Síntese e análise conformacional de derivados da 3-fenilsulfanilciclohexanonas 4'-substituídas

Abstract

The green synthesis of organic compounds has emerged and gained strength with the association of environmental damage with human activity. New methods and procedures are being developed in order to reduce the environmental impact in obtained chemicals. In this context the catalyst Bis[(L)-prolinato-N,O]Zn allows obtaining chemicals meeting the concepts of green chemistry to enable the development of methodologies that do not use solvents, reducing the reaction time and still be reusable. Making use of these characteristics and associating the ultrasound irradiation as a green alternative for further reducing the reaction time has developed a methodology for the synthesis of 3-phenylsulfanylcyclohexanone and 4-substituted derivatives, through the mechanism of addition to conjugate carbon also designated Michael addition. The use of thiol functional group give the name tio-Michael to the mechanism, which showed a good performance when compared to the similar methodologies. The product obtained was characterized by infrared spectroscopy and nuclear magnetic resonance of proton and carbon. The second prong of the research consisted of the conformational analysis of the substance 3-phenylsulfanylcyclohexanone by infrared spectroscopy, configured by the analysis of the carbonyl stretching band in the fundamental region and first overtone in solvents of increasing coefficient of permittivity, and theoretical calculations using the Hartree-Fock and basis set 6-31G, the solvent effect was calculated by Onsager. It has been found a reversal of the frequency component of the doublet as well as the molar fraction in polar solvents, still observing the pronounced effect of solvation.