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13C and 19F NMR Spectra of substituted ethyl α-fluorocinnamates. Application of the DSP-NLR equation

✍ Scribed by Charles N. Robinson; Gregory E. Stablein; Carl D. Slater

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
460 KB
Volume
46
Category
Article
ISSN
0040-4020

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✦ Synopsis

1% and t9F NMR spectra of 12 psubstltuted and 9 msubstituted ethyl a-fluorocinnamates, along with that of the parent compound, have been recorded and analyzed by DSP and LISP-NLR equatlons. E values found for the correlation of chemical shifts of both the warbon atom of the styrene skeleton and the F atom show near additivtty of the effect of individual substituents on C4 shifts in pdisubstitutad benzenes. Despite this, correlations using the DSP-NLR equation are not greatly Improved over those of the DSP equation, either for sites showing excellent or poor correlations. Also, the magnitude of the E values appropriate for different sites on the side chain show no significant relationship to the percentage of the sensitivity at the she attributed to resonance interaction. Consequently, the utility of the DSP-NLR method seems limited. Substituent effects at F are normal, in contrast to the expectation based on charge alternation that they would be inverse. CNDCV2 charge densities calculated for representative methyl a-fiuorocinnamates reveal that n densities at both F and the Farbon atom of the styrene skeleton accord with normal substituent effects.

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