The quest for determining one-electron redox potentials of azulene-1-carbonitriles by calculation

Physical Chemistry Chemical Physics : PCCP
Nicolai ReeKurt V Mikkelsen

Abstract

Electrochemical processes drive many chemical and biochemical reactions. Theoretical methods to accurately predict redox potentials are therefore crucial for understanding these reactions and designing new chemical species with desired properties. We have investigated a theoretical methodology using electronic structure methods based on density functional theory and continuum solvation models. These methods have been validated with linear correlation plots comparing theoretical and experimental results for the redox properties of a series of azulene derivatives. The results showed excellent correlations despite only minor structural variations of the azulenes, which support this rather simple theoretical methodology for determining redox potentials of organic molecules. Furthermore, we have estimated the absolute redox potential of the ferrocene/ferrocenium redox couple to be 4.8 ± 0.1 V in dichloromethane, which is slightly lower than previous estimates.

References

Jul 7, 1988·Nature·C A ReynoldsW G Richards
Apr 25, 2006·Physical Chemistry Chemical Physics : PCCP·Florian Weigend
May 19, 2006·The Journal of Physical Chemistry. a·Alberto ModelliDaniele Fabbri
Dec 22, 2006·The Journal of Physical Chemistry. a·Kirk A PetersonHermann Stoll
Apr 13, 2007·Chemical Reviews·Serap GünesNiyazi Serdar Sariciftci
Jun 19, 2010·Chemical Reviews·Jürgen HeinzeSabine Ludwigs
Mar 8, 2011·Chemical Reviews·Zhenguo YangJun Liu
Apr 22, 2011·The Journal of Organic Chemistry·Gilbert NöllKnut Rurack
May 20, 2011·The Journal of Physical Chemistry. B·Ksenia B BravayaAnna I Krylov
Oct 11, 2011·Journal of Cheminformatics·Noel M O'BoyleGeoffrey R Hutchison
Nov 19, 2011·Science·Bruce DunnJean-Marie Tarascon
Dec 10, 2013·The Journal of Organic Chemistry·Søren Lindbæk BromanMogens Brøndsted Nielsen
Jun 25, 2014·Physical Chemistry Chemical Physics : PCCP·Aleksandr V MarenichDonald G Truhlar
Jan 9, 2015·The Journal of Physical Chemistry. a·Stine T OlsenKurt V Mikkelsen
Sep 14, 2010·Journal of Chemical Theory and Computation·Mansoor NamazianMichelle L Coote
Jan 23, 2016·Organic & Biomolecular Chemistry·Anne Ugleholdt PetersenMogens Brøndsted Nielsen
Aug 24, 2016·Chemistry : a European Journal·Anders B SkovMogens Brøndsted Nielsen
Feb 1, 2015·Chemical Science·Süleyman ErAlán Aspuru-Guzik

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Citations

Oct 26, 2018·PLoS Computational Biology·Adrian JinichArren Bar-Even
Aug 7, 2019·Organic & Biomolecular Chemistry·Martin Drøhse KildeMogens Brøndsted Nielsen
Jan 17, 2020·ChemPlusChem·Cecilie Lindholm AndersenMogens Brøndsted Nielsen
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mason D HartMikhail V Barybin
Jul 10, 2021·The Journal of Physical Chemistry. a·Bo LiAlexander M Spokoyny
Sep 7, 2021·Physical Chemistry Chemical Physics : PCCP·Cecilie L AndersenOle Hammerich

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Software Mentioned

Gaussian
PCM
SciPy library
Open Babel
GaussView
SMD
Nova
IEF

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