Can two molecules have the same NMR spectrum? Hexacyclinol revisited

Organic Letters

Volumn 11, Issue 6, 2009, Pages 1409-1412

  Saielli, Giacomo ^a   Bagno, Alessandro ^b  

^a INSTITUTE ON MEMBRANE TECHNOLOGY   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; HEXACYCLINOL; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; EPOXY COMPOUNDS; ISOMERISM; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYCYCLIC COMPOUNDS;

EID: 64049093768     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900164a     Document Type: Article

References (18)

1. Kwan, E. E.; Huang, S. G. Eur. J. Org. Chem. 2008, 2671.
2. Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012.
3. Schlegel, B.; Hartl, A.; Dahse, H. M.; Gollmick, F. A.; Grafe, U.; Dorfelt, H.; Kappes, B. J. Antibiot. 2002, 55, 814.
4. La Clair, J. J. Angew. Chem., Int. Ed. 2006, 45, 2769.
5. Rychnovsky, S. D. Org. Lett. 2006, 8, 2895.
6. Porco, J. A., Jr.; Su, S.; Lei, X.; Bardhan, S.; Rychnovsky, S. D. Aneew. Chem., Int. Ed. 2006, 45, 5790.
7. Marris, E. Nature 2006, 442, 492.
8. Williams, A. J.; Elyashberg, M. E.; Blinov, K. A.; Lankin, D. C.; Martin, G. E.; Reynolds, W. F.; Porco, J. A., Jr.; Singleton, C. A.; Su, S. J. Nat. Prod. 2008, 71, 581.
9. Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 293.
10. Bagno, A.; Rastrelli, F.; Saielli, G. Chem.-Eur. J. 2006, 12, 5514.
11. Bagno, A.; Saielli, G. Theor. Chem. Acc. 2007, 117, 603.
12. Tähtinen, P.; Saielli, G.; Guella, G.; Mancini, I.; Bagno, A. Chem.-Eur. J. 2008, 14, 10445.
13. Wilson, P. J.; Bradley, T. J.; Tozer, D. J. J. Chem. Phys. 2001, 115, 9233.
14. Maximoff, S. N.; Peralta, J. E.; Barone, V.; Scuseria, G. E. J. Chem. Theory Comput. 2005, 1, 541.
15. Keal, T. W.; Helgaker, T.; Salstrockek, P.; Tozer, D. J. Chem. Phys. Lett. 2006, 425, 163.
16. Frisch, M. J. et al. Gaussian 03, revision D.02; Gaussian, Inc.: Wallingford, CT, 2004.
17. 3J (H4, H5) and methyl proton H1. However, the conformation of the olefinic moiety is not a critical issue.
18. 1D spectra were simulated with the nmrsimmodule in Topspin 2.0 by Bruker, including strong coupling effects. 2-D COSY spectra were sketched as a superposition of 2-D Lorentzian functions at the calculated chemical shift (s). Off-diagonal peaks were added for all pairs of spins having [J] > 1 Hz, with an intensity scaled by a factor proportional to J. Hence, peak contours are only intended to convey qualitative connectivity informa-tion.