Figure 1
Chemical structures of indaziflam and its three metabolites a) IND, b) ITI, c) ICA and d) FDAT
Figure 2
Chemical structures of a) IND, b) ITI, c) ICA and d) FDAT optimized at the wB97XD/6-311++G(2d,2p) level of theory in the aqueous phase employing the PCM solvation model. Bond distances are given in Angstroms, DA=Dihedral Angle
Figure 3
HOMO and LUMO’s distributions on IND, ITI, ICA and FDAT obtained at the wB97XD/6-311++G(2d,2p) level of theory in the aqueous phase employing the PCM solvation model. In all cases the isosurfaces were obtained at 0.08 e/u.a33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285.
Figure 4
Isosurfaces of the Fukui Functions for IND according to equations (10), (11) and (12) at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model. In the case of (a) electrophilic, b) nucleophilic and c) free radical attacks. In all cases the isosurfaces were obtained at 0.008 e/u.a.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285., broken circles show the more reactive zones in each molecule
Figure 5
Isosurfaces of the Fukui Functions for ITI according to equations (10), (11) and (12) at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model. In the case of (a) electrophilic, b) nucleophilic and c) free radical attacks. In all cases the isosurfaces were obtained at 0.008 e/u.a.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285., broken circles show the more reactive zones in each molecule
Figure 6
Isosurfaces of the Fukui Functions for ICA according to equations (10), (11) and (12) at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model. In the case of (a) electrophilic, b) nucleophilic and c) free radical attacks. In all cases the isosurfaces were obtained at 0.008 e/u.a.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285., broken circles show the more reactive zones in each molecule
Figure 7
Isosurfaces of the Fukui Functions for FDAT according to equations (10), (11) and (12) at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model In the case of (a) electrophilic, b) nucleophilic and c) free radical attacks. In all cases the isosurfaces were obtained at 0.008 e/u.a.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285., broken circles show the more reactive zones in each molecule
Figure 8
Condensed Fukui Function values for electrophilic attacks on IND at the X/6-311++G (2d,2p) (where X=B3LYP, M06, M06L and WB97XD) level of theory, in the aqueous phase employing Hirshfeld population and equations (13)-(15), broken circles show the more reactive zones in each molecule
Figure 9
Condensed Fukui Function values for nucleophilic attacks on IND at the X/6-311++G (2d,2p) (where X=B3LYP, M06, M06L and WB97XD) level of theory, in the aqueous phase employing Hirshfeld population and equations (13)-(15), broken circles show the more reactive zones in each molecule
Figure 10
Condensed Fukui Function values for free radical attacks on IND at the X/6-311++G (2d,2p) (where X=B3LYP, M06, M06L and WB97XD) level of theory, in the aqueous phase employing Hirshfeld population and equations (13)-(15), broken circles show the more reactive zones in each molecule
Figure 11
Dual descriptors evaluated at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model according to equation (17). In all cases, the isosurfaces were obtained at 0.008 e/u.a.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285. a). IND, b) ITI, c) ICA and d) FDAT
Figure 12
Mapping of the electrostatic potentials evaluated at the wB97XD/6-311++G(2d,2p) level of theory employing the PCM solvation model, onto a density isosurface (value =0.002 e/a.u.33 Guerra, N.; Silvério de Oliveira, R.; Constantin, J.; Mendes de Oliveira, A.; Braga, G.; Revista Brasileira de Herbicidas
2013, 12, 285.) for a) IND, b) ITI, c) ICA, and d) FDAT
Table 1
Evaluation of the Fukui function following different approximations, for an electrophilic (f-(r)), nucleophilic (f+(r)) or free radical attack (f0(r)) on the reference molecule
Table 2
Global reactivity parameters evaluated at the X/6-311++G(2d,2p) (where X=B3LYP, M06, M06L and WB97XD) level of theory and in the aqueous phase, employing equations (1)-(6)
Table 3
Global reactivity parameters evaluated at the X/6-311++G(2d,2p) (where X=B3LYP, M06, M06L and WB97XD) level of theory and in the aqueous phase, employing the equations (1)-(6) and the Koopmans's theorem
Table 4
More reactive sites obtained for IND and its metabolites employing different levels of theory, and approximations to evaluate the Fukui function. Atomic labels are reported in
Figures 4-
7