Title

Proton transfer between carbon acids and methoxide: Studies in methanol, the gas phase and by Ab initio MO calculations

Document Type

Article

Publication Date

1-1-1998

Abstract

A detailed mechanism that features hydrogen-bonded carbanions as well as free carbanions is presented for hydrogen transfer between carbon acids and methoxide ion in methanol. This is refined for several compounds by measuring their gas phase acidities, ΔG kcal/mol: C H CH(CF ) [335.3]; p-C H CHClCF [337.4]; 9-phenylfluorene [335.6]; C F H [349.2]. Ab inilio molecular orbital calculations are reported to evaluate the stability of possible intermediates along the reaction pathway from 2-hydro-2-phenyl-perfluoropropane and methoxide ion to the carbanion and methanol. The intermediate, {C H C(CF ) } ·HOCH , is 6.8 kcal/mol more stable than the separated species, {C H C(CF ) } and CH3OH, and 43.2 kcal/rnol more stable than C H CH(CF ) and OCH . © WILEY-VCH Verlag GmbH, 1998. Acid 6 5 3 2 6 4 3 6 5 6 5 3 2 3 6 5 3 2 6 5 3 2 3 0 - - -

Publication Name

Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics

Volume Number

102

First Page

567

Last Page

572

Issue Number

3

DOI

10.1002/bbpc.19981020341

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