New Quantum Chemical Method for Assessing the Relative Activity of Antioxidants

A new method for evaluating the antioxidant activity of organic compounds based on quantum chemical calculations of their electronic structure using the DFT B3LYP/6-31G (d, p) method has been proposed. The geometric parameters of antioxidant molecules were optimized and the reactivity indices were determined from the energy values of the highest occupied and the lowest unoccupied molecular orbitals: absolute electronegativity; electronic chemical potential; absolute "chemical hardness". The found indicators allow us to quantify the antioxidant activity by building their dependence on the energy of the lower vacant molecular orbitals. The correlation of the obtained parameters with the standard, such as trolox, allows determining the relative antioxidant activity of the test substance

References

[1] Zefirov N.S., Palyulin V.A. Fragmental approach in QSPR. J. Chem. Inf. Comput. Sci., 2002, vol. 42, no. 5, pp. 1112--1122. DOI: 10.1021/ci020010e

[2] Lazareva N.V. O kolichestvennoy svyazi mezhdu strukturoy organicheskikh soedineniy i ikh biologicheskoy aktivnostyu [About quantitative relationship between the structure of organic compounds and their biological activity.]. Istoriya khimii: oblast nauki i uchebnaya distsiplina [History of Chemistry: Field of Science and Academic Discipline]. Moscow, MSU Publ., 2001, pp. 60–81 (in Russ.).

[3] Khasanov V.V., Ryzhova G.L., Maltseva E.V. Methods of the antioxidant investigations. Khimiya rastitelnogo syrya [Chemistry of Plant Raw Material], 2004, no. 3, pp. 63–75 (in Russ.).

[4] Perevozkina M.G. Testirovanie antioksidantnoy aktivnosti polifunktsionalnykh soedineniy kineticheskimi metodami [Testing antioxidant activity of polyfunctional compounds by kinetic methods]. Novosibirsk, SibAK Publ., 2014.

[5] Masek A., Chrzescijanska E., Latos M., et al. Antioxidant and antiradical properties of green tea extract compounds. Int. J. Electrochem. Sci., 2017, no. 12, pp. 6600–6610.

[6] Ilyasov I.R., Beloborodov V.L., Tyukavkina N.A. The induction period of formation of ABTS

[7] Alekseev A.V., Proskurnina E.V., Vladimirov Yu.A. Determination of antioxidants by sensitized chemiluminescence using 2,22,2-azo-bis(2-amidinopropane). Moscow Univ. Chem. Bull., 2012, vol. 67, iss. 3, pp. 127–132. DOI:https://doi.org/10.3103/S0027131412030029

[8] Granovsky A.A. Introduction to the Firefly. Available at: http://classic.chem.msu.su/gran/gamess/index.html (accessed: 15.08.2018).

[9] Shubin L. Dynamic behavior of chemical reactivity indices in density functional theory: a Bohn --- Oppenheimer quantum molecular dynamics study. J. Chem. Sci., 2005, vol. 117, iss. 5, pp. 477–483. DOI: https://doi.org/10.1007/BF02708352

[10] Pearson R.G. Absolute electronegativity and hardness correlated with molecular orbital theory. PNAS, 1986, vol. 83, no. 22, pp. 8440–8441. DOI: https://doi.org/10.1073/pnas.83.22.8440