The Dual Roles of Phenylenediamines : Using their Voltammetric Behavior to Measure the Hydrogen Donor and Acceptor Abilities of Alcohols in Acetonitrile

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

2 Scopus Citations
View graph of relations

Author(s)

  • Malcolm E. Tessensohn
  • Sihao Lim
  • Miechie
  • Yu Rong Koh
  • Richard D. Webster

Detail(s)

Original languageEnglish
Pages (from-to)3562-3569
Journal / PublicationChemPhysChem
Volume18
Issue number24
Online published28 Sep 2017
Publication statusPublished - 15 Dec 2017
Externally publishedYes

Abstract

Cyclic voltammetry experiments on 2,3,5,6-tetramethyl-1,4-phenylenediamine (P) in acetonitrile in the presence of varying concentrations of alcohols indicate that the oxidized forms of the compound (P.+ and P2+) interact with the alcohols through a hydrogen-bonding mechanism where P.+ and P2+ act as the hydrogen donor and the alcohols act as acceptors. However, the neutral form (P) largely acts as a hydrogen acceptor but only for strong hydrogen donors that do not undergo proton-transfer reactions with the phenylenediamine. These results were ascertained based on measuring the difference in potential of the two one-electron transfer reactions (ΔEP ox(1, 2)=|EP ox(1)EP ox(2)|) in the oxidative electrochemistry of P, which thereby allows a simple measure of relative hydrogen bonding strengths.

Research Area(s)

  • density functional theory, electrochemistry, oxidation, quinones, voltammetry

Citation Format(s)

The Dual Roles of Phenylenediamines : Using their Voltammetric Behavior to Measure the Hydrogen Donor and Acceptor Abilities of Alcohols in Acetonitrile. / Tessensohn, Malcolm E.; Lim, Sihao; Miechie; Koh, Yu Rong; Hirao, Hajime; Webster, Richard D.

In: ChemPhysChem, Vol. 18, No. 24, 15.12.2017, p. 3562-3569.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review