Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.

Issue 101, 2014
Previous Article Next Article

Reduction potential predictions of some aromatic nitrogen-containing molecules

Author affiliations


Accurate quantum chemical methods offer a reliable alternative to time-consuming experimental evaluations for obtaining a priori electrochemical knowledge of a large number of redox active molecules. In this contribution, quantum chemical calculations are performed to investigate the redox behavior of quinoxalines, a promising family of active materials for non-aqueous flow batteries, as a function of substituent group. The reduction potentials of 40 quinoxaline derivatives with a range of electron-donating and electron-withdrawing groups are computed. Calculations indicate the addition of electron-donating groups, particularly alkyl groups, can significantly lower the reduction potential albeit with a concomitant decrease in oxidative stability. A simple descriptor is derived for computing reduction potentials of quinoxaline derivatives from the LUMO energies of the neutral molecules without time-consuming free energy calculations. The relationship was validated for a broader set of aromatic nitrogen-containing molecules including pyrazine, phenazine, bipyridine, pyridine, pyrimidine, pyridazine, and quinoline, suggesting that it is a good starting point for large high-throughput computations to screen reduction windows of novel molecules.

Graphical abstract: Reduction potential predictions of some aromatic nitrogen-containing molecules

Back to tab navigation

Supplementary files

Article information

12 Aug 2014
17 Oct 2014
First published
20 Oct 2014

RSC Adv., 2014,4, 57442-57451
Article type
Author version available

Reduction potential predictions of some aromatic nitrogen-containing molecules

R. S. Assary, F. R. Brushett and L. A. Curtiss, RSC Adv., 2014, 4, 57442
DOI: 10.1039/C4RA08563A

Social activity

Search articles by author