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Nitroxyl disulfides, novel intermediates in transnitrosation reactions.

Publication ,  Journal Article
Houk, KN; Hietbrink, BN; Bartberger, MD; McCarren, PR; Choi, BY; Voyksner, RD; Stamler, JS; Toone, EJ
Published in: Journal of the American Chemical Society
June 2003

A novel anionic RSN(O)SR species, the intermediate in transnitrosation reactions, was explored computationally with B3LYP and CBS-QB3 methods. The species resembles a nitroxyl coordinated to a highly distorted disulfide, and it differs significantly from intermediates in nucleophilic acyl substitution. Reactions of the following species were computed for comparison: MeS(-) + MeSNO; MeO(-) + MeONO; MeS(-) + MeSCHO; MeO(-) + MeOCHO. The last two have very different intermediates from the first two. Mass spectrometric experimental evidence is presented that is consistent with the formation of a nitroxyl disulfide in the gas phase. The calculated proton affinity and redox potentials of the intermediate are also reported.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

June 2003

Volume

125

Issue

23

Start / End Page

6972 / 6976

Related Subject Headings

  • Thermodynamics
  • Sulfhydryl Compounds
  • Nitroso Compounds
  • Nitrosation
  • Nitrogen Oxides
  • Models, Molecular
  • General Chemistry
  • Disulfides
  • 40 Engineering
  • 34 Chemical sciences
 

Citation

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Houk, K. N., Hietbrink, B. N., Bartberger, M. D., McCarren, P. R., Choi, B. Y., Voyksner, R. D., … Toone, E. J. (2003). Nitroxyl disulfides, novel intermediates in transnitrosation reactions. Journal of the American Chemical Society, 125(23), 6972–6976. https://doi.org/10.1021/ja029655l
Houk, K. N., Bruce N. Hietbrink, Michael D. Bartberger, Patrick R. McCarren, Bo Yoon Choi, Robert D. Voyksner, Jonathan S. Stamler, and Eric J. Toone. “Nitroxyl disulfides, novel intermediates in transnitrosation reactions.Journal of the American Chemical Society 125, no. 23 (June 2003): 6972–76. https://doi.org/10.1021/ja029655l.
Houk KN, Hietbrink BN, Bartberger MD, McCarren PR, Choi BY, Voyksner RD, et al. Nitroxyl disulfides, novel intermediates in transnitrosation reactions. Journal of the American Chemical Society. 2003 Jun;125(23):6972–6.
Houk, K. N., et al. “Nitroxyl disulfides, novel intermediates in transnitrosation reactions.Journal of the American Chemical Society, vol. 125, no. 23, June 2003, pp. 6972–76. Epmc, doi:10.1021/ja029655l.
Houk KN, Hietbrink BN, Bartberger MD, McCarren PR, Choi BY, Voyksner RD, Stamler JS, Toone EJ. Nitroxyl disulfides, novel intermediates in transnitrosation reactions. Journal of the American Chemical Society. 2003 Jun;125(23):6972–6976.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

June 2003

Volume

125

Issue

23

Start / End Page

6972 / 6976

Related Subject Headings

  • Thermodynamics
  • Sulfhydryl Compounds
  • Nitroso Compounds
  • Nitrosation
  • Nitrogen Oxides
  • Models, Molecular
  • General Chemistry
  • Disulfides
  • 40 Engineering
  • 34 Chemical sciences