INIFTA   05425
INSTITUTO DE INVESTIGACIONES FISICO-QUIMICAS TEORICAS Y APLICADAS
Unidad Ejecutora - UE
artículos
Título:
Theoretical characterization of some amides and ester derivatives of valproic acid
Autor/es:
A. H. JUBERT; N. C. COMMELLI; P. FUENTEALBA; E. A. CASTRO
Revista:
JOURNAL OF MOLECULAR MODELING - (Print)
Editorial:
SPRINGER
Referencias:
Lugar: Heidelberg; Año: 2009 vol. 16 p. 343 - 359
ISSN:
1610-2940
Resumen:
The equilibrium structures, the planarity of the C 12 (=O)X linkage and the nature of the chemical bond in the(=O)X linkage and the nature of the chemical bond in the 13 Y−C(=O)−XR1R2 [where: Y= −CH−(CH2−CH2−CH3)2,Y−C(=O)−XR1R2 [where: Y= −CH−(CH2−CH2−CH3)2, 14 X=N,O and R1, R2= H; alkyl and aryl groups and loneX=N,O and R1, R2= H; alkyl and aryl groups and lone 15 pair electrons (lp)] molecular fragment of derivates ofpair electrons (lp)] molecular fragment of derivates of 16 Valproic acid (Vpa) with antiepileptic activity were studiedValproic acid (Vpa) with antiepileptic activity were studied 17 systematically by means of B3LYP calculations andsystematically by means of B3LYP calculations and 18 topological analysis of the electron localization functiontopological analysis of the electron localization function 19 (ELF). The covariance parameter cov[Ùi, Ùj] reveals a(ELF). The covariance parameter cov[Ùi, Ùj] reveals a 20 dominating delocalization effect between the lone pair Vdominating delocalization effect between the lone pair V 21 (O1), V(X) and the electron density of the H−C and H−X1(O1), V(X) and the electron density of the H−C and H−X1 22 bonds resulting from the existence of not only non-bonds resulting from the existence of not only non- 23 conventional intramolecular hydrogen bonding patterns asconventional intramolecular hydrogen bonding patterns as 24 C−H...O/N but also a weak closed-shell stabilizing interac-C−H...O/N but also a weak closed-shell stabilizing interac- 25 tion type arising from a dihydrogen bonding as C−H...H−N,tion type arising from a dihydrogen bonding as C−H...H−N, 26 where H...H contacts at a significantly shorter distance thanwhere H...H contacts at a significantly shorter distance than 27 twice the hydrogen atom van der Waals radius. The analyzedtwice the hydrogen atom van der Waals radius. The analyzed 28 data derived from ELF domains were found to be indata derived from ELF domains were found to be in 29 agreement with the known features and properties of theagreement with the known features and properties of the 30 hydrogen bonding interactions discussed in this work.hydrogen bonding interactions discussed in this work.