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Int. J. Mol. Sci. 2007, 8(4), 346-362; doi:10.3390/i8040346
Article

Correlations of the Specific Rates of Solvolysis of Aromatic Carbamoyl Chlorides, Chloroformates, Chlorothionoformates, and Chlorodithioformates Revisited

1,* , 2 and 2,*
Received: 22 March 2007 / Accepted: 24 April 2007 / Published: 30 April 2007
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Abstract

Additional specific rates of solvolysis are determined for phenyl chloroformate.These values are combined with literature values to give a total of 49 data points, which areused within simple and extended Grunwald-Winstein treatments. Literature values are alsobrought together to allow treatments in more solvents than previously for three N-aryl-N-methylcarbamoyl chlorides, phenyl chlorothionoformate, phenyl chlorodithioformate, andN,N-diphenylcarbamoyl chloride. For the last two listed, moderately strong evidence for ameaningful inclusion of a term governed by the aromatic ring parameter (I) was indicated.No evidence was found requiring inclusion of this parameter for ionization reactions withonly one aromatic ring on the nitrogen of carbamoyl chlorides or for the solvolyses of thechloroformate or chlorothionoformate proceeding by an addition-elimination (association-dissociation) mechanism.
Keywords: solvolysis; carbamoyl chlorides; chloroformates; chlorothionoformates; chlorodithioformates; Grunwald-Winstein equation; aromatic ring parameter (I). solvolysis; carbamoyl chlorides; chloroformates; chlorothionoformates; chlorodithioformates; Grunwald-Winstein equation; aromatic ring parameter (I).
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Kevill, D.N.; Koyoshi, F.; D’Souza, M.J. Correlations of the Specific Rates of Solvolysis of Aromatic Carbamoyl Chlorides, Chloroformates, Chlorothionoformates, and Chlorodithioformates Revisited. Int. J. Mol. Sci. 2007, 8, 346-362.

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