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Issue 1, 2008
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Effects of the alkyl substituent in the π-donor heteroatom on the kinetic and thermodynamic acidities of Fischer thiocarbene complexes

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Abstract

Rate constants for the proton transfer reaction from Fischer thiocarbene complexes (CO)5M[double bond, length as m-dash]C(SR1)CH3 (M = Cr or W; R1 = n-butyl, isopropyl, tert-butyl, cyclohexyl) to OH and various primary and secondary amines were determined in 50% acetonitrile–50% water at 25 °C. These measurements allowed the determination of the thermodynamic and kinetic acidities for these substrates. The results obtained show that there is a slight effect of the substituent on the thermodynamic acidity, which is governed by its hydrophobicity; whereas the effect on the kinetic acidity is more noticeable and is due to the steric effect of the substituent.

Graphical abstract: Effects of the alkyl substituent in the π-donor heteroatom on the kinetic and thermodynamic acidities of Fischer thiocarbene complexes

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Article information


Submitted
27 Jun 2007
Accepted
07 Aug 2007
First published
24 Aug 2007

New J. Chem., 2008,32, 65-72
Article type
Paper

Effects of the alkyl substituent in the π-donor heteroatom on the kinetic and thermodynamic acidities of Fischer thiocarbene complexes

M. E. Zoloff Michoff, D. M. Andrada, A. M. Granados and R. H. de Rossi, New J. Chem., 2008, 32, 65
DOI: 10.1039/B709504J

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