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1 H NMR and 13 C NMR spectra of disulfides, thiosulfinates and thiosulfonates
Author(s) -
Freeman Fillmore,
Angeletakis Christos N.,
Maricich Tom J.
Publication year - 1981
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270170113
Subject(s) - chemistry , nmr spectra database , methylene , carbon 13 nmr , proton nmr , medicinal chemistry , chemical shift , spectral line , nuclear magnetic resonance spectroscopy , sulfonic acid , stereochemistry , polymer chemistry , physics , astronomy
The 1 H NMR and 13 C NMR spectra of neopentyl and benzyl substituted disulfides, thiosulfinates, thiosulfonates, thiols, sulfides, sulfinic acids and sulfonic acids are reported. The deshielding electron withdrawing effects of −SO, −SO 2 , −SO 2 − , −SO 2 H, −SO 3 − , −SO 3 H and SO 3 CH 3 on α‐methylene and benzylic protons are observed. The 1 H NMR spectra show, except for two dialkylthiosulfinates, that the α'‐protons of thiosulfinates absorb farther downfield than those of the thiosulfonates. Although the 13 C NMR spectra show that α SO effects are deshielding and are smaller than the α SO 2 effects, the α' SO values are more shielding than the α' SO 2 values for some compounds. The effects on 13 C NMR spectra which result from substituting a phenyl group for a neopentyl or benzyl group are discussed. The α‐methylene carbon shifts for neopentanesulfinic acid and α‐toluenesulfinic acid are further downfield than those for the corresponding sulfonic acids.