Measuring the relative hydrogen-bonding strengths of alcohols in aprotic organic solvents

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

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Author(s)

  • Malcolm E. Tessensohn
  • Melvyn Lee
  • Hajime Hirao
  • Richard D. Webster

Detail(s)

Original languageEnglish
Pages (from-to)160-168
Journal / PublicationChemPhysChem
Volume16
Issue number1
Publication statusPublished - 2 Jan 2015
Externally publishedYes

Abstract

Voltammetric experiments with 9,10-anthraquinone and 1,4-benzoquinone performed under controlled moisture conditions indicate that the hydrogen-bond strengths of alcohols in aprotic organic solvents can be differentiated by the electrochemical parameter ▵Ered p = · ▵Ered(1) p - ▵Ered(2) p ·, which is the potential separation between the two one-electron reduction processes. This electrochemical parameter is inversely related to the strength of the interactions and can be used to differentiate between primary, secondary, tertiary alcohols, and even diols, as it is sensitive to both their steric and electronic properties. red was illustrated The results are highly reproducible across two solvents with substantially different hydrogen-bonding properties (CH3CN and CH2Cl2) and are supported by density functional theory calculations. This indicates that the numerous solvent-alcohol interactions are less significant than the quinone-alcohol hydrogen-bonding interactions. The utility of ▵Ered p was illustrated by comparisons between 1) 3,3,3-trifluoro-n-propanol and 1,3-difluoroisopropanol and 2) ethylene glycol and 2,2,2-trifluoroethanol.

Research Area(s)

  • Alcohols, Electrochemistry, Hydrogen bonding, Quinones, Voltammetry

Citation Format(s)

Measuring the relative hydrogen-bonding strengths of alcohols in aprotic organic solvents. / Tessensohn, Malcolm E.; Lee, Melvyn; Hirao, Hajime; Webster, Richard D.

In: ChemPhysChem, Vol. 16, No. 1, 02.01.2015, p. 160-168.

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