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Synthesis, 1 H NMR spectral properties and conformational preferences of some open‐chain and cyclic aromatic sulphides containing pyridine or 1,3,4‐thiadiazole units
Author(s) -
Bottino Francesco,
Pappalardo Sebastiano
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.1270160102
Subject(s) - chemistry , steric effects , pyridine , thiophene , alkane stereochemistry , aromaticity , proton nmr , stereochemistry , nuclear magnetic resonance spectroscopy , crystallography , medicinal chemistry , organic chemistry , molecule , crystal structure
The conformational preferences in solution of eight new open‐chain and cyclic aromatic sulphides containing pyridine or 1,3,4‐thiadiazole units have been investigated, parallel to those of some structurally related phenyl sulphides, by means of 1 H NMR spectroscopy. The results obtained have shown that replacement of phenyl by the pyridyl or the 1,3,4‐thiadiazolyl moieties induces slightly different propeller arrangements, ascribed to the higher conjugative tendency of both electron‐deficient heteroaromatic rings, in all open‐chain mixed sulphides, in opposition to the skew arrangements observed for phenyl sulphide derivatives. No prominent differences have been found for cyclic sulphides, which preferentially adopt the sterically unhindered saddle shape conformation.