Effect of solvation on ion binding to imidazole and methylimidazole

Sharma, Bhaskar ; Rao, J. Srinivasa ; Sastry, G. Narahari (2011) Effect of solvation on ion binding to imidazole and methylimidazole The Journal of Physical Chemistry A, 115 (10). pp. 1971-1984. ISSN 1089-5639

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jp1120492

Related URL: http://dx.doi.org/10.1021/jp1120492

Abstract

Quantum chemical [MP2(FULL)/6-311++G-(d,p)] calculations are done on the binding of hydrated Li+, Na+, K+, Mg2+, Cu+, and Zn2+ metal ions with biologically relevant heteroaromatics such as imidazole and methylimidazole. The computed interaction energies are found to be in good agreement with the available experimental data. The effect of hydration on hydrogen bonding has been studied in detail and it shows that the hydrogen bond strength between H2O···H−N(1) substantially increases in the presence of metal ions. The present study quantifies the cooperativity between M···imidazole (M = Li+, Na+, K+, Mg2+, Cu+, and Zn2+) and N(1)−H···OH2 interactions. Topological atoms in molecules (AIM) analysis and charge analysis support the variation in hydrogen-bonding strength and the variation in M···imidazole binding strength. Effect of hydration on N(1)−H stretching frequency is studied, and it shows a clear shift in the stretching frequency after sequential hydration of metal ion as well as the N(1) of imidazole. The present study provides a detailed account on the biologically important M−histidine motif interaction with metal ions, where histidine is modeled by imidazole and methylimidazole.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:108277
Deposited On:28 Jul 2017 04:51
Last Modified:28 Jul 2017 04:51

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