Theoretical characterization of SOME amides and esters DERIVATIVES of valproic acid |
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Authors: | Nieves C Comelli Patricio Fuentealba Eduardo A Castro Alicia H Jubert |
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Institution: | 1. INIFTA, Theoretical Chemistry Division, Suc. 4, C.C. 16, La Plata 1900, Buenos Aires, Argentina 2. Departamento de Física, Facultad de Ciencias, Universidad de Chile, Las Palmeras 3425, ?u?oa, 653, Santiago, Chile 3. Departamento de Química, Facultad de Ciencias Exactas, UNLP, CEQUINOR, Centro de Química Inorgánica (CONICET, UNLP), C. C. 962, 1900 La Plata. Facultad de Ingeniería, UNLP, 1 y 47, 1900, La Plata, Argentina
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Abstract: | The equilibrium structures, the planarity of the C(=O)X linkage and the nature of the chemical bond in the Y−C(=O)−XR1R2 where: Y= −CH−(CH2−CH2−CH3)2, X=N,O and R1, R2= H; alkyl and aryl groups and lone pair electrons (lp)] molecular fragment of derivates of Valproic acid (Vpa) with antiepileptic
activity were studied systematically by means of B3LYP calculations and topological analysis of the electron localization
function (ELF). The covariance parameter covΩi, Ωj] reveals a dominating delocalization effect between the lone pair V(O1), V(X) and the electron density of the H−C and H−X1 bonds resulting from the existence of not only non-conventional intramolecular hydrogen bonding patterns as C−H...O/N but
also a weak closed-shell stabilizing interaction type arising from a dihydrogen bonding as C−H...H−N, where H...H contacts
at a significantly shorter distance than twice the hydrogen atom van der Waals radius. The analyzed data derived from ELF
domains were found to be in agreement with the known features and properties of the hydrogen bonding interactions discussed
in this work. |
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