Analizando the effects of halogen on properties of a halogenated series of R and S enantiomers analogues alkaloid cocaine-X, X=F, Cl, Br, I.

Abstract

The volumes and weight molecular of all members of both series are relationed with the Van der Waals radius X distances with the electronegativities and R of X suggesting that these two properties have influence on the positions of the CO CH groups of VdW 2 3 both series. The NBO calculations have evidenced that the F and Cl derivatives of both series present the higher variations in the total energies while the AIM analyses reveal that the presence of halogen X in the benzyl rings generate a new H bonds no observed in the free base of cocaine whose topological properties are strongly dependent from the electronegativity of the halogen. Hence, the properties for the F derivatives are higher than the observed for the other ones. The NBO calculations also show clearly that the presence of the halogen X generates variations in the bond orders related to the inter-rings C-C bonds formed between the piperidine and benzyl rings and, in the C atoms that contain the CO CH groups. The frontier orbitals 2 3 demonstrate that the effects of halogen X on the halogenated series are to increase the gaps values and, as consequence decrease the reactivities of all members of both series. Finally, the higher dipole moment values observed for the Cl derivatives of both R and S series could be clearly explained by the higher Merz-Kollman (MK) charges values observed on all C atoms belong to the benzyl rings that contain the halogen X.