chaudhuri |first4=TK |last5=Yagi-Utsumi |first5=M |last6=Chen |first6=J |last7=Kuwajima |first7=K |date=22 January 2013 |title=The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments |url=https://onlinelibrary.wiley.com/doi/10.1002/pro.2221 |journal=[[Protein Sci]] |language=en |location=Hoboken, New Jersey, USA |publisher=[[Wiley-Blackwell]] |volume=22 |issue=4 |pages=486–91 |doi=10.1002/pro.2221 |pmc=3610054 |pmid=23339068 |url-access=subscription |access-date=2 June 2023}}</ref> However commercially available samples are not 100% pure and a residual DMSO-d₅ ¹H NMR signal is observed at 2.50ppm (quintet, J_HD=1.9Hz). The ¹³C chemical shift of DMSO-d₆ is 39.52ppm (septet).<ref>{{Cite journal |last=Gottlieb |first=Hugo E. |last2=Kotlyar |first2=Vadim |last3=Nudelman |first3=Abraham |date=17 October 1997 |title=NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities |url=https://pubs.acs.org/doi/full/10.1021/jo971176v |journal=[[The Journal of Organic Chemistry]] |language=en |location=Washington, D.C., USA |publisher=[[American Chemical Society]] |volume=62 |issue=21 |pages=7512–7515 |doi=10.1021/jo971176v |pmid=11671879 |url-access=subscription |access-date=18 June 2011}}</ref>

==References==

{{reflist}}

{{List of NMR solvents}}

[[Category:Deuterated solvents]]