Reestimation of the Taft's substituent constant of the pentafluorophenyl group

Toshinobu Korenaga, Koichi Kadowaki, Tadashi Ema, Takashi Sakai

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22 Citations (Scopus)

Abstract

The Taft's substituent constant of the pentafluorophenyl group (σ*C6F5)) was reestimated to be 1.50 by correlation between IR spectral data (vC=O) and σ* constants for a series of esters (involving the pentafluorobenzyl group) of 3-phenylpropanoic acid and butanoic acid. The possibility of the disturbance of the correlation by the intramolecular π-π interaction between C 6F5 and C6H5 groups in pentafluorobenzyl 3-phenylpropanoate was excluded by ab initio and DFT calculations of the stable conformations and their carbonyl frequencies. The reestimated σ* (C6F5) value was used for calculation of the pKa value of pentafluorobenzyl alcohol [14.5 (or 14.3)].

Original languageEnglish
Pages (from-to)7340-7343
Number of pages4
JournalJournal of Organic Chemistry
Volume69
Issue number21
DOIs
Publication statusPublished - Oct 15 2004

ASJC Scopus subject areas

  • Organic Chemistry

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