Synthesis and physic-chemical properties of a novel chromate compound with potential biological applications, bis(2-phenylethylammonium) chromate(VI)

Journal of Molecular Structure - Tập 1185 - Trang 168-182 - 2019
Sonia Trabelsi1, Noureddine Issaoui2, Silvia A. Brandán3, Fehmi Bardak4, Thierry Roisnel5, Ahmet Atac4, Houda Marouani1
1Université de Carthage, Faculté des Sciences de Bizerte, LR13ES08 Laboratoire de Chimie des Matériaux, 7021, Bizerte, Tunisie
2University of Monastir, Laboratory of Quantum and Statistical Physics (LR18ES18), Faculty of Sciences, Monastir 5079, Tunisia
3Cátedra de Química General, Instituto de Química Inorgánica, Facultad de Bioquímica, Química y Farmacia. Universidad Nacional de Tucumán. Ayacucho 471, San Miguel de Tucumán, 4000, Tucumán R, Argentina
4Department of Physics, Celal Bayar University, Manisa, Turkey
5Centre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042, Rennes, France

Tài liệu tham khảo

Balasubramanian, 1986, Ind. J. Chem., 25B, 326 Muzart, 1992, Chromium-catalyzed oxidations in organic synthesis, Chem. Rev., 92, 113, 10.1021/cr00009a005 Le Flem, 1991, Eur. J. Solid State Inorg. Chem., 28 Aakerôy, 1989, A novel class of salts for second harmonic generation, J. Chem. Soc. Chem. Commun., 23, 1856, 10.1039/C39890001856 Sabbagh, 2015, Docking studies of flavonoid compounds as inhibitors of β-ketoacyl acyl carrier protein synthase I (Kas I) of Escherichia coli, J. Mol. Graph. Model., 61, 214, 10.1016/j.jmgm.2015.07.005 Ramesh, 2012, Antibacterial activity of Cr2O3 nanoparticles against E.coli; reduction of chromate ions by Arachis hypogaea leaves, Aech. Appl. Sci. Res., 4, 1894 Moudgal, 2010, Antifungals to treat Candida albicans, Expert Opin. Pharmacother., 11, 2037, 10.1517/14656566.2010.493875 Abad-Zapatero, 1996, Structure of a secreted aspartic protease from C. albicans complexed with a potent inhibitor: implications for the design of antifungal agents, Protein Sci., 5, 640, 10.1002/pro.5560050408 Li, 2014, Role of Candida albicans-secreted aspartyl proteinases (Saps) in severe early childhood caries, Int. J. Mol. Sci., 15, 10766, 10.3390/ijms150610766 Paterson, 1990, A modulator of catecholamine transmission in the mammalian central nervous system?, J. Neurochem., 55, 1827, 10.1111/j.1471-4159.1990.tb05764.x Parrott, 1987, 2-Phenylethylamine catabolism by Escherichia coli K12, J. Gen. Microbiol., 133, 347 Altomare, 1999, SIR97: a new tool for crystal structure determination and refinement, J. Appl. Crystallogr., 32, 115, 10.1107/S0021889898007717 Bruker, 2006 Sheldrick, 2015, Crystal structure refinement with SHELXL, ActaCryst, C71, 3 Farrugia, 2012, WinGX and ORTEP for windows: an update, J. Appl. Crystallogr., 45, 849, 10.1107/S0021889812029111 Frisch, 2010 Computer Program Gauss View 5.0.9, Gaussian Inc, Wallingford, CT 06492 USA. Bader, 1990 Lu, 2012, Multiwfn: a multifunctional wavefunction analyzer, J. Comput. Chem., 33, 580, 10.1002/jcc.22885 Humphrey, 1996, VMD—visual molecular dynamics, J. Mol. Graph., 14, 33, 10.1016/0263-7855(96)00018-5 Borelli, 2008, X-ray structures of Sap1 and Sap5: structural comparison of the secreted aspartic proteinases from Candida albicans, Proteins Struct. Funct. Bioinforma., 72, 1308, 10.1002/prot.22021 Borelli, 2007, The crystal structure of the secreted aspartic proteinase 3 from Candida albicans and its complex with pepstatin A, Proteins Struct. Funct. Bioinforma., 68, 738, 10.1002/prot.21425 Pappenberger, 2007, Structure-assisted discovery of an aminothiazole derivative as a lead molecule for inhibition of bacterial fatty-acid synthesis, Acta Crystallogr., D63, 1208 Trajtenberg, 2014, Structural insights into bacterial resistance to cerulenin, FEBS J., 281, 2324, 10.1111/febs.12785 Gajiwala, 2009, Crystal structures of bacterial FabH suggest a molecular basis for the substrate specificity of the enzyme, FEBS Lett., 583, 2939, 10.1016/j.febslet.2009.08.001 Morris, 2009, AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility, J. Comput. Chem., 30, 2785, 10.1002/jcc.21256 Hsu, 2011, iGEMDOCK: a graphical environment of enhancing GEMDOCK using pharmacological interactions and post-screening analysis, BMC Bioinf., 12, S33, 10.1186/1471-2105-12-S1-S33 Yang, 2004, GEMDOCK: a generic evolutionary method for molecular docking, Proteins Struct. Funct. Bioinforma., 55, 288, 10.1002/prot.20035 Delano, 2015 Tadesse, 2005, Assessment of the antimicrobial activity of lactic acid bacteria isolated from Borde and Shamita, traditional Ethiopian fermented beverages, on some foodborne pathogens and effect of growth medium on the inhibitory activity, 5, Int. J. Food Saf., 13 Celikatas, 2007, In vitro antioxidant activities of Rosmarinus officinalis extracts treated with supercritical carbon dioxide, Food Chem., 101, 1457, 10.1016/j.foodchem.2006.03.055 Sacchetti, 2005, Comparative evaluation of 11 essential oils of different origin as functional antioxidants, antiradicals and antimicrobials in foods, Food Chem., 91, 621, 10.1016/j.foodchem.2004.06.031 Gopalakrishnan, 2011, Antibacterial activity of azo compounds synthesized from the natural renewable source, cardanol, J. Chem. Pharmaceut. Res., 3, 490 Trabelsi, 2014, Propane-1,2-diammonium chromate(VI), Acta Crystallogr., E70, m84 Sudhahar, 2014, 2-Phenylethylammonium p-hydroxybenzoate: growth, structural, spectral, thermal, optical and mechanical characterization, Optik Int. J.Light Electr. Opt., 125, 4327, 10.1016/j.ijleo.2014.03.030 Billing, 2007, Bis(1-phenylethylammonium) hexachloridostannate(IV) and bis(2-phenylethylammonium) hexachloridostannate(IV), Acta Crystallogr., C63, m101 Oh, 2011, Bis(2-phenylethylammonium) tetrachloridocobaltate(II), Acta Crystallogr., E67, m522 Blessing, 1986, Hydrogen bonding and thermal vibrations in crystalline phosphate salts of histidine and imidazole, ActaCryst, B42, 613 Brown, 1976, On the geometry of O–H⋯O hydrogen bonds, ActaCryst, A32, 24 Benzon, 2015, Spectroscopic and theoretical characterization of 2-(4-methoxyphenyl)-4,5-dimethyl-1H-imidazole 3-oxide, Spectrochim. Acta, 151, 965, 10.1016/j.saa.2015.07.020 Bhagyasree, 2013, Vibrational spectroscopic (FT-IR, FT-Raman, 1H NMR and UV) investigations and computational study of 5-nitro-2-(4-nitrobenzyl) benzoxazole, Spectrochim. Acta, 102, 99, 10.1016/j.saa.2012.09.032 McKinnon, 1998, Hirshfeld surfaces: a new tool for visualising and exploring molecular crystals, Chem. A Eur., 4, 2136, 10.1002/(SICI)1521-3765(19981102)4:11<2136::AID-CHEM2136>3.0.CO;2-G Spackman, 2002, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm, 4, 378, 10.1039/B203191B Wolff, 2013 Jelsch, 2014, The enrichment ratio of atomic contacts in crystals, an indicator derived from the Hirshfeld surface analysis, IUCrJ, 1, 119, 10.1107/S2052252514003327 Rauhut, 1995, J. Phys. Chem., 99, 3093, 10.1021/j100010a019 Rauhut, 1995, J. Phys. Chem., 99, 14572, 10.1021/j100039a056 Sundius, 2002, Scaling of ab initio force fields by MOLVIB, Vib. Spectrosc., 29, 89, 10.1016/S0924-2031(01)00189-8 Gatfaoui, 2018, Synthesis and Characterization of p-Xylylenediaminium bis(nitrate). Effects of the Coordination Modes of Nitrate Groups on Their Structural and Vibrational properties, J. Mol. Struct., 1151, 152, 10.1016/j.molstruc.2017.09.027 Gatfaoui, 2017, Synthesis, structural and spectroscopic features, and investigation of bioactive nature of a novel organic-inorganic hybrid material 1H-1,2,4-triazole-4-ium trioxonitrate, J. Mol. Struct., 1150, 242, 10.1016/j.molstruc.2017.08.092 Höppe, 2013, A structural and vibrational study on the first potassium borosulfate, K5[B(SO4)4] by using the FTIR-Raman and DFT calculations, J. Mol. Struct., 1037, 294, 10.1016/j.molstruc.2012.12.042 Keresztury, 1993, Vibrational spectra of monothiocarbamates-II. IR and Raman spectra, vibrational assignment, conformational analysis and ab initio calculations of S-methyl-N,N-dimethylthiocarbamate Spectrochim, Acta, 49A, 2007 Michalska, 2005, The prediction of Raman spectra of platinum(II) anticancer drugs by density functional theory, Chem. Phys. Lett., 403, 211, 10.1016/j.cplett.2004.12.096 S. A. Brandán, Volume 1: A structural and vibrational study of the chromyl chlorosulfate, fluorosulfate, and nitrate compounds, Editor by Ken Derham, Springer Science, Business Media B.V., Van Godewijckstraat vol. 30, 3311 GZ Dordrecht, Netherlands. ISBN: 978-94-007-5762-2 (Print) 978-94-007-5763-9 (Online) October 2012. S. A. Brandán, Volume 2: a structural and vibrational investigation into chromylazide, acetate, perchlorate, and thiocyanate compounds, Editor by Ken Derham, Springer Science, Business Media B.V., Van Godewijckstraat vol. 30, 3311 GZ Dordrecht, Netherlands. ISBN: 978-94-007-5753-0 (Print) 978-94-007-5754-7 (Online) October 2012. Sudhahar, 2014, Optik, 125, 4327, 10.1016/j.ijleo.2014.03.030 Ben M’leh, 2018, Synthesis, molecular structure, vibrational and theoretical studies of a new non-centrosymmetric organic sulphate with promising NLO properties, J. Mol. Struct., 1171, 771, 10.1016/j.molstruc.2018.06.041 Marchewka, 2002, Infrared and Raman spectra of melaminium chloride hemihydrate, Mater. Sci. Eng. B, 95, 214, 10.1016/S0921-5107(02)00235-0 Weckhuysen, 1997, Diffuse reflectance spectroscopy of supported chromium oxide catalysts: a self-modeling mixture analysis, J. Catal., 166, 160, 10.1006/jcat.1997.1518 Tauc, 1968, Optical properties and electronic structure of amorphous Ge and Si, Mater. Res. Bull., 3, 37, 10.1016/0025-5408(68)90023-8 Rui-Feng, 2006, Synthesis and crystal structure of 7-nitro-5-sulfo-napthalene-1,4-dicarboxylate acid, Chin. J. Struct. Chem., 25, 849 Parr, 1991, Principle of maximum hardness, J. Am. Chem. Soc., 113, 1854, 10.1021/ja00005a072 Parr, 1999, Electrophilicity index, J. Am. Chem. Soc., 121, 1922, 10.1021/ja983494x Koch, 1995, Characterization of C-H-O hydrogen bonds on the basis of the charge density, J. Phys. Chem. Soc., A99, 9747, 10.1021/j100024a016 Rozas, 2000, Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors, J. Am. Chem. Soc., 122, 11154, 10.1021/ja0017864 Espinosa, 1998, Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities, Chem. Phys. Lett., 285, 170, 10.1016/S0009-2614(98)00036-0 Ott, 2000 Zhang, 2010, Experimental and theoretical studies on o-, m- and p-chlorobenzylideneaminoantipyrines, Spectrochim, Acta, 75, 1115 Johnson, 2010, Revealing noncovalent interactions, J. Am. Chem. Soc., 132, 6498, 10.1021/ja100936w Scrocco, 1978, Electronic molecular structure, reactivity and intermolecular forces: an euristic interpretation by means of electrostatic molecular potentials, Adv. Quantum. Chem., 11, 115, 10.1016/S0065-3276(08)60236-1 Luque, 2000, Perspective on “Electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects”, Theor. Chem. Acc., 103, 343, 10.1007/s002149900013 Politzer, 2002, The fundamental nature and role of the electrostatic potential in atoms and molecules, Theor. Chem. Acc., 108, 134, 10.1007/s00214-002-0363-9 Thul, 2010, Structural and spectroscopic studies on 2-pyranones, Spectrochim. Acta, 75, 251, 10.1016/j.saa.2009.10.020