Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents.

NIEVES C. COMELLI ; ROSANA M. LOBAYAN; ALICIA H. JUBERT; EDUARDO A. CASTRO

JOURNAL OF PHYSICAL CHEMISTRY A

AMER CHEMICAL SOC

Lugar: 1155 Sixteenth Street N.W., Washington, DC 20036; Año: 2011 vol. 115 p. 1686 - 1700

1089-5639

The conformational and electronic characteristics of the polar O9=C8-X10 moiety in the anticonvulsant   Valproic acid (Vpa) drug and some of their amides and esters derivatives are analyzed at B3LYP level using the 6-31+G(d,p) and 6-311++G(d,p) 6d,10f basis sets. Exploring the delocalization of the electron density of the O9=C8-X10 moiety by means of ELF, NBO and AIM calculations, we found that the bending away from co-planarity of the atoms in O9=C8-X10 are accompanied by a three dimensional arrangement of donor and acceptor proton units closing nearly planar pseudo-rings of four, five and six members arising from stabilizing interactions around the O9=C8-X10 backbone. From the structure-property relationship analysis we explain the origin of the change in the structural    parameters and atomic charges in the polar moiety.