Gas-phase reactivity of aromatic σ,σ-biradicals toward dinucleoside phosphates

Organic Letters

Volumn 10, Issue 10, 2008, Pages 1889-1892

  Yang, Linan ^a   Nash, John J ^a   Yurkovich, Michael J ^a   Jin, Zhicheng ^a   Vinueza, Nelson R ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DINUCLEOSIDE PHOSPHATE; DNA; FREE RADICAL; ISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GAS; LASER; MASS SPECTROMETRY; STEREOISOMERISM; SYNTHESIS;

DINUCLEOSIDE PHOSPHATES; DNA; FREE RADICALS; GASES; ISOQUINOLINES; LASERS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 47049111459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800312g     Document Type: Article

References (39)

1. See, for example: (a) Nicolaou, K. C; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
2. (b) Nicolaou, K. C; Dai, W.-M.; Tsay, S.-C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172.
3. (c) Borders, D. B.; Doyle, T. W. Eds. Enediyne Antibiotics as Antitumor Agents; Marcel Dekker: New York, 1995.
4. (d) Pogozelski, W. K.; Tullius, T. D. Chem. Rev. 1998, 98, 1089.
5. (e) Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502.
6. Liu, J,; Petzold, C. J.; Ramírez-Arizmendi, L. E.; Pérez, J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2005, 127, 12758.
7. (a) Adeuya, A.; Yang, L.; Amegayibor, F. S.; Nash, J. J.; Kenttamaa, H. I. J. Am. Soc. Mass Spectrom. 2006, 17, 1325.
8. (b) Yang, L. Ph.D. Thesis, Purdue University, 2007.
9. See, for example: (a) Chyall, L. J.; Kenttamaa, H. I. J. Am. Chem. Soc. 1994, 116, 3135.
10. (b) Smith, R. L.; Kenttamaa, H. I. J. Am. Chem. Soc. 1995. 117, 1393.
11. (c) Petucci, C; Nyman, M.; Guler. L.: Kenttamaa. H. I. J. Am. Chem. Soc. 2002, 124, 4108.
12. (d) Amegayibor, F. S.: Nash, J. J.; Lee, A. S.; Thoen, J.; Petzold, C. J.; Kenttamaa, H. T. J. Am. Chem. Soc. 2002, 124, 12066.
13. (a) Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896.
14. (b) Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113.
15. (c) Hoffner, J.: Schottelius, M. J.; Feichtinger, D.; Chen, P. J. Am, Chem. Soc. 1998. 120, 376.
16. (d) Roth, W. R.; Hopf. H.; Wasser, T.; Zimmermann, H.; Werner. C. Liebigs Ann. 1996, 1691.
17. (a) Nelson, E. D.: Artau, A.; Price, J. M.; Kenttämaa. H. I. .J, Am. Chem. Soc. 2000, 122, 8781.
18. (b) Nelson, E. D.; Artau, A.; Price, J. M.; Tichy, S. E.; Jing, L.; Kenttämaa, H. I. J. Phys. Chem. A 2001, 105, 10155.
19. (a) Pérez, J.; Ramfrez-Arizmendi, L. E.; Petzold, D. J.; Guler, L. P.; Nelson, E. D.; Kenttamaa, H. I. Int. J. Mass Spectrom. 2000, 198, 173.
20. (b) Petzold, D. J.; Ramírez-Arizmendi, L. E.; Heidbrink, J. L.; Perez, J.; Kenttämaa, H. I. J. Am,. Soc. Mass Spectrom. 2002, 13, 192.
21. (a) Campbell, J. L.; Fiddler, M. N.; Crawford, K. E.; Gqamana, P. P.; Kenttamaa, H. I. Anal. Chem. 2005, 77, 4020.
22. (b) Crawford, K. E.; Campbell, J. L.; Fiddler. M. N.; Duan, P.; Qian, K.; Gorbaty, M. L.; Kenttamaa, H. I. Anal. Chem. 2005, 77, 7916.
23. Gamage, S. A.; Spicer, J. A.; Rewcastle, G. W.; Milton, J.; Sohal, S.; Dangerfield, W.; Mistry. P.; Vicker, N.; Charlton, P. A.: Denny, W. A. J. Med. Chem. 2002, 45, 740.
24. Petzold, C. J.; Nelson. E. D.; Lardin. H. A.; Kenttamaa, H. I. J. Phys. Chem. A 2002, 106, 9767.
25. Price, J. M.: Nizzi, K. R.; Campbell, J. L.; Kenttamaa, H. I. J. Am. Chem. Soc. 2003, 125, 131.
26. CASPT2/cc-pVDZ//MCSCF/cc-pVDZ level of theory.
27. UT3LYP/aug-cc-pVDZ//MCSCF/cc-pVDZ level of theory.
28. UBLYP/aug-cc-pVDZ//UBLYP/cc-pVDZ level of theory.
29. (a) Johnson. W. T. G.: Cramer, C. J. J. Am. Chem. Soc. 2001,123, 923.
30. (b) Johnson, W. T. G.; Cramer, C. J. J. Phys. Org. Chem. 2001, 14, 597.
31. (c) Nash, J. J.; Nizzi, K.: Adeuya. A.; Yurkovich, M. J.; Cramer, C. J.; Kenttämaa, H. I. J. Am. Chem. Soc. 2005, 127, 5760.
32. The (U)BLYP functional provides the best agreement with highly correlated levels of theory for the structures of m-benzynes: (a) Winkler. M; Sander, W. J. Phys. Chem. A 2001,105, 10422.
33. (b) Winkler, M; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135.
34. (c) See also: Schreiner, P.; R.; Navarro-Vazuez, A.; Prall, M. Acc. Chem. Res. 2005, 38, 29.
35. Ramirez-Arizmendi, L. E.; Heidbrink, J. L,; Guler, L. P.; Kenttamaa, H. I. J. Am. Chem. Soc. 2003, 125, 2272.
36. Huang, Y.; Kenttämaa, H. I. J. Am. Chem. Soc. 2003, 125, 987.
37. Clarke, J. S.; Rypkema, H. A.; Kroll, J, H,; Donahue, N. M.; Anderson, J. G. J. Phys. Chem. A 2000, 104, 4458.
38. Lias, S. G.; Levin, R. D.; Kafafi, S. A. In Ion Energetics Data. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, June 2005.
39. Sherman, C. L.; Pierce, S. E.; Brodbelt, J. S.; Tuesuwan, B.; Kerwin, S. M. J. Am. Soc. Mass Spectrom. 2006, 17, 1342.