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Kinetics and Dynamics pp 35–75Cite as

From the Gas Phase to a Lipid Membrane Environment: DFT and MD Simulations of Structure and Dynamics of Hydrogen-Bonded Solvates of Bifunctional Heteroazaaromatic Compounds

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Part of the book series: Challenges and Advances in Computational Chemistry and Physics ((COCH,volume 12))

Abstract

We present a review of our recent developments in computational modeling of hydrogen-bonding-induced phenomena in a series of biologically relevant bifunctional proton donor–acceptor heteroazaaromatic compounds. Different types of hydrogen-bonded solvates, in which water or alcohol molecules form a bridge connecting the proton donor (pyrrole NH group) and the acceptor (pyridine or quinoline nitrogen) atoms of bifunctional solutes, are explored by combining density functional theory (DFT) and molecular dynamics (MD) simulation approaches. Structure and dynamics of multiple hydrogen-bonded solute-solvent complexes are studied starting from isolated complexes in the gas phase, elucidating their solvation dynamics in solutions and, finally, in a heterogeneous environment of a lipid bilayer. Our results indicate that the structure, stoichiometry and hydrogen bond strength in such solvates are tuned by local topologies of the hydrogen-bonding sites of a bifunctional proton donor–acceptor molecule. A role of such solvates in hydrogen-bond-dependent photophysics and in controlling excited-state behavior of heteroazaaromatic compounds is discussed.

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Acknowledgements

JW acknowledges support by the grant N N204 3329 33 from the Polish Ministry of Science and Higher Education. The experiments referred to in this work were based on a long-time collaboration with the groups of Prof. R.P. Thummel (University of Houston) and Prof. B. Brutschy (University of Frankfurt).

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Authors and Affiliations

  1. Institute of Chemistry, V.N. Karazin Kharkov National University, 4 Svobody Sq., 61077, Kharkov, Ukraine

    Alexander Kyrychenko

  2. Institute of Physical Chemistry, Polish Academy of Science, Kasprzaka 44, 01-224, Warsaw, Poland

    Jacek Waluk

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  1. Alexander Kyrychenko
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  2. Jacek Waluk
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Correspondence to Jacek Waluk .

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Editors and Affiliations

  1. Inst. Applied Radiation Chemistry, Dept. Chemistry, Technical University of Lodz, Zeromskiego 116, Lodz, 90-924, Poland

    Piotr Paneth

  2. Inst. Applied Radiation Chemistry, Dept. Chemistry, Technical University of Lodz, Zeromskiego 116, Lodz, 90-924, Poland

    Agnieszka Dybala-Defratyka

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Kyrychenko, A., Waluk, J. (2010). From the Gas Phase to a Lipid Membrane Environment: DFT and MD Simulations of Structure and Dynamics of Hydrogen-Bonded Solvates of Bifunctional Heteroazaaromatic Compounds. In: Paneth, P., Dybala-Defratyka, A. (eds) Kinetics and Dynamics. Challenges and Advances in Computational Chemistry and Physics, vol 12. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3034-4_2

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