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Steric Effects and Steric Hindrance to Resonance in tert-Butylbenzoic Acids in the Gas Phase and in Solution

✍ Scribed by Jiří Kulhánek; Michèle Decouzon; Jean-François Gal; Pierre-Charles Maria; Pavel Fiedler; Pilar Jiménez; Maria-Victoria Roux; Otto Exner

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
258 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Substituent effects of the tert-butyl group in isomeric tert-acidity in the gas phase has been found for all isomers and attributed to a pole-induced dipole interaction in the anion butylbenzoic acids have been investigated on the basis of enthalpies of formation, gas-phase acidities, acidities in (polarizability effect); in the ortho isomer the steric inhibition of resonance is only responsible for a minor part of the methanol and in dimethyl sulfoxide, and the IR spectra in tetrachloromethane. In contrast to 2-methylbenzoic acid, observed effect. In solution, the electrostatic interaction is attenuated, but remains strong in the case of the ortho 2-tert-butylbenzoic acid must adopt a non-planar conformation, as is confirmed by its IR spectrum. Enhanced isomer.

substituent. [1,3] In acids with two ortho-methyl groups it is [a

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