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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 2, Number 1
January 20, 1981 

Studies on the Linear Free Energy Relationship in Methyl Cinnamates by 1H-NMR Spectrometry
Sang Chul Shim, Joon Won Park
Chemical shift values of α-proton of trans- and cis-methyl cinnamates are well correlated with σ (σI, σRo), and (F, R) (r = 0.999 - 0.879). It is observed that (1) the degree of variation of δHα value by varying the substituents in trans-cinnamates is similar to that of cis-cinnamates (ρtrans = 0.296, ρcis = 0.284), (2) resonance contribution is larger in the trans-cinnamates than that in the cis-cinnamates, but inductive contribution is reversed, (3) for m-substituted derivatives, resonance contribution is very small compared to that for p-substituted derivatives.
29 - 34
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