ISSN:
0894-3230
Keywords:
electrostatic interaction energies
;
dipole moments
;
hydrogen bond basicity
;
nitriles
;
ammonia
;
amines
;
Chemistry
;
Theoretical, Physical and Computational Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Experimental molecular dipole moments and related bond and mesomeric moments were used to calculate the energy WA of the electrostatic attraction between N-containing acceptor molecules and the attracted H atom, the hydrogen bond N···H being along the symmetry axis of N. A satisfactory but family-dependent linear relationship is obtained between WA and the hydrogen-bond basicity scale pKHB in 36 nitriles, ammonia and 11 primary and tertiary amines. The energy WR of the electrostatic repulsion between the acceptor molecule and the moment of the created N⇐H bond is calculated in a similar way. WR is strongly family dependent but the total energy WA+WR is closely correlated with pKHB in the 48 derivatives studied without a significant family dependence. This analysis clarifies and completes a previous similar study and confirms that dipolmetry and classical electrostatic calculations can be a useful and practicable method for the prediction of the strength of hydrogen bonding. © 1997 by John Wiley & Sons, Ltd.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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