G. Sánchez-Sanz, C. Trujillo, I. Alkorta and J. Elguero
Enhancing Intramolecular Chalcogen Interactions in 1-Hydroxy-8-YH-Naphthalenes Derivatives
Forty-two peri-substituted naphthalenes presenting chalcogen weak interactions have been studied. They correspond to O···Y interactions, Y being O, S and Se. While the O atom bear H or CH3 substituents (OH and OCH3 groups), the Y atom is substituted by H, F and CN in order to explore the effect of these electron-donating and electron-withdrawing substituents on the chalcogen bond strength. The effect of F and CH3 substituents on positions ortho/para (2,4,5,7 of the naphthalene ring) was also studied. Optimizations were carried out at the MP2/augl-cc-pVDZ and binding energies at the MP2/aug-cc-pVTZ followed by an MP2/CBS estimation. The main properties studied were geometries, energies (Eb, Eiso and Edef), the Molecular Electrostatic Potential (MEP), Electron density shifts and NBO E(2) energies and the relationship between these properties.