𝔖 Bobbio Scriptorium
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Substituent Conformational effects in vicinal 13C13C spin–spin coupling constants

✍ Scribed by James L. Marshall; Larry G. Faehl; Richard Kattner; Poul Erik Hansen

Publisher
John Wiley and Sons
Year
1979
Tongue
English
Weight
424 KB
Volume
12
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

A series of 7‐^13^C‐labeled o‐substituted toluene derivatives and carboxyl‐^13^C‐isocrotonic and crotonic acid were synthesized and studied by ^13^C NMR spectroscopy to obtain ^13^C^13^C spin‐spin coupling constants involving the labeled carbon. The cis ^3^J(CC) values were different from those in previous studies in that these J(CC) values were relatively small and the usual dependence of ^3^J(CC) on the s‐character of the terminal carbon was reversed. Further, a strong dependence of ^3^J(CC) on the conformational orientation of a terminal carbonyl group was shown to exist. Through‐space interactions of the two coupling carbons were shown to contribute to these ‘anomalous’ results, and thus it was shown the cis carbon‐carbon couplings may not be directly related to geometrically equivalent proton‐proton couplings, as are other carbon‐carbon couplings.

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