Simultaneous effect of nitrogen, trifluoromethyl and dimethyl amino group on the radical trapping capacity of diphenylamine: a quantum chemical study

Authors

  • Thong Nguyen Minh The University of Danang, Campus in Kon Tum

DOI:

https://doi.org/10.15625/2525-2518/58/5/15021

Keywords:

Radical trapping antioxidant, bond dissociation enthalpies, ionization energy, potential energy surface, DFT

Abstract

In order to maximize the peroxyl radical trapping capacity of diphenynlamines, the substituents such as N, NMe2, and CF3 are suggested to add to their phenolic rings. The reasonable combination of these substituents at right position can reduce the bond strength of the N-H bond, but still keep the derivatives stable in air.

References

Ingold K. U.,Pratt D. A. - Advances in radical-trapping antioxidant chemistry in the 21st century: a kinetics and mechanisms perspective, Chemical reviews, 114(18) (2014) 9022-9046.

Valgimigli L.,Pratt D. A. - Maximizing the reactivity of phenolic and aminic radical-trapping antioxidants: just add nitrogen!, Accounts of chemical research, 48(4) (2015) 966-975.

Poliak P. V., Adam; Lukeš, Vladimír; Klein, Erik. - Substitution and torsional effects on the energetics of homolytic N–H bond cleavage in diphenylamines, Polym. Degrad. Stabil., 114 (2015) 37-44.

Chandra A. K., Nam P.-C., Nguyen M. T. - The S− H bond dissociation enthalpies and acidities of para and meta substituted thiophenols: a quantum chemical study, The Journal of Physical Chemistry A, 107(43) (2003) 9182-9188.

Thao P. T. T., Chon N. H., Vo V. Q., Thong N. M., Nam P. C. - Effect of Substituents on N-H bond Dissociation Enthalpies and Proton Affinities of Anions of Diphenylamine Derivatives: A DFT Study using B3P86 Functional, Hue University Journal of Science: Natural Science, 127(1B) (2018) 99-112.

Thong N. M., Quang D. T., Bui N. H. T., Dao D. Q., Nam P. C. - Antioxidant properties of xanthones extracted from the pericarp of Garcinia mangostana (Mangosteen): A theoretical study, Chemical Physics Letters, 625 (2015) 30-35.

Frisch M., Trucks G., Schlegel H., Scuseria G., Robb M., Cheeseman J., Scalmani G., Barone V., Mennucci B., Petersson G. - Gaussian 09, Revision A, Gaussian, Inc., Wallingford CT, (2009).

Dzib E., Cabellos J. L., Ortíz‐Chi F., Pan S., Galano A., Merino G. - Eyringpy: A program for computing rate constants in the gas phase and in solution, International Journal of Quantum Chemistry, 119(2) (2018) e25686.

Dzib E., Cabellos J. L., Ortiz-Chi F., Pan S., Galano A., Merino G. ( 2018), Eyringpy 1.0.2, Cinvestav, Mérida, Yucatán.

http://webbook.nist.gov/chemistry/ NIST Chemistry WebBook.

Galano A.,Alvarez‐Idaboy J. R. - A computational methodology for accurate predictions of rate constants in solution: Application to the assessment of primary antioxidant activity, J. Comput. Chem., 34(28) (2013) 2430-2445.

Downloads

Published

2020-10-16

Issue

Section

Materials