1, 8??Bis (tetramethylguanidino) naphthalene (TMGN): A New, Superbasic and Kinetically Active “Proton Sponge”

…, RM Gschwind, J Sundermeyer

Index: Raab, Volker; Kipke, Jennifer; Gschwind, Ruth M.; Sundermeyer, Joerg Chemistry - A European Journal, 2002 , vol. 8, # 7 p. 1682 - 1693

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Citation Number: 165

Abstract

Abstract 1, 8-Bis (tetramethylguanidino) naphthalene (TMGN, 1) is a new, readily accessible, and stable “proton sponge” with an experimental pK math image value of 25.1 in MeCN, which is nearly seven orders of magnitude higher in basicity than the classical proton sponge 1, 8-bis (dimethylamino)-naphthalene (DMAN). Because of the sterically less crowded character of the proton-accepting sp 2-nitrogen atoms, TMGN also has a higher ...