Computational study of the intramolecular proton transfer reactions of 3-hydroxytropolone (2,7-dihydroxycyclohepta-2,4,6-trien-1-one) and its dimers

The proton transfer reaction and dimerization processes of 3-hydroxytropolone (3-OHTRN) have been investigated using density functional theory (DFT) at the B3LYP/6–31+G** level. The influence of the solvent on the proton transfer reaction of 3-OHTRN was examined using the self-consistent isodensity...

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Bibliographic Details
Published in:Journal of molecular modeling 2010-12, Vol.16 (12), p.1877-1882
Main Authors: Isin, Dilara Özbakir, Karakus, Nihat
Format: Article
Language:English
Subjects:
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Computer Appl. in Life Sciences
Computer Applications in Chemistry
Computer Simulation
Dimerization
Hydrogen Bonding
Models, Chemical
Models, Molecular
Molecular Medicine
Original Paper
Protons
Solvents
Theoretical and Computational Chemistry
Thermodynamics
Tropolone - analogs & derivatives
Tropolone - chemistry
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Summary:The proton transfer reaction and dimerization processes of 3-hydroxytropolone (3-OHTRN) have been investigated using density functional theory (DFT) at the B3LYP/6–31+G** level. The influence of the solvent on the proton transfer reaction of 3-OHTRN was examined using the self-consistent isodensity polarized continuum model (SCI-PCM) with different dielectric constants (ε = 4.9, CHCI 3 ; ε = 32.63, CH 3 OH; ε = 78.39, H 2 O). The intramolecular proton transfer reaction occurs more readily in the gas phase than in solution. Results also show that the stability of 3-OHTRN dimers in the gas phase is directly affected by the hydrogen bond length in the dimer structure.
ISSN:1610-2940
0948-5023
DOI:10.1007/s00894-010-0674-z