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Studies on the substituent dependence of 1 H chemical shifts. Unusual 1 H shifts in trans ‐9‐halogenodecalins
Author(s) -
Schrumpf G.,
Sanwald W.,
Machinek R.
Publication year - 1987
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.1260250104
Subject(s) - chemistry , alkane stereochemistry , chemical shift , electronegativity , substituent , stereochemistry , halogen , spectral line , crystallography , medicinal chemistry , organic chemistry , crystal structure , alkyl , physics , astronomy
The 1 H, 2 H and 13 C spectra of trans ‐9‐chloro, ‐bromo‐ and ‐iodo‐decalins and their deuteriated analogues have been recorded in order to study the effect of chloro, bromo and iodo substituents on β antiperiplanar protons. All shifts were completely assigned. Unusually large upfield shifts were detected for β protons antiperiplanar to the halogen substituents. The electronegativity dependence of the β shifts is opposite to that hitherto reported.