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N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding

Publication ,  Journal Article
Eliel, EL; Koskimies, J; McPhail, AT; Swern, D
Published in: Journal of Organic Chemistry
June 1, 1976

The crystal structure of N-(p-nitrophenyl)-S,S-dimethyliminosulfurane is reported. The short N-S bond (1.651 Å) implies a substantial amount of double bonding and bond length distortions in the aromatic ring suggest extensive resonance involvement of the p-nitrophenyl moiety. The dipole moments of five para-substituted N-aryl-S,S-dimethyliminosulfuranes (para substituents: F, Cl, Br, CN, NO2) imply 45–58% ionic character in the N-S bond, least for p-F, most for P-NO2. It is concluded that the two canonic forms Ar-N--S+Me2 ⟷ Ar-N=SMe2 contribute about equally to the resonance hybrid with the dipolar form predominating only when there are strongly electron- withdrawing substituents at the para position in the benzene ring. © 1976, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

June 1, 1976

Volume

41

Issue

12

Start / End Page

2137 / 2140

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Eliel, E. L., Koskimies, J., McPhail, A. T., & Swern, D. (1976). N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding. Journal of Organic Chemistry, 41(12), 2137–2140. https://doi.org/10.1021/jo00874a015
Eliel, E. L., J. Koskimies, A. T. McPhail, and D. Swern. “N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding.” Journal of Organic Chemistry 41, no. 12 (June 1, 1976): 2137–40. https://doi.org/10.1021/jo00874a015.
Eliel EL, Koskimies J, McPhail AT, Swern D. N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding. Journal of Organic Chemistry. 1976 Jun 1;41(12):2137–40.
Eliel, E. L., et al. “N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding.” Journal of Organic Chemistry, vol. 41, no. 12, June 1976, pp. 2137–40. Scopus, doi:10.1021/jo00874a015.
Eliel EL, Koskimies J, McPhail AT, Swern D. N-Aryl-S,S-dimethyliminosulfuranes. Structure, Dipole Moments, and Extent of Double Bonding. Journal of Organic Chemistry. 1976 Jun 1;41(12):2137–2140.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

June 1, 1976

Volume

41

Issue

12

Start / End Page

2137 / 2140

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry