Determination of the absolute configuration of [32](1,4) barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism

Journal of the American Chemical Society

Volumn 126, Issue 24, 2004, Pages 7514-7521

  Stephens, P J ^a   McCann, D M ^a   Devlin, F J ^a   Cheeseman, J R ^b   Frisch, M J ^b  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b GAUSSIAN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CONFORMATIONS; ELECTRONIC STRUCTURE; PROBABILITY DENSITY FUNCTION; X RAY CRYSTALLOGRAPHY;

ELECTRONIC CIRCULAR DICHROISM (CD); TIME DEPENDENT DENSITY FUNCTIONAL THEORY (TDDFT);

STEREOCHEMISTRY;

BARRELENOPHANE; BARRELENOPHANEDICARBONITRILE; CYANIDE; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; CONFORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DENSITY FUNCTIONAL THEORY; OPTICAL ROTATION; RELIABILITY; X RAY CRYSTALLOGRAPHY;

EID: 2942665493     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049185q     Document Type: Article

References (36)

1. (a) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. J. Phys. Chem. A 2001, 105, 5356.
2. (b) Mennucci, B.; Tomasi, J.; Cammi, R.; Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Gabriel, S.; Stephens, P. J. J. Phys. Chem. A 2002, 106, 6102.
3. (c) Grimme, S. Chem. Phys. Lett. 2001, 339, 380.
4. (d) Grimme, S.; Furche, F.; Ahlrichs R. Chem. Phys. Lett. 2002, 361, 321.
5. (e) Autschbach, J.; Patchkovskii, S.; Ziegler, T.; van Gisbergen, S. J. A.; Baerends, E. J. J. Chem. Phys. 2002, 117, 581.
6. (f) Ruud, K.; Helgaker, T. Chem. Phys. Lett. 2002, 352, 533.
7. (g) Furche, F.; Ahlrichs, R.; Wachsmann, C.; Weber, E.; Sobanski, A.; Vogtle, F.; Grimme, S. J. Am. Chem. Soc. 2000, 122, 1717.
8. (h) Autschbach, J.; Ziegler, T.; van Gisbergen, S. J. A.; Baerends, E. J. J. Chem. Phys. 2002, 116, 6930.
9. (a) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Mennucci, B.; Tomasi, J. Tetrahedron Asymmetry 2000, 11, 2443.
10. (b) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Chirality 2002, 14, 288.
11. (c) Grimme, S.; Bahlmann, A.; Haufe, G. Chirality 2002, 14, 793.
12. (d) Polavarapu, P. L. Chirality 2002, 14, 768.
13. (e) Polavarapu, P. L.; Petrovic, A.; Wang, F. Chirality 2003, 15, S143.
14. (f) Wiberg, K. H.; Vaccaro, P. H.; Cheeseman, J. R. J. Am. Chem. Soc. 2003, 125, 1888.
15. (g) Diedrich, C.; Grimme, S. J. Phys. Chem. A 2003, 107, 2524.
16. (a) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Rosini, C. Org. Lett. 2002, 4, 4595.
17. (b) Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Bortolini, O.; Besse, P. Chirality 2003, 15, S57.
18. (c) Wang, F.; Wang, Y.; Polavarapu, P. L.; Li, T.; Drabowicz, J.; Pietrusiewicz, K. M.; Zygo, K. J. Org. Chem. 2002, 67, 6539.
19. (d) Polavarapu, P. L. Angew. Chem., Int. Ed. 2002, 41, 4544.
20. (e) Wang, Y.; Raabe, G.; Repges, C.; Fleischhauer, J. Int. J. Quantum Chem. 2003, 93, 265.
21. For concerted TDDFT calculations of the optical rotations and circular dichroism spectra of four bicyclo[3.3.1]nonanediones whose ACs had been assigned previously, see: Stephens, P. J.; McCann, D. M.; Butkus, E.; Stončius, S.; Cheeseman, J. R.; Frisch, M. J. J. Org. Chem. 2004, 69, 1948.
22. Matsuda-Sentou, W.; Shinmyozu, T. Tetrahedron: Asymmetry 2001, 12, 839.
23. MMFF94: Halgren, T. A. J. Comput. Chem. 1996, 17, 490.
24. AM1: Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
25. Spartan 02; Wavefunction Inc., Irvine, CA.
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98 and 03; Gaussian, Inc.: Pittsburgh, PA.
27. Cheeseman, J. R.; Frisch, M. J.; Devlin, F. J.; Stephens, P. J. J. Phys. Chem. A 2000, 104, 1039.
28. Matsuda-Sentou, W.; Shinmyozu, T. Eur. J. Org. Chem. 2000, 3195.
29. The difference density is the difference between the ground-state density and the unrelaxed excited-state density formed from the CI one-particle density matrix (Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135). Note that the unrelaxed excited state density constructed in this way only recovers some of the gross features of charge redistribution in the excited state, as orbital relaxation effects are not included.
30. Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction Inc., Irvine, CA, 2003; Chapter 8.
31. Sakamoto, Y.; Miyoshi, N.; Hirakida, M.; Kusumoto, S.; Kawase, H.; Rudzinski, J. M.; Shinmyozu, T. J. Am. Chem. Soc. 1996, 118, 12267.
32. D values (calculated using the aug-cc-pVDZ basis set and at B3LYP/6-31G* geometries) are -1216 for norbomenone and -342 for Tröger's Base.1a Using BLYP in place of B3LYP yields -1762 and -615, respectively (unpublished results).
33. See, for example, ref 1g wherein absorption and CD spectra calculated using TDDFT for several helicenes are blue-shifted by 0.45 eV to optimize agreement with experimental spectra.
34. Tozer, D. J.; Amos, R. D.; Handy, N. C.; Roos, B. O.; Serrano-Andres, L. Mol. Phys. 1999, 97, 859.
35. Djerassi, C. Optical Rotatory Dispersion; McGraw-Hill: New York, 1960; Chapter 12 by A. Moscowitz, p 166.
36. See, for example, the case of 2-(1-hydroxyethyl)-chromen-4-one; ref 3b.