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33 S NMR spectroscopy: Substituent γ‐effect. Halogen derivatives of tetrahydrothiophene 1,1‐dioxide
Author(s) -
Rozhenko A. B.,
Bzhezovsky V. M.,
Polovinko V. V.,
Makarenko A. G.
Publication year - 1995
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260331102
Subject(s) - tetrahydrothiophene , chemistry , substituent , halogen , bromine , nuclear magnetic resonance spectroscopy , ring (chemistry) , spectroscopy , chemical shift , photochemistry , stereochemistry , organic chemistry , alkyl , physics , quantum mechanics
A series of halogen‐substituted tetrahydrothiophene 1,1‐dioxides (sulpholanes) were investigated by 13 C, 17 O and 33 S NMR spectroscopy. It was shown that successive replacement of hydrogen atoms in positions 3 and 4 of the sulpholane ring led to an increase in 33 S nuclei shielding. The 33 S NMR chemical shift range exceeded 39 ppm. The variation of the 33 S nuclei shielding with increasing number of chlorine or bromine atoms was caused by an electrostatic through‐space effect of the halogen atoms and the strongly polarized CHal bonds.