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Downfield γ‐ gauche and γ‐antiperiplanar effects on 13 C NMR chemical shifts exerted by thiophene sulphur
Author(s) -
de Haan J. W.,
van Dommelen M. E.,
van de Ven L. J. M.,
Corvers A.
Publication year - 1978
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.1270110611
Subject(s) - alkane stereochemistry , thiophene , sulfur , chemical shift , chemistry , ring (chemistry) , molecule , stereochemistry , crystallography , organic chemistry
The γ‐effects of sulphur on 13 C NMR chemical shifts have been measured in a series of steroidal compounds containing the thiophene ring in different configurations with respect to the rest of the molecule. The data constitute the first example of downfield effects exerted by sulphur on both gauche and antiperiplanar γ‐carbons. The γ‐ gauche effect of sulphur amounts to 1.6–1.8 ppm, the γ‐antiperiplanar effect from practically zero to almost 1 ppm.