Bulletin of the Korean Chemical Society

  • 제30권4호
  • /
  • Pages.975-978
  • /
  • 2009
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Kinetics and Mechanism of the Aminolysis of Dimethyl Thiophosphinic Chloride with Anilines

  • 발행 : 2009.04.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

키워드

참고문헌

  1. Guha, A. K.; Lee, H. W.; Lee, I. J. Chem. Soc., Perkin Trans. 2 1999, 765
  2. Lee, H. W.; Guha, A. K.; Lee, I. Int. J. Chem. Kinet. 2002, 34, 632 https://doi.org/10.1002/kin.10081
  3. Hoque, M. E. U.; Dey, S.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Org. Chem. 2007, 72, 5493 https://doi.org/10.1021/jo0700934
  4. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936 https://doi.org/10.5012/bkcs.2007.28.6.936
  5. Dey, N. K.; Han, I. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 2003 https://doi.org/10.5012/bkcs.2007.28.11.2003
  6. Hoque, M. E. U.; Dey, N. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Org. Biomol. Chem. 2007, 5, 3944 https://doi.org/10.1039/b713167d
  7. Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2008, 21, 544 https://doi.org/10.1002/poc.1314
  8. Lumbiny, B. J.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 2065 https://doi.org/10.5012/bkcs.2008.29.10.2065
  9. Dey, N. K.; Hoque, M. E. U.; Kim, C. K.; Lee, B. S.; Lee, H. W. J. Phys. Org. Chem. 2009, 22, 425. Pyridinolysis https://doi.org/10.1002/poc.1478
  10. Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12 https://doi.org/10.1021/jo990671j
  11. Lee, H. W.; Guha, A. K.; Kim, C. K.; Lee, I. J. Org. Chem. 2002, 67, 2215 https://doi.org/10.1021/jo0162742
  12. Adhikary, K. K.; Lee, H. W.; Lee, I. Bull. Korean Chem. Soc. 2003, 24, 1135 https://doi.org/10.5012/bkcs.2003.24.8.1135
  13. Hoque, M. E. U.; Dey, N. K.; Guha, A. K.; Kim, C. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 1797 https://doi.org/10.5012/bkcs.2007.28.10.1797
  14. Adhikary, K. K.; Lumbiny, B. J.; Kim, C. K.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 851 https://doi.org/10.5012/bkcs.2008.29.4.851
  15. Lumbiny, B. J.; Adhikary, K. K.; Lee, B. S.; Lee, H. W. Bull. Korean Chem. Soc. 2008, 29, 1769. https://doi.org/10.5012/bkcs.2008.29.9.1769
  16. Lee, I.; Kim, C. K.; Li, H. G.; Sohn, C. K.; Kim, C. K.; Lee, H. W.; Lee, B. S. J. Am. Chem. Soc. 2000, 122, 11162 https://doi.org/10.1021/ja001814i
  17. Crumpler, T. B.; Yoh, J. H. Chemical Computations and Errors; John Wiley: New York, 1940; p 178
  18. Hengge, A. C.; Onyido, I. Curr. Org. Chem. 2005, 9, 61 https://doi.org/10.2174/1385272053369349
  19. Omakor, J. E.; Onyido, I.; vanLoon, G. W.; Buncel, E. J. Chem. Soc., Perkin Trans. 2 2001, 324
  20. Gregersen, B. A.; Lopez, X.; York, D. M. J. Am. Chem. Soc. 2003, 125, 7178 https://doi.org/10.1021/ja035167h
  21. Hondal, R. J.; Bruzik, K. S.; Zhao, Z.; Tsai, M. D. J. Am. Chem. Soc. 1997, 119, 5477 https://doi.org/10.1021/ja964217y
  22. Onyido, I.; Swierczek, K.; Purcell, J.; Hengge, A. C. J. Am. Chem. Soc. 2005, 127, 7703 https://doi.org/10.1021/ja0501565
  23. Holtz, K. M.; Catrina, I. E.; Hengge, A. C.; Kantrowitz, E. R. Biochemistry 2000, 39, 9451 https://doi.org/10.1021/bi000899x
  24. Liu, Y.; Gregersen, B. A.; Hengge, A. C.; York, D. M. Biochemistry 2006, 45, 10043 https://doi.org/10.1021/bi060869f
  25. Oivanen, M.; Ora, M.; Lonnberg, H. Collect. Czech. Chem. Commun. 1996, 61, S-1
  26. Zhang, L.; Xie, D.; Xu, D.; Guo, H. J. Phys. Chem. A 2005, 109, 11295 https://doi.org/10.1021/jp054430t
  27. Hehre, W. J.; Random, L.; Schleyer, P. V. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986; Chapter 4
  28. Charton, M. Prog. Phys. Org. Chem. 1987, 16, 287 https://doi.org/10.1002/9780470171950.ch6
  29. Hansch, C.; Leo, A.; Taft, R.W. Chem. Rev. 1991, 91, 165 https://doi.org/10.1021/cr00002a004
  30. Streitwieser, A., Jr.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry, 4th ed.; Macmillan publishing Co.: New York, 1992; p 735
  31. Ritchie, C. D. Solute-Solvent Interactions, Coetzee, J. F.; Ritchie, C. D., Eds.; Marcel Dekker: New York, 1969; Ch. 4.
  32. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 54
  33. Spillane, W. J.; Hogan, G.; McGrath, P.; King, J.; Brack, C. J. Chem. Soc. Perkin Trans. 2 1996, 2099
  34. Oh, H. K.; Woo, S. Y.; Shin, C. H.; Park, Y. S.; Lee, I. J. Org. Chem. 1997, 62, 5780 https://doi.org/10.1021/jo970413r
  35. Poirier, R. A.; Youliang, W.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526 https://doi.org/10.1021/ja00085a037
  36. Yamata, H.; Ando, T.; Nagase, S.; Hanamusa, M.; Morokuma, K. J. Org. Chem. 1984, 49, 631 https://doi.org/10.1021/jo00178a010
  37. Xhao, X. G.; Tucker, S. C.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 826 https://doi.org/10.1021/ja00003a015
  38. Melander, L., Jr.; Saunders, W. H. Reaction Rates of Isotopic Molecules; Wiley-Interscience: New York, 1980
  39. Lee, I.; Koh, H. J.; Lee, B. S.; Lee, H. W. J. Chem. Soc., Chem. Commun. 1990, 335
  40. Lee, I. Chem. Soc. Rev. 1990, 19, 317 https://doi.org/10.1039/cs9901900317
  41. Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57
  42. Lee, I.; Lee, H. W. Collect. Czech. Chem. Commun. 1999, 64, 1529 https://doi.org/10.1135/cccc19991529

피인용 문헌

  1. Kinetics and Mechanism of the Anilinolysis of Diisopropyl Thiophosphinic Chloride in Acetonitrile vol.32, pp.11, 2011, https://doi.org/10.5012/bkcs.2011.32.11.3880
  2. Kinetics and Mechanism of the Benzylaminolysis of O,O-Diphenyl S-Aryl Phosphorothioates in Dimethyl Sulfoxide vol.32, pp.5, 2011, https://doi.org/10.5012/bkcs.2011.32.5.1625
  3. Kinetics and Mechanism of the Anilinolysis of Bis(aryl) Chlorophosphates in Acetonitrile vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.1939
  4. Kinetics and Mechanism of the Pyridinolysis of Methyl Phenyl Phosphinic Chloride in Acetonitrile vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.1945
  5. Pyridinolysis of Dicyclohexyl Phosphinic Chloride in Acetonitrile vol.32, pp.6, 2011, https://doi.org/10.5012/bkcs.2011.32.6.2109
  6. Kinetics and Mechanism of the Pyridinolysis of Diethyl Thiophosphinic Chloride in Acetonitrile vol.32, pp.8, 2011, https://doi.org/10.5012/bkcs.2011.32.8.2805
  7. Kinetics and mechanism of the anilinolyses of aryl dimethyl, methyl phenyl and diphenyl phosphinates vol.9, pp.3, 2011, https://doi.org/10.1039/C0OB00517G
  8. Kinetics and Mechanism of the Pyridinolysis of 1,2-Phenylene Phosphorochloridate in Acetonitrile vol.33, pp.1, 2012, https://doi.org/10.5012/bkcs.2012.33.1.270
  9. Pyridinolysis of Dipropyl Chlorothiophosphate in Acetonitrile vol.33, pp.1, 2012, https://doi.org/10.5012/bkcs.2012.33.1.325
  10. Kinetics and Mechanism of the Anilinolysis of Dibutyl Chlorophosphate in Acetonitrile vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.663
  11. A Kinetic Study on Aminolysis of 2-Pyridyl X-Substituted Benzoates: Effect of Changing Leaving Group from 4-Nitrophenolate to 2-Pyridinolate on Reactivity and Mechanism vol.31, pp.12, 2010, https://doi.org/10.5012/bkcs.2010.31.12.3588
  12. Kinetics and Mechanism of the Pyridinolyses of Dimethyl Phosphinic and Thiophosphinic Chlorides in Acetonitrile vol.31, pp.12, 2009, https://doi.org/10.5012/bkcs.2010.31.12.3856
  13. Anilinolysis of Diethyl Phosphinic Chloride in Acetonitrile vol.31, pp.5, 2009, https://doi.org/10.5012/bkcs.2010.31.5.1403
  14. Kinetics and mechanism of the pyridinolyses of dimethyl and diethyl chloro(thiono)phosphates in acetonitrile vol.23, pp.11, 2009, https://doi.org/10.1002/poc.1709
  15. Kinetics and mechanism of the pyridinolysis of N‐aryl‐P,P‐diphenyl phosphinic amides in dimethyl sulfoxide vol.24, pp.6, 2011, https://doi.org/10.1002/poc.1788
  16. Kinetics and Mechanism of the Pyridinolysis of Aryl Ethyl Chlorothiophosphates in Acetonitrile vol.32, pp.11, 2009, https://doi.org/10.5012/bkcs.2011.32.11.3947
  17. Kinetics and Mechanism of the Pyridinolysis of Bis(2,6-dimethylphenyl) Chlorophosphate in Acetonitrile vol.32, pp.12, 2011, https://doi.org/10.5012/bkcs.2011.32.12.4179
  18. Kinetics and Mechanism of the Anilinolysis of Ethylene Phosphorochloridate in Acetonitrile vol.32, pp.12, 2009, https://doi.org/10.5012/bkcs.2011.32.12.4185
  19. Kinetics and Mechanism of the Benzylaminolysis of O,O-Dimethyl S-Aryl Phosphorothioates in Dimethyl Sulfoxide vol.32, pp.12, 2009, https://doi.org/10.5012/bkcs.2011.32.12.4304
  20. Kinetics and Mechanism of the Anilinolysis of Bis(N,N-dimethylamino) Phosphinic Chloride in Acetonitrile vol.32, pp.12, 2009, https://doi.org/10.5012/bkcs.2011.32.12.4361
  21. Kinetics and Mechanism of the Pyridinolysis of Diisopropyl Thiophosphinic Chloride in Acetonitrile vol.32, pp.12, 2009, https://doi.org/10.5012/bkcs.2011.32.12.4387
  22. Kinetics and Mechanism of the Anilinolysis of Dipropyl Chlorothiophosphate in Acetonitrile vol.32, pp.12, 2009, https://doi.org/10.5012/bkcs.2011.32.12.4403
  23. Pyridinolysis of Diethyl Phosphinic Chloride in Acetonitrile vol.32, pp.2, 2009, https://doi.org/10.5012/bkcs.2011.32.2.709
  24. Theoretical Study of Phosphoryl Transfer Reactions vol.32, pp.3, 2009, https://doi.org/10.5012/bkcs.2011.32.3.889
  25. Kinetic Study on Aminolysis of 4-Pyridyl X-Substituted Benzoates: Effect of Substituent X on Reactivity and Reaction Mechanism vol.32, pp.6, 2009, https://doi.org/10.5012/bkcs.2011.32.6.1907
  26. Kinetics and Mechanism of the Anilinolysis of Dicyclohexyl Phosphinic Chloride in Acetonitrile vol.32, pp.6, 2009, https://doi.org/10.5012/bkcs.2011.32.6.1997
  27. Kinetics and Mechanism of the Pyridinolysis of Aryl Phenyl Chlorothiophosphates in Acetonitrile vol.32, pp.4, 2009, https://doi.org/10.5012/bkcs.2011.32.4.1138
  28. Kinetics and Mechanism of the Pyridinolysis of O-Aryl Methyl Phosphonochloridothioates in Acetonitrile vol.32, pp.4, 2011, https://doi.org/10.5012/bkcs.2011.32.4.1375
  29. Kinetics and Mechanism of the Anilinolysis of Diethyl Thiophosphinic Chloride in Acetonitrile vol.32, pp.7, 2009, https://doi.org/10.5012/bkcs.2011.32.7.2306
  30. Kinetics and Mechanism of the Pyridinolysis of O,O-Dimethyl S-Aryl Phosphorothioates in Dimethyl Sulfoxide vol.32, pp.7, 2011, https://doi.org/10.5012/bkcs.2011.32.7.2339
  31. Transition State Variation in the Anilinolysis of O-Aryl Phenyl Phosphonochloridothioates in Acetonitrile vol.32, pp.8, 2009, https://doi.org/10.5012/bkcs.2011.32.8.2628
  32. Kinetics and Mechanism of the Anilinolysis of Diisopropyl Chlorophosphate in Acetonitrile vol.32, pp.9, 2011, https://doi.org/10.5012/bkcs.2011.32.9.3245
  33. Kinetics and Mechanism of the Anilinolysis of 1,2-Phenylene Phosphorochloridate in Acetonitrile vol.32, pp.9, 2009, https://doi.org/10.5012/bkcs.2011.32.9.3355
  34. Kinetics and Mechanism of the Benzylaminolysis of O,O-Diethyl S-Aryl Phosphorothioates in Dimethyl Sulfoxide vol.32, pp.10, 2011, https://doi.org/10.5012/bkcs.2011.32.10.3587
  35. Kinetics and Mechanism of the Pyridinolysis of S-Aryl Phenyl Phosphonochloridothioates in Acetonitrile vol.32, pp.10, 2011, https://doi.org/10.5012/bkcs.2011.32.10.3743
  36. Kinetics and Mechanism of the Anilinolysis of (2R,4R,5S)-(+)-2-Chloro-3,4-dimethyl -5-phenyl-1,3,2-oxazaphospholidine 2-Sulfide in Acetonitrile vol.33, pp.3, 2009, https://doi.org/10.5012/bkcs.2012.33.3.1037
  37. Pyridinolysis of Dibutyl Chlorophosphate in Acetonitrile vol.33, pp.3, 2009, https://doi.org/10.5012/bkcs.2012.33.3.1055
  38. Kinetics and Mechanism of the Anilinolysis of Dibutyl Chlorothiophosphate in Acetonitrile vol.33, pp.3, 2009, https://doi.org/10.5012/bkcs.2012.33.3.843
  39. Kinetics and Mechanism of the Anilinolysis of Dipropyl Chlorophosphate in Acetonitrile vol.33, pp.6, 2012, https://doi.org/10.5012/bkcs.2012.33.6.1879