Citation: GÜL Vedat, IŞIN Dilara Özbakir. Computational Investigation of the Substituent Effect on the Intramolecular Proton Transfer Reaction of 3-Hydroxytropolone[J]. Chinese Journal of Structural Chemistry, ;2014, 33(12): 1757-1767. doi: 10.14102/j.cnki.0254-5861.2010-1628 shu

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

GÜL Vedat ,
IŞIN Dilara Özbakir ^,

1.
Chemistry Department, Faculty of Science, Cumhuriyet University 58140 Sivas, Turkey

Corresponding author: IŞIN Dilara Özbakir,
Received Date: 2 August 2014
Available Online: 20 October 2014

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.
- tropolone derivative,
- 3-hydroxytropolone,
- the proton transfer reaction,
- density functional theory
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