Synthetic, XRD, non-covalent interactions and solvent dependent nonlinear optical studies of Sulfadiazine-Ortho-Vanillin Schiff base: (E)-4-((2-hydroxy-3-methoxy-benzylidene) amino)-N-(pyrimidin-2-yl)benzene-sulfonamide

Author(s)

Shahid, Muhammad ^[1] ; Salim, Muhammad ^[2] ; Khalid, Muhammad ^{[3, 4]} ; Tahir, Muhammad Nawaz ^[5] ; Khan, Muhammad Usman ^[6] ; Carmo Braga, Ataualpa Albert ^[7]

Affiliation

^[1] Govt Community Coll Township, Dept Chem, Lahore - Pakistan

^[2] Govt Islamia Coll Civil Lines, Dept Chem, Lahore - Pakistan

^[3] Univ Educ Lahore, Dept Chem, Faisalabad Campus, Faisalabad - Pakistan

^[4] Khwaja Fareed Univ Engn & Informat Technol, Dept Basic Sci & Humanities, Rahim Yar Khan - Pakistan

^[5] Univ Sargodha, Dept Phys, Sargodha - Pakistan

^[6] Govt Coll Univ, Dept Appl Chem, Faisalabad - Pakistan

^[7] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo - Brazil

• Document type: Journal article
• Source: Journal of Molecular Structure; v. 1161, p. 66-75, JUN 5 2018.
• Web of Science Citations: 20

Abstract

In this study, Sulfadiazine-Ortho-Vanillin Schiff base namely (E)-4-((2-hydroxy-3-methoxybeniylidene) amino)-N-(pyrimidin-2-yl)benzene-sulfonamide (BS) was synthesized. Chemical characterization and computational studies using different techniques like XRD, FT-IR, UV-Vis, NBO, FMO, and MEP have been employed. Density functional theory (DFT) calculations have been performed at M06-2X/6-311 + G(d,p) level of theory to obtain optimized geometry and vibrational wave numbers for (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)-N-(pyrimidin-2-yl)benzene- sulfonamide (BS). The DFT optimized geometry supports the experimental XRD parameters. Frontier molecular orbital (FMO) energies and molecular electrostatic potential (MEP) surfaces have been executed at M06-2X/6-311 + G(d,p) level of theory. NBO analysis has been carried out at M06-2X/6-311 + G(d,p) level which not only discovered the hyper conjugative interactions and stability in title molecule but also reconfirmed the existence of N-H center dot center dot center dot N hydrogen bonds between the dimer. The findings of small E-HOMO-E-LUMO gap shows less hardness and larger softness values which suggested the bioactiveness of the title molecule. Finally, the effect of solvent on nonlinear optical (NLO) properties has been executed using M06-2X level of theory and 6-311 + G (d,p) basis set. The solvent polarity enhanced the NLO response from 3.62 x 10(-30) esu to 4.66 x 10(-30) esu indicating the considerable NLO character hence in general may have potential applications in the development of non-linear optical materials. (c) 2018 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support Opportunities: Regular Research Grants