Transmission of substituent effects through unsaturated systems Part 71. Influence of substituent on infrared and 13C NMR properties in rigid cisoid and transoid Conformations of α-enones

Serge Geribaldi, Yvonne Girault, Pal Perjesi, Jeanine Tortajada

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Dual substituent parameter (DSP) analysis is applied to model substituent effects on 13C substituent chemical shifts (SCS) and νCO stretching frequencies in two series of α-enones with rigid cisoïd and transoïd conformations. The regression coefficients of DSP analysis for the 13C SCS of the conjugated systems are discussed in terms of the relative importance of the various mechanisms of transmission of electronic effects. The differences between the regression coefficients relative to the field and resonance effects for the cisoïd and transoïd systems reflect very well the variations of geometries between both series. Concerning the i.r. data, the DSP analysis leads to an apparently unprecedented observation since it appears that the stretching frequencies of the carbonyl group are more sensitive towards substituent effect in the aplanar cisoïd system than in the more planar transoïd system. This surprising result is discussed.

Original languageEnglish
Pages (from-to)879-892
Number of pages14
JournalSpectrochimica Acta Part A: Molecular Spectroscopy
Volume48
Issue number6
DOIs
Publication statusPublished - Jun 1992

ASJC Scopus subject areas

  • Engineering(all)

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