Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities

Fluorine, the heterosubstituent par excellence, which can have a stronger impact on the reactivity in its vicinity than any other element, may serve as a crucial test of any model of the origin and transmission of electronic effects. To what extent fluoro substituents in organic compounds (A−H) incr...

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Veröffentlicht in:Angewandte Chemie International Edition 1998-06, Vol.37 (11), p.1496-1513
1. Verfasser: Schlosser, Manfred
Format: Artikel
Sprache:eng
Schlagworte:
Acidity
Fluorine
Gas-phase chemistry
Metalations
Substituent effects
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description Fluorine, the heterosubstituent par excellence, which can have a stronger impact on the reactivity in its vicinity than any other element, may serve as a crucial test of any model of the origin and transmission of electronic effects. To what extent fluoro substituents in organic compounds (A−H) increase their kinetic proton mobility (H/D and H/metal (M) exchange) and thermodynamic acidity in aqueous media and in the gas phase (see below) depends on many factors such as induction, resonance, polarization, hyperconjugation, and dipolar interactions.
doi_str_mv 10.1002/(SICI)1521-3773(19980619)37:11<1496::AID-ANIE1496>3.0.CO;2-U
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subjects Acidity
Fluorine
Gas-phase chemistry
Metalations
Substituent effects
title Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH, NH, and CH Acidities
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