Severe energy costs of double steric interactions: Towards a molecular clamp

European Journal of Organic Chemistry

Volumn , Issue 27, 2010, Pages 5203-5216

  Nikitin, Kirill ^a   Fleming, Conor ^a   Müller Bunz, Helge ^a   Ortin, Yannick ^a   McGlinchey, Michael J ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Molecular devices; Molecular machinery; Rotational barrier; Steric hindrance; Strained molecules

Indexed keywords

EID: 77956492373     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000847     Document Type: Article

References (64)

1. a) V. Pophristic, L. Goodman, Nature 2001, 411, 565;
2. M. Oki, Top. Stereochem. 1983, 14, 1-81;
3. S. Brydges, L. E. Harrington, M. J. McGlinchey, Coord. Chem. Rev. 2002, 233/234, 75-105.
4. a) M. J. Hafezi, F. J. Sharif, THEOCHEM 2008, 814, 43-49;
5. J. R. Durig, D. A. C. Compton, J. Phys. Chem. 1979, 83, 265-268.
6. a) M. Nakamura, M. Oki, Bull. Chem. Soc. Jpn. 1975, 48, 2106-2111;
7. M. Oki, I. Fujino, D. Kawaguchi, K. Chuda, Y. Moritaka, Y. Yamamoto, S. Tsuda, T. Akinaga, M. Aki, H. Kojima, N. Morita, M. Sakurai, S. Toyota, Y. Tanaka, T. Tanuma, G. Yamamoto, Bull. Chem. Soc. Jpn. 1997, 70, 457-469;
8. G. Yamamoto, M. Suzuki, M. Oki, Angew. Chem. 1981, 93, 580-581;
9. Angew. Chem. Int. Ed. Engl. 1981, 20, 607-608;
10. D. Zehm, W. Fudickar, M. Hans, U. Schilde, A. Kelling, T. Linker, Chem. Eur. J. 2008, 14, 11429-11441;
11. A. Caspar, S. Altenburger-Combrisson, F. Gobert, Org. Magn. Reson. 1978, 11, 603-606;
12. P. J. Marriott, Y.-H. Lai, J. Chromatogr. 1988, 447, 29-41.
13. a) K. M. Mislow, Introduction to Stereochemistry, W. A. Benjamin, Inc., 1965, pp. 78-79;
14. G. H. Christie, J. J. Kenner, J. Chem. Soc. 1922, 121, 614-620;
15. R. Adams, H. C. Yuan, Chem. Rev. 1933, 12, 261-338;
16. G. Yamamoto, T. Nemoto, Y. Ohashi, Bull. Chem. Soc. Jpn. 1992, 65, 1957-1966;
17. A. Mazzanti, L. Lunazzi, M. Minzoni, J. E. Anderson, J. Org. Chem. 2006, 71, 5474-5481;
18. G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518-5563;
19. Angew. Chem. Int. Ed. 2005, 44, 5384-5427.
20. a) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. Garcia, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657-3658;
21. T. R. Kelly, J. P. Sestelo, I. N. Tellitu, J. Org. Chem. 1998, 63, 3655-3665;
22. T. R. Kelly, Acc. Chem. Res. 2001, 34, 514-522;
23. M. Llunell, P. Alemany, J. M. Bofill, ChemPhysChem 2008, 9, 1117-1119;
24. T. F. Magnera, J. Michl, Top. Curr. Chem. 2005, 262, 63-97, and references cited therein;
25. I. Yoon, D. Bentez, Y.-L. Zhao, O. Miljanic, S.-Y. Kim, E. Tkatchouk, K. C.-F. Leung, S. I. Khan, W. A. Goddard, J. F. Stoddart, Chem. Eur. J. 2009, 15, 1115-1122;
26. R. D. Rasberry, K. D. Shimizu, Org. Biomol. Chem. 2009, 7, 3899-3905;
27. V. Serreli, C.-F. Lee, E. R. Kay, D. A. Leigh, Nature 2007, 445, 523-527;
28. J. Hernandez, E. R. Kay, D. A. Leigh, Science 2004, 306, 1532-1537;
29. G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281-1376.
30. a) H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 21, 175-182;
31. T. R. Kelly, R. A. Silva, H. De Silva, S. Jasmin, Y. Zhao, J. Am. Chem. Soc. 2000, 122, 6935-6949;
32. L. Grill, K.-H. Rieder, F. Moresco, G. Rapenne, S. Stojkovic, X. Bouju, C. Joachim, Nat. Nanotechnol 2007, 2, 95-98.
33. a) T. A. Albright, P. Hofmann, R. Hoffmann, C. P. Lillya, P. A. Dobosh, J. Am. Chem. Soc. 1983, 105, 3396-3411;
34. Y. F. Oprunenko, Russ. Chem. Rev. 2000, 69, 683-704;
35. S. Brydges, N. Reginato, L. P. Cuffe, C. M. Seward, M. J. McGlinchey, C. R. Chim. 2005, 8, 1497-1505;
36. E. Kirillov, S. Kahlal, T. Roisnel, T. Georgelin, J.-Y. Saillard, J. F. Carpentier, Organometallics 2008, 27, 387-393;
37. G. Yamamoto, Pure Appl. Chem. 1990, 62, 569-574.
38. a) L. E. Harrington, L. S. Cahill, M. J. McGlinchey, Organometallics 2004, 23, 2884-2891;
39. K. Nikitin, H. Müller-Bunz, Y. Ortin, M. J. McGlinchey, Org. Biomol. Chem. 2007, 5, 1952-1960.
40. a) H. Förster, F. Vögtle, Angew. Chem. 1977, 89, 443-455;
41. Angew. Chem. Int. Ed. Engl. 1977, 16, 429-441;
42. G. Bott, L. D. Field, S. Sternhell, J. Am. Chem. Soc. 1980, 102, 5618-5626;
43. L. Lunazzi, A. Mazzanti, M. Minzoni, J. Org. Chem. 2006, 71, 9297-9301;
44. R. Ruzziconi, S. Spizzichino, L. Lunazzi, A. Mazzanti, M. Schlosser, Chem. Eur. J. 2009, 15, 2645-2652.
45. K. Nikitin, H. Müller-Bunz, Y. Ortin, M. J. McGlinchey, Chem. Eur. J. 2009, 15, 1836-1843.
46. * have been introduced merely as a convenient measure of the severity of non-bonded interactions and give no insight into the actual details of geometry of the transition state.
47. D.-W. Lee, J. Yun, Bull. Korean Chem. Soc. 2004, 25, 29-30.
48. H. Dang, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2001, 123, 355-356.
49. K. Nikitin, H. Müller-Bunz, Y. Ortin, W. Risse, M. J. McGlinchey, Eur. J. Org. Chem. 2008, 3079-3084.
50. N. M. Sergeyev, K. F. Abdulla, V. R. Skvarchenko, J. Chem. Soc. Chem. Commun. 1972, 368-370.
51. J. P. N. Brewer, I. F. Eckhard, H. Heaney, B. A. Marples, J. Chem. Soc. C 1968, 664-676.
52. J. Trotter, F. C. Wireko, Acta Crystallogr., Sect. C 1991, 47, 1275-1277.
53. L. R. C. Barclay, R. A. Chapman, Can. J. Chem. 1965, 43, 1754-1760.
54. W. J. Wasserman, M. C. Kloetzel, J. Am. Chem. Soc. 1953, 75, 3036-3038.
55. P. Reutenauer, P. J. Boul, J.-M. Lehn, Eur. J. Org. Chem. 2009, 1691-1697.
56. C. Pinazzi, Ann. Chim. 1962, 7, 397-408.
57. J. L. Cook, C. A. Hunter, C. M. R. Low, A. Perez-Velasco, J. G. Vinter, Angew. Chem. 2007, 119, 3780-3783;
58. Angew. Chem. Int. Ed. 2007, 46, 3706-3709.
59. D. B. Li, W. F. Paxton, R. H. Baughman, T. J. Huang, J. F. Stoddart, P. S. Weiss, MRS Bull. 2009, 34, 671-681, and references cited therein.
60. H. S. Gutowsky, C. H. Holm, J. Chem. Phys. 1956, 25, 1228-1234.
61. B. H. Klandermann, T. R. Criswell, J. Org. Chem. 1969, 34, 3426-3430.
62. G. M. Sheldrick, SADABS, Bruker AXS Inc., Madison, WI 53711, 2000.
63. G. M. Sheldrick, SHELXS-97, University of Göttingen, Germany, 1997.
64. G. M. Sheldrick, SHELXL-97-2, University of Göttingen, Germany, 1997.