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Hydrogen bond structural group constants.

M H Abraham¹, J A Platts

¹Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, U.K. m.h.abraham@ucl.ac.uk

The Journal of Organic Chemistry

|May 12, 2001

Summary

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This study quantifies functional group hydrogen bonding abilities using equilibrium and overall constants. Constants derived from overall hydrogen bond data are more effective for analyzing chemical and biological properties.

Area of Science:

Chemistry
Biochemistry
Physical Chemistry

Background:

Functional groups' roles in hydrogen bonding are crucial for understanding molecular interactions.
Quantifying hydrogen bond acidity and basicity is essential for predicting chemical and biological behavior.

Purpose of the Study:

To determine and compare methods for obtaining functional group hydrogen bonding constants.
To assess the utility of different hydrogen bonding constants in analyzing physicochemical and biochemical properties.

Main Methods:

Utilizing equilibrium constants for 1:1 hydrogen bonding.
Calculating overall hydrogen bond constants.
Comparing the predictive power of constants derived from both methods.

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Main Results:

Established methods for deriving structural constants for hydrogen bonding from functional groups.
Reported extensive lists of these functional group constants.
Demonstrated that constants from overall hydrogen bond data are superior for property analysis.

Conclusions:

Overall hydrogen bond constants provide a more robust measure of functional group hydrogen bonding.
These constants are valuable tools for analyzing a wide range of physicochemical and biochemical properties.
The findings offer a refined approach to structure-property relationship studies.