Abstract
The work verifies the application of a “resonance model” in description of the structure of tautomers in the so-called resonance-assisted hydrogen bonds. The results of B3LYP/6-31G + G(d,p) calculations are presented for N-methyl-2-hydroxy benzylidene amine and its 2,- and 2,4-chloroderivatives (Schiff bases) as well as for related Mannich bases. The influence of surrounding permittivity and the phenol acidity on the structure is discussed. It is demonstrated that enhancement of both the factors leads to the increase of the content of keto resonance forms in Mannich bases. In the case of Schiff bases, a decrease of the content of such forms with surrounding permittivity increase has been found. The differences in dipole moments of particular forms explain such tendencies.
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