Phenolysis of 2, 2′-Biphenoxy Thiophosphinic Chloride: Crystal Structures and DFT Calculations of 2, 2′-Biphenyl 4-Tert-Butylphenyl Thiophosphinate and 2, 2′-Biphenyl 3,4-di-Methylphenyl Thiophosphinate

References

• F. Ekström, C. Akfur, A. K. Tunemalm, and S. Lundberg, “Structural Changes of Phenylalanine 338 and Histidine 447 Revealed by the Crystal Structures of Tabun-Inhibited Murine Acetylcholinesterase,” Biochemistry 45, no. 1 (2006): 74–81.
   PubMed Web of Science ®Google Scholar
• S. Pignard, C. Lopin, G. Gouhier, and S. R. Piettre, “Phosphonodifluoromethyl and Phosphonothiodifluoromethyl Radicals. Generation and Addition onto Alkenes and Alkynes,” The Journal of Organic Chemistry 71, no. 1 (2006): 31–7.
   PubMed Web of Science ®Google Scholar
• V. A. Milyukov, Y. H. Budnikova, and O. G. Sinyashin, “Organic Chemistry of Elemental Phosphorus,” Russian Chemical Reviews 74, no. 9 (2005): 781–805.
   Google Scholar
• O. I. Kolodiazhnyi, “Asymmetric Synthesis of Hydroxyphosphonate,” Tetrahedron: Asymmetry 16, no. 20 (2005): 3295–340.
   Google Scholar
• H. Schulze, R. D. Schmid, and T. T. Bachmann, “Activation of Phosphorothionate Pesticides Based on a Cytochrome P450 BM-3 (CYP102 A1) Mutant for Expanded Neurotoxin Detection in Food Using Acetylcholinesterase Biosensors,” Analytical Chemistry 76, no. 6 (2004): 1720–5.
   PubMed Web of Science ®Google Scholar
• K. A. Kumar, C. S. Reddy, L. N. Rao, and C. N. Raju, “Synthesis and Characterization of 6- Substituted Dibenzo [d,f] [1,3,2] Dioxa Phosphepin 6-Oxides,” Journal of Heterocyclic Chemistry 7, no. 3 (2001): 253–6.
   Google Scholar
• M. P. Koroteev, A. A. Nazarov, S. Y. Burmmistrov, G. Z. Kaziev, and E. E. Nifantév, (Patent No. RU 2180666, Application No. RU 2000-109683, 2002).
   Google Scholar
• T. Ishida, K. Usıki, H. Hashimoto, and T. Okita, (Patent No. 07192253, Application No. JP 93-333031, 1995).
   Google Scholar
• Y. Yamamoto, CA, 1987. 107:99.589 m.
   Google Scholar
• L. R. Wolf, CA, 1992. 117:73,002w.
   Google Scholar
• J. J. Talley, CA, 1987. 106: 12,0850f.
   Google Scholar
• P. Miles, CA, 1989. 110: 11, 8138u.
   Google Scholar
• R. S. Edmunson, “Cyclic Organophosphorus Compounds—III: Some Sterically Hindered Pyrophosphates,” Tetrahedron 21, no. 9 (1965): 2379–87.
   Web of Science ®Google Scholar
• J. J. Talley, and C. B. Berman, “Phase-Transfer-Catalyzed Preparation of Triaryl Phosphorothionates,” Journal of Chemical & Engineering Data 32, no. 2 (1987): 279–80.
   Web of Science ®Google Scholar
• W. ReimschüSsel, M. Mikołajczyk, H. Ślebocka-Tilk, and M. Gajl, “The Kinetics of the Chlorine Isotopic Exchange between Chloride Ion at O,O-Diarylphosphorochloridates or O,O-Diarylphosphorochloridothionates,” International Journal of Chemical Kinetics 12, no. 12 (1980): 979–91.
   Web of Science ®Google Scholar
• D. C. Nonhebel, J. M. Tedder, and J. C. Walton, Cambridge Radicals (Cambridge: Cambridge University Press, 1979).
   Google Scholar
• M. B. Abou-Donia, “Organophosphorus Ester-Induced Chronic Neurotoxicity, Arch,” Archives of Environmental Health 58, no. 8 (2003): 484–97.
   PubMed Web of Science ®Google Scholar
• E. Denisov, Handbook of Antioxidants (Boca Raton, FL: CRC Press, 1995).
   Google Scholar
• H. A. Mohammed, Y. Sert, M. R. Albayati, N. Dege, and F. Şen, “Structure Elucidation, Hirshfeld Surface Analysis, Molecular Docking and Computational Studies of a Jahn-Teller Distorted Octahedral Cobalt (II) Complex with Saccharin Ligand,” Polycyclic Aromatic Compounds
   Web of Science ®Google Scholar
• S. Kansız, A. Tolan, M. Azam, N. Dege, M. Alam, Y. Sert, Saud. I. Al-Resayes, and H. Içbudak, “Acesulfame Based Co(II) Complex: Synthesis, Structural Investigations, Solvatochromism, Hirshfeld Surface Analysis and Molecular Docking Studies,” Polyhedron 218 (2022): 115762.
   Web of Science ®Google Scholar
• Bruker, Sadabs (Madison, WI: Bruker AXS Inc., 2005).
   Google Scholar
• Bruker, APEX2 (Version 2011.4-1) (Madison, WI: Bruker AXS Inc., 2008).
   Google Scholar
• G. M. Sheldrick, “A Short History of SHELX,” Acta Crystallographica Section A, Foundations of Crystallography 64, no. Pt 1 (2008): 112–22.
   PubMedGoogle Scholar
• A. L. Spek, “Structure Validation in Chemical Crystallography,” Acta Crystallogr D65 (2009): 148–55.
   Web of Science ®Google Scholar
• C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P. A. Wood, “Mercury CSD 2.0 – New Features for the Visualization and Investigation of Crystal Structures,” Journal of Applied Crystallography 41, no. 2 (2008): 466–70.
   Web of Science ®Google Scholar
• K. Brandenburg, DIAMOND 3.1 for Windows. Crystal Impact GbR (Bonn, Germany: 2006).
   Google Scholar
• A. R. Sande, M. T. Thorat, P. P. Wadgaonkar, and M. M. Salunkhe, “European Polymer Journal,” Use of Polymer Supported Phenoxide Ions for the Synthesis of Triaryl Phosphorothionates 35, no. 6 (1999): 1179–81.
   Google Scholar
• S. Begeç, “Heteroatom Chem,” Synthesis of Phenoxy-Substituted Spiro-Ansa Phosphazene Derivative 18, no. 4 (2007): 372–5.
   Google Scholar
• S. Begeç, S. Alatş, and A. Kılıç, “Phosphorus, Sulfur, and Silicon Ant the Related Elements,” Synthesis and Characterization of Novel Alkyl-Substituted Aryl Diphenylphosphinate Esters 186, no. 7 (2011): 1531–7.
   Google Scholar
• G. M. Fazleeva, V. P. Gubskaya, F. G. Sibgatullina, V. V. Yanilkin, N. V. Nastapova, Sh K. Latypov, A. A. Balandina, I. E. Ismaev, V. V. Zverev, Yu Ya Efremov, et al., “Synthesis, Structures, and Properties of New Thiophosphorylated Fullerenopyrrolidines,” Russian Chemical Bulletin 55, no. 3 (2006): 507–16.
   Web of Science ®Google Scholar
• J. Hernández, F. M. Goycoolea, D. Zepeda-Rivera, J. Juárez-Onofre, K. Martínez, J. Lizardi, M. Salas-Reyes, B. Gordillo, C. Velázquez-Contreras, O. García-Barradas, et al., “Substituent Effects on the 31P NMR Chemical Shifts of Arylphosphorothionates,” Tetrahedron 62, no. 11 (2006): 2520–8.
   Web of Science ®Google Scholar
• K. Sivakumar, K. Subramanian, and S. Natarayan, “6-(4-Chlorophenoxy)Dibenzo [d,f] [1,3,2] Dioxaphosphepin 6-Sulfide,” Acta Crystallographica C45, no. 5 (1989): 806–8.
   Google Scholar
• M. Krishnaiah, V. H. H. Surendra Babu, J. Radha Krishna, K. Ananda Kumar, C. Suresh Reddy, and V. G. Puranik, “6-(2,4-Dichlorophenoxy)Dibenzo[d,f][1,3,2]Dioxaphosphepine-6-Sulfide,” Acta Crystallographica E61 (2005): o1646–o1648.
   Google Scholar
• Frisch, M. J., et al., Gaussian 16, Revision C.01 (Wallingford CT: Gaussian, Inc., 2016).
   Google Scholar
• D. M. Chipman, “Comparison of Solvent Reaction Field Representations,” Theoretical Chemistry Accounts. 107, no. 2 (2002): 80–9.
   Web of Science ®Google Scholar
• J. R. Cheeseman, G. W. Trucks, T. A. Keith, and M. J. Frisch, “A Comparison of Models for Calculating Nuclear Magnetic Resonance Shielding Tensors,” Journal of Chemical Physics 104, no. 14 (1996): 5497–509.
   Web of Science ®Google Scholar
• S. K. Latypov, F. M. Polyancev, D. G. Yakhvarov, and O. G. Sinyashin, “Quantum Chemical Calculations of 31P NMR Chemical Shifts: Scopes and Limitations,” Physical Chemistry Chemical Physics 17, no. 10 (2015): 6976–87.
   PubMed Web of Science ®Google Scholar