Substitution effect of phenol derivatives on electrochemical oxidation potentials: Correlation of theoretical reaction Gibbs free energies

Andrea Kováčová

doi:10.2478/acs-2024-0002

Abstract

Reaction Gibbs free energies for electron abstraction from phenol and its 74 derivatives were calculated using the composite ab-initio approach (G4) in combination with the implicit solvation model. Resulting values were correlated with 38 oxidation potentials obtained from cyclic voltammetry measurements. Substitution effect and the role of substituents in ortho-, meta-, and para-position were also quantified by Hammett constants. The evaluated linear dependences can be used to reliably estimate electrochemical potentials of substituted phenols solvated in water.

References

Albuquerque BR, Heleno SA, Oliveira B, Barros L, Ferreira ICFR (2021) Food Funct. 12: 14—29.
Search in Google Scholar Back to article
Atkins PW, De Paula J (2006) Atkins’ Physical Chemistry. 8^th Edition, Oxford University Press, Oxford, New York.
Search in Google Scholar Back to article
Biela M, Kleinová A, Uhliar M, Klein E (2023) J. Mol. Graph. Model. 122: 1—6.
Search in Google Scholar Back to article
Bordwell FG, Zhang XM, Satish AV, Cheng JP (1994) J. Am. Chem. Soc. 116: 6605—6610.
Search in Google Scholar Back to article
Brown HC, Okamoto Y (1957) J. Am. Chem. Soc. 79: 1913—1917.
Search in Google Scholar Back to article
Cagardová D, Michalík M, Klein E, Lukeš V, Marković Z (2019) Acta Chim. Slovaca 12: 225—240.
Search in Google Scholar Back to article
Curtiss LA, Redfern PC, Raghavachari K (2007) J. Chem. Phys. 126: 084108.
Search in Google Scholar Back to article
Fifen JJ (2013) J. Chem. Theory Comput. 9: 3165—3169.
Search in Google Scholar Back to article
Frisch MJ, Trucks GW, Schlegel HB, GE Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS,Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J and Fox DJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc. Wallingford CT.
Search in Google Scholar Back to article
Guerra R (2001) Chemosphere 44: 1737—1747.
Search in Google Scholar Back to article
Hansch C, Leo A, Taft R (1991) Chem. Rev. 91: 165—195.
Search in Google Scholar Back to article
Ho J, Coote LM, Cramer CJ, Truhlar DG (2016) Theoretical Calculation of Reduction Potentials. In: Organic Electrochemistry, 5^th edn. CRC Press, pp 229—259.
Search in Google Scholar Back to article
Ignaczak M, Dziegiec’ J, Prawicki K (1987) Kinet. Catal. (Engl Transl); (United States) 27(6): 1305–1309.
Search in Google Scholar Back to article
Ishikawa A, Nakai H (2016) Chem. Phys. Lett. 650: 159—164.
Search in Google Scholar Back to article
Jmol development team (2016) Jmol: an open-source Java viewer for chemical structures in 3D (14.6). http://jmol.sourceforge.net/.
Search in Google Scholar Back to article
Klein E, Lukeš V (2006) J. Phys. Chem. A 110: 12312—12320.
Search in Google Scholar Back to article
Klein E, Rimarčík J, Lukeš V (2009) Acta Chim. Slovaca 2: 37—51.
Search in Google Scholar Back to article
Lukeš V, Hartmann H (2021) Color. Technol. 137: 389—398.
Search in Google Scholar Back to article
Lukeš V, Škorňa P, Michalík M, Klein E (2017) Chem. Phys. Lett. 687: 66—72.
Search in Google Scholar Back to article
Marenich AV, Cramer CJ, Truhlar DG (2009) J. Phys. Chem. B 113: 6378—6396.
Search in Google Scholar Back to article
Mennucci B, Tomasi J, Cammi R, Cheeseman JR, Frisch MJ, Devlin FJ, Gabriel S, Stephens PJ (2002) J. Phys. Chem. A 106: 6102—6113.
Search in Google Scholar Back to article
Michalík M, Biela M, Cagardová D, Lukeš V (2021) Chem. Phys. Lett. 762: 138142.
Search in Google Scholar Back to article
Michalík M, Lukeš V (2016) Acta Chim. Slovaca 9: 89—94.
Search in Google Scholar Back to article
Michalík M, Poliak P, Lukeš V, Klein E (2019a) Phytochemistry 166: 112077.
Search in Google Scholar Back to article
Michalík M, Rimarčík J, Lukeš V, Klein E (2019b) Acta Chim. Slovaca 12: 108—118.
Search in Google Scholar Back to article
Michalík M, Sádecká L, Lukeš V (2017) Acta Chim. Slovaca 10: 91—95.
Search in Google Scholar Back to article
Pavitt AS, Bylaska EJ, Tratnyek PG (2017) Environ. Sci.: Process Impacts 19: 339—349.
Search in Google Scholar Back to article
Rimarčík J, Lukeš V, Klein E, Ilčin M (2010) J. Mol. Struct. theochem. 952: 25—30.
Search in Google Scholar Back to article
Šimunková M, Biela M, Štekláč M, Hlinčík A, Klein E, Malček M (2022) J. Mol. Liq. 359: 119230
Search in Google Scholar Back to article
Štellerová D, Lukeš V (2021) Acta Chim. Slovaca 14: 32—37.
Search in Google Scholar Back to article
Štellerová D, Michalík M, Lukeš V (2022) Phytochemistry 203: 113387.
Search in Google Scholar Back to article
Takahata Y, Chong DP (2005) Int. J. Quantum Chem. 103: 509—515.
Search in Google Scholar Back to article
Tawa GJ, Topol IA, Burt SK, Caldwell RA, Rashin AA (1998) J. Chem. Phys. 109: 4852—4863.
Search in Google Scholar Back to article
Žemlička L, Fodran P, Lukeš V, Vagánek A, Slováková M, Staško A, Dubaj T, Liptaj T, Karabín M, Birošová L, Rapta P (2014) Monatsh. Chem. 145: 1307—1318.
Search in Google Scholar Back to article
Zhan CG, Dixon DA (2003) J. Phys. Chem. B 107: 4403—4417.
Search in Google Scholar Back to article

Substitution effect of phenol derivatives on electrochemical oxidation potentials: Correlation of theoretical reaction Gibbs free energies

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