title: Synthesis, crystal structure, spectroscopic and density functional theory (DFT) study of N-[3-anthracen-9-yl-1-(4-bromo-phenyl)-allylidene]-N-benzenesulfonohydrazine.
abstract: N-[3-anthracen-9-yl-1-(4-bromo-phenyl)-allylidene]-N-benzenesulfonohydrazine has been synthesized and characterized by various spectroscopic techniques including FT-IR, UV-vis, (1)H-NMR, (13)C-NMR spectroscopy, and the structure was unequivocally confirmed by single crystal X-ray diffraction studies. The compound crystallized in monoclinic system with P21/n space group, and adopted cis-geometry around the azomethine CN double bond. The X-ray crystal structure revealed that the intermolecular packing was stabilized by C-H⋯O type hydrogen bonding interaction, whereas NH was not involved in hydrogen bonding due to steric hindrance. Absorption wavelength was studied by scanning UV-vis. absorption spectrum in different solvents to explore excited state stability of the molecule in polar solvent. Density functional theory calculations were performed at B3LYP/6-31G (d, p) level in order to compare the experimental results with the theoretical results. The simulated molecular electrostatic potential (MEP), Mulliken charges and NPA (natural population analysis) also confirmed the presence of specific intermolecular hydrogen bonding (C-H⋯O). In addition natural bond orbital (NBO) analysis (intra and inter molecular bonding and interaction among bonds), frontier molecular orbital analysis (electronic properties) and first hyperpolarizability analysis (nonlinear optical response) were simulated at B3LYP/6-31G (d, p) level of theory.
authors.affiliation: Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
authors.forename: Muhammad Nadeem
authors.initials: MN
authors.lastname: Arshad
authors.affiliation: Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
authors.forename: Abdullah M
authors.initials: AM
authors.lastname: Asiri
authors.affiliation: Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
authors.forename: Khalid A
authors.initials: KA
authors.lastname: Alamry
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan. Electronic address: mahmood@ciit.net.pk.
authors.forename: Tariq
authors.initials: T
authors.lastname: Mahmood
authors.affiliation: Department of Chemical Engineering, COMSATS Institute of Information Technology, Defence Road, Off Raiwind Road, Lahore, Pakistan. Electronic address: mazhargilani@ciitlahore.edu.pk.
authors.forename: Mazhar Amjad
authors.initials: MA
authors.lastname: Gilani
authors.affiliation: Department of Chemistry, COMSATS Institute of Information Technology, University Road, Tobe Camp, 22060 Abbottabad, Pakistan; Department of Chemistry, College of Science, King Faisal University, Al-Hafouf 31982, Saudi Arabia.
authors.forename: Khurshid
authors.initials: K
authors.lastname: Ayub
authors.affiliation: Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia.
authors.forename: Abdulhadi Salih
authors.initials: AS
authors.lastname: Birinji
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D011789:Quantum Theory; D013056:Spectrophotometry, Ultraviolet; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D001555:Benzene Derivatives; D006834:Hydrazines; D013450:Sulfones; C034020:anthracene
keywords: DFT; First hyperpolarizability; Hydrazone; MEP; Mulliken and NPA; NBO