NDLI: Correlation of the rates of solvolysis of i-butyl fluoroformate and a consideration of leaving-group effects (2011).

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Correlation of the rates of solvolysis of i-butyl fluoroformate and a consideration of leaving-group effects (2011).

Content Provider	CiteSeerX
Author	Lee, Yelin Park, Kyoung-Ho Seong, Mi Hye Kyong, Jin Burm Kevill, Dennis N.
Abstract	Abstract: The specific rates of solvolysis of isobutyl fluoroformate (1) have been measured at 40.0 °C in 22 pure and binary solvents. These results correlated well with the extended Grunwald-Winstein (G-W) equation, which incorporated the NT solvent nucleophilicity scale and the YCl solvent ionizing power scale. The sensitivities (l and m-values) to changes in solvent nucleophilicity and solvent ionizing power, and the kF/kCl values are very similar to those observed previously for solvolyses of n-octyl fluoroformate, consistent with the additional step of an addition-elimination pathway being rate-determining. The solvent deuterium isotope effect value (kMeOH/kMeOD) for methanolysis of 1 was determined, and for solvolyses in ethanol, methanol, 80 % ethanol, and 70 % TFE, the values of the enthalpy and the entropy of activation for the solvolysis of 1 were also determined. The results are compared with those reported earlier for isobutyl chloroformate (2) and other alkyl haloformate esters and mechanistic conclusions are drawn. Keywords: i-butyl fluoroformate; Grunwald-Winstein equation; leaving group effect; addition-elimination; solvolysisInt. J. Mol. Sci. 2011, 12 7807 1.
File Format	PDF
Publisher Date	2011-01-01
Access Restriction	Open
Subject Keyword	I-butyl Fluoroformate Leaving-group Effect Alkyl Haloformate Ester Additional Step Ycl Solvent N-octyl Fluoroformate Nt Solvent Nucleophilicity Scale Addition-elimination Pathway Kf Kcl Value Solvent Nucleophilicity Isobutyl Chloroformate Specific Rate Binary Solvent Solvent Deuterium Isotope Effect Value Mechanistic Conclusion Power Scale Group Effect Isobutyl Fluoroformate Grunwald-winstein Equation Extended Grunwald-winstein
Content Type	Text
Resource Type	Article

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