X-ray quality geometries of geodesic polyarenes from theoretical calculations: What levels of theory are reliable?

Journal of Organic Chemistry

Volumn 70, Issue 14, 2005, Pages 5713-5716

  Petrukhina, Marina A ^a   Andreini, Kristian W ^a   Mack, James ^b   Scott, Lawrence T ^c  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF CINCINNATI   (United States)

^c BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CALIBRATION; COMPUTATIONAL METHODS;

BOND ANGLES; CRYSTAL PACKING FORCES; GEODESIC POLYARENES; MOLECULAR DISTORTIONS; MOLECULAR GEOMETRIES;

X RAY ANALYSIS;

CORANNULENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; GEOMETRY; MATHEMATICAL ANALYSIS; RELIABILITY; THEORETICAL MODEL; X RAY CRYSTALLOGRAPHY;

EID: 22144466217     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050233e     Document Type: Article

References (25)

1. Lovas, F. J.; McMahon, R. J.; Grabow, J.; Schnell, M.; Mack, J.; Scott, L. T.; Kuczkowski, R. L. J. Am. Chem. Soc. 2005, 127, 4345-4349.
2. Hanson, J. C.; Nordman, C. E. Acta Crystallogr., Sect. B 1976, B32, 1147-1153.
3. 2 was performed using crystals grown from solution. For the new X-ray crystal structures reported here, crystals were grown by subliming corannulene at 175 °C. See the Supporting Information for complete crystallographic tables and details.
4. Skoog, D. A.; West, D. M.; Holler, F. J.; Crouch, S. R. Analytical Chemistry, 7th ed.; Saunders: New York, 2000; Chapter 7.
5. Geometry optimizations were performed using the programs packaged in Spartan '02 (Linux version, 2002; Wavefunction, Inc., Irvine, CA 92612), with the following exceptions: MM2 calculations were performed using the program in Chem-3D (v 5.0, 1999; CambridgeSoft Corp., Cambridge, MA 02140); MM3 and MMX calculations were performed using the program in PCModel (v 8.0 for Linux, 2002; Serena Software, Bloomington, IN 47402). Default termination thresholds were used in all cases.
6. (a) Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-381.
7. (b) Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-1745.
8. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162-163.
9. The first new methods were introduced in the early 1990s: (a) Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-7084.
10. (b) Scott, L. T.; Hashemi, M. M.; Brateher, M. S. J. Am. Chem. Soc. 1992, 114, 1920-1921.
11. (c) Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-1923.
12. (a) Boorum, M. M.; Vasil'ev, Y. V.; Drewello, T.; Scott, L. T. Science 2001, 294, 828-831.
13. (b) Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; de Meijere, A. Science 2002, 295, 1500-1503.
14. (c) Scott, L. T. Angew. Chem. Int. Ed. 2004, 43, 4995-5007.
15. Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Ansems, R. B. M.; Brateher, M. S.; Hagen, S. Pure Appl. Chem. 1999, 71, 209-219. See also ref 9c and references therein.
16. Ansems, R. B. M. Ph.D. dissertation, Boston College, Chestnut Hill, MA 2004.
17. For examples, see: (a) Sygula, A.; Sygula, R.; Ellern, A.; Rabideau, P. W. Org. Lett. 2003, 5, 2595-2597 and references therein,
18. (b) Petrukhina, M. A.; Andreini, K. W.; Peng, L.; Scott, L. T. Angew. Chem., Int. Ed. 2004, 43, 5477-5481.
19. (c) Petrukhina, M. A.; Andreini, K. W.; Tsefrikas, V. M.; Scott, L. T. Organometallics 2005, 24, 1394-1397.
20. (a) Priyakumar, U. D.; Punnagai, M.; Mohan, G. P. K.; Sastry, G. N. Tetrahedron 2004, 60, 3037-3043 and many earlier publications by Sastry and co-workers.
21. (b) Schulman, J. M.; Disch, R. L. J. Comput. Chem. 1998, 19, 189-194.
22. (c) Ferrer, S. M.; Molina, J. M. J. Comput. Chem. 1999, 20, 1412.
23. (d) Biedermann, P. U.; Pogodin, S.; Agranat, I. J. Org. Chem. 1999, 64, 3655-3662.
24. (e) Marcinow, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett. 2001, 3, 3527-3529 and earlier papers from Rabideau et al.
25. As with corannulene, the high symmetries of fullerenes also offer opportunities to take into account explicitly the molecular distortions that crystal packing forces can impart. For a comparison of various ab initio and DFT treatments of fullerenes, see: Andreoni, W. Annu. Rev. Phys. Chem. 1998, 49, 405-439.