Demonstration of tunable reactivity for meta-benzynes

Journal of the American Chemical Society

Volumn 127, Issue 16, 2005, Pages 5760-5761

  Nash, John J ^a   Nizzi, Katrina E ^a   Adeuya, Anthony ^a   Yurkovich, Michael J ^a   Cramer, Christopher J ^b   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

^b University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 ARYNE; BENZYL DERIVATIVE; BENZYNE DERIVATIVE; HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; GAS; ION CYCLOTRON RESONANCE MASS SPECTROMETRY; SUBSTITUTION REACTION;

BENZENE DERIVATIVES; DRUG DESIGN; FREE RADICALS; THERMODYNAMICS;

EID: 17744367443     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0449473     Document Type: Article

References (30)

1. See for example: Winkler, M.; Wenk, H. H.; Sander, W. Arynes. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; John Wiley & Sons: New York, 2004.
2. See for example: Nicolau, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
3. (a) Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113.
4. (b) Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896.
5. (c) Chen, P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1478.
6. (d) Hoffner, J.; Schottelius, M. J.; Feichtinger, D.; Chen, P. J. Am. Chem. Soc. 1998, 120, 376.
7. (a) Cramer, C. J.; Debbert, S. Chem. Phys. Lett. 1998, 287, 320.
8. (b) Debbert, S. L.; Cramer, C. J. Int. J. Mass Spectrom. 2000, 201, 1.
9. (c) Johnson, W. T. G.; Cramer, C. J. J. Phys. Org. Chem. 2001, 14, 597.
10. (d) Johnson, W. T. G.; Cramer, C. J. J. Am. Chem. Soc. 2001, 123, 923.
11. Sander, W.; Exner, M.; Winkler, M.; Balster, A.; Hjerpe, A.; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 2002, 124, 13072.
12. The BLYP functional provides the best agreement with highly correlated levels of theory for the structures of meta-benzynes: (a) Winkler, M.; Sander, W. J. Phys. Chem. A 2001, 105, 10422. (b) Winkler, M.; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135. (c) See also: Schreiner, P. R.; Navarro-Vazuez, A.; Prall, M. Acc. Chem. Res. 2005, 38, 29.
13. The BLYP functional provides the best agreement with highly correlated levels of theory for the structures of meta-benzynes: (a) Winkler, M.; Sander, W. J. Phys. Chem. A 2001, 105, 10422. (b) Winkler, M.; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135. (c) See also: Schreiner, P. R.; Navarro-Vazuez, A.; Prall, M. Acc. Chem. Res. 2005, 38, 29.
14. The BLYP functional provides the best agreement with highly correlated levels of theory for the structures of meta-benzynes: (a) Winkler, M.; Sander, W. J. Phys. Chem. A 2001, 105, 10422. (b) Winkler, M.; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135. (c) See also: Schreiner, P. R.; Navarro-Vazuez, A.; Prall, M. Acc. Chem. Res. 2005, 38, 29.
15. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J. Am. Chem. Soc. 1998, 120, 5279.
16. Price, J. M.; Kenttämaa, H. I. J. Phys. Chem. A 2003, 107, 8985.
17. Amegayibor, F. S.; Nash, J. J.; Lee, A. S.; Thoen, J.; Petzold, C. J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2002, 124, 12066.
18. Clark, A. E.; Davidson, E. R. J. Am. Chem. Soc. 2001, 123, 10691.
19. See for example: Nelson, E. D.; Artau, A.; Price, J. M.; Tichy, S. E.; Jing, L.; Kenttämaa, H. I. J. Phys. Chem. A 2001, 105, 10155.
20. The (U)BLYP/cc-pVTZ//(U)BLYP/cc-pVTZ surfaces for a and c are virtually identical to those obtained at the (U)BLYP/cc-pVDZ//(U)BLYP/ cc-pVDZ level of theory.
21. For b, the CCSD(T)/cc-pVTZ/(U)BLYP/cc-pVDZ surface is very similar to the (U)BLYP/cc-pVDZ//(U)BLYP/cc-pVDZ surface.
22. CASPT2/cc-pVDZ//(U)BLYP/cc-pVDZ level of theory.
23. (U)BLYP/aug-cc-pVDZ//MCSCF/cc-pVDZ level of theory.
24. Amegayibor, F. S.; Nash, J. J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2003, 125, 14256.
25. Rousseau, G.; Robin, S. Tetrahedron Lett. 1997, 38, 2467.
26. (a) Kaufman, A.; Hussy, H. Chem. Ber. 1908, 41, 1735.
27. (b) Serban, A. U.S. Patent, ICI, 3930837, 1972, 84, 180075.
28. Rieche, A.; Schmitz, E.; Dietrich, P. Chem. Ber. 1959, 92, 2239.
29. Petucci, C.; Nyman, M.; Guler, L.; Kenttämaa, H. I. J. Am. Chem. Soc. 2002, 124, 4108.
30. 4 by b-d are consistent with the H atom abstraction rate differences measured for THF.