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Issue 8, 2003
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The effect of intramolecular interactions on hydrogen bond acidity

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Abstract

DFT calculations on a range of molecules containing intramolecular hydrogen bonds are reported, with a view to establishing how intramolecular hydrogen bonding affects their intermolecular interactions. It is shown that properties such as the energy of the intramolecular H-bond are unrelated to the ability to form external H-bonds. Conversely, several properties of complexes with a reference base correlate well with an experimental scale of H-bond acidity, and accurate predictive models are determined. A more detailed study, using electrostatic and overlap properties of complexes with a reference base, is used to predict the location, as well as strength, of hydrogen bond acidity. The effects of intramolecular hydrogen bonding on acidity can be seen not just on O–H and N–H, where acidity is greatly reduced, but also on certain C–H groups, which in some cases become the primary source of acidity.

Graphical abstract: The effect of intramolecular interactions on hydrogen bond acidity

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Supplementary files

Article information


Submitted
21 Jan 2003
Accepted
10 Mar 2003
First published
26 Mar 2003

Org. Biomol. Chem., 2003,1, 1419-1424
Article type
Paper

The effect of intramolecular interactions on hydrogen bond acidity

F. T. T. Huque and J. A. Platts, Org. Biomol. Chem., 2003, 1, 1419
DOI: 10.1039/B300598D

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