A detailed exploration of intermolecular interactions in 4-(4-dimethylaminobenzylideneamino)-N-(5-methyl-3-isoxazolyl)benzenesulfonamide and related Schiff bases: Crystal structure, spectral studies, DFT methods, Pixel energies and Hirshfeld surface analysis

GIL, DIEGO M.; SALOMÓN, FERNANDO F.; ECHEVERRÍA, G.A.; PIRO, OSCAR E.; PÉREZ, HIRAM; BEN ALTABEF, AIDA

SPECTROCHIMICA ACTA. PART A, MOLECULAR AND BIOMOLECULAR SPECTROSCOPY.

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2017 vol. 185 p. 286 - 297

1386-1425

The Schiff base of the title has been synthesized and its crystal structure determined by single-crystal X-ray diffraction.The compound was characterized by IR, Raman, 1H NMR, 13C NMR and electronic absorption spectra.DFT calculations provide the quantumchemical basis for the observed molecular conformation. A study of intermolecularinteractions of the title compound is comparedwith seven other closely related structures and revealsthat molecules in most of the compounds are linked by a cooperative effect of strong and weak hydrogen bonds,CH?π, and π?π stacking interactions, and also lp?π contacts. Lattice energy calculations indicate that thedispersion component is the major contribution, with the coulombic term playing a significant role in the totalenergy. Interaction energies for molecular pairs involving NH···N bonds indicate a dominant contribution topacking stabilization coming from coulomb component. Hirshfeld surfaces and 2D?fingerprint plots allowed usto visualize different intermolecular contacts and its relative contributions to total surface in each compound.The analysis of electrostatic potential (ESP) maps correlates well with the computed energies providingevidences on the dominant electrostatic nature of NH···N and NH···O interactions.