INFLUENCE OF AROMATIC SUBSTITUENTS ON THE SYNTHESIS OF SCHIFF BASES DERIVED FROM TRANS-(R,R)-DIAMINOCYCLOHEXANE: A SPECTROPHOTOMETRIC AND DFT B3LYP STUDY
Author(s):
Lili Dahiana Becerra, Carlos Coy-Barrera*, Diego Quiroga
Field: Organic chemistry Type: Research paper Pages:
Graphycal Abstract: In this work, the synthesis of Schiff bases derived from trans-(R,R)-diaminocyclohexane by microwave irradiation (MW) is presented. The reaction yields varied between 31% and 69%, being influenced by the electronic nature of the substituents (H, Cl, Br, NO2, MeO, t-BuO, BnO, and 4-(4-Me)PhO) and the reaction temperature. The spectrophotometric properties of the products were investigated by UV-Vis spectrophotometry, revealing bathochromic and hypso-chromic effects attributable to the different substituent groups. These effects were interpreted by DFT calculations with the B3LYP functional at the 6-311G(d,p) level. The results suggest that the electronic properties of the substituents in the para position have a significant impact on the spectroscopic characteristics of the Schiff bases.