Gas-Phase Acidities of α-and α, α-SO 2 CF 3-Substituted Toluenes. Varying Resonance Demand in the Electron-Rich System

…, MMR Badal, IA Koppel, M Mishima

Index: Zhang, Min; Badal, Md. Mizanur Rahman; Koppel, Ilmar A.; Mishima, Masaaki Bulletin of the Chemical Society of Japan, 2013 , vol. 86, # 7 p. 813 - 820

Full Text: HTML

Citation Number: 24

Abstract

The gas-phase acidities (GA) of aryl (trifluoromethylsulfonyl) methanes (ArCH 2 SO 2 CF 3; 1) and arylbis (trifluoromethylsulfonyl) methanes (ArCH (SO 2 CF 3) 2; 2) were determined by measuring proton-transfer equilibria. Substituent effects for acidities of a series of ArCH (R 1) R 2 including 1 and 2 have been analyzed successfully in terms of the Yukawa–Tsuno equation. The resonance demand parameter r− value was found to decrease linearly with ...