THEORETICAL ANALYSIS OF THE STRUCTURE OF CHIRAL JASMONIC ACID

Year 2020, Volume: 21 , 55 - 62, 27.11.2020

Nihal Kuş

https://doi.org/10.18038/estubtda.820129

Abstract

Jasmonic acid, also known as jasmonates, (JA), a molecule formed by the oxygenation of fatty acids, is an organic compound and is found in many plants, especially jasmine. The conformation of this compound is found according to the location in the chiral centers. In this study, the molecular structure of JA (labeled C-4 and C-5 in this study) which has two chiral centers was investigated by DFT and TD-DFT methods. These structures have been found to have RR, RS and SS configurations relative to their chiral centers. Each configuration has cis and trans conformations depending on the orientation of the chain groups attached to the five atom ring. The minimum energies of each conformation were calculated with DFT/B3LYP/6-311++G(d,p) method and the structures of their stable form were drawn. JA_RR_trans conformer was found most stable than the other conformers. Excited state energies were calculated using TD-DFT calculations and also HOMO-LUMO energy gaps were found for all chiral conformers.

Keywords

Jasmonic acid, DFT/ TD-DFT, B3LYP, HOMO-LUMO energy

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