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According to calculations, ortho-diethynylbenzene dianion is the strongest superbase and has a proton affinity of 1,843.987 kJ/mol (440.723 kcal/mol). [1] The meta isomer is the second-strongest, and the para isomer is the third. All three are readily able to accept any proton to its ethynyl tails, from almost any compound.
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.
In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH −. These ions can react with hydrogen ions (H + according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction. A base was therefore a metal hydroxide such as NaOH or Ca(OH) 2.
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]
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 ...
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P 4-t-Bu is a readily accessible chemical from the group of neutral, peralkylated sterically hindered polyaminophosphazenes, which are extremely strong bases but very weak nucleophiles, with the formula (CH 3) 3 C−N=P(−N=P(−N(CH 3) 2) 3) 3. "t-Bu" stands for tert-butyl (CH 3) 3 C –.