Theoretical characterization of SOME amides and esters DERIVATIVES of valproic acid
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Comelli, Nieves C.
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Theoretical characterization of SOME amides and esters DERIVATIVES of valproic acid
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 cov[Ωi, 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 nonconventional
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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J Mol Model (2010) 16:343–359
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