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

✍ Scribed by Manfred Schlosser

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 343 KB
Volume: 37
Category: Article
ISSN: 0044-8249
DOI: 10.1002/(sici)1521-3773(19980619)37:11<1496::aid-anie1496>3.0.co;2-u

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✦ Synopsis

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.

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