Naslov
Influence of different free radicals on scavenging potency of gallic acid

Autori
Đorović, Jelena ; Dimitrić Marković, Jasmina ; Stepanić, Višnja ; Begović, Nebojša ; Amić, Dragan ; Marković, Zoran

Izvornik
Journal of molecular modeling (1610-2940) 20 (2014), 7; 2345-1

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Bond dissociation enthalpy ; DFT ; Gallic acid ; Proton affinity

Sažetak
The M05-2X/6-311++G(d, p) and B3LYP-D2/6-311++G(d, p) models are used to evaluate scavenging potency of gallic acid. The hydrogen atom transfer (HAT), sequential proton loss electron transfer (SPLET), and single electron transfer followed by proton transfer (SET-PT) mechanisms of gallic acid with some radicals (•OO−, •OH, and CH3OO•) were investigated using the corresponding thermodynamic quantities: bond dissociation enthalpy (BDE), ionization potential (IP), and proton affinity (PA). Namely, the ΔHBDE, ΔHIP, and ΔHPA values of the corresponding reactions in some solvents (water, DMSO, pentylethanoate, and benzene) are investigated using an implicit solvation model (SMD). An approach based on the reactions enthalpies related to the examined mechanisms is applied. This approach shows that a thermodynamically favored mechanism depends on the polarity of reaction media and properties of free radical reactive species. The most acidic 4-OH group of gallic acid is the active site for radical inactivation. The results of this investigation indicate that the SPLET mechanism can be a favored reaction pathway for all three radicals in all solvents, except for •OH in the aqueous solution. In water, gallic acid can inactivate •OH by the HAT mechanism.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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