info:eu-repo/semantics/article
Solvent and substituent effects on the conformational equilibria and intramolecular hydrogen bonding of 4-substituted-2-hydroxybenzaldehydes
Fecha
2007-04-02Registro en:
Blanco, Sonia Encarnacion; Ferretti, Ferdinando Hector; Solvent and substituent effects on the conformational equilibria and intramolecular hydrogen bonding of 4-substituted-2-hydroxybenzaldehydes; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 48; 14; 2-4-2007; 2577-2581
0040-4039
CONICET Digital
CONICET
Autor
Blanco, Sonia Encarnacion
Ferretti, Ferdinando Hector
Resumen
By applying the B3LYP/6-31G(d) method with the SCIPCM model on seven 4X substituted 2-hydroxybenzaldehydes, some structural characteristics related with their conformational equilibria and intramolecular hydrogen bonds have been clarified. The compounds are almost completely under the planar conformation characterized by a strong intramolecular hydrogen bond, which decreases in those solvents that possess a higher hydrogen bond donating capability and polarity. The substituents exert a marked influence on the conformational equilibrium constants and the strength of the IHB. Moreover, the excellent Hammett-type equations obtained support the proposed conformational reactions to quantify the IHB in the o-hydroxybenzaldehydes studied.