메뉴 건너뛰기




Volumn 68, Issue 16, 2003, Pages 6470-6473

Role of face-to-face and edge-to-face aromatic interactions in the inclusion complexation of cyclobis(paraquat-p-phenylene): A theoretical study

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COMPLEXATION; ELECTROSTATICS;

EID: 0042074624     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026887u     Document Type: Article
Times cited : (26)

References (52)
  • 1
    • 0034852567 scopus 로고    scopus 로고
    • (a) Molecular Machines Special Issue: Acc. Chem. Res. 2001, 34, 409-522.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 409-522
  • 2
    • 0003705758 scopus 로고    scopus 로고
    • Structure And Bonding; Sauvage, J.-P., Ed.; Springer: Berlin, Germany
    • (b) Molecular Machines and Motors; Structure And Bonding, Vol. 99; Sauvage, J.-P., Ed.; Springer: Berlin, Germany, 2001.
    • (2001) Molecular Machines and Motors , vol.99
  • 5
    • 33748716824 scopus 로고    scopus 로고
    • Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Sauvage, J.-P., Hosseini, M. W., Eds.; Pergamon: Oxford, UK, Chapter 3
    • (c) Amabilino, D. B.; Raymo, F. M.; Stoddart, J. F. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Sauvage, J.-P., Hosseini, M. W., Eds.; Pergamon: Oxford, UK, 1996; Vol. 9, Chapter 3.
    • (1996) Comprehensive Supramolecular Chemistry , vol.9
    • Amabilino, D.B.1    Raymo, F.M.2    Stoddart, J.F.3
  • 9
    • 0001227655 scopus 로고
    • For accounts and reviews on π-π stacking interactions, see: (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (b) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (c) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5525-5534
    • Hunter, C.A.1    Sanders, J.K.M.2
  • 10
    • 33748228968 scopus 로고
    • For accounts and reviews on π-π stacking interactions, see: (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (b) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (c) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 1584-1586
    • Hunter, C.A.1
  • 11
    • 0343417831 scopus 로고
    • For accounts and reviews on π-π stacking interactions, see: (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (b) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (c) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
    • (1995) Pure Appl. Chem. , vol.67 , pp. 683-689
    • Cozzi, F.1    Siegel, J.S.2
  • 12
    • 0029935228 scopus 로고    scopus 로고
    • For accounts and reviews on π-π stacking interactions, see: (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534. (b) Hunter, C. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1584-1586. (c) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 683-689. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1019-1027
    • Shetty, A.S.1    Zhang, J.2    Moore, J.S.3
  • 13
    • 0029117927 scopus 로고
    • For accounts and reviews on [C-H⋯π] interactions, see: (a) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213. (c) Nishio, M.; Hirota, M.; Umezawa, Y. The [C-H⋯π] Interaction. Evidence, Nature, and Consequences; Wiley: New York, 1998. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894. (e) Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M. Chem. Eur. J. 2002, 8, 2848-2858.
    • (1995) Tetrahedron , vol.51 , pp. 8665-8701
    • Nishio, M.1    Umezawa, Y.2    Hirota, M.3    Takeuchi, Y.4
  • 14
    • 0001679930 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯π] interactions, see: (a) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213. (c) Nishio, M.; Hirota, M.; Umezawa, Y. The [C-H⋯π] Interaction. Evidence, Nature, and Consequences; Wiley: New York, 1998. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894. (e) Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M. Chem. Eur. J. 2002, 8, 2848-2858.
    • (1998) Bull. Chem. Soc. Jpn. , vol.71 , pp. 1207-1213
    • Umezawa, Y.1    Tsuboyama, S.2    Honda, K.3    Uzawa, J.4    Nishio, M.5
  • 15
    • 0003505803 scopus 로고    scopus 로고
    • Wiley: New York
    • For accounts and reviews on [C-H⋯π] interactions, see: (a) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213. (c) Nishio, M.; Hirota, M.; Umezawa, Y. The [C-H⋯π] Interaction. Evidence, Nature, and Consequences; Wiley: New York, 1998. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894. (e) Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M. Chem. Eur. J. 2002, 8, 2848-2858.
    • (1998) The [C-H⋯π] Interaction. Evidence Nature, and Consequences
    • Nishio, M.1    Hirota, M.2    Umezawa, Y.3
  • 16
    • 0035200608 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯π] interactions, see: (a) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213. (c) Nishio, M.; Hirota, M.; Umezawa, Y. The [C-H⋯π] Interaction. Evidence, Nature, and Consequences; Wiley: New York, 1998. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894. (e) Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M. Chem. Eur. J. 2002, 8, 2848-2858.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 885-894
    • Jennings, W.B.1    Farrell, B.M.2    Malone, J.F.3
  • 17
    • 85044702121 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯π] interactions, see: (a) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665-8701. (b) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213. (c) Nishio, M.; Hirota, M.; Umezawa, Y. The [C-H⋯π] Interaction. Evidence, Nature, and Consequences; Wiley: New York, 1998. (d) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894. (e) Carver, F. J.; Hunter, C. A.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M. Chem. Eur. J. 2002, 8, 2848-2858.
    • (2002) Chem. Eur. J. , vol.8 , pp. 2848-2858
    • Carver, F.J.1    Hunter, C.A.2    Livingstone, D.J.3    McCabe, J.F.4    Seward, E.M.5
  • 18
    • 0007116617 scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 290-296
    • Desiraju, G.R.1
  • 19
    • 0000216832 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 441-449
    • Desiraju, G.R.1
  • 20
    • 0006168009 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1996) Chem. Commun. , pp. 2655-2656
    • Krishnamohan Sharma, C.V.1    Zaworotko, M.J.2
  • 21
    • 1842763826 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1997) Chem. Commun. , pp. 727-734
    • Steiner, T.1
  • 22
    • 0030767082 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1997) Chem.-Eur. J. , vol.3 , pp. 1400-1404
    • Berger, I.1    Egli, M.2
  • 23
    • 0002271366 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1997) Chem. Commun. , pp. 1669-1670
    • Bodige, S.G.1    Rogers, R.D.2    Blackstock, S.C.3
  • 24
    • 0003465684 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (1998) Top. Curr. Chem. , vol.198 , pp. 57-95
    • Desiraju, G.R.1
  • 25
    • 0035955230 scopus 로고    scopus 로고
    • For accounts and reviews on [C-H⋯O] hydrogen-bonding interactions, see: (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449. (c) Krishnamohan Sharma, C. V.; Zaworotko, M. J. Chem. Commun. 1996, 2655-2656. (d) Steiner, T. Chem. Commun. 1997, 727-734. (e) Berger, I.; Egli, M. Chem.-Eur. J. 1997, 3, 1400-1404. (f) Bodige, S. G.; Rogers, R. D.; Blackstock, S. C. Chem. Commun. 1997, 1669-1670. (g) Desiraju., G. R. Top. Curr. Chem. 1998, 198, 57-95. (h) Raymo, F. M.; Bartberger, M. D.; Houk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9264-9267
    • Raymo, F.M.1    Bartberger, M.D.2    Houk, K.N.3    Stoddart, J.F.4
  • 32
    • 84989504610 scopus 로고
    • Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem. 1988, 101, 1605; Angew. Chem., Int. Ed. Engl. 1988, 27, 1547-1550.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 1547-1550
  • 40
    • 0043229764 scopus 로고    scopus 로고
    • note
    • (b). MP2 calculations were carried out with the default "frozen-core" option.
  • 46
    • 0043229763 scopus 로고
    • Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, Chapter 7
    • Electrostatic potential was calculated at a distance of 1.75 A from the center of mass of the guest in the direction perpendicular to the average molecular plane, as suggested in: Politzer, P.; Murray, J. S. Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1991; Vol. 2, Chapter 7.
    • (1991) Computational Chemistry , vol.2
    • Politzer, P.1    Murray, J.S.2
  • 47
  • 50
    • 0041727277 scopus 로고    scopus 로고
    • note
    • -1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.