Comparison of gas??phase acidities of some carbon acids with their rates of hydron exchange in methanolic methoxide

VF DeTuri, HF Koch, JG Koch, G Lodder…

Index: DeTuri, Vincent F.; Koch, Heinz F.; Koch, Judith G.; Lodder, Gerrit; Mishima, Masaaki; Zuilhof, Han; Abrams, Neal M.; Anders, Cecily E.; Biffinger, Justin C.; Han, Patrick; Kurland, Adam R.; Nichols, Jason M.; Ruminski, Anne M.; Smith, Patricia R.; Vasey, Karen D. Journal of Physical Organic Chemistry, 2006 , vol. 19, # 5 p. 308 - 317

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Citation Number: 8

Abstract

Abstract Hydron exchange reaction rates, k exch M− 1 s− 1, using methanolic sodium methoxide are compared with gas-phase acidities, ΔG math image kcal/mol, for four 9- YPhenylfluorenes-9-i H, seven YC 6 H 4 C i H (CF 3) 2, seven YC 6 H 4 C i HClCF 3, and C 6 F 5 i H. Fourteen of the fluorinated benzylic compounds and pentafluorobenzene result in near unity experimental hydrogen isotope effects that suggest substantial amounts of ...