Time-resolved infrared spectroscopy of intermediates and products from photolysis of 1-(2-nitrophenyl)ethyl phosphates: Reaction of the 2- nitrosoacetophenone byproduct with thiols

Journal of the American Chemical Society

Volumn 119, Issue 18, 1997, Pages 4149-4159

  Barth, Andreas ^a   Corrie, John E T ^b   Gradwell, Michael J ^b   Maeda, Yashusi ^a   Mäntele, Werner ^a   Meier, Tanja ^a   Trentham, David R ^b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b NATIONAL INSTITUTE FOR MEDICAL RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; ANION; DITHIOTHREITOL; DITHRANOL; PHOSPHATE; THIOL DERIVATIVE;

ARTICLE; DIMERIZATION; INFRARED SPECTROSCOPY; KINETICS; PHOTOCHEMISTRY; PHOTOLYSIS; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROSCOPY;

EID: 0030949448     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964430u     Document Type: Article

References (39)

1. Barth, A.; Hauser, K.; Mäntele, W.; Corrie, J. E. T.; Trentham, D. R. J. Am. Chem. Soc. 1995, 117, 10311-10316.
2. Walker, J. W.; Reid, G. P.; McCray, J. A.; Trentham, D. R. J. Am. Chem. Soc. 1988, 110, 7170-7177.
3. McCray, J. A.; Trentham, D. R. Annu. Rev. Biophys. Biophys. Chem. 1989, 18, 239-270.
4. Kaplan, J. H.; Forbush, B.; Hoffman, J. F. Biochemistry 1978, 17, 1929-1935.
5. Dähne, S.; Stanko, H. Spectrochim. Acta 1962, 18, 561-567.
6. Feuer, H.; Savides, C.; Rao, C. N. R. Spectrochim. Acta 1963, 19, 431-434.
7. Takeuchi, H.; Murata, H.; Harada, I. J. Am. Chem. Soc. 1988, 110, 392-397.
8. Barabás, K.; Keszthelyi, L. Acta Biochim. Biophys. Acad. Sci. Hung. 1984, 19, 305-309.
9. Colthup, N. B.; Daly, L. H.; Wiberley, S. E. Introduction to Infrared and Roman Spectroscopy, 3rd ed.; Academic Press: San Diego, 1990; p 296.
10. Reference 9, p 353.
11. Azoulay, M.; Fischer, E. J. Chem. Soc., Perkin Trans. 2 1982, 637-642.
12. Zuman, P.; Shah, B. Chem. Rev. 1994, 94, 1621-1641 and references therein.
13. Weast, R. C. Handbook of Chemistry and Physics, 50th ed.; Chemical Rubber Co.: Cleveland, OH, 1969; p C-93.
14. Diepold, C. H.; Eyer, P.; Kampffmeyer, H.; Reinhardt, K. Adv. Exp. Med. Biol. 1982, 136B, 1173-1181.
15. (a) Whitesides, G. M.; Lilburb, J. E.; Szajewski, R. P. J. Org. Chem. 1977, 42, 332-338.
16. (b) Burns, J. A.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 6296-6303.
17. Valters, R. E.; Ritsch, W. Ring-Chain Tautomerism; Plenum Press: New York, 1985; Chapter 2.
18. Cayley, P. J.; Albrand, J. P.; Feeney, J.; Roberts, G. C. K.; Piper, E. A.; Burgen, A. S. V. Biochemistry 1979, 18, 3886-3895. Hyde, E. I.; Birdsall, B.; Roberts, G. C. K.; Feeney, J.; Burgen, A. S. V. Biochemistry 1980, 19, 3738-3746.
19. Cayley, P. J.; Albrand, J. P.; Feeney, J.; Roberts, G. C. K.; Piper, E. A.; Burgen, A. S. V. Biochemistry 1979, 18, 3886-3895. Hyde, E. I.; Birdsall, B.; Roberts, G. C. K.; Feeney, J.; Burgen, A. S. V. Biochemistry 1980, 19, 3738-3746.
20. Yates, P.; Hand, E. S. J. Am. Chem. Soc. 1969, 91, 4749-4760.
21. Brodersen, S.; Christoffersen, J.; Bak, B.; Nielsen, J. T. Spectrochim. Acta 1965, 21, 2077-2084.
22. McCray, J. A.; Herbette, L.; Kihara, T.; Trentham, D. R. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 7237-7241.
23. Le Guyader, M. C. R. Seances Acad. Sci., Ser. C 1966, 262, 1383-1386.
24. Shabarov, Y. S.; Mochalov, S. S.; Fedotov, A. N.; Kalashnikov, V. V. Khim. Geterotsikl. Soedin. 1974, 9, 1195-1197.
25. Fedotov, A. N.; Mochalov, S. S.; Shabarov, Y. S. Zh. Prikl. Khim. 1977, 50, 1775-1777.
26. Wettermark, G.; Black, E.; Dogliotti, L. Photochem. Photobiol. 1965, 4, 229-239. DeMayo, P.; Reid, S. T. Quart. Rev. (London) 1961, 15, 393-417. Morrison, H.; Migdalof, B. H. J. Am. Chem. Soc. 1965, 30, 3996.
27. Wettermark, G.; Black, E.; Dogliotti, L. Photochem. Photobiol. 1965, 4, 229-239. DeMayo, P.; Reid, S. T. Quart. Rev. (London) 1961, 15, 393-417. Morrison, H.; Migdalof, B. H. J. Am. Chem. Soc. 1965, 30, 3996.
28. Wettermark, G.; Black, E.; Dogliotti, L. Photochem. Photobiol. 1965, 4, 229-239. DeMayo, P.; Reid, S. T. Quart. Rev. (London) 1961, 15, 393-417. Morrison, H.; Migdalof, B. H. J. Am. Chem. Soc. 1965, 30, 3996.
29. Corrie, J. E. T. J. Chem. Soc., Perkin Trans. 1 1993, 2161-2166. Peng, L; Goeldner, M. J. Org. Chem. 1996, 61, 185-191. Ellis-Davies, G. C. R.; Kaplan, J. H.; Barsotti, R. J. Biophys. J. 1996, 70, 1006-1016.
30. Corrie, J. E. T. J. Chem. Soc., Perkin Trans. 1 1993, 2161-2166. Peng, L; Goeldner, M. J. Org. Chem. 1996, 61, 185-191. Ellis-Davies, G. C. R.; Kaplan, J. H.; Barsotti, R. J. Biophys. J. 1996, 70, 1006-1016.
31. Corrie, J. E. T. J. Chem. Soc., Perkin Trans. 1 1993, 2161-2166. Peng, L; Goeldner, M. J. Org. Chem. 1996, 61, 185-191. Ellis-Davies, G. C. R.; Kaplan, J. H.; Barsotti, R. J. Biophys. J. 1996, 70, 1006-1016.
32. Corrie, J. E. T.; Papageorgiou, G. J. Chem. Soc., Perkin Trans. 1 1996, 1583-1592.
33. Cohn, M.; Hu, A. J. Am. Chem. Soc. 1980, 102, 913-916.
34. Corrie, J. E. T. J. Labelled Compd. Radiopharm. 1996, 38, 403-410.
35. Corrie, J. E. T.; Reid, G. P. J. Labelled Compd. Radiopharm. 1995, 36, 289-300.
36. Shabarov, Y. S.; Mochalov, S. S.; Stepanova, I. P. Dokl. Akad. Nauk SSSR 1969, 189, 1028-1030.
37. VNMR Version 5.1; Varian Associates, Palo Alto, CA, 1995.
38. Harris, R. K. Nuclear Magnetic Resonance Spectroscopy; Pitman, London 1983; p 81.
39. Kaleidagraph; Synergy Software, Reading, PA, 1994.