Excited-state intramolecular proton transfer in 2-(2'-arylsulfonamidophenyl) benzimidazole derivatives: The effect of donor and acceptor substituents

…, J Cody, S Sumalekshmy, J Li, S Mandal…

Index: Henary, Maged M.; Wu, Yonggang; Cody, John; Sumalekshmy; Li, Jing; Mandal, Subrata; Fahrni, Christoph J. Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4784 - 4797

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Citation Number: 52

Abstract

A series of water-soluble 2-(2'-arylsulfonamidophenyl) benzimidazole derivatives containing electron-donating and accepting groups attached to various positions of the fluorophore π- system has been synthesized and characterized in aqueous solution at 0.1 M ionic strength. The measured p K a's for deprotonation of the sulfonamide group of monosubstituted derivatives range between 6.75 and 9.33 and follow closely Hammett's free energy ...