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 polarized continuum model (SCI-PCM) with different dielectric constants (ε = 4.9, CHCI₃; ε = 32.63, CH₃OH; ε = 78.39, H₂O). 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.
Chemistry Department, Faculty of Science and Literature, Cumhuriyet University, 58140 Sivas, Turkey. dozbakir@cumhuriyet.edu.tr
Dilara Ozbakir
DO
Isin
Nihat
N
Karakus
D003198:Computer Simulation; D019281:Dimerization; D006860:Hydrogen Bonding; D008956:Models, Chemical; D008958:Models, Molecular; D011522:Protons; D012997:Solvents; D013816:Thermodynamics; D014334:Tropolone / Q000031:analogs & derivatives* / Q000737:chemistry
D011522:Protons; D012997:Solvents; C035995:7-hydroxytropolone; D014334:Tropolone