DSS (NMR standard)

{{Chembox

| ImageFile = Me3SiC2SO3Na.png

| ImageAlt =

| ImageFile1 =

| ImageSize1 =

| ImageAlt1 =

| PIN = Sodium 3-(trimethylsilyl)propane-1-sulfonate

| OtherNames = 3-trimethylsilyl-1-propanesulfonate, sodium salt; 2,2-Dimethyl-2-silapentane-5-sulfonate sodium salt; DSS sodium salt(trimethylsilyl)-1-propanesulfonate

|Section1={{Chembox Identifiers

| Abbreviations = DSS

| CASNo = 2039-96-5

| CASNo_Ref = {{cascite|correct|??}}

| PubChem = 5167273

| PubChem1 =

| PubChem1_Comment =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI =

| ChemSpiderID = 67436

| ChemSpiderID_Ref = {{Chemspidercite|correct|ChemSpider}}

| EC_number = 218-031-5

| DTXSID = DTXSID7062118

| StdInChI=1S/C6H16O3SSi.Na/c1-11(2,3)6-4-5-10(7,8)9;/h4-6H2,1-3H3,(H,7,8,9);/q;+1/p-1

| StdInChIKey = HWEXKRHYVOGVDA-UHFFFAOYSA-M

| SMILES = C[Si](C)(C)CCCS(=O)(=O)[O-].[Na+]

}}

|Section2={{Chembox Properties

| C=6 | H=15 | O=3 | S=1 | Si=1 | Na =1

| Appearance = White solid

| BoilingPtC =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Sodium trimethylsilylpropanesulfonate (DSS) is the organosilicon compound with the formula (CH3)3SiCH2CH2CH2SO3Na+. It is the sodium salt of trimethylsilylpropanesulfonic acid. A white, water-soluble solid, it is used as a chemical shift standard for proton NMR spectroscopy of aqueous solutions.{{cite journal|doi=10.1351/pac200880010059|title=Further Conventions for NMR Shielding and Chemical Shifts (IUPAC Recommendations 2008)|journal=Pure and Applied Chemistry|volume=80|issue=2|pages=59–84|year=2008|last1=Harris|first1=Robin K.|last2=Becker|first2=Edwin D.|last3=Cabral De Menezes|first3=Sonia M.|last4=Granger|first4=Pierre|last5=Hoffman|first5=Roy E.|last6=Zilm|first6=Kurt W.|bibcode=2008JMagR.191..340.|doi-access=free}} The chemical shift, specifically the signal for the trimethylsilyl group, is relatively insensitive to pH.{{cite journal|doi=10.1016/0022-2364(77)90104-4|title=pH Dependence of Internal References|journal=Journal of Magnetic Resonance |volume=26|issue=3|pages=527–528|year=1977|last1=De Marco|first1=Antonio|bibcode=1977JMagR..26..527D}}

The proton spectrum of DSS also exhibits resonances at 2.91 ppm (m), 1.75 ppm (m), and 0.63 ppm (m) at an intensity of 22% of the reference resonance at 0 ppm.

Alternatives

Sodium trimethylsilyl propionate (TSP) is a related compound used as an NMR standard. It uses a carboxylic acid instead of the sulfonic acid found in DSS to confer water solubility. As a weak acid, TSP is more sensitive to changes in pH.

4,4-Dimethyl-4-silapentane-1-ammonium trifluoroacetate (DSA) has also been proposed as an alternative, to overcome certain drawbacks of DSS.{{cite journal | title = DSA: A New Internal Standard for NMR Studies in Aqueous Solution | first1= James S.|last1= Nowick|first2= Omid|last2= Khakshoor|first3= Mehrnoosh|last3= Hashemzadeh|first4= Justin O.|last4= Brower | journal = Org. Lett. | year = 2003 | volume = 5 | issue = 19 | pages = 3511–3513 | doi = 10.1021/ol035347w | pmid = 12967312}}

References