18,18′-dihexyl[9,9′]biphenanthro[9,10-b]triphenylene: Construction and consequences of a profoundly hindered aryl-aryl single bond

Journal of the American Chemical Society

Volumn 130, Issue 40, 2008, Pages 13392-13399

  Hilton, Cameron L ^a   Crowfoot, Jeremy M ^a   Rempala, Pawel ^a   King, Benjamin T ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ZIRCONIUM;

SINGLE BONDS; TRIPHENYLENE;

LITHIUM;

18,18' DIHEXYL[9,9']BIPHENANTHRO[9,10 B]TRIPHENYLENE; ANTHRACENE DERIVATIVE; LIGAND; PHENANTHRENE DERIVATIVE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG; 18,18' DIHEXYL(9,9')BIPHENANTHRO(9,10 B)TRIPHENYLENE; 18,18'-DIHEXYL(9,9')BIPHENANTHRO(9,10-B)TRIPHENYLENE; CHRYSENE DERIVATIVE; PHENOL DERIVATIVE;

ADIABATICITY; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ENERGY; MEASUREMENT; MOLECULAR DYNAMICS; PHASE TRANSITION; SYNTHESIS; TEMPERATURE DEPENDENCE; X RAY DIFFRACTION; ALKYLATION; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE;

ALKYLATION; CHRYSENES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; TEMPERATURE; X-RAY DIFFRACTION;

EID: 53549115949     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803396n     Document Type: Article

References (34)

1. Fetzer, J. C. Large (C ≤ 24) Polycyclic Aromatic Hydrocarbons: Chemistry and Analysis; Wiley & Sons: New York, 2000; p 6.
2. Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D. J. Am. Chem. Soc. 1986, 108, 5652-5653.
3. Pascal, R. A., Jr.; McMillan, W. D.; Van Engen, D.; Eason, R. G. J. Am. Chem. Soc. 1987, 109, 4660-4665.
4. Pascal, R. A., Jr Pure Appl. Chem. 1993, 65, 105-110.
5. Gill, R. D.; Beltran, L.; Nettikumara, A. N.; Harvey, R. G.; Koostra, A.; DiGiovanni, J. Mol. Carcinog. 1992, 6, 53-59.
6. Zimmerman, S. C. Tetrahedron Lett. 1988, 29, 983-986.
7. Zimmerman, S. C.; Zeng, Z.; Wu, W.; Reichert, D. E. J. Am. Chem. Soc. 1991, 113, 183-196.
8. Yang, Y.; Dai, W.; Zhang, Y.; Petersen, J. L.; Wang, K. K. Tetrahedron 2006, 62, 4364-4371.
9. Lambert, P.; Martin, R. H. Bull. Soc. Chim. Belg. 1952, 61, 513-523.
10. Mondal, S.; Bandyopadhyay, K.; Bhattacharya, A. J. Curr. Sci. 1985, 54, 455-458.
11. Eshdat, L.; Ayalon, A.; Beust, R.; Shenhar, R.; Rabinovitz, M. J. Am. Chem. Soc. 2000, 122, 12637-12645.
12. Hilton, C. L.; Jamison, C. R.; King, B. T. J. Am. Chem. Soc. 2006, 128, 14824-14824.
13. Hilton, C. L.; King, B. T. Organometallics 2006, 25, 4058-4061.
14. Xue, X.; Scott, L. T. Org. Lett. 2007, 9, 3937-3940.
15. 3; temp 100 K; Z = 2; R = 0.054; GOF = 0.92.
16. Barnett, L.; Ho, D. M.; Baldridge, K. K.; Pascal, R. A., Jr J. Am. Chem. Soc. 1999, 121, 727-733.
17. Pascal, R. A., Jr Chem. Rev 2006, 106, 4809-4819.
18. Kyziol, J. B.; Zaleski, J. Acta Crystallogr, Sect. E 2007, 63, o1235.
19. Lu, J.; Ho, D. M.; Vogelaar, N. J.; Kraml, C. M.; Bernhard, S.; Byrne, N.; Kim, L. R.; Pascal, R. A., Jr J. Am. Chem. Soc. 2006, 128, 17043-17050.
20. Hehre, W. J. A Guide to Molecular Mechanics and Quantum Mechanical Calculations; Wavefunction Inc.: Irvine, CA, 2003; p 94.
21. (a) Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Steele, W. V. J. Chem. Thermodyn. 1989, 21, 1307-1331.
22. (b) Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590-2599.
23. Allen, F.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 1987, 2, S1.
24. Peyman, A.; Beckhaus, H.-D. J. Comput. Chem. 1992, 13, 541-550.
25. Rüchardt, C.; Backhaus, H.-D. Top. Curr. Chem. 1986, 130, S1.
26. Colmsjö, A. L. Anal. Chim. Acta 1987, 197, 71-75.
27. The modified Amber model chemistry also would have been appropriate, but transition states were more difficult to locate.
28. (a) Weinhold, F. Angew. Chem., Int. Ed. 2003, 42, 4188-4194.
29. (b) Bickelhaupt, F. M.; Baerends, E. J. Angew. Chem., Int. Ed. 2003, 42, 4183-4188.
30. Nori-shargha, D.; Asadzadeha, S.; Ghanizadehb, F.-R.; Deyhimic, F. THEOCHEM 2005, 717, 41-51.
31. Rashidi-Ranjbar, P.; Sandström, J.; Schriver, G. W.; Wong, H. N. C. Iran. J. Chem. Chem. Eng. 1996, 15, 18-22.
32. Schurig, V.; Reich, S. Chirality 1998, 10, 316-320.
33. Grein, F. J. Phys. Chem. A 2002, 106, 3823-3827.
34. Cioslowski, J.; Scott, A. P.; Radom, L. Mol. Phys. 1997, 91, 413- 420.