Abstract
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 quantum chemical basis for the observed molecular conformation. A study of intermolecular interactions of the title compound is compared with seven other closely related structures and reveals that 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 the dispersion component is the major contribution, with the coulombic term playing a significant role in the total energy. Interaction energies for molecular pairs involving NH···N bonds indicate a dominant contribution to packing stabilization coming from coulomb component. Hirshfeld surfaces and 2D–fingerprint plots allowed us to 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 providing evidences on the dominant electrostatic nature of NH···N and NH···O interactions.
Highlights
Sulfonamides are considered potent antimicrobial agents [1]
A Calculated at B3LYP/6–311++G(d,p) approximation taking into account implicitly solvent. b Oscillator strengths of calculated transitions are in atomic units. c Major contributions are shown in parentheses
Intermolecular interactions in title compound and seven related structures were studied with Pixel energies and Hirshfeld surfaces showing that the crystal packing is stabilized by strong N\\H···N or N\\H···O hydrogen bonds and weaker C\\H···O hydrogen bonds, together with short π···π and/or C-H···π stacking contacts for six structures
Summary
Sulfonamides are considered potent antimicrobial agents [1]. Nowadays there are some problems associated with the occurrence of drug-resistant microbial strains and the demand for new and better antibacterial compounds makes relevant the research on this field and the search for new antimicrobial agents. Sulfonamides can be used for the treatment of different infections including chancroid, nocardiosis and infections in the urinary tract caused by some microorganism like E. coli and others. These compounds can exhibit a wide variety of pharmacological activities such as anti-tumor, anti-viral, anti-fungal, anticarbonic anhydrase, diuretic, among others [2,3,4,5]. Mondal and co-workers have reported the synthesis and structural characterization of Schiff bases derived from sulfamethoxazole and substituted salicylaldehydes [13] These compounds exhibit antimicrobial activity against several Gram-positive and Gram-negative bacteria
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