title: Synthesis, structural and computational characterization of 2-amino-3,5-diiodobenzoic acid and 2-amino-3,5-dibromobenzoic acid.
abstract: The benzoic acid compounds 2-amino-3,5-dibromobenzoic acid (2A35Br) and 2-amino-3,5-diiodobenzoic (2A35I) acid have been synthesized and characterized by single-crystal X-ray diffraction, FT-IR spectroscopy, UV-Vis spectroscopy and computational methods. Molecular geometry, intra- and inter-molecular interactions have been investigated by using X-ray diffraction technique. Fundamental vibrational bands of the title compounds were founded by FT-IR and UV-Vis method was used to obtain electronic bands. Geometry optimizations and the calculation of IR frequencies were performed both Gaussian type orbitals at Gaussian 09W and Slater type orbitals at ADF2009.01 software. The calculations are compatible with the experiment results. In addition, geometrical parameters, energies, HOMO-LUMO gaps and electrophilicity indexes have been calculated for thirty possible positional isomers of 2A35Br and 2A35I. Calculations show that 2A35Br and 2A35I isomers have the lowest energy, the narrowest HOMO-LUMO gap and the highest electrophilicity index values. Molecular electrostatic potential maps, Fukui indices, natural bond orbital analysis, thermodynamic parameters and non-linear optical properties of the 2A35Br and 2A35I were also investigated by theoretical calculations.
authors: Department of Property Protection and Security, Dereli Vocational School, Giresun University, 28950 Giresun, Turkey. Electronic address: hakki.yildirim@giresun.edu.tr.
authors: M Hakkı
authors: MH
authors: Yıldırım
authors: Department of Physics, Faculty of Arts and Science, Ondokuz Mayıs University, 55139 Samsun, Turkey.
authors: Hümeyra
authors: H
authors: Paşaoğlu
authors: Department of Textile Engineering, Faculty of Engineering, Pamukkale University, 20070 Denizli, Turkey.
authors: Hakkı Yasin
authors: HY
authors: Odabaşoğlu
authors: Department of Chemistry and Chemical Processing Technology, Denizli Vocational School of Tech. Sci., Pamukkale Univ., 20070 Denizli, Turkey.
authors: Mustafa
authors: M
authors: Odabaşoğlu
authors: Department of Physics, Faculty of Arts and Science, Giresun University, 28200 Giresun, Turkey.
authors: Arzu Özek
authors: AÖ
authors: Yıldırım
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis* / Q000737:chemistry*; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D012984:Software
chemical_list: D001565:Benzoates
keywords: 2-Amino-3,5-dibromobenzoic; 2-Amino-3,5-diiodobenzoic; Aminobenzoic acids; Crystal structures; DFT