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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The authors are highly thankful to Council of Scientific and Industrial Research (CSIR), New Delhi for financial assistance.
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Below is the link to the electronic supplementary material. Supplementary data of the paper can be obtained from journal website. Data include Tables (S1–S15) incorporating electron delocalizations, atomic charges, and geometrical parameters of aggregates of both the HAs with MeNH2, MeOH, and AcOH.
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kaur, D., Kohli, R. Understanding hydrogen bonding of hydroxamic acids with some amino acid side chain model molecules. Struct Chem 23, 161–173 (2012). https://doi.org/10.1007/s11224-011-9840-x
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DOI: https://doi.org/10.1007/s11224-011-9840-x