DSS (NMR standard)

DSS (NMR standard)
Names
	Preferred IUPAC name Sodium 3-(trimethylsilyl)propane-1-sulfonate
	Other names 3-trimethylsilyl-1-propanesulfonate, sodium salt; 2,2-Dimethyl-2-silapentane-5-sulfonate sodium salt; DSS sodium salt(trimethylsilyl)-1-propanesulfonate
Identifiers
CAS Number	2039-96-5 ;
3D model (JSmol)	Interactive image;
Abbreviations	DSS
ChemSpider	67436 ;
EC Number	218-031-5;
PubChem CID	5167273;
CompTox Dashboard (EPA)	DTXSID7062118;
	InChI InChI=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 Key: HWEXKRHYVOGVDA-UHFFFAOYSA-M;
	SMILES C[Si](C)(C)CCCS(=O)(=O)[O-].[Na+];
Properties
Chemical formula	C6H15NaO3SSi
Molar mass	218.32 g·mol−1
Appearance	White solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sodium trimethylsilylpropanesulfonate (DSS) is the organosilicon compound with the formula (CH₃)₃SiCH₂CH₂CH₂SO₃⁻Na⁺. 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.[1] The chemical shift, specifically the signal for the trimethylsilyl group, is relatively insensitive to pH.[2]

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.[3]

References

Harris, Robin K.; Becker, Edwin D.; Cabral De Menezes, Sonia M.; Granger, Pierre; Hoffman, Roy E.; Zilm, Kurt W. (2008). "Further Conventions for NMR Shielding and Chemical Shifts (IUPAC Recommendations 2008)". Pure and Applied Chemistry. 80 (2): 59–84. Bibcode:2008JMagR.191..340.. doi:10.1351/pac200880010059.
De Marco, Antonio (1977). "pH Dependence of Internal References". Journal of Magnetic Resonance. 26 (3): 527–528. Bibcode:1977JMagR..26..527D. doi:10.1016/0022-2364(77)90104-4.
Nowick, James S.; Khakshoor, Omid; Hashemzadeh, Mehrnoosh; Brower, Justin O. (2003). "DSA: A New Internal Standard for NMR Studies in Aqueous Solution". Org. Lett. 5 (19): 3511–3513. doi:10.1021/ol035347w. PMID 12967312.

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[1] Harris, Robin K.; Becker, Edwin D.; Cabral De Menezes, Sonia M.; Granger, Pierre; Hoffman, Roy E.; Zilm, Kurt W. (2008). "Further Conventions for NMR Shielding and Chemical Shifts (IUPAC Recommendations 2008)". Pure and Applied Chemistry. 80 (2): 59–84. Bibcode:2008JMagR.191..340.. doi:10.1351/pac200880010059.

[2] De Marco, Antonio (1977). "pH Dependence of Internal References". Journal of Magnetic Resonance. 26 (3): 527–528. Bibcode:1977JMagR..26..527D. doi:10.1016/0022-2364(77)90104-4.

[3] Nowick, James S.; Khakshoor, Omid; Hashemzadeh, Mehrnoosh; Brower, Justin O. (2003). "DSA: A New Internal Standard for NMR Studies in Aqueous Solution". Org. Lett. 5 (19): 3511–3513. doi:10.1021/ol035347w. PMID 12967312.