Bulletin of the Chemical Society of Japan

Gas-phase acidities of acetophenone oximes. Substituent effect and solvent effects

MMR Badal, M Mishima

Index: Badal, Mizanur Rahman; Mishima, Masaaki Bulletin of the Chemical Society of Japan, 2010 , vol. 83, # 1 p. 58 - 65

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Citation Number: 9

Abstract

Gas-phase acidities (GA) of ring-substituted (E)-acetophenone oximes, XC 6 H 4 C (CH 3)= NOH, were determined by measuring proton-transfer equilibria using an FT-ICR mass spectrometer. The magnitude of the substituent effect on the acidity was found to be smaller than that of corresponding phenols by a factor of 0.70. The effects of strong para π-acceptors such as p-NO 2 and p-CN are somewhat enhanced compared with those of phenols, ...