Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Reaction Mechanism and Structure of Transition State Determined from Analysis of Bronsted βnuc for Aminolysis of 4-Nitrophenyl Diphenylphosphinate

  • Shin, Young-Hee (Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Kim, Eun-Hee (Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Um, Ik-Hwan (Department of Chemistry and Nano Science, Ewha Womans University)
  • Published : 2008.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Jencks, W. P. Chem. Rev. 1985, 85, 511-527 https://doi.org/10.1021/cr00070a001
  2. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345-375 https://doi.org/10.1039/cs9811000345
  3. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451-464 https://doi.org/10.1021/ja00444a023
  4. Jencks, W. P.; Gilchrist, M. J. Am. Chem. Soc. 1968, 90, 2622-2637 https://doi.org/10.1021/ja01012a030
  5. Kirsch, J. F.; Clewell, W.; Simon, A. J. Org. Chem. 1968, 33, 127-132 https://doi.org/10.1021/jo01265a023
  6. Castro, E. A.; Echevarria, G. R.; Opazo, A.; Robert, P. S.; Santos, J. G. J. Phys. Org. Chem. 2008, 21, 62-67 https://doi.org/10.1002/poc.1285
  7. Castro, E. A.; Aliaga, M.; Campodonico, P. R.; Leis, J. R.; Garcia-Rio, L.; Santos, J. G. J. Phys. Org. Chem. 2006, 19, 683-688 https://doi.org/10.1002/poc.1116
  8. Castro, E. A.; Aliaga, M.; Gazitua, M.; Santos, J. G. Tetrahedron 2006, 62, 4863-4869 https://doi.org/10.1016/j.tet.2006.03.013
  9. Oh, H. K.; Oh, J. Y.; Sung, D. D.; Lee, I. J. Org. Chem. 2005, 70, 5624-5629 https://doi.org/10.1021/jo050606b
  10. Sung, D. D.; Koo, I. S.; Yang, K. Y.; Lee, I. Chem. Phys. Lett. 2006, 432, 426-430 https://doi.org/10.1016/j.cplett.2006.11.002
  11. Jeong, K. S.; Oh, H. K. Bull. Korean Chem. Soc. 2007, 28, 2535-2538 https://doi.org/10.5012/bkcs.2007.28.12.2535
  12. 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, 1797-1802 https://doi.org/10.5012/bkcs.2007.28.10.1797
  13. Hoque, M. E. U.; Lee, H. W. Bull. Korean Chem. Soc. 2007, 28, 936-940 https://doi.org/10.5012/bkcs.2007.28.6.936
  14. Um, I. H.; Kim, K. H.; Park, H. R.; Fujio, M.; Tsuno, Y. J. Org. Chem. 2004, 69, 3937-3942 https://doi.org/10.1021/jo049694a
  15. Um, I. H.; Min, J. S.; Ahn, J. A.; Hahn, H. J. J. Org. Chem. 2000, 65, 5659-5663 https://doi.org/10.1021/jo000482x
  16. Um, I. H.; Chun, S. M.; Akhtar, K. Bull. Korean Chem. Soc. 2007, 28, 220-224 https://doi.org/10.5012/bkcs.2007.28.2.220
  17. Um, I. H.; Jeon, S. E.; Seok, J. A. Chem. Eur. J. 2006, 12, 1237-1243 https://doi.org/10.1002/chem.200500647
  18. Um, I. H.; Seok, J. A.; Kim, H. T.; Bae, S. K. J. Org. Chem. 2003, 68, 7742-7746 https://doi.org/10.1021/jo034637n
  19. Menger, F. M.; Smith, J. H. J. Am. Chem. Soc. 1969, 91, 5346-5349 https://doi.org/10.1021/ja01047a025
  20. Um, I. H.; Yoon, S. R.; Park, H. R.; Han, H. J. Org. Biomol. Chem. 2008, 6, 1618-1624 https://doi.org/10.1039/b801422a
  21. Um, I. H.; Kim, E. Y.; Park, H. R.; Jeon, S. E. J. Org. Chem. 2006, 71, 2302-2306 https://doi.org/10.1021/jo052417z
  22. Um, I. H.; Han, H. J.; Baek, M. H.; Bae, S. Y. J. Org. Chem. 2004, 69, 6365-6370 https://doi.org/10.1021/jo0492160
  23. Um, I. H.; Lee, S. E.; Kwon, H. J. J. Org. Chem. 2002, 67, 8999-9005 https://doi.org/10.1021/jo0259360
  24. Castro, E. A.; Aguayo, R.; Bessolo, J.; Santos, J. G. J. Phys. Org. Chem. 2006, 19, 555-561 https://doi.org/10.1002/poc.1055
  25. Campodonico, P. R.; Fuentealba, P.; Castro, E. A.; Santos, J. G.; Contreras, R. J. Org. Chem. 2005, 70, 1754-1760 https://doi.org/10.1021/jo048127k
  26. Castro, E. A.; Vivanco, M.; Aguayo, R.; Santos, J. G. J. Org. Chem. 2004, 69, 5399-5404 https://doi.org/10.1021/jo049260f
  27. Castro, E. A.; Cubillos, M.; Aliaga, M.; Evangelisti, S.; Santos, J. G. J. Org. Chem. 2004, 69, 2411-2416 https://doi.org/10.1021/jo035451r
  28. Castro, E. A. Chem. Rev. 1999, 99, 3505-3524 https://doi.org/10.1021/cr990001d
  29. Oh, H. K.; Lee, J. M.; Lee, H. W.; Lee, I. Int. J. Chem. 2004, 36, 434-440
  30. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 8995-8998 https://doi.org/10.1021/jo0264269
  31. Oh, H. K.; Ku, M. H.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 3874-3877 https://doi.org/10.1021/jo025637a
  32. Um, I. H.; Shin, Y. H.; Han, J. Y.; Mishima, M. J. Org. Chem. 2006, 71, 7715-7720 https://doi.org/10.1021/jo061308x
  33. Um, I. H.; Akhtar, K.; Shin, Y. H.; Han, J. Y. J. Org. Chem. 2007, 72, 3823-3829 https://doi.org/10.1021/jo070171n
  34. Quin, L. D. A Guide to Organophosphorus Chemistry; Wiley: New York, 2000
  35. Wu, T. G.; Qiu, J. U. Environ. Sci. Technol. 2006, 40, 5428-5434 https://doi.org/10.1021/es060711i
  36. Stairs, R. A.; Buncel, E. Can. J. Chem. 2006, 84, 1580-1591 https://doi.org/10.1139/V06-160
  37. Han, X.; Balakrishnan, V. K.; VanLoon, G. W.; Buncel, E. Langmuir 2006, 22, 9009-9017 https://doi.org/10.1021/la060641t
  38. Churchill, D.; Cheung, J. C. F.; Park, Y. S.; Smith, V. H.; VanLoon, G. W.; Buncel, E. Can. J. Chem. 2006, 84, 702-708 https://doi.org/10.1139/V06-053
  39. Balakrishnan, V. K.; Buncel, E.; VanLoon, G. W. Environ. Sci. Technol. 2005, 39, 5824-5830 https://doi.org/10.1021/es050234o
  40. Terrier, F.; Rodriguez-Dafonte, P.; Le Guevel, E.; Moutiers, G. Org. Biomol. Chem. 2006, 4, 4352-4363 https://doi.org/10.1039/b609658c
  41. Gomez-Tagle, P.; Vargas-Zuniga, I.; Taran, O.; Yatsimirsky, A. K. J. Org. Chem. 2006, 71, 9713-9722 https://doi.org/10.1021/jo061780i
  42. Buncel, E.; Albright, K. G.; Onyido, I. Org. Biomol. Chem. 2004, 2, 601-610 https://doi.org/10.1039/b314886f
  43. Zalatan, J.; Herschlag, D. J. Am. Chem. Soc. 2006, 128, 1293-1303 https://doi.org/10.1021/ja056528r
  44. Maxwell, C.; Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2005, 3, 4329-4336 https://doi.org/10.1039/b512378j
  45. Lu, Z. L.; Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2005, 3, 3379-3387 https://doi.org/10.1039/b508917d
  46. Gibson, G. T. T.; Neverov, A. A.; Teng, A. C. T.; Brown, R. S. Can. J. Chem. 2005, 83, 1268-1276 https://doi.org/10.1139/v05-065
  47. Tsang, J. S. W.; Neverov, A. A.; Brown, R. S. Org. Biomol. Chem. 2004, 2, 3457-3463 https://doi.org/10.1039/b412132e
  48. Cook, R. D.; Daouk, W. A.; Hajj, A. N.; Kabbani, A.; Kurku, A.; Samaha, M.; Shayban, F.; Tanielian, O. V. Can. J. Chem. 1986, 64, 213-219 https://doi.org/10.1139/v86-037
  49. Guha, A. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2000, 65, 12-15 https://doi.org/10.1021/jo990671j
  50. Guha, A. K.; Lee, H. W.; Lee. I. J. Chem. Soc., Perkin Trans. 1999, 2, 765-770
  51. Pross, A. Advances in Physical Organic Chemistry; Academic Press: London, 1977; vol. 14, pp 69-132

Cited by

  1. 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