Natural Flavonoids Interact with Dinitrobenzene System in Aprotic Media: An Electrochemical Probing

Abstract

Three structurally related natural flavonoids (FlOH), quercetin (Q), rutin (R) and morin (M), were investigated by cyclic voltammetry to probe their interactions with hazardous 1,4-dinitrobenzene (1,4-DNB) using a glassy carbon electrode. Scavenging of 1,4-DNB by FlOH was inferred from a positive shift in reduction potential, decrease in anodic peak current, and irreversible electrochemical behavior of 1,4-DNB on increasing the flavonoid concentration. The homogeneous bi-molecular rate constant (k2) was determined using the Nicholson-Shain equation and found to be higher for the dianion. Morin posed a comparatively higher k2 value for its interaction with the 1,4-DNB electrochemical system owing to its more acidic nature and least intramolecular hydrogen bonding. The cyclic voltammetric (CV) results were further supported by HyperchemPM3 quantum mechanical semi-empirical calculations, which point towards ErCi interactions between flavonoids and 1,4-DNB. The present investigation is biologically significant in terms of natural flavonoidal scavenging activity toward toxins such as dinitroaromatics.