Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Solvent Effect on the Nature of the Metallamacrocycles Formed: Formation of Octanuclear and Dodecanuclear Manganese Metalladiazamacrocycles

  • John, Rohith P. (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Lee, Kyung-Jin (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Lee, Kyung-Jae (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Park, Mi-Ra (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Lah, Myoung-Soo (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University)
  • Published : 2007.11.20
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Abstract

The aminolysis of diphenyl thiophosphinic chloride (2) with substituted anilines in acetonitrile at 55.0 oC is investigated kinetically. Kinetic results yield large Hammett ρX (ρnuc = ?3.97) and Bronsted βX (βnuc = 1.40) values. A concerted mechanism involving a partial frontside nucleophilic attack through a hydrogen-bonded, four-center type transition state is proposed on the basis of the primary normal kinetic isotope effects (kH/kD = 1.0-1.1) with deuterated aniline (XC6H4ND2) nucleophiles. The natural bond order charges on P and the degrees of distortion of 42 compounds: chlorophosphates [(R1O)(R2O)P(=O)Cl], chlorothiophosphates [(R1O)(R2O)P(=S)Cl], phosphonochloridates [(R1O)R2P(=O)Cl], phosphonochlorothioates [(R1O)R2P(=S)Cl], chlorophosphinates [R1R2P(=O)Cl], and chlorothiophosphinates [R1R2P(=S)Cl] are calculated at the B3LYP/ 6-311+G(d,p) level in the gas phase.

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References

  1. Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853 https://doi.org/10.1021/cr9601324
  2. Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629 https://doi.org/10.1021/cr9900432
  3. Holliday, B. J.; Mirkin, C. A. Angew. Chem. Int. Ed. Engl. 2001, 40, 2022 https://doi.org/10.1002/1521-3773(20010601)40:11<2022::AID-ANIE2022>3.0.CO;2-D
  4. Bodwin, J. J.; Cutland, A. D.; Malkani, R. G.; Pecoraro, V. L. Coord. Chem. Rev. 2001, 216-217, 489
  5. Severin, K. Chem. Commun. 2006, 3859
  6. Fujita, M.; Tominaga, M.; Hori, A.; Therrien, B. Acc. Chem. Res. 2005, 38, 371
  7. Kubota, Y.; Biradha, K.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. Bull. Chem. Soc. Jpn. 2002, 75, 559 https://doi.org/10.1246/bcsj.75.559
  8. Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185
  9. Dong, V. M.; Fiedler, D.; Carl, B.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 14464 https://doi.org/10.1021/ja0657915
  10. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem. Int. Ed. Engl. 2006, 45, 745 https://doi.org/10.1002/anie.200501938
  11. Kawano, M.; Kobayashi, Y.; Ozeki, T.; Fujita, M. J. Am. Chem. Soc. 2006, 128, 6558 https://doi.org/10.1021/ja0609250
  12. Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. J. Am. Chem. Soc. 2000, 122, 6311 https://doi.org/10.1021/ja000779c
  13. Yoshizawa, M.; Miyagi, S.; Kawano, M.; Ishiguro, K.; Fujita, M. J. Am. Chem. Soc. 2004, 126, 9172 https://doi.org/10.1021/ja047612u
  14. Yoshizawa, M.; Takeyama, Y.; Okano, T.; Fujita, M. J. Am. Chem. Soc. 2003, 125, 3243 https://doi.org/10.1021/ja020718+
  15. Tominaga, M.; Suzuki, K.; Kawano, M.; Kusukawa, T.; Ozeki, T.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Angew. Chem. Int. Ed. Engl. 2004, 43, 5621 https://doi.org/10.1002/anie.200461422
  16. Yoshizawa, M.; Nakagawa, J.; Kumazawa, K.; Nagao, M.; Kawano, M.; Ozeki, T.; Fujita, M. Angew. Chem. Int. Ed. Engl. 2005, 44, 1810 https://doi.org/10.1002/anie.200462171
  17. Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keeffe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319 https://doi.org/10.1021/ar000034b
  18. Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759 https://doi.org/10.1021/ar010062+
  19. Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705 https://doi.org/10.1038/nature01650
  20. Chae, H. K.; Siberio-Perez, D. Y.; Kim, J.; Go, Y.; Eddaoudi, M.; Matzger, A.; O'Keeffe, M.; Yaghi, O. M. Nature 2004, 427, 523 https://doi.org/10.1038/nature02311
  21. Li, H.; Laine, A.; O'Keeffe, M.; Yaghi, O. M. Science 1999, 283, 1145 https://doi.org/10.1126/science.283.5405.1145
  22. Kitagawa, S.; Kitaura, R.; Noro, S.-I. Angew. Chem. Int. Ed. Engl. 2004, 43, 2334 https://doi.org/10.1002/anie.200300610
  23. Glaser, T.; Heidemeier, M.; Weyhermuller, T.; Hoffmann, R.-D.; Rupp, H.; Muller, P. Angew. Chem. Int. Ed. Engl. 2006, 45, 6033 https://doi.org/10.1002/anie.200600712
  24. Miyasaka, H.; Nakata, K.; Lecren, L.; Coulon, C.; Nakazawa, Y.; Fujisaki, T.; Sugiura, K.-I.; Yamashita, M.; Clerac, R. J. Am. Chem. Soc. 2006, 128, 3770 https://doi.org/10.1021/ja0574062
  25. Dendrinou-Samara, C.; Alexiou, M.; Zaleski, C. M.; Kampf, J. W.; Kirk, M. L.; Kessissoglou, D. P.; Pecoraro, V. L. Angew. Chem. Int. Ed. Engl. 2003, 42, 3763 https://doi.org/10.1002/anie.200351246
  26. Bell, A.; Aromi, G.; Teat, S. J.; Wernsdorfer, W.; Winpenny, R. E. P. Chem. Commun. 2005, 2808
  27. Hill, S.; Edwards, R. S.; Aliaga-Alcalde, N.; Christou, G. Science 2003, 302, 1015 https://doi.org/10.1126/science.1090082
  28. Stamatatos, T. C.; Foguet-Albiol, D.; Stoumpos, C. C.; Raptopoulou, C. P.; Terzis, A.; Wernsdorfer, W.; Perlepes, S. P.; Christou, G. J. Am. Chem. Soc. 2005, 127, 15380 https://doi.org/10.1021/ja0558138
  29. Hwang, S.-H.; Moorefield, C. N.; Wang, P.; Fronczek, F. R.; Courtney, B. H.; Newkome, G. R. Dalton Trans. 2006, 3518
  30. Hwang, S.-H.; Wang, P.; Moorefield, C. N.; Jung, J.-C.; Kim, J.-Y.; Lee, S.-W.; Newkome, G. R. Macromol. Rapid Commun. 2006, 27, 1809 https://doi.org/10.1002/marc.200600516
  31. Wong-Foy, A. G.; Matzger, A. J.; Yaghi, O. M. J. Am. Chem. Soc. 2006, 128, 3494 https://doi.org/10.1021/ja058213h
  32. Rowsell, J. L. C.; Millward, A. R.; Park, K. S.; Yaghi, O. M. J. Am. Chem. Soc. 2004, 126, 5666 https://doi.org/10.1021/ja049408c
  33. Kubota, Y.; Takata, M.; Matsuda, R.; Kitaura, R.; Kitagawa, S.; Kato, K.; Sakata, M.; Kobayashi, T. C. Angew. Chem. Int. Ed. Engl. 2005, 44, 920 https://doi.org/10.1002/anie.200461895
  34. Matsuda, R.; Kitaura, R.; Kitagawa, S.; Kubota, Y.; Belosludov, R. V.; Kobayashi, T. C.; Sakamoto, H.; Chiba, T.; Takata, M.; Kawazoe, Y.; Mita, Y. Nature 2005, 436, 238 https://doi.org/10.1038/nature03852
  35. Millward, A. R.; Yaghi, O. M. J. Am. Chem. Soc. 2005, 127, 17998 https://doi.org/10.1021/ja0570032
  36. Uemura, K.; Kitagawa, S.; Fukui, K.; Saito, K. J. Am. Chem. Soc. 2004, 126, 3817 https://doi.org/10.1021/ja039914m
  37. Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251 https://doi.org/10.1126/science.1124985
  38. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 351
  39. Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem. Int. Ed. Engl. 2004, 43, 6748 https://doi.org/10.1002/anie.200461776
  40. Leung, D. H.; Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem. Int. Ed. Engl. 2004, 43, 963 https://doi.org/10.1002/anie.200352772
  41. Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kim, K. Nature 2000, 404, 982 https://doi.org/10.1038/35010088
  42. Kwak, B.; Rhee, H.; Park, S.; Lah, M. S. Inorg. Chem. 1998, 37, 3599 https://doi.org/10.1021/ic971538h
  43. Kwak, B.; Rhee, H.; Lah, M. S. Polyhedron 2000, 19, 1985 https://doi.org/10.1016/S0277-5387(00)00499-X
  44. John, R. P.; Lee, K.; Kim, B. J.; Suh, B. J.; Rhee, H.; Lah, M. S. Inorg. Chem. 2005, 44, 7109 https://doi.org/10.1021/ic050891h
  45. Moon, D.; Lee, K.; John, R. P.; Kim, G. H.; Suh, B. J.; Lah, M. S. Inorg. Chem. 2006, 45, 7991 https://doi.org/10.1021/ic060646d
  46. Lin, S.; Liu, S.-X.; Huang, J.-Q.; Lin, C.-C. J. Chem. Soc., Dalton Trans. 2002, 1595
  47. Lin, S.; Liu, S.-X.; Chen, Z.; Lin, B.-Z.; Gao, S. Inorg. Chem. 2004, 43, 2222 https://doi.org/10.1021/ic035145w
  48. Liu, S.-X.; Lin, S.-L.; Lin, B.-Z.; Lin, C.-C.; Huang, J.-Q. Angew. Chem. Int. Ed. Engl. 2001, 40, 1084
  49. Song, J.; Moon, D.; Lah, M. S. Bull. Korean Chem. Soc. 2002, 23, 708 https://doi.org/10.5012/bkcs.2002.23.5.708
  50. John, R. P.; Lee, K.; Lah, M. S. Chem. Commun. 2004, 2660
  51. SMART and SAINT, Area Detector Software Package and SAX Area detector Integration Program; Bruker Analytical X-ray: Madison, WI, 1997
  52. SADABS, Area Detector Absorption Correction Program; Bruker Analytical X-ray: Madison, WI, 1997
  53. Sheldrick, G. M. SHELXTLPLUS, Crystal Structure Analysis Package; Bruker Analytical X-ray: Madison, WI, 1997
  54. Spek, A. L. Acta Crystallogr. Sect. A 1990, 46, 194 https://doi.org/10.1107/S0108767389011189

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