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Please use this identifier to cite or link to this item: https://dspace.ffh.bg.ac.rs/handle/123456789/290
Title: Elucidating Solvent Effects on Strong Intramolecular Hydrogen Bond: DFT-MD Study of Dibenzoylmethane in Methanol Solution
Authors: Milovanović, Branislav 
Stanković, Ivana M
Petković, Milena 
Etinski, Mihajlo 
Keywords: density functional theory;hydrogen bond;molecular dynamics;proton transfer;solvation
Issue Date: 5-Nov-2019
Journal: Chemphyschem : a European journal of chemical physics and physical chemistry
Abstract: 
The dynamic aspect of solvation plays a crucial role in determining properties of strong intramolecular hydrogen bonds since solvent fluctuations modify instantaneous hydrogen-bonded proton transfer barriers. Previous studies pointed out that solvent-solute interactions in the first solvation shell govern the position of the proton but the ability of the electric field due to other solvent molecules to localize the proton remains an important issue. In this work, we examine the structure of the O-H⋅⋅⋅O intramolecular hydrogen bond of dibenzoylmethane in methanol solution by employing density functional theory-based molecular dynamics and quantum chemical calculations. Our computations showed that homogeneous electric fields with intensities corresponding to those found in polar solvents are able to considerably alter the proton transfer barrier height in the gas phase. In methanol solution, the proton position is correlated with the difference in electrostatic potentials on the oxygen atoms of dibenzoylmethane even when dibenzoylmethane-methanol hydrogen bonding is lacking. On a timescale of our simulation, the hydrogen bonding and solvent electrostatics tend to localize the proton on different oxygen atoms. These findings provide an insight into the importance of the solvent electric field on the structure of a strong intramolecular hydrogen bond.
URI: https://dspace.ffh.bg.ac.rs/handle/123456789/290
ISSN: 1439-4235
DOI: 10.1002/cphc.201900704
Appears in Collections:Journal Article

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University of Belgrade
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University of Belgrade Faculty of Physical Chemistry