An AM1 Semiempirical Study of Host-Guest Complexation in Hemicarcerand Complexes

Journal of Computational Chemistry

Volumn 25, Issue 4, 2004, Pages 542-557

  Liddell, Michael J ^a   Margetic, Davor ^b,c   Mitchell, Anthony S ^b,d   Warrener, Ronald N ^b  

^a JAMES COOK UNIVERSITY   (Australia)

^b CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

^d UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

AMI; Carceplex; Hemicarcerand; Host guest; Theoretical

Indexed keywords

ACTIVATION ENERGY; COMPLEXATION; COMPUTATIONAL METHODS; CONSTRAINT THEORY; DATA REDUCTION; HAMILTONIANS; MOLECULAR DYNAMICS; X RAY ANALYSIS;

AMI; CARCEPLEX; HEMICARCERAND; HOST-GUEST;

SUPRAMOLECULAR CHEMISTRY;

EID: 1442330382     PISSN: 01928651     EISSN: None     Source Type: Journal    
DOI: 10.1002/jcc.10404     Document Type: Article

References (50)

1. (a) Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, England, 1994;
2. (b) Cram, D. J. Nature 1992, 356, 29.
3. (a) Sherman, J. C. Tetrahedron 1995, 51, 3395;
4. (b) Warmuth, R.; Yoon, J. Acc Chem Res 2001, 34, 95.
5. Sheu, C.; Houk, K. N. J Am Chem Soc 1996, 118, 8056.
6. Jasat, A.; Sherman, J. C. Chem Rev 1999, 99, 931.
7. (a) Cram, D. J.; Tanner, M. E.; Thomas, R. Agnew Chem Int Ed Engl 1991, 30, 1024;
8. (b) Sherman, J. C.; Cram, D. J. J Am Chem Soc 1989, 111, 4527.
9. Piatnitski, E. L.; Deshayes, K. D. Angew Chem Int Ed Engl 1998, 37, 970.
10. Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50.
11. Warmuth, R.; Kerdelhué, J.-L.; Sánchez Carrera, S.; Langenwalter, K. J.; Brown, N. Angew Chem Int Ed 2002, 41, 96.
12. Warrener, R. N. In Advances in Theoretically Interesting Moledules; JAI Press: Greenwich, CT, 1992, p. 143, vol. 2, and references cited therein.
13. Warrener, R. N.; Amarasekara, A. S.; Russell, R. A. Chem Commun 1996, 1519.
14. (a) Houk, K. N.; Nakamura, K.; Sheu, C.; Keating, A. E. Science 1996, 273, 627;
15. (b) Beno, B. R.; Sheu, C.; Houk. K. N.; Warmuth, R.; Cram, D. J. Chem Commun 1998, 301.
16. Nakamura, K.; Houk, K. N. J Am Chem Soc 1995, 117, 1853.
17. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J Am Chem Soc 1991, 113, 2194.
18. Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. F.; Cram, D. J. J Am Chem Soc 1996, 188, 5590.
19. von dem Bussche-Hünnefeld, C.; Bühring, D.; Knobler, C. B.; Cram, D. J. J Chem Soc, Chem Commun 1995, 1085.
20. Nakamura, K.; Chimin, S.; Keating, A. E.; Houk, K. N.; Sherman, J. C.; Chapman, R. G.; Jorgensen, W. L. J Am Chem Soc 1997, 119, 4321.
21. (a) Mecozzi, S.; Rebek, J., Jr. Chem Eur 1998, 4, 1016;
22. (b) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J Am Chem Soc 1997, 119, 77.
23. Warmuth, R. Eur J Org Chem 2001, 423.
24. Pina, F.; Parola, A. J.; Ferreira, E.; Maestri, M.; Armaroli, N.; Ballardini, R.; Balzani, V. J Phys Chem 1995, 99, 12701.
25. Robbins, T. A.; Cram, D. J. J Am Chem Soc 1993, 115, 12199.
26. Streitweiser, A.; Heathcock, C. H. Introduction to Organic Chemistry; Macmillan: New York, 1976, p. 1028.
27. Warmuth, R.; Marvel, M. A. Chem Eur J 2001, 7, 1209.
28. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J Am Chem Soc 1985, 107, 3902;
29. (b) Stewart, J. J. P. In Reviews in Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; VCH Publishers: New York, 1991, 2, 45.
30. Stewart, J. J. P. J Comp Chem 1989, 10, 209.
31. Dewar, M. J. S.; Thiel, W. J Am Chem Soc 1997, 99, 4899.
32. Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J Am Chem Soc 1988, 100, 2229.
33. Tanner, M. E.; Knobler, C. B.; Cram, D. J. J Am Chem Soc 1990, 112, 1659.
34. Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J Am Chem Soc 1994, 116, 111.
35. Cram, D. J.; Tanner, M. E.; Knobler, C. B. J Am Chem Soc 1991, 113, 7717.
36. Cram, D. J.; Blanda, M. T.; Paek, K.; Knobler, C. B. J Am Chem Soc 1992, 114, 7765.
37. Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman, J. C.; J Org Chem 1995, 60, 1207.
38. Mitchell, A.Unpublished results. GAMESS RHF geometry optimisations of 5a.pyrazine made use of 3-21 G* and Huzinaga MINI basis sets. Calculations were carried out at the South Australian Centre for High Performance Computing.
39. Chapman, R. G.; Olovsson, G.; Trotter, J.; Sherman, J. C. J Am Chem Soc 1998, 120, 6252.
40. Spartan User's Guide; Wavefunction. Inc.: Irvine, CA, 1997, p. 169.
41. Romanova, Z. S.; Deshayes, K.; Piotrowiak, P. J Am Chem Soc 2001, 123, 11029.
42. Silberberg, M. S. Chemistry: The Molecular Nature of Matter and Change; McGraw Hill: Boston, 2000, p. 344, 2nd ed.
43. Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Angew Chem Int Ed Engl 1994, 33, 2345.
44. +, 18%, 1a.furan).
45. Robbins, T. A.; Cram, D. J. J Chem Soc Chem Commun 1995, 1515.
46. Yoon, J.; Cram, D. J. Chem Commun 1997, 1505.
47. Place, D.; Brown, J.; Deshayes, K. Tetrahedron Lett 1998 39, 5915.
48. Nuwaysir, L. M.; Castoro, J. A.; Yang, C. L.-C.; Wilkins, C. L. J Am Chem Soc 1992, 114, 5748.
49. Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J Am Chem Soc 1997, 119, 3229.
50. Warrener, R. N.; Elsey, G. M. The Royal Australian Chemical Institute 14th National Organic Conference, Wollongong, NSW, Australia, July 1994.