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Submitted
Jul 16, 2020
Published
Dec 21, 2019
SUBSTITUENT EFFECTS ON THE ANTIOXIDANT ACTIVITY OF MONOSUBSTITUTED 3,3’-DIINDOLYLMETHANE: A DFT STUDY
Corresponding Author(s) : Mai Van Bay
mvbay@ued.udn.vn
UED Journal of Social Sciences, Humanities and Education,
Vol. 9 No. 5 (2019): UED JOURNAL OF SOCIAL SCIENCES, HUMANITIES AND EDUCATION
Abstract
3,3’-diindolylmethane (DIM) is an indole compound with proven health benefits and thus potential preventive medicine and therapeutic applications. Herein, the origins of the substituent effects on the antioxidant activity of monosubstituted 3,3’-diindolylmethanes (DIMs) were studied in silico by calculating their thermochemical properties using the RO)B3LYP/6−311++G(2df,2p)//B3LYP/6−31G(d) method. It was found that the compounds 2-NHMeDIM, 2-OH-DIM and 2−MeO-DIM have the lowest BDE(N1−H) values (78.4−78.9 kcal.mol−1 ), while that for the C8−H bond is observed in the 2-HO-DIM compound (67.0 kcal.mol-1). The presence of substitutes can decrease the ionization energies of the DIMs, however the effects of substitutes on the proton affinity were not clearly observed. The investigation on the HOO• radical scavenging following the hydrogen atom transfer mechanism indicated that the compound 2-NHMe-DIM has the highest rate constant with k = 9.72×109 L.mol−1.s−1. Thus, it is suggested that the 2-NHMe-DIM is a powerful antioxidant.
Keywords
Antioxidants; indole; Brassica; bond dissociation energies; substituent effects; 3,3’-diindolylmethane; glucosinolates
Mai Van Bay, Le Thi Kim Bong, Vo Thang Nguyen, Doan Van Quan, & Vo Van Quan. (2019). SUBSTITUENT EFFECTS ON THE ANTIOXIDANT ACTIVITY OF MONOSUBSTITUTED 3,3’-DIINDOLYLMETHANE: A DFT STUDY. UED Journal of Social Sciences, Humanities and Education, 9(5), 1-8. Retrieved from https://jshe.vn/index.php/jshe/article/view/93
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