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13 C chemical shifts and conformational analysis of methyl substituted thiacyclopentanes
Author(s) -
Barbarella G.,
Dembech P.
Publication year - 1980
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.1270130414
Subject(s) - heteroatom , conformational isomerism , chemical shift , chemistry , preference , methyl group , sulfur , group (periodic table) , nmr spectra database , spectral line , crystallography , orientation (vector space) , position (finance) , atom (system on chip) , stereochemistry , molecule , physics , mathematics , organic chemistry , geometry , computer science , ring (chemistry) , statistics , astronomy , finance , economics , embedded system
The 13 C NMR spectra of thiacyclopentane (thiolane) and its mono‐ and dimethyl derivatives at positions other than the heteroatom are reported. The 13 C shieldings are found to be consistent with a description of these compounds in terms of equilibria between half‐chair conformers. An attempt has been made to establish the axial or equatorial preference of methyl groups adjacent to, or removed from, the sulphur atom in these systems. In agreement with previous observations on thiacyclohexanes (thianes), the conformational preference of a methyl group for the equatorial orientation is greater at the β than at the α position.