A DENSITY FUNCTIONAL THEORY STUDY OF ANTIOXIDANT ACTIVITY OF ISOTHIOCYANATES IN BROCCOLI SPROUTS (BRASSICA OLERACEA L.)
Keywords:Brassica oleracea L., isothiocyanate, antioxidant, HAT, SET, DFT.
Antioxidant activity of 9 isothiocyanate derivatives (−N=C=S) extracted from Broccoli
sprouts (Brassica oleracea L.) has been investigated using density functional theory (DFT) –
based computational methods. Through the hydrogen atom transfer (HAT) and single electron
transfer (SET) mechanisms, three thermodynamic parameters including bond dissociation
enthalpy (BDE), vertical ionization energy (IE), and vertical electron affinity (EA) were
calculated in the gas phase using B3LYP/6-311++G(3df,3p)//B3LYP/6-311G(d,p) model
chemistry. As a result, the isothiocyanate (ITC) shows potential antioxidant activity via HAT
mechanism. The most potential antioxidant is 3-isothiocyanato pro-1-en (3ITCP) with
BDE(C−H) of 72.9 kcal/mol. The SET mechanism is not dominant in case of the studied ITCs.
Moreover, the radicals formed H• removal had more reactive and less stable than the intial
neutral compounds with lower IE, higher EA and ω.
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