title: Electrochemical and spectroscopic characteristics of p-acryloyloxybenzoyl chloride and p-acryloyloxybenzoic acid and antimicrobial activity of organic compounds.
abstract: The purpose of this multidisciplinary work is to characterize title compounds, p-acryloyloxybenzoyl chloride (ABC) and p-acryloyloxybenzoic acid (ABA) by means of experimental and theoretical evidences. As experimental research, Fourier transformation-infrared spectra (in the region 400-4000 cm(-1)) and nuclear magnetic resonance (NMR) chemical shifts (with a frequency of 400 MHz) are examined for spectroscopic properties belonging to the new synthesized compounds. Moreover, the compounds are investigated for antimicrobial activity against various microorganisms (Gram-positive and Gram-negative) by means of the visual inhibition zone technique on the agar media. The experimental results observed indicate that ABA exhibits more powerful inhibitors of microorganisms due to the presence of the hydroxyl group leading to higher reactive system, one of the most striking features of the paper. As for the theoretical studies, the optimized molecular structures, vibrational frequencies, corresponding vibrational spectra interpreted with the aid of normal coordinate analysis based on scaled density functional force field, atomic charges, thermodynamic properties at different temperature, 1H NMR chemical shifts by way of density functional theory (DFT) with the standard (B3LYP) methods at 6-311G++(d,p) basis set combination for the first time. According to findings, the 1H NMR chemical shifts and vibrational frequencies are obtained to be in good agreement with the suitable experimental results. Thus, it would be more precise to say that the calculation level chosen is powerful approach for understanding in the identification of the molecules investigated. At the same time, we determine the electrochemical characteristics belonging to the samples via the simulation of translation energy (HOMO-LUMO), molecular electrostatic potential (MEP) and electrostatic potential (ESP) investigations. It is observed that the strong intra-molecular charge transfer (ICT) appears between the donor and acceptor in the both compounds (especially ABA) due to the existence of the strong electronic donating groups and effective π-π* conjugated segments with high electronic donor ability for the electrophilic attack (intermolecular interactions).
authors.affiliation: Abant Izzet Baysal University, Department of Food Engineering, Bolu 14280, Turkey.
authors.forename: I
authors.initials: I
authors.lastname: Cakir
authors.affiliation: Abant Izzet Baysal University, Department of Chemistry, Bolu 14280, Turkey. Electronic address: ugursoykan@ibu.edu.tr.
authors.forename: U
authors.initials: U
authors.lastname: Soykan
authors.affiliation: Abant Izzet Baysal University, Department of Chemistry, Bolu 14280, Turkey.
authors.forename: S
authors.initials: S
authors.lastname: Cetin
authors.affiliation: Abant Izzet Baysal University, Department of Physics, Bolu 14280, Turkey.
authors.forename: F
authors.initials: F
authors.lastname: Karaboga
authors.affiliation: Abant Izzet Baysal University, Department of Physics, Bolu 14280, Turkey; Osmaniye Korkut Ata University, Department of Physics, Osmaniye 80000, Turkey.
authors.forename: Y
authors.initials: Y
authors.lastname: Zalaoglu
authors.affiliation: Abant Izzet Baysal University, Department of Physics, Bolu 14280, Turkey.
authors.forename: M
authors.initials: M
authors.lastname: Dogruer
authors.affiliation: Abant Izzet Baysal University, Department of Physics, Bolu 14280, Turkey.
authors.forename: C
authors.initials: C
authors.lastname: Terzioglu
authors.affiliation: Abant Izzet Baysal University, Department of Mechanical Engineering, Bolu 14280, Turkey.
authors.forename: G
authors.initials: G
authors.lastname: Yildirim
mesh_terms: D000179:Acrylates / Q000737:chemistry* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001565:Benzoates / Q000737:chemistry* / Q000494:pharmacology*; D019817:Benzoic Acid / Q000737:chemistry* / Q000494:pharmacology*; D004563:Electrochemistry; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D055672:Static Electricity; D013816:Thermodynamics
chemical_list: D000179:Acrylates; D000890:Anti-Infective Agents; D001565:Benzoates; C000595761:p-acryloyloxybenzoic acid; C000595758:p-acryloyloxybenzoyl chloride; D019817:Benzoic Acid; C013409:benzoyl chloride
keywords: ABA; ABC; Antimicrobial activity; B3LYP; ICT