Theoretical investigation of aniline derivatives: Correlation of theoretical reaction Gibbs free energies with experimental oxidation potentials

Andrea Kováčová; Martin Michalík

doi:10.2478/acs-2024-0010

Abstract

Anilines and their derivatives are used in industrial production of dyes, pharmaceuticals, plastics, and synthetic antioxidants. Abstraction of electron and formation of a cation radical represent a significant step in the reactivity of this group of substances. The aim of this study was to theoretically investigate the effect of a substituent on the oxidative electrochemical potential of 64 species of aniline derivatives. Quantum-chemical calculations were performed using the composite G4 method. The obtained linear dependences for reaction Gibbs free energies were correlated with the Hammett constants and available experimental values.

References

Anjalin M, Kanagathara N, Baby Suganthi AR (2020) Mater. Today Proc. 33: 4751—4755.
Search in Google Scholar Back to article
Bakalbassis EG, Lithoxoidou AT, Vafiadis AP (2003) J. Phys. Chem. A. 107(41): 8594—8606.
Search in Google Scholar Back to article
Bannwarth C, Caldeweyher E, Ehlert S, Hansen A, Pracht P, et al. (2021) Wiley Interdiscip. Rev. Comput. Mol. Sci. 11(2): 1—49.
Search in Google Scholar Back to article
Bannwarth C, Ehlert S, Grimme S (2019) J. Chem. Theory Comput. 15(3): 1652—1671.
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
Busch M, Ahlberg E, Ahlberg E, Laasonen K (2022) ACS Omega. 7(20): 17369—17383.
Search in Google Scholar Back to article
Curtiss LA, Redfern PC, Raghavachari K (2007) J. Chem. Phys. 127(12): 1—8.
Search in Google Scholar Back to article
Fifen JJ (2013) J. Chem. Theory Comput. 9(7): 3165—3169.
Search in Google Scholar Back to article
Frisch MJ, Trucks GW, Schlegel HB, 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
Fu Y, Liu L, Yu HZ, Wang YM, Guo QX (2005) J. Am. Chem. Soc. 127(19): 7227—7234.
Search in Google Scholar Back to article
Grimme S, Ehrlich S, Goerigk L (2011) J. Comput. Chem. 32(7): 1456—1465.
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) In Organic Electrochemistry, pp. 229—259. CRC Press. 5th ed.
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
Kleinová A, Biela M, Lukeš V, Klein E (2024) J. Mol. Struct. 1303: 137646.
Search in Google Scholar Back to article
Kováčová A (2024) Acta Chim. Slovaca. 17(1): 12—21.
Search in Google Scholar Back to article
Kováčová A, Michalík M, Hartmann H, Lukeš V (2023) J. Mol. Liq. 389: 122811.
Search in Google Scholar Back to article
Lukeš V, Hartmann H (2021) Color. Technol. 137(4): 389—398.
Search in Google Scholar Back to article
Lukeš V, Rapta P, Idzik KR, Beckert R, Dunsch L (2011) J. Phys. Chem. B. 115(13): 3344—3353.
Search in Google Scholar Back to article
Marenich AV, Cramer CJ, Truhlar DG (2009) J. Phys. Chem. B. 113(18): 6378—6396.
Search in Google Scholar Back to article
Pavitt AS, Bylaska EJ, Tratnyek PG (2017) Environ. Sci. Process. Impacts. 19(3): 339—349.
Search in Google Scholar Back to article
Pracht P, Bohle F, Grimme S (2020) Phys. Chem. Chem. Phys. 22(14): 7169—7192.
Search in Google Scholar Back to article
Rani M, Shanker U (2017) J. Environ. Chem. Eng. 5(6): 5298—5311.
Search in Google Scholar Back to article
Rappoport Z (2007) The chemistry of Anilines, Part 1, Vol. 11 New York: Wiley. 1163.
Search in Google Scholar Back to article
Skákalová V, Lukeš V, Breza M (1997) Macromol. Chem. Phys. 198(10): 3161—3172.
Search in Google Scholar Back to article
Takahata Y, Chong DP (2005) Int. J. Quantum Chem. 103(5): 509—515.
Search in Google Scholar Back to article
Vagánek A, Rimarčík J, Ilčin M, Škorňa P, Lukeš V, Klein E (2013) Comput. Theor. Chem. 1014: 60—67.
Search in Google Scholar Back to article
Weigend F, Ahlrichs R (2005) Phys. Chem. Chem. Phys. 7(18): 3297—3305.
Search in Google Scholar Back to article

Theoretical investigation of aniline derivatives: Correlation of theoretical reaction Gibbs free energies with experimental oxidation potentials

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