Computational Investigation of the Substituent Effect on the Intramolecular Proton Transfer Reaction of 3-Hydroxytropolone


Gul V., ÖZBAKIR IŞIN D.

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, vol.33, no.12, pp.1757-1767, 2014 (Peer-Reviewed Journal) identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 12
  • Publication Date: 2014
  • Journal Name: CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1757-1767

Abstract

The effects of substituent type and position on the proton transfer reaction of 3-hydroxytropolone (3-OHTRN) have been investigated theoretically by using density functional theory at the level of B3LYP/ 6-31+G** method. The influence of solvent on the proton transfer reactions of substituted 3-OHTRN has been examined using the self-consistent isodensity polarized continuum model (SCI-PCM) in water. As a result, while the proton transfer reaction is kinetically the easiest by substitution on position 3 of -NH2 group in the gas phase, it is kinetically the easiest by substitution on position 5 of the same group in water. In addition, these reactions are either kinetically or thermodynamically easier in the gas phase than that in water, except the reaction of structure with -NH2 group at position 6.