Intermolecular perturbation in the self‑assembly of melamine

• Autores: Petelski, André N.; Duarte, Darío Jorge Roberto; Pamies, Silvana Carina; Peruchena, Nélida María; Sosa, Gladis Laura
• Año de publicación: 2016
• Idioma: inglés
• Tipo de recurso: artículo
• Fuente: Theoretical Chemistry Accounts, 2016, vol. 135, no. 3, p. 1-13.
• Materia: Cyanuric acid; Supramolecular; Molecular building blocks; Hydrogen bond; Halogen bond
• Institución: Universidad Nacional del Nordeste

Fil: Petelski, André N. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura; Argentina.
Fil: Petelski, André N. Universidad Tecnológica Nacional. Facultad Regional Resistencia; Argentina.
Fil: Duarte, Darío Jorge Roberto. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura; Argentina.
Fil: Pamies, Silvana Carina. Universidad Tecnológica Nacional. Facultad Regional Resistencia; Argentina.
Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura; Argentina.
Fil: Sosa, Gladis Laura. Universidad Tecnológica Nacional. Facultad Regional Resistencia; Argentina.
A theoretical study has been conducted on a set of supramolecular complexes based on 1,3,5-triazine-2,4,6- triamine, or melamine (M), with cyanuric acid (CA), trithiocyanuric acid (TCA), and two mono-substituted derivatives of CA with chlorine (CACl) and bromine (CABr). The study was carried out on 12 complexes, M/(CA)n, M/ (TCA)n, M/(CACl)n, M/(CABr)n, with n = 1, 2 and 3, by the density functional theory employing the ω-B97XD functional with the 6-311++G(d,p) basis set. Information about the intermolecular perturbation over M and the interactions that drive the self-assembly of these species has been obtained from the quantum theory of atoms in molecules and a natural bond orbital analysis. The harmonic oscillator model of aromaticity, the para-delocalization index, the fluctuation aromatic index, and two electron charge density descriptors were used to evaluate the aromaticity of M in each complex. Results show that the hydrogen and halogen (XBs) bond interactions, which direct the self-assembly process in these complexes, are anti-cooperative. Binding energies decrease in the following order: M/ (CA)n > M/(TCA)n > M/(CABr)n > M/(CACl)n (for all values of n). Brominated CA arises as a potential compound to self-assembly with M via XBs.