56
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

A facile synthesis and comparative structural characterization with DFT, fluorescence behavior, and anti-microbial activity of O,O'-diethyl-S-(N-phthalimidomethyl) dithiophosphate

, ORCID Icon, , , , & show all
Pages 673-681 | Received 29 Apr 2022, Accepted 30 Jan 2023, Published online: 30 Mar 2023

References

  • Alimarin, I. P.; Rodionova, T. V.; Ivanov, V. M. Extraction with Thio and Dithio Phosphorus Acids. Russ. Chem. Rev. 1989, 58, 863–878. DOI: 10.1070/RC1989V058N09ABEH003483/XML.
  • Ma, R.; Van Mol, W.; Adams, F. Flow Injection Sorbent Extraction with Dialkyldithiophosphates as Chelating Agent for the Determination of Zinc by Flame Atomic Absorption Spectrometry. Anal. Chim. Acta 1995, 309, 395–403. DOI: 10.1016/0003-2670(95)00053-3.
  • Jaeger, D. A.; Roberts, T. L.; Zelenin, A. K. Quaternary Ammonium O,O′-Dialkylphosphorodithioate Surfactants and Their Reactions with 2-Chloroethyl Phenyl Sulfide, a Mustard Simulant. Colloids Surf. A 2002, 196, 209–216. DOI: 10.1016/S0927-7757(01)00878-0.
  • Costa, L. G.; Cole, T. B.; Vitalone, A.; Furlong, C. E. Measurement of Paraoxonase (PON1) Status as a Potential Biomarker of Susceptibility to Organophosphate Toxicity. Clin Chim Acta 2005, 352, 37–47. DOI: 10.1016/J.CCCN.2004.09.019.
  • Gogoi, P. K.; Juthika, S. Effectiveness of Bis(2-Methyl Piperazine Dithiocarbamato) Cu(II) and Zn(II), Bis(Diethyl Dithiophosphato) Ni(II) and Its ϒ-Picoline Diadduct and Bis(Pyrrolidine Dithiocarbamato) Cu(II) as Antioxidant Lubricating Oil Additives. Indian J. Chem. Technol. 2005, 12, 50–54. https://nopr.niscair.res.in/handle/123456789/8593.
  • Ferreira, S. L. C.; de Andrade, J. B.; Das, G. A.; Korn, M.; de G. Pereira, M.; Lemos, V. A.; do Santos, W. N. L. d M.; Rodrigues, F.; Souza, A. S.; Ferreira, H. S.; et al. Review of Procedures Involving Separation and Preconcentration for the Determination of Cadmium Using Spectrometric Techniques. J. Hazard Mater. 2007, 145, 358–367. DOI: 10.1016/J.JHAZMAT.2007.03.077.
  • Yamaguchi, T.; Saito, H.; Maki, T.; Ito, T. Syntheses and Structures of Bridge and Chelate Isomers of Tetraplatinum(II) Cluster Complex with Diethyldithiophosphate Ion (Et2dtp) at in-Plane Sites, [Pt4(CH3COO)4(Et2dtp)4], and Their Mutual Isomerization Via Cluster Core Rotation. J. Am. Chem. Soc. 1999, 121, 10738–10742. DOI: 10.1021/JA990596U/SUPPL_FILE/JA990596U_S.PDF.
  • Chauhan, H. P. S.; Kori, K.; Shaik, N. M.; Singh, U. P. Synthetic and Spectroscopic Studies on Some Bis(Dialkyldithiocarbomato)-Arsenic(III) O,O’-Dialkyldithiophosphates. Phosphorus Sulfur Silicon Relat. Elem. 2005, 180, 31–40. DOI: 10.1080/104265004904948.
  • Liu, X.; Zhang, Q. F.; Leung, W. H. Syntheses and Molecular Structures of Ruthenium Complexes with Dithiophosphate Ligands. J. Coord. Chem. 2005, 58, 1299–1305. DOI: 10.1080/00958970500174061.
  • Barrado, G.; Miguel, D.; Riera, V.; García-Granda, S. η3-Allyl Molybdenum Dithiophosphate and Dithiophosphinate Complexes with Uni- and Bidentate Nitrogen Donor Ligands. X-Ray Structure of [Mo2(η3-C3H5)2(CO)4. {S2P(OEt)2}2(μ-NH2NH2)]. J. Organomet. Chem. 1995, 489, 129–135. DOI: 10.1016/0022-328X(94)05116-S.
  • Lefferts, J. L.; Molloy, K. C.; Zuckerman, J. J.; Haiduc, I.; Guta, C.; Ruse, D. Oxy and Thio Phosphorus Acid Derivatives of Tin. 1. Triorganotin(IV) Dithiophosphate Esters. Inorg. Chem. 1980, 19, 1662–1670. DOI: 10.1021/ic50208a046.
  • Molloy, K. C.; Hossain, M. B.; van der Helm, D.; Zuckerman, J. J.; Haiduc, I. Phosphoric Acid Derivatives of Tin. 2. Crystal and Molecular Structure of (O,O’-Diethyl Dithiophosphato)Triphenyltin(IV) at 138 K. A Unique Monodentate Dithiophosphate Derivative. Inorg. Chem. 1979, 18, 3507–3511. DOI: 10.1021/ic50202a043.
  • Singh, B. P.; Srivastava, G.; Mehrotra, R. C. Synthesis of Diorganotin Dialkylditelophoshiates. Synth. React. Inorg. Met. Chem. 1980, 10, 359–371. DOI: 10.1080/00945718008058247.
  • Chen, L.; You, H.; Yang, C.; Ma, D.; Qin, J. Novel, Highly Efficient Blue-Emitting Heteroleptic Iridium(III) Complexes Based on Fluorinated 1,3,4-Oxadiazole: Tuning to Blue by Dithiolate Ancillary Ligands. Chem. Commun. 2007, 1352–1354. DOI: 10.1039/b616493e.
  • Livingstone, S. E.; Mihkelson, A. E. Metal Chelates of Biologically Important Compounds. II. Nickel Complexes of Dialkyldithiophosphates and Their Adducts with Nitrogen Heterocycles1. Inorg. Chem. 1970, 9, 2545–2551. DOI: 10.1021/ic50093a033.
  • White, L. K.; Belford, R. L. Quadrupole Coupling Constants of Square-Planar Copper(II)-Sulfur Complexes from Single-Crystal Electron Paramagnetic Resonance Spectroscopy. J. Am. Chem. Soc. 1976, 98, 4428–4438. DOI: 10.1021/ja00431a016.
  • Jian, F.; Wang, W.; Zhao, P. Structure-Controlled Self-Assembly of Impeller-Shaped Crystal on the Transition Metal Fullerene Complexes. Cryst. Growth Des. 2006, 6, 2563–2566. DOI: 10.1021/cg060257u.
  • Casarin, M.; Maccato, C.; Vittadini, A. A Comparative Theoretical Investigation of Three Sodalite Systems: Cd4S(AlO2)6, Zn4O(BO2)6, and Zn4S(BO2)6. J. Phys. Chem. B 2002, 106, 2569–2573. DOI: 10.1021/jp013854u.
  • Ide, Y.; Shibahara, T. Reaction of the Mo3S4 Cluster with Dimethylacetylenedicarboxylate: An ESR-Active Cluster and an Organometallic Cluster Formed by α,β-Conjugate Addition. Inorg. Chem. 2007, 46, 357–359. DOI: 10.1021/ic0617285.
  • Lin, X.; Chen, H. Y.; Chi, L. S.; Zhuang, H. H. Synthesis and Crystal Structures of Two New Trinuclear Molybdenum Cluster Compounds Containing a [Mo3Te7]4 Fragment. Polyhedron 1998, 18, 217–223. DOI: 10.1016/S0277-5387(98)00289-7.
  • Sokolov, M.; Esparza, P.; Hernandez-Molina, R.; Platas, J. G.; Mederos, A.; Gavin, J. A.; Lusar, L.; Vicent, R. C. Preparation and Properties of the Full Series of Cuboidal Clusters [Mo xW4-xSe4(H2O)12]n+ (n = 4–6) and Their Derivatives. Inorg. Chem. 2005, 44, 1132–1141. DOI: 10.1021/ic049298a.
  • Matsumoto, K.; Tanaka, R.; Shimomura, R.; Nakao, Y. Synthesis and X-Ray Structures of Octanuclear Silver(I) cluster [Ag8(μ6-S){S2P(OC2H5)2}6.] and Its Copper(I) analogue [Cu8(μ8-S){S2P(OC2H5)2}6]. Inorg. Chim. Acta 2000, 304, 293–296. DOI: 10.1016/S0020-1693(00)00084-0.
  • Liu, H.; Calhorda, M. J.; Félix, V.; Drew, M. G. B.; Veiros, L. F. Heptacoordinate Dithiophosphate W(II) and Mo(II) Complexes of Diphosphines and Iodide. Inorg. Chim. Acta 2002, 327, 169–178. DOI: 10.1016/S0020-1693(01)00699-5.
  • Galakhov, M. V.; Gómez-Sal, P. T.; Pedraz, T.; Pellinghelli, M. A.; Royo, P.; Tiripicchio, A.; Vázquez De Miguel, A. Cyclopentadienyl Dithiocarbamate and Dithiophosphate Molybdenum and Tungsten Complexes. J. Organomet. Chem. 1999, 579, 190–197. DOI: 10.1016/S0022-328X(98)01222-4.
  • Pantaleo, D. C.; Johnson, R. C. Synthesis and Characterization of Dialkyldithiophosphate Complexes of Niobium (V). Inorg. Chem. 1971, 10, 1298–1301. DOI: 10.1021/ic50100a040.
  • Yih, K. H.; Lee, G. H.; Huang, S. L.; Wang, Y. Reactivity and Crystal Structures of the First Dithiocarbamate Chromium(0) and Dithiophosphate Tungsten(0) Complexes: crystal Structures of [Et4N][Cr(η2-S2CNC5H. 10)(CO)4] and [Et4N][W{η2-S2P(OEt)2(CO)4]. J. Organomet. Chem. 2003, 665, 114–121. DOI: 10.1016/S0022-328X(02)02073-9.
  • Dakternieks, D.; Di Giacomo, R.; Gable, R. W.; Hoskins, B. F. Observation of Secondary Bonding in Solution: Synthesis, NMR Studies, and the Crystal Structure of TeVI[OTeIV(C8H8)(S,P(OEt)2)]6. J. Am. Chem. Soc. 1988, 110, 6541–6546. DOI: 10.1021/ja00227a040.
  • Yih, K. H.; Lee, G. H.; Huang, S. L.; Wang, Y. Synthesis, Reactivity and Structures of Diethyldithiophosphate Molybdenum Complexes: crystal Structures of [Mo{η2-S2P(OEt2)}2. (PhC–CPh)2] and [Mo(η3-C3H5){η1-S2P(OEt2)}(Phen)(CO)2]. J. Organomet. Chem. 2002, 658, 191–197. DOI: 10.1016/S0022-328X(02)01654-6.
  • Yih, K. H.; Lee, G. H.; Wang, Y. Synthesis, Fluxional Behavior and Structures of Diethyldithiophosphate Molybdenum Complexes: Crystal Structures of [Et4N][Mo(CO)4{η2-S2. P(OEt)2}] and [Mo(CH3CN)(η3-C3H5.) (CO)2{η2-S2P(OEt)2}]. J. Organomet. Chem. 1999, 588, 125–133. DOI: 10.1016/S0022-328X(99)00357-5.
  • Rastogi, R.; Gupta, S.; Tarannum, N.; Agarwal, R.; Butcher, R. J. Synthesis, Spectral Characterization, and Evaluation of Antimicrobial Activity of O,O′-Alkanediyl S-(N-Phthalimidomethyl) Dithiophosphates and Zinc Bis(O,O′-Alkanediyl) Dithiophosphates. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 300–306. DOI: 10.1080/10426507.2016.1237949.
  • Rao, R. J.; Srivastava, G.; Mehrotra, R. C. Triorganotin(IV) O,O-Alkylene Dithiophosphates. J. Organomet. Chem. 1983, 258, 155–161. DOI: 10.1016/S0022-328X(00)99252-0.
  • Chauhan, H. P. S.; Bhasin, C. P.; Srivastava, G.; Mehrotra, R. C. Synthesis and Characterization of 2-Mercapto-2-Thiono-1,3,2-Dioxaphospholanes and Dioxaphosphorinanes. Phosphorus Sulfur Relat. Elem. 1983, 15, 99–104. DOI: 10.1080/03086648308073283.
  • Rastogi, R.; Srivastava, S. K.; Asolia, S.; Butcher, R. J. Synthesis, Spectral Characterization and Ligation of N-[2-(Phenylseleno)Ethyl]Phthalimide. J. Cryst. Process Technol. 2013, 2013, 31–34. DOI: 10.4236/JCPT.2013.31005.
  • Rastogi, R.; Krishna, G.; Tarannum, N.; Mishra, S.; Rastogi, A.; Butcher, R. J. Study Based on Docking of Antimicrobial Activity and Fluorescence Behavior of Ammonium Salt of Diisopropyl Dithiophosphate, O,O′- Diisopropanediyl S-(N-Phthalimido Methyl) and Zinc Diisopropyl Dithiophosphates. Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 501–512. DOI: 10.1080/10426507.2020.1860983.
  • Srivastava, S. K.; Sihare, S.; Rastogi, R.; Gaur, A. Synthesis, Structural Aspects and Ligation Behaviour of Phenylmercury(II) Dithio Complexes Having Hg-S Bonds. J. Indian Chem. Soc. 2007, 84, 867–871. DOI: 10.5281/ZENODO.5827036.
  • Balachandran, V.; Lalitha, S.; Rajeswari, S. Density Functional Theory, Comparative Vibrational Spectroscopic Studies, NBO, HOMO–LUMO Analyses and Thermodynamic Functions of N-(Bromomethyl)Phthalimide and N-(Chloromethyl)Phthalimide. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 91, 146–157. DOI: 10.1016/J.SAA.2012.01.034.
  • Gunasekaran, S.; Balaji, A. R.; Anand, G.; Srinivasan, S. Experimental and Theoretical Investigations of Spectroscopic Properties of N-Acetyl-5-Methoxytryptamine, Can. J. Anal. Sci. Spectrosc. 2008, 53, 149–162. https://www.researchgate.net/publication/237723908.
  • Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds; Wiley International Edition, 1981.
  • Amalanathan, M.; Hubert Joe, I.; Kostova, I. Density Functional Theory Calculation and Vibrational Spectral Analysis of 4-Hydroxy-3-(3-Oxo-1-Phenylbutyl)-2H-1-Benzopyran-2-One. J. Raman Spectrosc. 2010, 41, 1076–1084. DOI: 10.1002/jrs.2543.
  • Matulková, I.; Němec, I.; Teubner, K.; Němec, P.; Mička, Z. Novel Compounds of 4-Amino-1,2,4-Triazole with Dicarboxylic Acids – Crystal Structures, Vibrational Spectra and Non-Linear Optical Properties. J. Mol. Struct. 2008, 873, 46–60. DOI: 10.1016/j.molstruc.2007.03.007.
  • Karabacak, M.; Kurt, M. Comparison of Experimental and Density Functional Study on the Molecular Structure, Infrared and Raman Spectra and Vibrational Assignments of 6-Chloronicotinic Acid. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2008, 71, 876–883. DOI: 10.1016/J.SAA.2008.02.014.
  • Sathyanarayana, D. N. Vibrational Spectroscopy: Theory and Applications, 2nd ed.; New Age International (P) Limited: New Delhi, 2004.
  • Komboz, R. A. E.; Khaldy, A. A. S. E.; Nasman, O. S.; Baraka, R. M. Synthesis Properties and Characterization of Di Cyclopentadienyl Vanadium Bis Dialkyl and Alkylene Dithiophosphate Complexes. Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 567–575. DOI: 10.1080/10426500210264.
  • Glidewell, C. Ambident Nucleophiles: VI. Solution Metal-Ligand Binding Modes in Phosphorodithioate Complexes. A Phosphorus-31 N.M.R. Study. Inorg. Chim. Acta 1977, 25, 159–163. DOI: 10.1016/S0020-1693(00)95706-2.
  • Tripathi, U. N. Synthesis and Spectroscopic Studies of P,O′ Alkylenedithiophosphato Complexes of Metallocenes: Cp2ML2[M = Ti or Zr]. Phosphorus Sulfur Silicon Relat. Elem. 2000, 159, 47–54. DOI: 10.1080/10426500008043649.
  • Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds, 7th ed.; Wiley: New York, 2005.
  • Huber, K. P.; Herzberg, G. Molecular Spectra and Molecular Structure, 1st ed.; Springer: New York, 1979.
  • Onwudiwe, D. C.; Ajibade, P. A. Thermal Studies of Zn(II), Cd(II) and Hg(II) Complexes of Some N-Alkyl-N-Phenyl-Dithiocarbamates. Int. J. Mol. Sci. 2012, 13, 9502–9513. DOI: 10.3390/IJMS13089502.
  • Govindasamy, P.; Gunasekaran, S.; Srinivasan, S. Molecular Geometry, Conformational, Vibrational Spectroscopic, Molecular Orbital and Mulliken Charge Analysis of 2-Acetoxybenzoic Acid. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 130, 329–336. DOI: 10.1016/J.SAA.2014.03.056.
  • Irişli, S.; Yanar, S.; Büyükgüngör, O. Ionic Platinum(II)–Imidobis(Diphenylthiophosphinato) Complexes: Preparation, Structure, and Thermal Behavior. Phosphorus Sulfur Silicon Relat. Elem. 2010, 185, 2036–2044. DOI: 10.1080/10426500903463721.
  • Rastogi, R.; Srivastava, S. K.; Butcher, R. J.; Jasinski, J. P. Synthesis, Structural Characterization and Crystal Structure of Selenium Bearing 3-(Phenylseleno) Propylammonium Acetate Salt and Its Cleavage on Reaction with Mercury(II) and Tin(IV) Salts. J. Chem. Crystallogr. 2011, 41, 391–400. DOI: 10.1007/s10870-010-9895-3.
  • Xiang, S.; Wang, J. Study on DFT Based Computation for Quantum Chemical Descriptors of Neodymium Carboxylate Molecules. Comput. Aided Chem. Eng. 2018, 44, 2449–2454. DOI: 10.1016/B978-0-444-64241-7.50403-1.
  • Radicchi, E.; Kachmar, A.; Mosconi, E.; Bizzarri, B.; Nunzi, F.; De Angelis, F. Structural and Optical Properties of Solvated PbI2 in γ-Butyrolactone: Insight into the Solution Chemistry of Lead Halide Perovskite Precursors. J. Phys. Chem. Lett. 2020, 11, 6139–6145. DOI: 10.1021/acs.jpclett.0c01890.
  • Ji, Y.; Yang, X.; Ji, Z.; Zhu, L.; Ma, N.; Chen, D.; Jia, X.; Tang, J.; Cao, Y. DFT-Calculated IR Spectrum Amide I, II, and III Band Contributions of N-Methylacetamide Fine Components. ACS Omega 2020, 5, 8572–8578. DOI: 10.1021/acsomega.9b04421.
  • ADF. SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands; http://www.scm.com, 2014.
  • Rastogi, R.; Tarannum, N.; Butcher, R. J. A Facile Approach towards Synthesis, Characterization, Single Crystal Structure, and DFT Study of 5-Bromosalicylalcohol. Crystallogr. Rep. 2016, 61, 234–238. DOI: 10.1134/S1063774516020164.
  • Te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Fonseca Guerra, C.; van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. Chemistry with ADF. J. Comput. Chem. 2001, 22, 931–967. DOI: 10.1002/jcc.1056.
  • Balachandran, V.; Murugan, M.; Nataraj, A.; Karnan, M.; Ilango, G. Comparative Vibrational Spectroscopic Studies, HOMO-LUMO, NBO Analyses and Thermodynamic Functions of p-Cresol and 2-Methyl-p-Cresol Based on DFT Calculations. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 132, 538–549. DOI: 10.1016/j.saa.2014.04.194.
  • Geerlings, P.; De Proft, F.; Langenaeker, W. Conceptual Density Functional Theory. Chem. Rev. 2003, 103, 1793–1873. DOI: 10.1021/cr990029p.
  • Sheehan, D. J.; Hitchcock, C. A.; Sibley, C. M. Current and Emerging Azole Antifungal Agents. Clin. Microbiol. Rev. 1999, 12, 40–79. DOI: 10.1128/CMR.12.1.40.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.