Gallic acid: thermodynamics of the homolytic and heterolytic phenolic O—H bonds splitting-off

Škorňa, Peter; Michalík, Martin; Klein, Erik

doi:10.1515/acs-2016-0020

Abstract

The DFT study of primary antioxidant action of gallic acid and its carboxylic anion is presented in the gas-phase, benzene and water. Corresponding reaction enthalpies for three possible mechanisms was calculated using B3LYP/6-311++G** method. Bond dissociation enthalpy (BDE) and proton dissociation enthalpy (PDE) of 4-OH group was found to be the lowest in gas-phase as well as in both solvents approximated by IEF-PCM model. Ionization potentials (IPs) were higher than BDEs in all cases. Deprotonation of carboxylic group result in increased antioxidant potency as drop in BDE, proton affinities (PAs) and IPs was indicated in all environments.

References

Alberti A, Amorati R, Campredon M, Lucarini M, Macciantelli D, Pedulli GF (2009) Acta Alimentaria 38: 427—436.10.1556/AAlim.38.2009.4.3
Search in Google Scholar Back to article
Álvarez-Diduk R, Ramírez-Silva MT, Galano A, Merkoçi A (2013) J. Phys. Chem. B 117: 12347—12359.
Search in Google Scholar Back to article
Bartmess JE (1994) J. Phys. Chem. 98: 6420—6424.
Search in Google Scholar Back to article
Becke A (1993) J. Chem. Phys. 98: 5648—5652.
Search in Google Scholar Back to article
Binkley JS, Pople JA, Hehre WJ (1980) J. Am. Chem. Soc. 102: 939—947.
Search in Google Scholar Back to article
Cances E, Mennucci B, Tomasi J (1997) J. Chem. Phys. 107: 3032—3041.
Search in Google Scholar Back to article
Cances E, Mennucci B (1998) J. Math. Chem. 23: 309—326.
Search in Google Scholar Back to article
Chen Y, Xiao H, Zheng J, Liang G (2015) PLoS ONE 10(3): e0121276.10.1371/journal.pone.0121276437240725803685
Search in Google Scholar Back to article
Denisova TG, Denisov ET (2008) Russ. Chem. Bull. 57: 1858—1866.
Search in Google Scholar Back to article
Đorović J, Dimitrić Marković JM, Stepanić V, Begović N, Amić D, Marković Z (2014) J. Mol. Model. (2014) 20: 2345.
Search in Google Scholar Back to article
Eslami AC, Pasanphan W, Wagner BA, Buettner GR (2010) Chemistry Central Journal 4: 15.10.1186/1752-153X-4-15292433820687941
Search in Google Scholar Back to article
Galaverna RS, Bataglion GA, Heerdt G, De Sa GF, Daroda R, Cunha VS, Morgon NH, Eberlin MN (2015) Eur. J. Org. Chem. 2015: 2189—2196.
Search in Google Scholar Back to article
Gülçin İ (2012) Arch. Toxicol. 86: 345—391.
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, 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 Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT
Search in Google Scholar Back to article
Huguenin J, Hamadya SOS, Bourson P (2015) J. Raman Spectrosc. 46: 1062—1066.10.1002/jrs.4752
Search in Google Scholar Back to article
Ji H-F, Zhang H-Y, Shen L (2006) Bioorg. Med. Chem. Lett. 16: 4095—4098.
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, Lukes V, Ilčin M (2007) Chem Phys. 336: 51—57.
Search in Google Scholar Back to article
Klein E, Rimarčík J, Senajová E, Vagánek A, Lengyel J (2016) Comp. Theor. Chem. 1085: 7—17.
Search in Google Scholar Back to article
Koroleva O, Torkova A, Nikolaev I, Khrameeva E, Fedorova T, Tsentalovich M, Amarowicz R (2014) Int. J. Mol. Sci. 15: 16351—16380.
Search in Google Scholar Back to article
Lee C, Yang W, Parr RG (1988) Phys. Rev. B 37: 785—789.
Search in Google Scholar Back to article
Lemańska K, Szymusiak H, Tyrakowska B, Zieliński R, Soffers AEMF, Rietjens IMCM (2001) Free Rad. Biol. Med. 31: 869—881.
Search in Google Scholar Back to article
Lengyel J, Rimarčík J, Vagánek A, Klein E (2013) Phys. Chem. Chem. Phys. 15: 10895—10903.
Search in Google Scholar Back to article
Leopoldini M, Marino T, Russo N, Toscano M (2004) J. Phys. Chem. A 108: 4916—4922.
Search in Google Scholar Back to article
Lu Z, Nie G, Belton PS, Tang H, Zhao B (2006) Neurochemistry International 48: 263—274.10.1016/j.neuint.2005.10.01016343693
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
Marković Z, Amić D, Milenković D, Dimitrić-Marković JM, Marković S (2013) Phys. Chem. Chem. Phys. 15: 7370—7378.
Search in Google Scholar Back to article
Marković Z, Đorović J, Dimitrić Marković JM, Biočanin R, Amić D (2016) Turk. J. Chem. 40: 499—509.
Search in Google Scholar Back to article
Michalík M, Škorňa P, Lukeš V (2015) Acta Chimica Slovaca 8: 120—125.10.1515/acs-2015-0021
Search in Google Scholar Back to article
Mohajeri A, Asemani SS (2009) J. Mol. Struct. 930: 15—20.
Search in Google Scholar Back to article
Musialik M, Kuzmicz R, Pawlowski TS, Litwinienko G (2009) J. Org. Chem. 74: 2699—2709.
Search in Google Scholar Back to article
Rimarčík J, Lukeš V, Klein E, Ilčin M (2010) J. Mol. Struct. THEOCHEM 952: 25—30.10.1016/j.theochem.2010.04.002
Search in Google Scholar Back to article
Saqib M, Mahmood A, Akram R, Khalid B, Afzal S, Kamal GM (2015) J. Pharm. Appl. Chem. 1: 65—71.
Search in Google Scholar Back to article
Škorňa P, Rimarčík J, Poliak P, Lukeš V, Klein E (2016) Comp. Theor. Chem. 1077: 32—38.
Search in Google Scholar Back to article
Šolc R, Gerzabek MH, Lischka H, Tunega D (2014) Comp. Theor. Chem. 1032: 42—49.
Search in Google Scholar Back to article
Toscano M, Russo N (2016) Comp. Theor. Chem. 1077: 119—124.
Search in Google Scholar Back to article
Vagánek A, Rimarčík J, Dropková K, Lengyel J, Klein E (2014) Comp. Theor. Chem. 1050: 31—38.
Search in Google Scholar Back to article
Yin J, Andersen ML, Skibsted LH (2013) J. Agric. Food Chem. 61: 3159—3166.10.1021/jf400219r23461366
Search in Google Scholar Back to article
Zhao Y, Truhlar DG (2008) Theor. Chem. Acc. 120: 215—241.
Search in Google Scholar Back to article

Gallic acid: thermodynamics of the homolytic and heterolytic phenolic O—H bonds splitting-off

Abstract

Paradigm

My account