Two Equilibria of (N-Methyl-3-pyridinium)chlorocarbene, a Cationic Carbene

The Journal of Physical Chemistry. a
Hui CangKarsten Krogh-Jespersen

Abstract

Equilibrium constants and the associated thermodynamic parameters are reported for the equilibria established between the cationic carbene (N-methyl-3-pyridinium)chlorocarbene tetrafluoroborate (MePyr(+)CCl BF4(-), 3) and 1,3,5-trimethoxybenzene (TMB) to form a carbene-TMB complex, as well as between carbene 3 and chloride ion to form the zwitterion, N-methyl-3-pyridinium dichloromethide (10). These equilibrium constants and thermodynamic parameters are contrasted with analogous data for several related carbenes, and the influence of the pyridinium unit in carbene 3 is thereby highlighted. Computational studies augment and elucidate the experimental results.

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Citations

Jan 20, 2017·The Journal of Organic Chemistry·Robert A Moss

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