Intermolecular Perturbation In The Self-Assembly Of Melamine

ANDRE N. PETELSKI; PAMIES, SILVANA; DUARTE, DARIO J. R.; PERUCHENA, N. M.; SOSA, G. L.

TORINO

Congreso; 41 Congreso Internacional de Químicos Teóricos de Expresión Latina, CHITEL2015; 2015

ASOCIACION INTERNACIONAL DE Químicos Teóricos de Expresión Latina

A theoretical study has been carried out on a set of supramolecular complexes based on melamine (M), 1,3,5-Triazine-2,4,6-triamine, with cyanuric acid (CA), thiocyanuric acid (TCA) and two homo-substituted derivatives of CA with chlorine (CACl) and bromine (CABr). The study was carried out in twelve complexes by density functionally theory employing the B3LYP functional with the 6-311++G(d,p) basis set. Information of the intermolecular perturbation over M and the interactions that drive the self-assembly of these species has been gained by the Atoms in Molecules Theory and a Natural Bond Orbital (NBO) analysis. The Harmonic Oscillator Model of Aromacity (HOMA), the Para Delocalization Index (PDI), the Fluctuation Aromatic Index (FLU) and two topological charge density descriptors were used to verify the aromaticity of M in each complex. Our results show that the process of self-assembly is anticooperative for hydrogen bonds (HB) as well as for halogen bonds (XB). The strength of the binding energies decreases in the following order: M/(CA)n> M/(CABr)n> M/(TCA)n> M/(CACl)n. The homo-brominated CA arises as a potential compound to self-assembly with M via XB.