Ultrafast spectroscopy and computational study of the photochemistry of diphenylphosphoryl azide: Direct spectroscopic observation of a singlet phosphorylnitrene

Journal of the American Chemical Society

Volumn 132, Issue 47, 2010, Pages 16796-16804

  Vyas, Shubham ^a,b   Muthukrishnan, Sivaramakrishnan ^a,b   Kubicki, Jacek ^a,b   McCulla, Ryan D ^a,b   Burdzinski, Gotard ^a,b   Sliwa, Michel ^c   Platz, Matthew S ^a,b   Hadad, Christopher M ^a,b  

^a OHIO STATE UNIVERSITY   (United States)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

^c UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION BAND; COMPUTATIONAL RESULTS; COMPUTATIONAL STUDIES; DIRECT IRRADIATION; EXCITED SINGLET STATE; FEMTOSECOND TRANSIENT ABSORPTION SPECTROSCOPY; LIGHT INDUCED REACTION; MOLECULAR NITROGEN; NITRENES; PHENYL RINGS; PHOSPHORAMIDATES; SINGLET EXCITED STATE; TIME RESOLVED STUDIES; TRANSIENT ABSORPTION; TRANSIENT SPECIES; TRIS(TRIMETHYLSILYL)SILANE; ULTRA-FAST; ULTRAFAST SPECTROSCOPY;

ABSORPTION; CHEMICAL REACTIONS; ENERGY TRANSFER; EXCITED STATES; NITROGEN; PHOTOLYSIS;

ABSORPTION SPECTROSCOPY;

AZIDE; BIPHENYL; DIPHENYLPHOSPHORYL AZIDE; DIPHENYLPHOSPHORYLNITRENE; NITROGEN; PHENYL GROUP; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENERGY TRANSFER; IRRADIATION; PHOTOCHEMISTRY; PHOTOLYSIS;

ABSORPTION; AZIDES; ENERGY TRANSFER; IMINES; LIGHT; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; SPECTRUM ANALYSIS; TIME FACTORS;

EID: 78649507741     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja909327z     Document Type: Article

References (66)

1. Bartels, C. F., James, K., and La Du, B. N. Am. J. Hum. Genet. 1992, 50, 1104-1114
2. Main, A. R. Pharmacol. Ther. 1979, 6, 579-628
3. Rozenbeny, T. L. Adv. Enzymol. 1975, 43, 103
4. Quinn, D. M. Chem. Rev. 1987, 87, 955-979
5. Michel, H. O., Hackley, B. E., Jr., Berkowitz, L., List, G., Hackley, E. B., Gilliam, W., and Paukan, M. Arch. Biochem. Biophys. 1967, 121, 29-34
6. Bennet, A. J., Kovach, I. M., and Schowen, R. L. J. Am. Chem. Soc. 1988, 110, 7892-7893
7. Bencsura, A., Enyedy, I., and Kovach, I. M. Biochemistry 1995, 34, 8989-8999
8. Bencsura, A., Enyedy, I. Y., and Kovach, I. M. J. Am. Chem. Soc. 1996, 118, 8531-8541
9. Millard, C. B., Kryger, G., Ordentlich, A., Greenblatt, H. M., Harel, M., Raves, M. L., Segall, Y., Barak, D., Shafferman, A., Silman, I., and Sussman, J. L. Biochemistry 1999, 38, 7032-7039
10. Viragh, C., Kovach, I. M., and Pannell, L. Biochemistry 1999, 38, 9557-9561
11. Elhanany, E., Ordentlich, A., Dgany, O., Kaplan, D., Segall, Y., Barak, R., Velan, B., and Shafferman, A. Chem. Res. Toxicol. 2001, 14, 912-918
12. George, K. M., Schule, T., Sandoval, L. E., Jennings, L. L., Taylor, P., and Thompson, C. M. J. Biol. Chem. 2003, 278, 45512-45518
13. Nachon, F., Asojo, O. A., Borgstahl, G. E. O., Masson, P., and Lockridge, O. Biochemistry 2005, 44, 1154-1162
14. Clement, J. G. Arch. Toxicol. 1992, 66, 143-144
15. Lundy, P. M., Hansen, A. S., Hand, B. T., and Boulet, C. A. Toxicology 1992, 72, 99-105
16. Worek, F., Eyer, P., and Szinicz, L. Arch. Toxicol. 1998, 72, 580-587
17. Raveh, L., Grauer, E., Grunwald, J., Cohen, E., and Ashani, Y. Toxicol. Appl. Pharmacol. 1997, 145, 43-53
18. Cerasoli, D. M., Griffiths, E. M., Doctor, B. P., Saxena, A., Fedorko, J. M., Greig, N. H., Yu, Q. S., Huang, Y., Wilgus, H., Karatzas, C. N., Koplovitz, I., and Lenz, D. E. Chem. Biol. Int. 2005, 157, 362-365
19. Josse, D., Xie, W., Renault, F., Rochu, D., Schopfer, L. M., Masson, P., and Lockridge, O. Biochemistry 1999, 38, 2816-2825
20. Harel, M., Aharoni, A., Gaidukov, L., Brumshtein, B., Khersonsky, O., Meged, R., Dvir, H., Ravelli, R. B., McCarthy, A., Toker, L., Silman, I., Sussman, J. L., and Tawfik, D. S. Nat. Struct. Mol. Biol. 2004, 11, 412-419
21. Khersonsky, O. and Tawfik, D. S. Biochemistry 2005, 44, 6371-6382
22. Khersonsky, O. and Tawfik, D. S. J. Biol. Chem. 2006, 281, 7649-7656
23. Harel, M., Aharoni, A., Gaidukov, L., Brumshtein, B., Khersonsky, O., Meged, R., Dvir, H., Ravelli, R., Mccarthy, A., Toker, L., Silman, I., Sussman, J., and Tawfik, D. Nat. Struct. Mol. Biol. 2004, 11, 412-419
24. Yueng, D. T., Lenz, D. E., and Cerasoli, D. M. FEBS J. 2005, 272, 2225-2230
25. Yeung, D. T., Josse, D., Nicholson, J. D., Khanal, A., McAndrew, C. W., Bahnson, B. J., Lenz, D. E., and Cerasoli, D. M. Biochim. Biophys. Acta 2004, 1702, 67-77
26. Staros, J. V. Trends Biochem. Sci (Pers. Ed.) 1980, 5, 320-322
27. BayLey, H. Photogenerated Reagent in Biochemistry and Molecular Biology; Elsevier: New York, 1983.
28. Bayley, H. and Straos, J. In Azides and Nitrenes; Reactivity and Utility; Academic Press: New York, 1984; p 434.
29. Torres, M. J., Zayas, J., and Platz, M. S. Tetrahedron Lett. 1986, 27, 791-794
30. Leyva, E., Chang, D. H. S., Platz, M. S., Watt, D. S., Crocker, P. J., and Kawada, K. Photochem. Photobiol. 1991, 54, 329-333
31. Pandurangi, R. S., Katti, K. V., Barnes, C. L., Volkert, W. A., and Kuntz, R. R. J. Chem. Commun. 1994, 16, 1841-1842
32. Mueller, P. and Fruit, C. Chem. Rev. 2003, 103, 2905-2919
33. Shioiri, T., Ninomiya, K., and Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205
34. Breslow, R., Feiring, A., and Herman, F. J. Am. Chem. Soc. 1974, 96, 5937-5939
35. Maslak, P. J. Am. Chem. Soc. 1989, 111, 8201-8207
36. Houser, M., Kelley, S., Maloney, V., Marlow, M., Steininger, K., and Zhou, H. J. Phys. Chem. 1995, 99, 7946-7950
37. Gohar, G. A. and Platz, M. S. J. Phys. Chem. A 2003, 107, 3704-3707
38. McCulla, R. D., Gohar, G. A., Hadad, C. M., and Platz, M. S. J. Org. Chem. 2007, 72, 9426-9438
39. Hättig, C. and Weigend, F. J. Chem. Phys. 2000, 113, 5154-5161
40. Hättig, C., Kõhn, A., and Hald, K. J. Chem. Phys. 2002, 116, 5401-5410
41. Hättig, C. J. Chem. Phys. 2003, 118, 7751-7761
42. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
43. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1988, 37, 785-789
44. Ahlrichs, R., Bär, M., Häser, M., Horn, H., and Kölmel, C. Chem. Phys. Lett. 1989, 162, 165
45. For the current version of TURBOMOLE, see http://www.turbomole.de.
46. Treutler, O. and Ahlrichs, R. J. Chem. Phys. 1995, 102, 346
47. Burdzinski, G., Gustafson, T. L., Hackett, J. C., Hadad, C. M., and Platz, M. S. J. Am. Chem. Soc. 2005, 127, 13764-13765
48. Burdzinski, G., Hackett, J. C., Wang, J., Gustafson, T. L., Hadad, C. M., and Platz, M. S. J. Am. Chem. Soc. 2006, 128, 13402-13411
49. Wang, J., Kubicki, J., Burdzinski, G., Hackett, J. C., Gustafson, T. L., Hadad, C. M., and Platz, M. S. J. Org. Chem. 2007, 72, 7581-7586
50. Sliwa, M., Mouton, N., Ruckebusch, C., Poisson, L., Idrissi, A., Aloise, S., Potier, L., Poizat, O., and Buntinx, G. Photochem. Photobiol. Sci. 2010, 9, 661-669
51. Voskresenska, V., Wilson, R. M., Panov, M., Tarnovsky, A. N., Krause, J. A., Vyas, S., Winter, A. H., and Hadad, C. M. J. Am. Chem. Soc. 2009, 131, 11535-11547
52. Olivucci, M. Computational Photochemistry; Elsevier: Amsterdam, 2005; pp 92 - 128.
53. Kucheryvavy, P., Li, G., Vyas, S., Hadad, C. M., and Glusac, K. D. J. Phys. Chem. A 2009, 113, 6453-6461
54. Li, G., Parimal, K., Vyas, S., Hadad, C. M., Flood, A. H., and Glusac, K. D. J. Am. Chem. Soc. 2009, 131, 1156-11657
55. Vyas, S., Onchoke, K. K., Hadad, C. M., and Dutta, P. K. J. Phys. Chem. A 2009, 113, 12558-12565
56. Vyas, S., Hadad, C. M., and Modarelli, D. A. J. Phys. Chem. A 2008, 112, 6533-6549
57. Wiberg, K. B., Hadad, C. M., Breneman, C. M., Laidig, K. E., Murcko, M. A., and LePage, T. J. Science 1991, 252, 1266-1272
58. Wiberg, K. B., Hadad, C. M., LePage, T. J., Breneman, C. M., and Frisch, M. J. J. Phys. Chem. 1992, 96, 671-679
59. Wiberg, K. B., Hadad, C. M., Foresman, J. B., and Chupka, W. A. J. Phys. Chem. 1992, 96, 10756-10768
60. Hadad, C. M., Foresman, J. B., and Wiberg, K. B. J. Phys. Chem. 1993, 97, 4293-4312
61. Wiberg, K. B., Hadad, C. M., Ellison, G. B., and Foresman, J. B. J. Phys. Chem. 1993, 97, 13586-13597
62. Weigend, F., Häser, F., Patzelt, H., and Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143-152
63. Gritsan, N. P., Zhai, H. B., Yuzawa, T., Karweik, D., Brooke, J., and Platz, M. S. J. Phys. Chem. A 1997, 101, 2833-2840
64. Martin, C. B., Shi, X., Tsao, M.-L., Karweik, D., Brooke, J., Hadad, C. M., and Platz, M. S. J. Phys. Chem. B 2002, 106, 10263-10271
65. Tsao, M.-L., Gritsan, N., James, T. R., Platz, M. S., Hrovat, D. A., and Borden, W. T. J. Am. Chem. Soc. 2003, 125, 9343-9358
66. Rajaram, S., Chary, K. P., and Iyengar, D. S. Synth. Commun. 2000, 30, 4495-4500