Single crystal exploration, supramolecular behaviour, Hirshfeld surface analysis, linear and non-linear theoretical optical properties of Schiff bases derived from Benzene sulfonamides

The current research work is about the efficient synthesis of three crystalline Schiff bases derived from benzene sulfonamides named as (E)-4-((3-ethoxy-2-hydroxybenzylidene)amino)benzenesulfonamide ( ASES ), (E)-4-((3-ethoxy-2-hydroxybenzylidene)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide ( SMB ), (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide ( SES ) and their characterization by single-crystal X-rays diffraction (SC-XRD) studies. The molecular configuration of ASES and SMB is stabilized by intramolecular O-H center dot center dot center dot N bonding, whereas C-H center dot center dot center dot O intramolecular H-bonding is responsible for the stabilization of the molecular configuration of SES . The N-H center dot center dot center dot O intermolecular H-bonding is the main aspect of the supramolecular behaviour of ASES , while the N-H center dot center dot center dot O and C-H center dot center dot center dot O intermolecular H-bonding are the major features of the supramolecular behaviour of SMB and SES , respectively. The S-O center dot center dot center dot zr interaction performs a significant role in the stabilization of the molecular assembly of the SMB , whereas the C-H center dot center dot center dot zr interaction stabilizes the molecular assembly of SES . The role of weak off-set zr center dot center dot center dot zr interaction in all three compounds is also explored. The non-covalent interactions of strong as well as comparatively weak nature are further comprehensively explored by Hirshfeld surface (HS) analysis for the further exploration of the molecular assembly. Furthermore, we have also applied quantum chemical methods to calculate the linear and nonlinear optical (NLO) properties of synthesized compounds. The average linear polarizability values for ASES, SMB , and SES are found to be 34.83 x 10 -24 esu, 40.14 x 10 -24 esu, and 42.67 x 10 -24 esu, respectively, while the third-order NLO average polarizability amplitudes of ASES, SMB , and SES are found to be reasonably larger, amounting to 58.89 x 10 -36 esu, 83.35 x 10 -36 esu, and 69.69 x 10 -36 esu at the M06-2X/6-311G * levels of theory, respectively. A comparison of average NLO polarizabilities shows that the amplitudes of SMB and SES are 41% and 18% larger than that of ASES , respectively, which are also 3 and 2.5 times larger than that of para -nitroaniline ( p -NA) as calculated using the same methodology. We believe that the above-synthesized compounds will have decent potential to be used as NLO materials. (c) 2022 Elsevier B.V. All rights reserved.

Automated summary

The current research focuses on the efficient synthesis and characterization of three crystalline Schiff bases derived from benzene sulfonamides. The study investigates the molecular assembly and optical properties of the synthesized compounds.