The equilibrium and kinetics of intermolecular hydrogen bonding in nitroarene anion radical-alcohol system: 1,3-dinitro-benzene anion radical - R-OH (R═CH3 -, C2 H5 -, (CH3 )2 CH-)

Abstract

To explore the possibility of hydrogen bonding of a stable anion radical with DNA – component sugar, hormones, steroid, and so on (through hydroxyl group), as a first step, the possibility of hydrogen bonding of 1,3-dinitrobenzene anion radical (1,3-DNB−•) with aliphatic alcohols was studied. It was found that 1,3-DNB−• anion radical undergoes hydrogen bonding with alcohols: methanol, ethanol, and 2-proponal. The hydrogen-bonding equilibrium constant Keq and the (hydrogen-bonding) rate constants k2 were evaluated through the use of linear scan and cyclic voltammetry theory and techniques. The Keq was found to be in the range of 1.4–6.0 m−1, whereas the rate constants k2 were found to be in the range of 1.5–3.6 m−1 s−1, depending upon the hydrogen-bonding agent and the equation used for the calculation of the rate constants. The hydrogen-bonding number n was found to be around 0.5 or 1.0. The implication of this study in, for example, the replication of DNA, the prevention of the formation of super oxide, and so on is discussed. Copyright © 2012 John Wiley & Sons, Ltd.