Stereodynamics and edge-to-face CH-π aromatic interactions in o-phenethyl-substituted biaryls

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2277-2282

  Jennings, W Brian ^a   Farrell, Brid M ^a,c   Malone, John F ^b  

^a UNIVERSITY COLLEGE CORK   (Ireland)

^b QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^c Marigot Group   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

BONDING; ISOMERS; MIXTURES; NUCLEAR MAGNETIC RESONANCE; PROTONS; X RAY CRYSTALLOGRAPHY;

BIARYL BOND; ENTROPICALLY DISFAVORED; INTRAMOLECULAR AROMATIC EDGE-TO-FACE INTERACTIONS; O-PHENETHYL-SUBSTITUTED BIARYLS; ORTHO-PROTON; PHENETHYL SIDE CHAIN; STEREODYNAMICS; X-RAY CRYSTAL STRUCTURE;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; ENTROPY; HYDROGEN BOND; ISOMER; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 33645037290     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0520902     Document Type: Article

References (30)

1. Cox, E. G.; Cruickshank, D. W. J.; Smith, J. A. S. Proc. R. Soc. London 1958, 247, 1-21.
2. (a) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
3. (b) Singh, J.; Thornton, J. M. FEBS Lett. 1985, 191, 1-6.
4. Burley, S.K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189.
5. For a review see: Nishio, M. CrystEngComm 2004, 6, 130-158.
6. Some recent examples: (a) Brayshaw, P. A.; Hall, A. K.; Harrison, W. T. A.; Harrowfield, J. M.; Pearce, D.; Shand, T. M.; Skelton, B. W.; Whitaker, C. R.; White, A. H. Eur. J. Inorg. Chem. 2005, 6, 1127-1141.
7. (b) Oh, M.; Stern, C. L.; Mirkin, C. A. Inorg. Chem. 2005, 44, 2647-2653.
8. (c) Abboud, K.; Harrowfield, J. M.; James, B. D.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2005, 358, 1293-1297.
9. (d) Soudi, A. A.; Marandi, F.; Ramazani, A.; Ahmadi, E.; Morsali, A. C. R. Chim. 2005, 8, 157-168.
10. (e) Reger, D. L.; Semeniuc, R. F.; Smith, M. D. Cryst. Growth Des. 2005, 5, 1181-1190.
11. (f) Harrowfield, J.; Matt, D. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 133-150.
12. (g) Emseis, P.; Hibbs, D. E.; Leverett, P.; Reddy, N.; Williams, P. A. Inorg. Chim. Acta 2004, 357, 3257-3263.
13. (h) Xu, W.; Lu, Y. X.; Liu, C. M.; Guo, P.; Lan, B. J.; Zhoua, H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2004, 60, 1049-1050.
14. Yang, J. S.; Liu, C. P.; Lin, B. C.; Tu, C. W.; Lee, G. H. J. Org. Chem. 2002, 67, 7343-7354.
15. (a) Reger, D. L.; Watson R. P.; Smith, M. D.; Pellechia, P. J. Organometallics 2005, 24, 1544-1555.
16. (b) Lukyanenko, N. G.; Kirichenko, T. I.; Lyapunov, A. Y.; Mazepa, A. V.; Simonov, Y. A.; Fonari, M. S.; Botoshansky, M. M. Chem.- Eur. J. 2004, 11, 262-270.
17. (c) Leonard, M. S.; Carroll, P. J.; Joullie, M. M. J. Org. Chem. 2004, 69, 2526-2531.
18. (d) Balog, M.; Grosu, I.; Ple, G.; Ramondenc, Y.; Condamine, E.; Varga, R. A. J. Org. Chem. 2004, 69, 1337-1345.
19. (a) Sukalovic, V.; Andric, D.; Roglic, G.; Kostic-Rajacic, S.; Schrattenholz, A.; Soskic, V. Eur. J. Med. Chem. 2005, 40, 481-493.
20. (b) Sukalovic, V.; Zlatovic, M.; Andric, D.; Roglic, G.; Kostic-Rajacic, S.; Soskic, V. Arzneim.-Forsch. 2005, 55, 145-152.
21. (c) Fatten, D. Drug Discovery Today 2004, 9, 229-238.
22. Shu, L. H.; Shi, Y. Tetrahedron Lett. 2004, 45, 8115-8117.
23. For a review, see: Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894.
24. (a) Boyd, D. R.; Evans, T. A.; Jennings, W. B.; Malone, J. F.; O'Sullivan, W. O.; Smith, A. Chem. Commun. 1996, 2269-2270.
25. (b) Hamor, T. A.; Jennings, W. B.; Proctor, L. D.; Tolley, M. S.; Boyd, D. R.; Mullan, T. J. Chem. Soc., Perkins Trans. 2 1990, 25-30.
26. (a) Boyd, D. R.; Al-Showiman, S.; Jennings, W. B. J. Org. Chem. 1978, 43, 3335-3339.
27. (b) Jennings, W. B.; Kochanewycz, M. J.; Lunazzi, L. J. Chem. Soc., Perkin Trans. 2 1997, 2271-2273.
28. The ring current shielding of a proton situated 2.59 A vertically above the face of a phenyl ring and offset from the center by 0.52 Å (as in the X-ray structure of 3a) was estimated to be -2.5 ppm using the tabular data given in Emsley, J. W.; Feeney, J.; Sutcliffe, L. H. High Resolution Nuclear Magnetic Resonance Spectroscopv; Pergamon Press: Oxford, 1965; Vol. 1, pp 595-604.
29. Tobias, J. K.; Knochel, P. Angew. Chem. Int. Ed. 2005, 44, 2947-2952.
30. de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans, 1 2000, 787-797.