Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Evaluation of Methylthio and Phenylthio Group Effects in the Solvolyses of 2-Chloro-2-(methylthio)acetone and 2-Chloro-2-(phenylthio)acetophenone Using Extended Grunwald-Winstein Equations

  • Published : 2008.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Swain, C. G.; Mosely, R. B. J. Am. Chem. Soc. 1955, 77, 327 https://doi.org/10.1021/ja01607a023
  2. Ryu, Z. H.; Lim, G. T.; Bentley, T. W. Bull. Korean Chem. Soc. 2003, 24, 1293 https://doi.org/10.5012/bkcs.2003.24.9.1293
  3. Oh, Y. H.; Jang, G. G.; Lim, G. T.; Ryu, Z. H. Bull. Korean Chem. Soc. 2002, 23, 1089 https://doi.org/10.5012/bkcs.2002.23.8.1089
  4. Lee, H. S.; Rhu, C. J.; Kyong, J. B.; Kim, D. K.; Kevill, D. N. Bull. Korean Chem. Soc. 2007, 28(4), 657 https://doi.org/10.5012/bkcs.2007.28.4.657
  5. Bentley, T. W.; Harris, H. C.; Ryu, Z. H.; Lim, G. T.; Sung, D. D.; Szajda, S. R. J. Org. Chem. 2005, 70, 8963 https://doi.org/10.1021/jo0514366
  6. D'Souza, M. J.; Ryu, Z. H.; Park, B.-C.; Kevill, D. N. Can. J. Chem. 2008, 86, 359 https://doi.org/10.1139/V08-028
  7. Kevill, D. N.; Park, B.-C.; Kyong, J. B. J. Org. Chem. 2005, 70, 9032 https://doi.org/10.1021/jo050998m
  8. Kevill, D. N.; D'Souza, M. J. J. Chem. Soc. Perkin Trans. 2 1997, 1721
  9. Queen, A. Can. J. Chem. 1967, 45, 1619 https://doi.org/10.1139/v67-264
  10. Kevill, D. N.; D'Souza, M. J. J. Org. Chem. 1998, 63, 1220
  11. Kevill, D. N.; Bond, M. W.; D'Souza, M. J. J. Org. Chem. 1997, 62, 7869 https://doi.org/10.1021/jo970657b
  12. Kevill, D. N.; D'Souza, M. J. Can. J. Chem. 1999, 77, 1118 https://doi.org/10.1139/cjc-77-5-6-1118
  13. Kyong, J. B.; Won, H.; Lee, Y. H.; Kevill, D. N. Bull. Korean Chem. Soc. 2005, 26, 661 https://doi.org/10.5012/bkcs.2005.26.4.661
  14. Kyong, J. B.; Park, B. C.; Kim, C. B.; Kevill, D. N. Bull. Korean Chem. Soc. 2000, 65, 8051
  15. Singh, A.; Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1968, 84, 1179 https://doi.org/10.1021/ja00866a024
  16. Strauss, M. J.; Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1968, 90, 3473 https://doi.org/10.1021/ja01015a033
  17. Friedrich, S. S.; Andrews, L. J.; Keefer, R. M. J. Org. Chem. 1972, 37, 3007 https://doi.org/10.1021/jo00984a021
  18. Apeloig, Y.; Karni, M. J. Chem. Soc., Perkin Trans. 2 1988, 625
  19. Jagannadham, V.; Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1993, 115, 8465 https://doi.org/10.1021/ja00071a073
  20. Brown, H. C.; Okamoto, Y.; Inuki, T. J. Am. Chem. Soc. 1958, 80, 4964 https://doi.org/10.1021/ja01551a051
  21. Hoffman, B. M.; Eames, T. J. Am. Chem. Soc. 1969, 91, 5170 https://doi.org/10.1021/ja01046a045
  22. McManus, S. P.; Sedaghat-Herati, M. R.; Karaman, R. M.; Neamati-Mazraeh, N.; Cowell, S. M.; Harris, J. M. J. Org. Chem. 1989, 54, 1911 https://doi.org/10.1021/jo00269a030
  23. Grunwald, E.; Winstein, S. J. Am. Chem. Soc. 1948, 70, 846 https://doi.org/10.1021/ja01182a117
  24. Bentley, T. W.; Llewellyn, G. Prog. Phys. Org. Chem. 1990, 17, 121 https://doi.org/10.1002/9780470171967.ch5
  25. Kevill, D. N.; D'Souza, M. J. J. Phys. Org. Chem. 1992, 5, 287 https://doi.org/10.1002/poc.610050602
  26. Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1976, 98, 7667 https://doi.org/10.1021/ja00440a037
  27. Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1 https://doi.org/10.1016/S0065-3160(08)60107-0
  28. Liu, K.-T. J. Chinese Chem. Soc. 1995, 42, 607 https://doi.org/10.1002/jccs.199500082
  29. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845
  30. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. (S) 1993, 174
  31. Kevill, D. N. In Advances in Quantitative Structure-Property Relationships; Charton, M, Ed.; JAI Press: Greenwich, CT, 1996; Vol 1, p 81.
  32. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. (S) 1996, 1649
  33. Kevill, D. N.; D'Souza, M. J. J. Chem. Res. 2008, 61
  34. Ryu, Z. H.; Shin, S. H.; Lim, G. T.; Lee, J. P. Bull. Korean Chem. Soc. 2004, 25, 307 https://doi.org/10.5012/bkcs.2004.25.2.307
  35. Ryu, Z. H.; Shin, S. H.; Lee, J. P.; Lim, G. T.; Bentley, T. W. J. Chem. Soc., Perkin Trans. 2 2002, 1283
  36. da Roza, D. A.; Andrews, L. J.; Keefer, R. M. J. Am. Chem. Soc. 1973, 95, 7003 https://doi.org/10.1021/ja00802a022
  37. Kevill, D. N.; Ryu, Z. H. Int. J. Mol. Sci. 2006, 7, 451 https://doi.org/10.3390/i7100451
  38. Kevill, D. N.; Koyoshi, F.; D'Souza, M. J. Int. J. Mol. Sci. 2007, 8, 346 https://doi.org/10.3390/i8040346
  39. Kevill, D. N.; Kim, C.-B. J. Org. Chem. 2005, 70, 1490 https://doi.org/10.1021/jo048103d
  40. Creary, X. Chem. Rev. 1991, 91, 1625 https://doi.org/10.1021/cr00008a001
  41. Creary, X. Chem. Rev. 1991, 91, 1625 https://doi.org/10.1021/cr00008a001
  42. Bentley, T. W.; Garley, M. S. J. Phys. Org. Chem. 2006, 19, 341 https://doi.org/10.1002/poc.1084
  43. Ryu, Z. H.; Ju. C.-K.; Sung, D. D.; Sung, N. C.; Bentley, T. W. Bull. Korean Chem. Soc. 2002, 23, 123 https://doi.org/10.5012/bkcs.2002.23.1.123
  44. Koo, I. S.; Lee, I.; Oh, J.; Yang, K.; Bentley, T. W. J. Phys. Org. Chem. 1993, 6, 223 https://doi.org/10.1002/poc.610060405
  45. Prepared as previously reported (Choi, H. D.; Seo, P. J.; Son, B. W. J. Korean Chem. Soc. 1999, 43, 494
  46. Bentley, T. W.; Jones, R. O. J. Chem. Soc. Perkin Trans. 2 1993, 2351-2357
  47. Koo, I. S.; Kwon, E.; Choi, H.; Yang, K.; Park, J. K.; Lee, J. P.; Lee, I.; Bentley, T. W. Bull. Korean Chem. Soc. 2007, 28(12), 2377 https://doi.org/10.5012/bkcs.2007.28.12.2377
  48. Guggenheim, E. A. Philos. Mag. 1926, 2, 538 https://doi.org/10.1080/14786442608564083

Cited by

  1. Correlation of the Rates of Solvolyses of 4-Methylthiophene-2-carbonyl Chloride Using the Extended Grunwald-Winstein Equation vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.499
  2. Correlation of the Rates of Solvolysis of 4-Morpholinecarbonyl Chloride Using the Extended Grunwald-Winstein Equation vol.31, pp.7, 2010, https://doi.org/10.5012/bkcs.2010.31.7.1963
  3. Correlation of the Rates of Solvolysis of 1-Piperidincarbonyl Chloride Using the Extended Grunwald-Winstein Equation vol.32, pp.11, 2008, https://doi.org/10.5012/bkcs.2011.32.11.3941
  4. Extent of Nucleophilic Participation in the Solvolyses of Alkyl Chloromethyl Ethers and Sulfides vol.36, pp.11, 2008, https://doi.org/10.3184/174751912x13469242440149
  5. Further Kinetic Studies of Solvolytic Reactions of Isobutyl Chloroformate in Solvents of High Ionizing Power Under Conductometric Conditions vol.34, pp.2, 2008, https://doi.org/10.5012/bkcs.2013.34.2.615