Abstract

M. Chandra Sekhar^1*, A. Venkatesulu², T.Madhu Mohan³, M. Gowrisankar⁴

DOI : http://dx.doi.org/10.13005/ojc/310233

In this study complexes formed via hydrogen bond interactions between 2-chloroaniline with carboxylic acids have been studied by density functional theory (DFT) using 6-311++G (d, p) atomic basis set. The relevant geometries, energies, and IR characteristics of hydrogen bonds have been systematically investigated. Thirteen 2-chloroaniline - carboxylic acid complexes were found involving N-H…N, H-O…H, N-H---O, O-H…N hydrogen bonds. The quantum theory of atoms in molecule (AIM) and natural bond orbital (NBO) have also been applied to understand the nature and strength of the hydrogen bonding interactions in complexes. Good correlations have been established between hydrogen bond lengths versus AIM topological parameter like electron density ( ) and its Laplacian ( ) at the bond critical points. The strength of the hydrogen bond between 2-chloroaniline – carboxylic acid complexes has been explored by calculation of stabilization energy (E (2)) between proton acceptor and proton donor under NBO analysis.

carboxylic acids; hydrogen bond; atoms in molecule (AIM); natural bond orbital (NBO)

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