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


ÖZBAKIR IŞIN D. , KARAKUŞ N.

JOURNAL OF MOLECULAR MODELING, cilt.16, ss.1877-1882, 2010 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 16 Konu: 12
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1007/s00894-010-0674-z
  • Dergi Adı: JOURNAL OF MOLECULAR MODELING
  • Sayfa Sayıları: ss.1877-1882

Özet

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 (epsilon = 4.9, CHCI(3); epsilon = 32.63, CH(3)OH; epsilon = 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.