Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy
Publication type: Journal Article
Publication date: 1979-07-01
scimago Q2
wos Q2
SJR: 0.678
CiteScore: 7.0
Impact factor: 3.8
ISSN: 00092673, 13480634
General Chemistry
Abstract
Thermodynamic parameters (ΔH=−4.9 kcal mol−1, ΔS=−11.3 cal mol−1 deg−1) were determined for cyclization of 2,4,6-tri-t-butyl-N-thiosulfinylaniline (1b) (the minor component) into 2,4,6-tri-t-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene (1a) (the major component) by means of NMR spectroscopy. Using these values, π-bond of thiosulfinylamino group (–N=S=S) was estimated to be weaker than that of sulfinylamino group (–N=S=O) by, at least, 25 kcal mol−1. The equilibrium ratio [1a]/[1b] is subject to considerable solvent effect, polar solvents favoring the cyclic form (1a). Similarity of the thiosulfinylamine-dithiazole equilibrium to that of azidoimine-tetrazole has been pointed out.
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INAGAKI Y. et al. Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy // Bulletin of the Chemical Society of Japan. 1979. Vol. 52. No. 7. pp. 2008-2009.
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INAGAKI Y., Okazaki R., Inamoto N., YAMADA K., KAWAZURA H. Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy // Bulletin of the Chemical Society of Japan. 1979. Vol. 52. No. 7. pp. 2008-2009.
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RIS
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TY - JOUR
DO - 10.1246/bcsj.52.2008
UR - https://doi.org/10.1246/bcsj.52.2008
TI - Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy
T2 - Bulletin of the Chemical Society of Japan
AU - INAGAKI, YOSHIO
AU - Okazaki, Renji
AU - Inamoto, Naoki
AU - YAMADA, Koh-ichi
AU - KAWAZURA, Hiroshi
PY - 1979
DA - 1979/07/01
PB - Oxford University Press
SP - 2008-2009
IS - 7
VL - 52
SN - 0009-2673
SN - 1348-0634
ER -
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@article{1979_INAGAKI,
author = {YOSHIO INAGAKI and Renji Okazaki and Naoki Inamoto and Koh-ichi YAMADA and Hiroshi KAWAZURA},
title = {Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy},
journal = {Bulletin of the Chemical Society of Japan},
year = {1979},
volume = {52},
publisher = {Oxford University Press},
month = {jul},
url = {https://doi.org/10.1246/bcsj.52.2008},
number = {7},
pages = {2008--2009},
doi = {10.1246/bcsj.52.2008}
}
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MLA
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INAGAKI, YOSHIO, et al. “Chemistry ofN-Thiosulfinylanilines. III. Thiosulfinylamine—5H-1,2,3-Dithiazole Equilibrium as Studied by NMR Spectroscopy.” Bulletin of the Chemical Society of Japan, vol. 52, no. 7, Jul. 1979, pp. 2008-2009. https://doi.org/10.1246/bcsj.52.2008.