Theoretical study of nitrodibenzofurans: A possible relationship between molecular properties and mutagenic activity
Abstract
In this study we present a theoretical investigation of the molecular properties of nitrodibenzofurans (NDFs) and dinitrodibenzofurans (DNDFs) and their relation to mutagenic activity. Equilibrium geometries, relative energies, vertical ionization potentials (IP), vertical electron activities (EA), electronic dipole polarizabilities, and dipole moments of all NDFs and three DNDFs calculated by Density Functional Theory (DFT) methods are reported. The Ziegler/Rauk Energy Decomposition Analysis (EDA) is employed for a direct estimate of the variations of the orbital interaction and steric repulsion terms corresponding to the nitro group and the oxygen of the central ring of NDFs. The results indicate differences among NDF isomers for the cleavage of the related bonds and steric effects in the active site. The results show a good linear relationship between polarizability ( LT alpha>), anisotropy of polarizability (Delta alpha), the summation of IR intensities (Sigma I-IR) and the summati...on of Raman activities (Sigma A(Raman)) over all 3N-6 vibrational modes and experimental mutagenic activities of NDF isomers in Salmonella typhimurium TA98 strain. The polarizability changes with respect to the nu(sNO+CN) vibrational mode are in correlation with the mutagenic activities of NDFs and suggest that intermolecular interactions are favoured along this coordinate.
Keywords:
Nitrodibenzofurans / Dinitrodibenzofurans / Environmental pollutants / Density functional theory / Mutagenic activitySource:
Journal of Hazardous Materials, 2016, 318, 623-630Publisher:
- Elsevier Science Bv, Amsterdam
Projects:
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
- The study of physicochemical and biochemical processes in living environment that have impacts on pollution and the investigation of possibilities for minimizing the consequences (RS-172001)
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1016/j.jhazmat.2016.07.035
ISSN: 0304-3894
PubMed: 27475460