ELECTROSTATIC INTERACTION ENERGIES FROM DIPOLE MOMENTS IN NITRILES, AMMONIA AND AMINES. CORRELATIONS WITH HYDROGEN BOND BASICITY
✍ Scribed by Marine Hérail; Eugène Megnassan; Alain Proutière
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 183 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0894-3230
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✦ Synopsis
Experimental molecular dipole moments and related bond and mesomeric moments were used to calculate the energy W A 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 W A and the hydrogen-bond basicity scale pK HB in 36 nitriles, ammonia and 11 primary and tertiary amines. The energy W R of the electrostatic repulsion between the acceptor molecule and the moment of the created N←H bond is calculated in a similar way. W R is strongly family dependent but the total energy W A + W R is closely correlated with pK HB 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.