1. bookVolume 12 (2019): Issue 2 (October 2019)
Journal Details
License
Format
Journal
First Published
10 Dec 2012
Publication timeframe
2 times per year
Languages
English
access type Open Access

Antioxidant action of phenols: Revisiting theoretical calculations of their thermodynamics

Published Online: 21 Jan 2020
Page range: 212 - 217
Journal Details
License
Format
Journal
First Published
10 Dec 2012
Publication timeframe
2 times per year
Languages
English

Theoretical prediction ability of M06-2X functional was tested for thermodynamics of phenol, 15 para and 15 meta phenol derivatives. Calculations were done for gas phase as well as for polar and nonpolar solvents. Although predicted values might be shifted from the experimental ones in the framework of the employed DFT functional and basis set, the calculated and experimental data sets correlate well together. Very good linearity was found especially for the correlation of experimental and theoretical proton affinities. Hammett type correlations between the environments considered were compared. The phenolic C—O bond length was also tested as an alternative substituent effect descriptor while the type and position of the functional group on the aromatic ring have a direct effect on the phenolic bond.

Keywords

Becke AD (1988) Phys. Rev. A. 38: 3098.Search in Google Scholar

Bordwell FG, Cheng J (1991) J. Am. Chem. Soc. 113: 1736—1743.Search in Google Scholar

Chen Y, Xiao H, Zheng J, Liang G (2015) PLoS One, 10: e0121276.Search in Google Scholar

Francl MM, Pietro WJ, Hehre WJ, Binkley JS, Gordon MS, DeFrees DJ, Pople JA (1982) J. Chem. Phys. 77: 3654—3665.Search in Google Scholar

Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr., Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB and Fox DJ (2016) Gaussian 16, Revision B.01, Gaussian, Inc. Wallingford CT.Search in Google Scholar

Fujio M, McIver Jr RT, Taft RW (1981) J. Am. Chem. Soc. 103: 4017—4029.Search in Google Scholar

Hammett LP (1937) J. Am. Chem. Soc. 59: 96—103.Search in Google Scholar

Hansch C, Leo A, Taft RW (1991) Chem. Rev. 91: 165—195.Search in Google Scholar

Hariharan PC, Pople JA (1973) Theor. Chim. Acta. 28: 213—222.Search in Google Scholar

Huang F, Jiang J, Wen M, Wang ZX (2014) J. Theor. Comput. Chem. 13: 1350074.Search in Google Scholar

Jaffé HH (1953) Chem. Rev. 53: 191—261.Search in Google Scholar

Klein E, Lukeš V (2006a) J. Phys. Chem. A, 110: 12312—12320.Search in Google Scholar

Klein E, Lukeš V (2006b) J. Mol. Struct.(THEOCHEM) 767: 43—50.Search in Google Scholar

Klein E. Lukeš V (2006c) Chem. Phys. 330: 515—525.Search in Google Scholar

Klein E, Rimarcik J, Lukes V (2009) Acta Chim. Slovaca, 2: 37—51.Search in Google Scholar

Lee C, Yang W, Parr RG (1988) Phys. Rev. B. 37: 785.Search in Google Scholar

Luo S, Zhao Y, Truhlar DG (2011) Phys. Chem. Chem. Phys. 13: 13683—13689.Search in Google Scholar

Marenich AV, Cramer CJ, Truhlar DG (2009) J. Phys. Chem. B. 113: 6378—6396.Search in Google Scholar

Michalík M, Vagánek A, Poliak P (2014) Acta Chim. Slovaca. 7: 123—128.Search in Google Scholar

Nazarparvar E, Zahedi M, Klein E (2012) J. Org. Chem. 77: 10093—10104.Search in Google Scholar

Peverati R, Truhlar DG (2011) J. Phys. Chem. Lett. 2: 2810—2817.Search in Google Scholar

Rassolov VA, Pople JA, Ratner MA, Windus TL (1998) J. Chem. Phys. 109: 1223—1229.Search in Google Scholar

Rimarčík J, Lukeš V, Klein E, Rottmannová L (2011) Comp. Theor. Chem. 967: 273—283.Search in Google Scholar

Škorňa P, Lengyel J, Rimarčík J, Klein E (2014) Comput. Theor. Chem. 1038: 26—32.Search in Google Scholar

Vagánek A, Rimarcik J, Lukes V, Rottmannová L, Klein E (2011) Acta Chim. Slovaca 4: 55—71.Search in Google Scholar

Zhao Y, Truhlar DG (2008) Theor. Chem. Acc. 120: 215—241.Search in Google Scholar

Recommended articles from Trend MD

Plan your remote conference with Sciendo