S-Nitrosotriphenylmethanethiol

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S-Nitrosotriphenylmethanethiol
Ph3CSNO.svg
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SN=O
Properties
C19H15NOS
Molar mass 305.40 g·mol−1
Appearancegreen 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).

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]

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Jonathan Stamler

Jonathan Solomon Stamler is an English-born American physician and scientist. He is known for his discovery of protein S-nitrosylation, the addition of a nitric oxide (NO) group to cysteine residues in proteins, as a ubiquitous cellular signal to regulate enzymatic activity and other key protein functions in bacteria, plants and animals, and particularly in transporting NO on cysteines in hemoglobin as the third gas in the respiratory cycle.

References

  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.