Understanding hydrogen bonding of hydroxamic acids with some amino acid side chain model molecules |
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Authors: | Damanjit kaur Ruchi Kohli |
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Institution: | (1) Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, India |
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Abstract: | The hydrogen-bonding abilities of a few amino acid side chains have been studied through aggregation of methylamine, methanol,
and acetic acid (as model molecules) with formo- and thioformo- hydroxamic acids using ab initio calculations. Forty six aggregates
representing all possible H-bond interactions between these amino acid side chain groups and two most stable keto and enol
tautomeric forms of both hydroxamic acids have been optimized. Although participation of conventional H-bond donors and acceptors
leads to significant stabilization energies, yet C–H···O, C–H···N, S–H···O, and S–H···N etc. unconventional H-bonds also contribute
to stabilize interactions in many aggregates. Strength of H-bonds of the molecules with formo- and thioformo- hydroxamic acid
studied follows the order acetic acid > methylamine > methanol. A comparative study of atomic charges and orbital interactions
employing NBO analysis has been carried out to explore the role of bond polarizations, charge transfer, and electron delocalizations
as contributors to stabilization energy. |
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Keywords: | |
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