Out-basicity of 1,8-bis(dimethylamino)naphthalene: the experimental and theoretical challenge.

Abstract

A possibility of non-conventional two-step protonation of 1,8-bis(dimethylamino)naphthalene (proton sponge) is discussed. Unlike the generally accepted mechanism, involving relatively slow direct penetration of a proton into the cleft between the peri-NMe2 groups, it consists of the rapid addition of a proton to the out-inverted NMe2 group with the… (More)
DOI: 10.1039/c3ob41986j

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