The determination of inductive effects by 13C nuclear magnetic resonance spectrometry

Abstract
A series of meta- and para-XCH2-substituted methyl cinnamates has been prepared and the 13C n.m.r. chemical shifts of the α- and β-side-chain carbons have been determined in ethanol. In the majority of cases the magnitudes of the substituent-induced chemical shifts are directly proportional to the inductive substituent constants of the group X. C–H Hyperconjugation appears to play a significant role in the relay of inductive effects from the substituent to the more distant ethenyl carbon in the para-series, but in the other three cases relay appears to be mainly via a direct field effect.

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