S-Nitrosotriphenylmethanethiol

S-Nitrosotriphenylmethanethiol
Identifiers
CAS Number	6316-86-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	85891;
PubChem CID	95186;
UNII	EDT6XKN756;
CompTox Dashboard (EPA)	DTXSID80212503 ;
	InChI InChI=1S/C19H15NOS/c21-20-22-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Key: YLEVRGODADSYBK-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SN=O;
Properties
Chemical formula	C19H15NOS
Molar mass	305.40 g·mol−1
Appearance	green solid
Melting point	110 °C (230 °F; 383 K) decomposition
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

S-Nitrosotriphenylmethanethiol is the organosulfur compound with the formula (C₆H₅)₃CSNO. It is a rare example of a nitrosothiol derivative that is robust solid at room temperature. The green compound can be produced by the reaction of triphenylmethanethiol with nitrous acid:

(C₆H₅)₃CSH + HONO → (C₆H₅)₃CSNO + H₂O

According to X-ray crystallography, S-nitrosotriphenylmethanethiol features a conventional trityl group appended to a bent SNO substituent. The S-N=O angle is 114°, while the S-N and N=O distances are 1.78 and 1.79 Å. Other S-nitrosothiols, e.g. MeSNO and SNAP have characterized by similar structures.^[1]

References

^ Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between Conformational Dynamics and the Redox Chemistry of S-Nitrosothiols". Journal of the American Chemical Society. 121 (30): 7115–7123. doi:10.1021/ja9901314.

[1] Arulsamy, N.; Bohle, D. S.; Butt, J. A.; Irvine, G. J.; Jordan, P. A.; Sagan, E. (1999). "Interrelationships between Conformational Dynamics and the Redox Chemistry of S-Nitrosothiols". Journal of the American Chemical Society. 121 (30): 7115–7123. doi:10.1021/ja9901314.

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