Detailed investigations of electronic effects taking place within the molecular system of o-hydroxy Schiff bases have been performed. The analysis of geometry, local and global aromaticity, selected AIM-based parameters, and finally, ð-electron currents induced in the systems under consideration have been performedon the basis of quantum chemical calculations at the B3LYP/6-311+G** level of theory. The relation between localization/delocalization of ð-electrons within the whole system has been described. It has been shown that the character of the bond which is common to the phenylic ring and the quasi-ring formed as a result of H-bond formation has a crucial impact on the strength of H-bonding. The strongest H-bonds can be observed for the systems in which the sequence of formally single and double bonds within the H-bridged quasi-ring enable a ð-electronic coupling. These observations indicate that ð-electron effects play a fundamental role in the stabilization of the hydrogen bridge within o-hydroxy Schiff bases.Analysis of ð-ring currents induced by a magnetic field perpendicular to the molecular plane of selected analyzed systems confirms these conclusions.

Relation between pi-electron localization/delocalization and H-bond strength in derivatives of o-hydroxy Schiff bases / TADEUSZ M., KRYGOWSKI; JOANNA E., ZACHARA HOREGLAD; MARCIN, PALUSIAK; STEFANO, PELLONI; LAZZERETTI, Paolo. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 73:(2008), pp. 2138-2145.

Relation between pi-electron localization/delocalization and H-bond strength in derivatives of o-hydroxy Schiff bases

LAZZERETTI, Paolo
2008-01-01

Abstract

Detailed investigations of electronic effects taking place within the molecular system of o-hydroxy Schiff bases have been performed. The analysis of geometry, local and global aromaticity, selected AIM-based parameters, and finally, ð-electron currents induced in the systems under consideration have been performedon the basis of quantum chemical calculations at the B3LYP/6-311+G** level of theory. The relation between localization/delocalization of ð-electrons within the whole system has been described. It has been shown that the character of the bond which is common to the phenylic ring and the quasi-ring formed as a result of H-bond formation has a crucial impact on the strength of H-bonding. The strongest H-bonds can be observed for the systems in which the sequence of formally single and double bonds within the H-bridged quasi-ring enable a ð-electronic coupling. These observations indicate that ð-electron effects play a fundamental role in the stabilization of the hydrogen bridge within o-hydroxy Schiff bases.Analysis of ð-ring currents induced by a magnetic field perpendicular to the molecular plane of selected analyzed systems confirms these conclusions.
73
2138
2145
Relation between pi-electron localization/delocalization and H-bond strength in derivatives of o-hydroxy Schiff bases / TADEUSZ M., KRYGOWSKI; JOANNA E., ZACHARA HOREGLAD; MARCIN, PALUSIAK; STEFANO, PELLONI; LAZZERETTI, Paolo. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 73:(2008), pp. 2138-2145.
TADEUSZ M., KRYGOWSKI; JOANNA E., ZACHARA HOREGLAD; MARCIN, PALUSIAK; STEFANO, PELLONI; LAZZERETTI, Paolo
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/421590
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