A theoretical study on vomitoxin and its tautomers

In the present work, the structural and electronic properties of vomitoxin (deoxynivalenol, a mycotoxin) and all of its possible tautomers have been investigated by the application of B3LYP/6-31 G(d,p) type quantum chemical calculations. According to the results of the calculations, tautomer V-4 has been found to be the most stable one among all the structures both in the gas and aqueous phases. The calculations also indicated that, vomitoxin and V-2 possess the deepest and the highest lying HOMO levels, respectively. Hence, V-2 is to be more susceptible to oxidations than the others. On the other hand, V-5(S) and vomitoxin have the lowest and the next lowest LUMO energies, respectively. Whereas, V-1 and V-2 possess quite highly lying (within the group) LUMO energy levels which result in comparatively unfavorable reduction potentials. Some important geometrical and physicochemical properties and the calculated IR spectra of the systems have also been reported in the study. (C) 2008 Elsevier B.V. All rights reserved.