Parametrization of Substituents: Effects of Fluorine and Other Heteroatoms on OH,NH, and CH Acidities |
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Authors: | Manfred Schlosser |
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Abstract: | 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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Keywords: | Acidity Fluorine Gas-phase chemistry Metalations Substituent effects |
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