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Intermolecular hydrogen bonds in hetero-complexes of biologically active aromatic ligands: Monte Carlo simulations results

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Abstract

We report results of the Monte Carlo simulations of systems containing heterodimers of biological active ligands and water molecules. The study was designed to identify the possible formation of intermolecular hydrogen bonds in such systems in order to investigate the molecular mechanisms of hetero-association of aromatic ligands in aqueous solution. The geometry optimization and the calculation of the atomic charges of free ligands were carried out at DFT/B3LYP level of theory. Monte Carlo simulations with Metropolis algorithm were used to determine the low energy conformations of heterodimers in water clusters. The analysis of the Monte Carlo simulation results allows us to describe in detail the hydration properties of all investigated heterodimers and to determine the intermolecular hydrogen bonds between the functional donor–acceptor groups for some of hetero-associates under investigation. In the case of heterodimers without intermolecular hydrogen bonds, the additional stabilization of these hetero-complexes can be explained by the formation the water bridges between donor and acceptor groups of the ligands.

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Acknowledgments

The study was supported in part by the SCST Programme of Implementation and Usage of GRID technologies for 2009–2013 years. The calculations were done using clusters of Institute for Scintillation Materials NASU and Institute for Radiophysics and Electronics NASU. The research which results are presented in the paper was fulfilled due to the collaboration with Prof. O. Shishkin. The authors also thank Roman Zubatyuk (ISMA NASU) and Darina Pesina (IRE NASU) for their assistance in quantum-chemical calculations.

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  1. Usikov Institute for Radiophysics and Electronics, National Academy of Sciences of Ukraine, 12 Ak. Proskura Str., Kharkiv, 61085, Ukraine

    Julia N. Blyzniuk, Michail A. Semenov & Anna Victorovna Shestopalova

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  1. Julia N. Blyzniuk
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  2. Michail A. Semenov
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  3. Anna Victorovna Shestopalova
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Correspondence to Anna Victorovna Shestopalova.

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Blyzniuk, J.N., Semenov, M.A. & Shestopalova, A.V. Intermolecular hydrogen bonds in hetero-complexes of biologically active aromatic ligands: Monte Carlo simulations results. Struct Chem 27, 77–89 (2016). https://doi.org/10.1007/s11224-015-0696-3

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