Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Coordination Chemistry, Spectral, and Structural Characterizations of Mercury (II) Complexes with a New Phosphorus Ylide and Confirmation Ylide Reactive Site Toward Interaction with Metal Atom by Computational Methods

Document Type : Research Article

Authors
Alireza Dadras 1
Shahla Ebrahimnezhad 1
Mahsa Pourmirza 1
Ali Ramezani 2
Ali Soldoozi 3
1 Department of Chemistry, Faculty of Science, Urmia University, Postal Fund 57153-165 Urmia, I.R. IRAN
2 Department of Chemistry, Zanjan Branch, Islamic Azad University, Zanjan I.R. IRAN
3 Physics Group, Urmia Branch, Islamic Azad University, Urmia, I.R. IRAN
Abstract
The reaction of 2-bromo-1-(3-nitrophenyl) ethan-1-one with (tri-p-tolylphosphane) in acetone as solvent was led to effective ylide of 1-(3-nitrophenyl)-2-(tri-p-tolyl- λ5-phosphanylidene) ethan -1- one (NTPPY) (1). Then binuclear complexes of the type [HgX2 (ptolyl)3PCHCOC6H4NO2)] (X = Cl, Br and I), were prepared by the reaction of title ylide with mercury (II) halides in equimolar ratios, using dry methanol as solvent. The final products were characterized by IR, 1H, 13C, 31P NMR spectroscopic methods. The solid-state structure of (1) was established by X-ray crystallography analysis. Computational studies at DFT (B3LYP/6-31G*) level of theory were used to confirm ylide reactive site
Keywords
Coordination chemistry
Phosphorus ylide complexes
Hg (II) binuclear complexes
Tri-p-tolylphosphane
Transition metal complexes

Subjects

[1] Bhatti R. S., Shah S., Suresh., Krishan P., Sandhu J. S., Recent Pharmacological Developments on Rhodanines and 2,4-Thiazolidinediones, J. Medicinal Chem, 2013: 16 pages (2013).      
[2] Sabounchei S. J., Ahmadianpoor M.,  Yousefi A.,  Hashemi A.,  Bayat M.,  Sedghi A., Akhlaghi B. F., Gable R. W., New Pd(II) complexes of sulfur ylides; synthesis, X-ray characterization, a theoretical study and catalytic activity toward the Mizoroki–Heck reaction,RSC Adv, 6: 28308-28315 (2016).
[3] ضیایی حلیمه جانی، عظیم؛ آقابزرگ نانوا، پریچهر؛ لطفی نوسود، یزدانبخش؛ خلیلی، بهزاد؛ تهیه 4 - آریلیدین - 2- آلکیلتیو - -4H  تیازول - 5 - اون ها با استفاده از آمینواسیدهای بر پایه دیوتیوکاربامات و آلدهیدها، نشریه شیمی و مهندسی شیمی ایران، (3) 35: )1395(.
[4] Heng S., Tieu W., Hautmann S., Kuan K., Pedersen D. S., Pietsch M., Gütschow M., Abell A D, New cholesterol esterase inhibitors based on rhodanine and thiazolidinedione scaffolds, J. Bioorg & Med. Chem, 19(24): 7453–7463 (2011).     
[5] Arimori S., Matsubara O., Takada M., Shiro M., Shibata N., Difluoromethanesulfonyl hypervalent iodonium ylide for electrophilic difluoromethylthiolation reactions under copper catalysis, J. Royal society of chem, (2016).
[6] Zhou H., Wang G. X., Zhang W. Z., Lu X. B., CO2 Adducts of Phosphorus Ylides: Highly Active Organocatalysts for Carbon Dioxide Transformation, J. ACS Catal, 5 (11): 6773–6779 (2015).
[7] Spengler G., Ocsovszki I., Tönki ÁS., Saijo R., Watanabe G., Kawase M., Molnár J., Fluorinated β-Diketo Phosphorus Ylides Are Novel Inhibitors of the ABCB1 Efflux Pump of Cancer Cells, J. Anticancer Res, 35(11): 5915-9 (2015).
[8] Kincses A., Szabó ÁM., Saijo R., Watanabe G., Kawase M., Molnár J., Spengler G., Fluorinated Beta-diketo Phosphorus Ylides Are Novel Efflux Pump Inhibitors in Bacteria, J. Vivo, 30(6): 813-817 (2016).
[9] Kalkeren H. A. V., Blom A. L., Rutjes F. P. J. T., Huijbregts M. A. J, On the usefulness of life cycle assessment in early chemical methodology development: the case of organophosphorus-catalyzed Appel and Wittig reactions, J. Green Chem, 15: 1255 (2013).
[10] Liu S., Chen W., Luo J., Yu Y., [3+3] Annulation of allylic phosphoryl-stabilized carbanions / phosphorus ylides and vinyl azide: a practice strategy for polyfunctionalized anilines, J. Chem. Commun, 50: 8539-8542 (2014).
[11] Maigali S. S., Abd-El-Maksoud M. A., El-Hussieny M., Soliman F. M., Abdel-Aziz M.S., Shalaby E. S. M., Chemistry of phosphorus ylides: Part 41 Synthesis of antimicrobial agents from the reaction of aminoantipyrine, coumarin- and quinoline-carbaldehyde with phosphacumulene and phosphaallene ylides, J. Chem. Research, 38:.0 754–761(2014).
[12] Karami K., Hosseini-K. M., Shirani-Sarmazeh Z., Zahedi-Nasab R., Corrado Rizzoli, Janusz Lipkowski. NC Palladacycles and C,C-chelating phosphorus ylide complexes: synthesis, X-ray characterization, and comparison of the catalytic activity in the Suzuki-Miyaura reaction, J. coordination Chemistry, 69(5) (2016).
[13] Kolodiazhnyi O. I., “Phosphorus Ylides: Chemistry and Applications in Organic Synthesis”, wiley, E-book, (2008).
[14] Sabounchei S. J.,  Hosseinzadeh M.,  Hashemi A.,   Salehzadeh S., Maleki F., P,C-Chelation versus P,P- coordination of unsymmetrical phosphorus ylides in palladacyclopropa[60] fullerene complexes; synthetic spectroscopic, and theoretical studies, J.Dalton Trans, 45: 13899-13906 (2016).
[15] Spencer E. C., Kalyanasundari B., Mariyatra M. B., Howard J. A.K., Panchanatheswaran K., The preparation and structural elucidation of uranium (VI) complexes and salts of the phosphorus ylides Ph3PCHCOPh, Ph3PC(COMe)(COPh) and Ph3PCHCOOCH2CH3, Inorg. Chim. Acta, 359:35–43 (2006).
[16] Karami K., Büyükgüngör O., Dalvand H., Synthesis, spectroscopic and structural characterization of orthopalladated complexes with 4-phenylbenzoylmethylene triphenyl phosphorane ylide, J. Transition Met.Chem, 35(5): 621–626 (2010).
[17] Li X., Sun H., Harms K., Sundermeyer J., Simple Synthesis and Structure Characterization of a Stable Niobium(V) Phosphoniomethylidyne Complex, J. Organomet, 24 (19): 4699–4701(2005).
[18] Fedorov A., Chen P., Mechanistic Insights from the Gas-Phase Reactivity of Phosphorus-Ylid-Supported Benzylidene Gold Complexes, J. Organomet, 29(13): 2994–3000 (2010).
[19] Lin Tzu-P., Gabbaï F. P., Bis- and tris-phosphinostannane gold complexes featuring Au → Sn dative interactions: Synthesis, structures, and DFT calculations, J. Polyhedron, 125(29): 18–25 (2017).
[20] Sabounchei S. J., Pourshahbaz M., Salehzadeh S., Bayat M., Karamian R., Asadbegy M., Khavasi H. R., New chlorine bridged binuclear silver (I) complexes of bidentate phosphorus ylides: Synthesis, spectroscopy, theoretical and anti-bacterial studies, J.  Polyhedron, 85: 652-664(2015).
[21] Brownie J. H., Baird Michael C., Coordination complexes of aryl- and alkylphosphonium cyclopentadienylides (cyclopentadienylidene ylides), C5R4PR′R′′R′′′ (R = H, alkyl, aryl; R′, R′′, R′′′ = alkyl, aryl), Coordination Chem Rev. 252: 1734–1754 (2008).
[22] Sabounchei S. J., Akhlaghi B. F., Boskovic C., Gable R. W., Karamian R., Asadbegy M., Reactivity of mercury (II) halides with the α-keto stabilized sulfonium ylides: crystal structures of two new polymer and binuclear complexes and in vitro antibacterial study, J Polyhedron, 53: 1-7 (2013).
[23] Estevez-Hernandez O., Duque J., Rodriguez-Hernandez J., Reguera E.,  Dinuclear and polymeric Hg(II) complexes with 1-(2-furoyl)thiourea derivatives: Their crystal structure and related properties, J. Polyhedron, 97: 148–156 (2015).
[24] Dadrass A., Rahchamani H., Khalafy J., Ramazani A., Parsa- Habashi B., Poursattar- Marjani A.,  Souldozi A., Slepokura K.,  Lis T., Rouhani M., Study Of Conversion Of Polymeric Organophosphorus Ylide Complexes Of  Mercury(Ii) Halides To Phenazine Complexes: X-Ray Crystal Structures And Spectral Characterizations,  J. Phosphorus, Sulfur, and Silicon, 190: 360–371 (2015).
[25] Garoufis A., Perlepes S., Schreiber A., Bau R., Hadjiliadis N., mercury (II) – Carbon bond cleavage due to the coordination of the metal by 2-(2/- pyridyl) quinoxaline(L): preparation and characterization of [Hg2I2L2] derived from the reaction of CH3HgI and L, J. Ppolyhedron, 15 (2): 177-182, (1996).
[26] Nascimento A. M., charton – Souza E., Operon mer: bacterial resistance to mercury and potential for bioremediation of contaminated environments, J. Genet. Mol. Res, 2 (1): 92-101 (2003).
[27] Wang D., Huang S., Liu P., Liu X., He Y., Chen W., Hu Q., Wei T., Gan J., Ma J., Chen H., Structural Analysis of the Hg(II)- Regulatory Protein Tn501 MerR from Pseudomonas aeruginosa, J. Scientific Reports, (2016).
[28] Sabounchei, S. J., Zamanian M., Pourshahbaz M., Bayat M., Karamian R., Asadbegy M., Synthesis, characterisation and theoretical and antibacterial studies of Hg(II), Cd(II) and Ag(I) complexes with a new monodentate phosphorus ylide, J. Chemical Research, 40: 127-191 (2016).
[29] Abdullah B. H.,  Salh y. M., Synthesis, characterization and biological activity of N-phenylÑ-(2-phenolyl)thiourea (PPTH) and its metal complexes of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Pd(II), Pt(II) and Hg(II), Oriental Journal of Chemistry, 26(3): 763-773 (2010).
[30] Shiekh A. R., Ab Rahman I., Malik A. M., Masudi M. S., Luddin N., Synthesis, Spectral, Electrochemical and Biological Studies of Nitrogen Donor Macrocyclic Ligand and its Transition Metal Complexes. Int. J. Electrochem. Sci., 7:12829 – 12845(2012).
[31] Sabounchei S. J., Akhlaghi B. F., Boskovic C., Gable W. R., Karamian R., Asadbegy M., Reactivity of mercury(II) halides with the a-keto stabilized sulfonium ylides: Crystal structures of two new polymer and binuclear complexes and in vitro antibacterial study, J. Polyhedron, 53: 1–7 (2013).
[32] Sabounchei S. J., Zamanian M., Pourshahbaz M., Bayat M., Karamian R. Asadbegy M., Synthesis, characterisation and theoretical and antibacterial studies of Hg(II), Cd(II) and Ag(I) complexes with a new monodentate phosphorus ylide, J. Chem. Research, 40: 130–136 (2016).
[33] Spencer E.C., Mariyatra M.B., Howard J.A.K., Kenwright A.M., Panchanatheswaran K., The synthesis and structural characterisation of the mercury (II) halide complexes of the phosphorus ylide Carbethoxymethylenetriphenylphosphorane, J. Organomet. Chem, 692(5): 1081–1086 (2007).
[34] CrysAlisCCD and CrysAlisRED in Xcalibur PX software., Agilent Technologies, Yarnton,Oxfordshire, England, (2010).
[35] Sheldrick G. M., Acta Crystallogr, Sect. A, 64: 112 - 122 (2008).
[36] Brandenburg K., DIAMOND Version 3.2k. Crystal Impact GbR, Bonn, Germany. (2014).
[37] Schmidt M. W., Baldridge K. K., Boatz J. A., Elbert S. T., Gordon M. S., Jensen J. H., Koseki S., Matsunaga N., et al. General atomic and molecular electronic structuresystem, J. Comput. Chem, 11, 1347–1363 (1993).
[38] Lee C., Yang W., Parr R. G., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B: Condens. Matter Mater. Phys.  37(2): 785- 789 (1988).      
[39] Foster P., Weinhold F., Natural hybrid orbitals, J. Am. Chem. Soc, 102(24): 7211-7218 (1980).
[40] Dadrass A.R.,  Ramazani A., Poursattar Marjani A., Rahchamani H., Nasri Koureh H., Souldozi A., Samiee S., Ślepokurae K., Lise T., Synthesis and Structural Characterization of Organophosphorus Ylide-1-(3-nitrophenyl)-2- (triphenyl phosphoranylidene)ethanone, Chinese J. Struct. Chem 34(3) 373-378 (2015).
[41]  Sabounchei S. J., Panahimehr M., Khavasi H. R., Akhlaghi Bagherjeri F., Boscovic C., Mercury (II) complexes of  new bidentate phosphorus ylides: synthesis, spectra and crystal structures. J. Chemical Papers, 68 (5) 624–632 (2014).
[42] Akbarzadeh-Torbati N., Shahraki M., Assignment of the Major Geometrical Isomer of the Synthesized Stable Phosphorus Ylide: Crystallography and Theoretical Approaches, J. Biomedical & Pharmacology, 9(1), 133-142 (2016).
[43] Spencer E.C., Kalyanasundari B., Mariyatra M.B., Howard J.A.K., Panchanatheswaran K., The preparation and structural elucidation of uranium (VI) complexes and salts of the phosphorus ylides Ph3PCHCOPh, Ph3PC(COMe)(COPh) and Ph3PCHCOOCH2CH3. J. Inorganica Chimica Acta. 359(1), 35–43 (2006).