DOI QR코드

DOI QR Code

Kinetics and Mechanism of the Aminolysis of Aryl N-Isopropyl Thiocarbamates in Acetonitrile

  • Oh, Hyuck-Keun (Department of Chemistry, Research Institute of Physics and Chemistry, Chonbuk National University)
  • Received : 2011.08.22
  • Accepted : 2011.09.16
  • Published : 2011.11.20

Abstract

Keywords

References

  1. Koh, H. J.; Lee, J.-W.; Lee, H. W.; Lee, I. Can. J. Chem. 1998, 76, 710. https://doi.org/10.1139/v98-038
  2. Koh, H. J.; Kim, O. S.; Lee, H. W.; Lee, I. J. Phys. Org. Chem. 1997, 10, 725. https://doi.org/10.1002/(SICI)1099-1395(199710)10:10<725::AID-POC943>3.0.CO;2-X
  3. Pross, A. Adv. Phys. Org. Chem. 1997, 14, 69.
  4. Buncel, E.; Wilson, H. J. Chem. Educ. 1987, 64, 475. https://doi.org/10.1021/ed064p475
  5. Oh, H. K.; Lee, Y. H.; Lee, I. Int. J. Chem. Kinet. 2000, 32, 131. https://doi.org/10.1002/(SICI)1097-4601(2000)32:3<131::AID-KIN2>3.0.CO;2-C
  6. Lee, I. Chem. Soc. Rev. 1990, 19, 317. https://doi.org/10.1039/cs9901900317
  7. Lee, I. Adv. Phys. Org. Chem. 1992, 27, 57.
  8. Lee, I.; Sung, D. D. Curr. Org. Chem. 2004, 8, 557. https://doi.org/10.2174/1385272043370753
  9. Ritchie, C. D. In Solute-Solvent Interactions; Coetzee, J. F., Ritchie, C. D., Eds; Marcel Dekker: New York, 1969; Chapter 4.
  10. Coetzee, J. F. Prog. Phys. Org. Chem. 1967, 4, 54.
  11. Spillane, W. J.; Hagan, G.; McGrath, P.; King, J.; Brack, C. J. Chem. Soc. Perkin Trans. 2 1996, 2099.
  12. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 3874. https://doi.org/10.1021/jo025637a
  13. Castro, E. A.; Pavez, P.; Santos, J. G. J. Org. Chem. 2001, 66, 3129. https://doi.org/10.1021/jo010022j
  14. Stefanidas, D.; Cho, S.; Dhe-Paganon, S.; Jencks, W. P. J. Am. Chem. Soc. 1993, 115, 1650. https://doi.org/10.1021/ja00058a006
  15. Skoog, M. T.; Jencks, W. P J. Am. Chem. Soc. 1984, 106, 7597. https://doi.org/10.1021/ja00336a047
  16. Ba-Saif, S.; Luthra, A. K.; Williams, A. J. Am. Chem. Soc. 1989, 111, 2647. https://doi.org/10.1021/ja00189a045
  17. Colthurst, M. J.; Nanni, M.; Williams, A. J. Chem. Soc. Perkin Trans. 2 1996, 2285.
  18. Maude, A. B.; Williams, A. J. Chem. Soc. Perkin Trans. 2 1997, 179.
  19. Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 1998, 63, 6820. https://doi.org/10.1021/jo980284u
  20. Castro, E. A. Chem. Rev. 1991, 99, 3505.
  21. Yamabe, S.; Minato, T. J. Org. Chem. 1983, 48, 2972. https://doi.org/10.1021/jo00166a007
  22. Lee, I.; Lee, D.; Kim, C. K. J. Phys. Chem. A 1997, 101, 879. https://doi.org/10.1021/jp961145o
  23. 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
  24. Lee, I. Int. Rev. Phys. Chem. 2003, 22, 263. https://doi.org/10.1080/0144235031000086058
  25. Castro, E. A.; Ibanez, F.; Salas, M.; Santos, J. G.; Sepulveda, P. J. Org. Chem. 1993, 58, 459. https://doi.org/10.1021/jo00054a033
  26. Castro, E. A.; Ruiz, M. G.; Santos, J. G. Int. J. Chem. Kinet. 2001, 33, 281. https://doi.org/10.1002/kin.1022
  27. Yew, K. H.; Koh, H. J.; Lee, H. W.; Lee, I. J. Chem. Soc. Perkin Trans. 2 1995, 2263.
  28. Castro, E. A.; Ruiz, M. G.; Salinas, S.; Santos, J. G. J. Org. Chem. 1999, 64, 4817. https://doi.org/10.1021/jo990146k
  29. Castro, E. A.; Cubillos, M.; Santos, J. G. J. Org. Chem. 2001, 66, 6000. https://doi.org/10.1021/jo0100695
  30. Oh, H. K.; Lee, J.-Y.; Park, Y. S.; Lee, I. Int. J. Chem. Kinet. 1998, 30, 419. https://doi.org/10.1002/(SICI)1097-4601(1998)30:6<419::AID-KIN4>3.0.CO;2-V
  31. Castro, E. A.; Cubillas, M.; Munoz, G.; Santos, J. G. Int. J. Chem. Kinet. 1994, 26, 571. https://doi.org/10.1002/kin.550260510
  32. Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of Organic Chemistry; Plenum: New York, 1975; Chapter 5.
  33. Lee, I. Chem. Soc. Rev. 1995, 24, 571.
  34. Lee, I. Chem. Soc. Rev. 1994, 24, 223.
  35. Guggenheim, E. A. Philos, Mag. 1926, 2, 538. https://doi.org/10.1080/14786442608564083
  36. Oh, H. K.; Hong, S. K. Bull. Korean Chem. Soc. 2009, 30, 2453. https://doi.org/10.5012/bkcs.2009.30.10.2453
  37. Lee, H.; Oh, H. K. Bull. Korean Chem. Soc. 2010, 31, 475. https://doi.org/10.5012/bkcs.2010.31.02.475
  38. Oh, H. K. Bull. Korean Chem. Soc. 2010, 31, 1785. https://doi.org/10.5012/bkcs.2010.31.6.1785

Cited by

  1. Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate in Acetonitrile vol.33, pp.5, 2012, https://doi.org/10.5012/bkcs.2012.33.5.1547
  2. Kinetics and Reaction Mechanism of Aminolyses of Benzyl 2-Pyridyl Carbonate and t-Butyl 2-Pyridyl Carbonate: Effect of Nonleaving Group on Reactivity and Reaction Mechanism vol.33, pp.5, 2012, https://doi.org/10.5012/bkcs.2012.33.5.1551
  3. Aminolysis of Benzyl 2-Pyridyl Thionocarbonate and t-Butyl 2-Pyridyl Thionocarbonate: Effects of Nonleaving Groups on Reactivity and Reaction Mechanism vol.34, pp.4, 2013, https://doi.org/10.5012/bkcs.2013.34.4.1115
  4. A Kinetic Study on Ethylaminolysis of Phenyl Y-Substituted-Phenyl Carbonates: Effect of Leaving-Group Substituents on Reactivity and Reaction Mechanism vol.34, pp.6, 2013, https://doi.org/10.5012/bkcs.2013.34.6.1722
  5. Kinetics and Reaction Mechanism for Aminolysis of Benzyl 4-Pyridyl Carbonate in H2O: Effect of Modification of Nucleofuge from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Me vol.33, pp.7, 2011, https://doi.org/10.5012/bkcs.2012.33.7.2269
  6. Aminolysis of Benzyl 4-Pyridyl Carbonate in Acetonitrile: Effect of Modification of Leaving Group from 2-Pyridyloxide to 4-Pyridyloxide on Reactivity and Reaction Mechanism vol.33, pp.8, 2011, https://doi.org/10.5012/bkcs.2012.33.8.2719