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Int. J. Mol. Sci. 2005, 6(1), 87-96; doi:10.3390/i6010087

Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Chloroformate

1
Department of Chemistry, Hanyang University, Ansan, Kyunggi-Do 425-791, Korea
2
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115-2862, USA
*
Authors to whom correspondence should be addressed.
Received: 30 November 2004 / Accepted: 10 December 2004 / Published: 31 January 2005
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Abstract

Application of the extended Grunwald-Winstein equation to solvolyses of n-propyl chloroformate in a variety of pure and binary solvents indicates an addition-elimination pathway in the majority of the solvents but an ionization pathway in the solvents of highest ionizing power and lowest nucleophilicity. For methanolysis, a solvent deuterium isotope effect of 2.17 is compatible with the incorporation of general-base catalysis into the substitution process. Activation parameters are consistent with the duality of mechanism. Very modest positive salt effects are observed on adding chloride or bromide salts to the ethanolysis.
Keywords: n-Propyl chloroformate; addition-elimination; ionization; solvent isotope effect; Grunwald-Winstein equation n-Propyl chloroformate; addition-elimination; ionization; solvent isotope effect; Grunwald-Winstein equation
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Kyong, J.B.; Won, H.; Kevill, D.N. Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Chloroformate. Int. J. Mol. Sci. 2005, 6, 87-96.

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