Synthesis and properties of 5, 6-Bis (dimethylamino) acenaphthylene: the first proton sponge with easily-modified basicity

…, AF Pozharskii, GR Milgizina, ST Howard

Index: Ozeryanskii; Pozharskii; Milgizina; Howard Journal of Organic Chemistry, 2000 , vol. 65, # 22 p. 7707 - 7709

Full Text: HTML

Citation Number: 24

Abstract

Some N-peralkylated aromatic diamines with unusually high basicity, due to repulsion of the nitrogen lonepairs which is relieved by enforced hydrogen bonding on protonation, are called proton sponges. 1 The first member of the proton sponge family is 1, 8-bis (dimethylamino) naphthalene (1, pKa 18.2 in MeCN, 1c 7.5 in DMSO2). Besides the high basicity, the repulsion between two amine sites in molecule 1 causes strong steric strain, ...