Organic superbases, such as the proton sponge (1,8-bis(dimethylamino)naphthalene), are strong bases due to the strain created by the proximity of the nitrogen lone pairs and the large relief of this strain when protonated. This study looks at the ability of chiral organic superbases analogous to the proton sponge to transfer chirality to an achiral acid, forming a chiral conjugate acid. Example superbases include <i>R</i>-2,2’-diphenyldiamine and (2S,3S)-butane-2,3-diamine. Comparison is made of the activation barriers (computed at ωb97X-D/6-311+G(d,p)) for deprotonation by a superbase of the pro-R or pro-S proton of as such as propanal and 1,1,1-trifluropropane.

DFT study of chiral organic superbase

251st National Meeting (2016)

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