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In chemistry, the Verkade base (or Verkade superbase) is a powerful superbase with the formula P(MeNCH 2 CH 2) 3 N. A colorless oil, it is an aminophosphine although its inventor John Verkade called it proazaphosphatrane. The trimethyl derivative or 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane is the simplest. [1]
A superbase is a compound that has a particularly high affinity for protons. Superbases are of theoretical interest and potentially valuable in organic synthesis . [ 1 ] [ 2 ] Superbases have been described and used since the 1850s.
Strongest superbases are synthesised in only gas phase: Ortho-diethynylbenzene dianion (C 6 H 4 (C 2) 2) 2− (the strongest superbase ever synthesized) Meta-diethynylbenzene dianion (C 6 H 4 (C 2) 2) 2− (second strongest superbase) Para-diethynylbenzene dianion (C 6 H 4 (C 2) 2) 2− (third strongest superbase)
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Lithium monoxide anion (LiO −) is a superbase existing in the gas phase. It was the strongest known base until 2008, when the isomeric diethynylbenzene dianions were determined to have a higher proton affinity. The methanide ion CH − 3 was the strongest known base before lithium monoxide anion was discovered. [2] LiO − has a proton ...
With a pK a of 12.34 [4] for its conjugate acid in aqueous solution, 1,8-bis(dimethylamino)naphthalene is one of the strongest organic bases. However, it only absorbs protons slowly—hence the trade name. The high basicity is attributed to the relief of strain upon protonation and/or the strong interaction between the nitrogen lone pairs. [3]
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