Conformational reactions of D2-symmetric twisted acenes

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8630-8637

  Pascal Jr , Robert A ^a   Qin, Qian ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

Acenes; Conformational analysis; Dynamic NMR spectroscopy; Polycyclic aromatic hydrocarbons; Transition state analysis

Indexed keywords

9,10,11,20,21,22 HEXAPHENYLTETRABENZO[A,C,L,N]PENTACENE; 9,10,19,20 TETRAPHENYLTETRABENZO[A,C,J,L]NAPHTHACENE; 9,18 DIPHENYLTETRABENZ[A,C,H,J]ANTHRACENE; POLYCYCLIC AROMATIC HYDROCARBON;

ANALYTIC METHOD; ARTICLE; CALCULATION; CHEMICAL ANALYSIS; COMPARATIVE STUDY; COMPUTATIONAL ANALYSIS; CONFORMATIONAL TRANSITION; ENANTIOMER; ENERGY; MOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIZATION; STRUCTURE ANALYSIS;

EID: 48049112608     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.030     Document Type: Article

References (23)

1. Review:. Pascal Jr. R.A. Chem. Rev. 106 (2006) 4809-4819
2. Pascal Jr. R.A., McMillan W.D., and Van Engen D. J. Am. Chem. Soc. 108 (1986) 5652-5653
3. Pascal Jr. R.A., McMillan W.D., Van Engen D., and Eason R.G. J. Am. Chem. Soc. 109 (1987) 4660-4665
4. Lu J., Ho D.M., Vogelaar N.J., Kraml C.M., and Pascal Jr. R.A. J. Am. Chem. Soc. 126 (2004) 11168-11169
5. Lu J., Ho D.M., Vogelaar N.J., Kraml C.M., Bernhard S., Byrne N., Kim L.R., and Pascal Jr. R.A. J. Am. Chem. Soc. 128 (2006) 17043-17050
6. Norton J.E., and Houk K.N. J. Am. Chem. Soc. 127 (2005) 4162-4163
7. Smyth N., Van Engen D., and Pascal Jr. R.A. J. Org. Chem. 55 (1990) 1937-1940
8. Meurer K.P., and Vogtle F. Top. Curr. Chem. 127 (1985) 1-76
9. Clark M., Cramer III R.D., and Van Opdenbosch N. J. Comput. Chem. 10 (1989) 982-1012
10. Halgren T.A. J. Comput. Chem. 17 (1996) 490-519
11. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
12. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), John Wiley & Sons, New York, NY pp 133-226
13. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
14. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
15. corr), which are generally similar, may be found in Table 1 for comparison.
16. Bock H., Havlas Z., Gharagozloo-Hubmann K., and Sievert M. Angew. Chem., Int. Ed. 38 (1999) 2240-2243
17. Pascal Jr. R.A., Kraml C.M., Byrne N., and Coughlin F.J. Tetrahedron 63 (2007) 11902-11910
18. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision C.02 (2004), Gaussian, Wallingford, CT
19. Gust D. J. Am. Chem. Soc. 99 (1977) 6980-6982
20. Gust D., and Patton A. J. Am. Chem. Soc. 100 (1978) 8175-8181
21. Komber H., Stumpe K., and Voit B. Tetrahedron Lett. 48 (2007) 2655-2659
22. Qiao X., Pelczer I., and Pascal Jr. R.A. Chirality 10 (1998) 154-158
23. D=559°, 460°, and 1737°, respectively. The last is obviously much lower than the experimentally determined value of 7400° for 3.