Insights into the self-assembly steps of cyanuric acid toward rosette motifs: a DFT study

PETELSKI, ANDRE N.; PERUCHENA, NÉLIDA M.; PAMIES, SILVANA C.; SOSA, GLADIS L.

JOURNAL OF MOLECULAR MODELING - (Print)

SPRINGER

Año: 2017 vol. 23

1610-2940

The nature of non-covalent interactions in self assemblingsystems is a topic that has aroused great attentionin literature. In this field, the 1,3,5-triazinane-2,4,6-trione orcyanuric acid (CA) is one of the most widely used moleculesto formulate self-assembled materials or monolayers. In thepresent work, a variety of molecular aggregates of CA areexamined using three different DFT functionals (B3LYP,B3LYP-D3, and ω-B97XD) in the framework of the quantumtheory of atoms in molecules (QTAIM) and natural bond orbital(NBO) analysis. Herein, a step by step aggregation pathis proposed and the origin of cooperative effects is also examined.It is shown that a greater cooperativity is not alwaysassociated with a greater binding energy, and the greatest cooperativeeffect occurs with highly directional hydrogen bonds. The intramolecular charge transfers play a key role inthis effect.