Synthesis, Characterization, Structural Study, Hirshfeld Surface Analysis and Antibacterial Activity of a New Dithiophosphorus Compound with a P(S)(S)(N)(C) Skeleton

Document Type : Research Article

Authors

1 Department of Chemistry, Germi Branch, Islamic Azad University, Germi, I.R. IRAN

2 Department of Chemistry, NUI Galway, Galway, Ireland

Abstract

In the present study, the new compound from Dithiophosphorus with the formula [(S–) (S)P(OC6H4-p-CH3) (NHCH2CH2NH(Me)2) +] was prepared and determined by IR spectroscopy, 1H, 13C NMR, 31P NMR, elemental analysis and single crystal X-ray diffraction analysis. Structural analysis revealed that the compound was crystallized in monoclinic crystal system with P21/c space group. The crystal structure of the compound showed that asymmetric unit contains two molecules and the phosphorus atom displayed P(S)(S)(N)(C) a distorted tetrahedral environment. In the crystal structure N-H…S=P H-bonding produced a one dimensional molecular structure along the b axis. This pattern contains  and  motifs. Hirshfeld surfaces and two-dimensional fingerprint plots are generated using the Crystal Explorer software program in which the CIF input file is used. These analyses revealed that H…H interactions had 51.1 % and 50.9 % portions of total interactions for the two molecules. Antibacterial properties of the new compound were additionally tested against E. coli, P. aeruginosa, S. aureus and B. cereus.

Keywords

Main Subjects

References

[1] Haiduc I., Thiophosphorus and Related Ligands in Coordination, Organometallic and Supramolecular Chemistry, J. Organomet. Chem., 623: 29–42 (2001).
[2] Silvestru C., Socaciu C., Bara A., Haiduc I., The First Organoantimony(III) Compounds Possessing Antitumor Properties: Diphenylantimony(III) Derivatives of Dithiophosphorus Ligands, Anticancer Res., 10: 803–804 (1990).
]3 [صمدی زاده، مرجانه؛ علیزاده، شیرین؛ کشاورز، شهریار؛ سنتز روی دی آلکیل دی تیو فسفات­ها به عنوان ماده افزودنی به روغن موتور و بررسی ویژگی­های آنتی اکسیدانی و ضد سایشی آن ها، نشریه شیمی و مهندسی شیمی ایران، (4)36: 71 تا 76 (1396)
[4] Tait B.K., Cobalt-nickel Separation: the Extraction of Cobalt(II) and Nickel(II) by Cyanex 301, Cyanex 302 and Cyanex 272, Hydrometallurgy, 32: 365–372 (1993).
[5] Ocio A., Almela A., Elizalde M.P., Cadmium(II) Extraction from Phosphoric Media by Bis(2,4,4‐Trimethylpentyl)Dithiophosphinic Acid (CYANEX 301), Solvent. Extr. Ion. Exch., 22: 961–977 (2004).
[6] Bhaattacharyya A., Mohapatra P.K., Manchanda V.K., Separation of Am3+ and Eu3+ Using an Extraction Chromatographic Resin Containing Bis(2,4,4-trimethylpentyl)dithiophosphinic Acid as the Stationary Phase, J. Chromatogr., 1123: 26–30 (2006).
[7] Singh R., Khwaja A.R., Gupta B., Tandon N.S., Extraction and Separation of Nickel(H) Using Bis (2,4,4-trimethylpentyl)dithiophosphinic Acid (cyanex 301) and its Recovery from Spent Catalyst and Electroplating Bath Residue, Solvent. Extr. Ion. Exch., 17: 367–390 (1999).
[8] Saadat A., Gholivand K., McArdle P., Synthesis, Characterization, Crystal Structure and Antibacterial Evaluation of Ni (II) Complex with New Dithiophosphorus Compound, Phosphorus, Sulfur, and Silicon and the Related Elements, 191: 1313–1317 (2016).
[9] Bina G., Zarena Begum I., Separation and Removal of Arsenic from Metallurgical Solutions Using Bis(2,4,4-trimethylpentyl)dithiophosphinic acid as Extractant, Sep. Purif. Technol., 63: 77–85 (2008).
[10] Eto M., Functions of Phosphorus Moiety in Agrochemical Molecules, Biosci. Biotech. Biochem., 61: 1–11 (1997).
[11] Shabana R., Atrees S.S., Studies on Organophosphorus Compounds Part XVII. the Reaction of Lawesson's Reagent with 1,2-Phenylenediamine Derivatives, 2-Aminophennol and 2-Amino-2-methyl-1-propanol, a New Rout to 1,3,2-Diazaphosphole-2-sulfide, Phosphorus, Sulfur and Silicon and the Related Elements, 105: 57–62 (1995).
[12] Fahmy A.A., Simple New Routes to Phosphorins from 2-Mercapto-1,3,4-oxa and Thiadiazole and 3-Mercapto-1,2,4-triazole, Phosphorus, Sulfur and Silicon and the Related Elements, 68: 139–145 (1992).
[13] van Zyl W.E., Fackler J.P., A General and Convenient Route to Dithiophosphonate Salt Derivatives, Phosphorus, Sulfur Silicon and the Related Elements, 167: 117–132 (2000).
[14] Banaei A., Saadat A., Mohammad Goli M., McArdle P., Pourbasheer E., Pargolghasemi P., Synthesis, Characterization, and Molecular Structures of Ni(II) and Cd(II) Complexes Derived from Dithiophosphonate, Heteroatom Chemistry, 27: 353–360 (2016).
[15] Banaei A., Saadat A., McArdle P., Mohammad Goli M., Crystal Structure, Antibacterial Activity and Nanoparticles of Cd(II) Complex Derived from Dithiophosphonate Ligand, Phosphorus, Sulfur Silicon and the Related Elements, 193: 369–374 (2018).
[16] Mehrotra R.C., Svrivastava G., Chauhan B.P.S., Dialkyldithiophosphate Derivatives of Non-transition Elements, Coord. Chem. Rev., 55: 207–259 (1984).
[17] Yed B., Yousif N.M., Pedersen U., Thomsen I., Lawesson S.O., Studies on Organophosphorus Compounds XLVII Preparation of Thiated Synthons of Amides, Lactams and Imides by use of Some New P,S-Containing Reagents, Tetrahedron, 40: 2047–2052 (1984).
[18] Scheibye S., Shabana R., Lawesson S.O., Studies on Organophosphorus Compounds XL: Reactions of Ketones with 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-Disulfide, Tetrahedron, 38: 993–1001 (1982).
[19] Albano V.G., Aragoni M.C., Arca M., Castellari C., Demartin F., Devillanova F.A., Isaia F., Lippolis V., Loddo L., Verani G., An Unprecedented Example of a Cis-Phosphonodithioato Nickel(ii) Complex Built by an Extensive Hhydrogen Bonding Supramolecular Network, Chem. Commun., 1170–1171 (2002).
[20] Aragoni M.C., Arca M., Demartin F., Devillanova F.A., Isaia F., Lippolis V., Verani G., An Unusual Cis-Phosphonodithioato Pd(II) Complex in an Extensive Hydrogen Bonding 3D Network, Inorg. Chim. Acta, 358: 213–216 (2005).
[21] Alberti E., Ardizzoia G.A., Brenna S., Castelli F., Galli S., Maspero A., The Synthesis of a New Dithiophosphonic Acid and its Coordination Properties Toward Ni(II): A Combined NMR and X-ray Diffraction Study, Polyhedron, 26: 958–966 (2007).
[22] Liu H.L., Mao H.Y., Xu C., Zhang H.Y., Hou H.W., Wu Q., Zhu Y., Ye B.X., Yuan L.J., Four Novel Sulfur-rich Complexes: Syntheses, Crystal Structures of Three Nickel(II) and One Cobalt(II) Complex with Derivatives of Lawesson's Reagent, Polyhedron, 23: 1799–1804 (2004).
[23] Sanchez G., Garcıa J., David J., Meseguer A., Jose L., Organometallic Nickel(II) Complexes with Dithiophosphate, Dithiophosphonate and Monothiophosphonate Ligands, Inorganica Chimica. Acta., 357: 677–683 (2004).
[24] Aragoni M.C., Arca M., Demartin F., Devillanova F.A., Graiff C., Isaia F., Lippolis V., Tiripicchio A., Verani G., Ring-Opening of Lawesson’s Reagent: New Syntheses of Phosphono- and Amidophosphono- Dithioato Complexes − Structural and CP-MAS 31P-NMR Characterization of [p-CH3OPh(X)PS2]2 M (X= MeO, iPrNH; M = NiII, PdII, and PtII), Eur. J. Inorg. Chem., 2239–2244 (2000).
[25] Clausen K., El Barbary A., Lawesson S., Studies on Organophosphorus Compounds XXXV1: A New Route to 4-Methoxyphenylphosphonothioic Diamides from 2,4-Bis(4-methoxyphenyl)-1,3,2,4-Dithiadiphosphetane-2,4-disulfide and Amines, Tetrahedron, 37: 1019–1025 (1981).
[26] Sheldrick G. M., SHELXT– Integrated Space-group and Crystalstructure Determination, Acta Crystallogr. A, 71: 3–8 (2015).
[27] Haiduc I., David L., Cozar O., Spectroscopic and Magnetic Studies of some Copper(II) and Chromium(III) Complexes with Dithiophosphonates as Ligands, J. Mol. Struct., 482: 153–157 (1999).
[28] Gilheany D.G., No d Orbitals but Walsh Diagrams and Maybe Banana Bonds: Chemical Bonding in Phosphines, Phosphine Oxides, and Phosphonium Ylides, Chem. Rev., 94: 1339–1374 (1994).
[29] (a) McKinnon J.J., Spackman M.A., Mitchell A.S., Novel Tools for Visualizing and Exploring Intermol­ecular Interactions in Molecular Crystals, Acta Crystallogr B, 60: 627–668 (2004).
(b) Spackman M. A., McKinnon J. J., Fingerprinting Intermolecular Interactions in Molecular Crystals, Cryst. Eng. Comm., 4: 378–392 (2002).
[30] Wolff S. K., Grimwood D. J., McKinnon J. J., Turner M. J., Jayatilaka D., Spackman M. A.," Crystal Explorer 3.1.", University of Western Australia, Crawley, Western, Australia, 2005–2013.
[31] Saadat A., Banaei A., Mcardle P., Zare K., Gholivand Kh., Ebramimi Valmoozi A.A., Ni(II) Complexes of Dithiophosphonic Acids, J. Chem. Sci., 126: 1125–1133 (2014)

Files

Share

How to cite

Statistics