Electronic structure and acid–base properties of Kojic acid and its dimers. A DFT and quantum topology study

ABSTRACT

Kojic acid is a polyfunctional heterocyclic compound, with several important reaction centres; it has a wide range of applications in the cosmetic, medicine, food, agriculture and chemical industries. The present study aims at better insight into its electronic structure and bonding characteristics. Thus, density functional theory at the M06-2x /6-311++G^** level of theory is used to investigate its ground state electronic and acid–base properties. Protonation and deprotonation enthalpies are computed and analysed. The ability of Kojic acid to form both water complexes and dimers is explored. Several different complexes and dimer structures were examined. Natural bond order and quantum topology features of the charge density were analysed. The origin of the stability of the studied complexes and dimer structures can be traced to hydrogen bonding, π-conjugative and non-covalent dispersive interactions.

KEYWORDS:

• Kojic acid
• electronic structure
• DFT
• acid–base properties
• dimers

Acknowledgments

This project was funded by Deanship of Scientific Research (DSR) of King Abdulaziz University, Jeddah under grant no. 455-130-1437G. The authors ,therfore, acknowledge with thanks DSR support for Scientific Research. The computational work described in this paper were supported by King Abdulaziz University High performane computing Center ( AZIZ supercomputer , http://hpc.kau.edu.sa).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

Deanship of Scientific Research (DSR) and King Abdulaziz University, Jeddah [grant number 455-130-1437-G].