Photochemical Reaction Mechanisms of 2-Nitrobenzyl Compounds: Methyl Ethers and Caged ATP

Journal of the American Chemical Society

Volumn 126, Issue 14, 2004, Pages 4581-4595

  Il'ichev, Yuri V ^a,b   Schwörer, Markus A ^a,c   Wirz, Jakob ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b WICHITA STATE UNIVERSITY   (United States)

^c MDL Information Systems GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; ETHERS; PH EFFECTS; PHOTOCHEMICAL REACTIONS; PHOTOLYSIS; ULTRAVIOLET SPECTROSCOPY;

BIOAGENTS; PHYSIOLOGICAL RESPONSE;

AROMATIC COMPOUNDS;

1,3 DIHYDROBENZ[C]ISOXAZOL 1 OL DERIVATIVE; 2 NITROBENZYL METHYL ETHER; 2 NITROSOBENZYL HEMIACETAL; ADENOSINE TRIPHOSPHATE; BENZENE DERIVATIVE; BUFFER; DIMETHYL ETHER; METHANOL; NITROBENZENE DERIVATIVE; PHOSPHATE; SOLVENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PH; PHOTOLYSIS; ULTRAVIOLET SPECTROSCOPY;

ADENOSINE TRIPHOSPHATE; HYDROGEN-ION CONCENTRATION; KINETICS; METHANOL; METHYL ETHERS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOLYSIS; SPECTROPHOTOMETRY, ULTRAVIOLET; WATER;

EID: 8644220844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039071z     Document Type: Article

References (75)

1. Pillai, V. N. R. Synthesis 1980, 1-26. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. 3rd ed.: Wiley-Interscience: New York, 1999.
2. Pillai, V. N. R. Synthesis 1980, 1-26. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. 3rd ed.: Wiley-Interscience: New York, 1999.
3. Chee, M.; Yang, R.; Hubbell, E.; Berno, A.; Huang, X. C.; Stern, D.; Winkler, J.; Lockhart, D. J.; Morris, M. S.; Fodor, S. P. A. Science 1996, 274, 610-614. Pirrung, M. C. Chem. Rev. 1997, 97. 473-488. Pirrung, M. C. Angew. Chem., Int. Ed. 2002, 41, 1276-1289.
4. Chee, M.; Yang, R.; Hubbell, E.; Berno, A.; Huang, X. C.; Stern, D.; Winkler, J.; Lockhart, D. J.; Morris, M. S.; Fodor, S. P. A. Science 1996, 274, 610-614. Pirrung, M. C. Chem. Rev. 1997, 97. 473-488. Pirrung, M. C. Angew. Chem., Int. Ed. 2002, 41, 1276-1289.
5. Chee, M.; Yang, R.; Hubbell, E.; Berno, A.; Huang, X. C.; Stern, D.; Winkler, J.; Lockhart, D. J.; Morris, M. S.; Fodor, S. P. A. Science 1996, 274, 610-614. Pirrung, M. C. Chem. Rev. 1997, 97. 473-488. Pirrung, M. C. Angew. Chem., Int. Ed. 2002, 41, 1276-1289.
6. Pelliccioli, A. P.; Wirz, J. Photochem. Photobiol. Sci. 2002, 1, 441-458.
7. Breitinger, H.-G. A.; Wieboldt, R.; Ramesh, D.; Carpenter, B. K.; Hess, G. P. Biochemistry 2000, 39, 5500-5508. Givens, R. S.; Weber, J. F. W.; Conrad, P. G.; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am Chem. Soc. 2000, 123, 2687-2697. Pollock, J.; Crawford, J. H.; Wootton, J. F.; Corrie, J. E. T.; Scott, R. H. Neurosci. Lett. 2003, 338, 143-146.
8. Breitinger, H.-G. A.; Wieboldt, R.; Ramesh, D.; Carpenter, B. K.; Hess, G. P. Biochemistry 2000, 39, 5500-5508. Givens, R. S.; Weber, J. F. W.; Conrad, P. G.; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am Chem. Soc. 2000, 123, 2687-2697. Pollock, J.; Crawford, J. H.; Wootton, J. F.; Corrie, J. E. T.; Scott, R. H. Neurosci. Lett. 2003, 338, 143-146.
9. Breitinger, H.-G. A.; Wieboldt, R.; Ramesh, D.; Carpenter, B. K.; Hess, G. P. Biochemistry 2000, 39, 5500-5508. Givens, R. S.; Weber, J. F. W.; Conrad, P. G.; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am Chem. Soc. 2000, 123, 2687-2697. Pollock, J.; Crawford, J. H.; Wootton, J. F.; Corrie, J. E. T.; Scott, R. H. Neurosci. Lett. 2003, 338, 143-146.
10. Kaplan, J. H.; Forbush, B.; Hoffman, J. F. Biochemistry 1978, 17, 1929-1935.
11. Corrie, J. E. T.; Barth, A.; Munasinghe, V. R. N.; Trentham, D. R.; Hutter, M. C. J. Am. Chem. Soc. 2003, 125, 8546-8554.
12. Schwörer, M. 'Mechanismen der lichtinduzierten Freisetzung von Abgangsgruppen aus 2-Nitrobenzylverbindungen'. Ph.D. thesis, University of Basel, 2002, and ref 3.
13. Schwörer, M.; Wirz, J. Helv. Chim. Acta 2001, 84, 1441-1458.
14. Il'ichev, Y. V.; Kombarova, S. V.; Mac, M.; Schwörer, M.; Wirz, J. in preparation.
15. Gauglitz, G.; Hubig, S. Z. Phys. Chem., N. F. 1984, 139, 237-246. Gauglitz, G.; Hubig, S. J. Photochem. 1985, 30, 121-125. Persy, G.; Wirz, J. EPA Newslett. 1987, 29, 45-46.
16. Gauglitz, G.; Hubig, S. Z. Phys. Chem., N. F. 1984, 139, 237-246. Gauglitz, G.; Hubig, S. J. Photochem. 1985, 30, 121-125. Persy, G.; Wirz, J. EPA Newslett. 1987, 29, 45-46.
17. Gauglitz, G.; Hubig, S. Z. Phys. Chem., N. F. 1984, 139, 237-246. Gauglitz, G.; Hubig, S. J. Photochem. 1985, 30, 121-125. Persy, G.; Wirz, J. EPA Newslett. 1987, 29, 45-46.
18. Hasler, E.; Hörmann, A.; Persy, G.; Platsch, H.; Wirz, J. J. Am. Chem. Soc. 1993, 115, 5400-5409.
19. Rödig, C.; Siebert F. Appl. Spectrosc. 1999, 55, 893-901.
20. Seebach, D.; Kalinowski, H.-O.; Bastani, B.; Crass, G.; Daum, H.; Dörr, H.; DuPreez, N. P.; Ehrig, V.; Langer, W.; Nüssler, C.; Oei, H.-A.; Schmidt, M. Helv. Chim. Acta 1977, 60, 301-325.
21. Merz, A. Angew. Chem. 1973, 85, 868-869.
22. Gonzalez, M. A.; Meyers, A. I. Tetrahedron Lett. 1989, 30, 47-55.
23. Bamberger, E.; Fodor, A. Ber. Dtsch. Chem. Ges. 1910, 43, 3321-3335.
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C. ; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.11, Gaussian, Inc., Pittsburgh, PA. 2002.
25. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
26. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-797.
27. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch M. J. J. Phys Chem. 1994, 98, 11 623-11 627.
28. Scott, A. P., Radom, L. J. Phys. Chem. 1996, 100, 16 502-16 513.
29. Il'ichev, Y. V.; Wirz, J. J. Phys. Chem. A 2000, 104, 7856-7870.
30. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117-129.
31. (b) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239-245.
32. (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327-335.
33. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449.
34. Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1986 33, 943-951.
35. Azoulay, M.; Wettermark, G. Tetrahedron 1978, 34, 2591-2596.
36. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1984, 88, 5770-5772. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1985, 89, 5328-5330. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Wen, Y. X. J. Phys. Chem. 1991, 95, 6078-6081. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Blanchet, D. Can. J. Chem. 1991, 69, 1193-1200.
37. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1984, 88, 5770-5772. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1985, 89, 5328-5330. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Wen, Y. X. J. Phys. Chem. 1991, 95, 6078-6081. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Blanchet, D. Can. J. Chem. 1991, 69, 1193-1200.
38. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1984, 88, 5770-5772. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1985, 89, 5328-5330. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Wen, Y. X. J. Phys. Chem. 1991, 95, 6078-6081. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Blanchet, D. Can. J. Chem. 1991, 69, 1193-1200.
39. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1984, 88, 5770-5772. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1985, 89, 5328-5330. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Wen, Y. X. J. Phys. Chem. 1991, 95, 6078-6081. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D.; Blanchet, D. Can. J. Chem. 1991, 69, 1193-1200.
40. The decay traces clearly deviated from a simple first-order rate law and gave excellent fits with two exponentials, but the two close-lying rate constants and their amplitudes were not defined with high accuracy.
41. This value is close to the time resolution of our instrument that was limited by the 30-ns duration of the laser pulse.
42. Supporting Information: See paragraph at the end of this paper regarding availability.
43. a = 3.6 determined independently.8
44. Walker, J. W.; Reid, G. P.; McCray, J. A.; Trentham, D. R. J. Am. Chem. Soc. 1988, 110, 7170-7177.
45. Bates, R. G. Determination of pH, Theory and Practice; Wiley: New York, 1973.
46. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. J. Chem. Soc., Perkin Trans. 2 2001, 1414-1425. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. Spectrochim. Acta, Part A 1997, 53A, 2553-2557. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. Spectrochim. Acta, Part A 1997, 53A, 2553-2557.
47. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. J. Chem. Soc., Perkin Trans. 2 2001, 1414-1425. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. Spectrochim. Acta, Part A 1997, 53A, 2553-2557. Dunkin, I. R.; Gebicki, J.; Kiszka, M.; Sanin-Leira, D. Spectrochim. Acta, Part A 1997, 53A, 2553-2557.
48. -1.
49. Il'ichev, Y. V. J. Phys. Chem. A 2003, 107, 10 159-10 170.
50. Bellamy, L. J. The Infrared Spectra of Complex Molecules. 3rd ed.; Chapman and Hall: London, 1975.
51. Barth, A.; Hauser, K.; Mäntele, W.; Corrie, J. E. T.; Trentham, D. R. J. Am. Chem. Soc. 1995. 117, 10311-10316. Barth, A.; Corrie, J. E. T.; Gradwell, M. J.; Maeda, Y.; Mäntele, W.; Meier, T.; Trentham, D. R. J. Am. Chem. Soc. 1997, 119, 4149-4159. Rammelsberg, R.; Boulas, S.; Chorongiewski, H. ; Gerwert, K. Vibr. Spectrosc. 1999, 19, 143-149.
52. Barth, A.; Hauser, K.; Mäntele, W.; Corrie, J. E. T.; Trentham, D. R. J. Am. Chem. Soc. 1995. 117, 10311-10316. Barth, A.; Corrie, J. E. T.; Gradwell, M. J.; Maeda, Y.; Mäntele, W.; Meier, T.; Trentham, D. R. J. Am. Chem. Soc. 1997, 119, 4149-4159. Rammelsberg, R.; Boulas, S.; Chorongiewski, H. ; Gerwert, K. Vibr. Spectrosc. 1999, 19, 143-149.
53. Barth, A.; Hauser, K.; Mäntele, W.; Corrie, J. E. T.; Trentham, D. R. J. Am. Chem. Soc. 1995. 117, 10311-10316. Barth, A.; Corrie, J. E. T.; Gradwell, M. J.; Maeda, Y.; Mäntele, W.; Meier, T.; Trentham, D. R. J. Am. Chem. Soc. 1997, 119, 4149-4159. Rammelsberg, R.; Boulas, S.; Chorongiewski, H. ; Gerwert, K. Vibr. Spectrosc. 1999, 19, 143-149.
54. Choi, J.; Terazima, M. Photochem. Photobiol. Sci. 2003, 2, 767-773.
55. Corrie, J. E. T.; Trentham, D. R. Bioorg. Photochem. Vol. 2, Morrison, H., Ed., 1993, 243-305.
56. Peng, L.; Nachon, F.; Wirz, J.; Goeldner, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2691-2693.
57. Schaper, K.; Dommaschke, D.; Globisch, S.; Madani-Mobarekeh, S. A. J. Inf. Rec. 2000, 25, 339-354.
58. Walbert, S.; Pfleiderer, W.; Steiner, U. E. Helv. Chim. Acta 2001, 84, 1601-1611.
59. This product could not be isolated from the strongly acidic solutions, but was tentatively identified on the basis of its transient UV spectrum and the rate of dehydration of its nitroso hydrate precursor.
60. - formed from 1, because reactions ab are rate-limiting for the formation of C at pH > 6. The case of 2 will be discussed below.
61. Peng, L.; Goeldner, M. J. Org. Chem. 1996, 61, 185-191.
62. (a) Schupp, H.; Wong, W. K.; Schnabel, W. J. Photochem. 1987, 36, 85-97.
63. (b) Zhu, Q. Q.; Schnabel, W.; Schupp, H. J. Photochem. 1987, 39, 317-332.
64. Quinkert, G. Wiersdorff, W.-W. Finke, M.; Opitz, K. von der Haar, F.-G. Chem. Ber. 1968, 101, 2302-2325.
65. 4 in this buffer system. Loudon, G. M.; Ryono, D. E. J. Org. Chem. 1975, 40, 3574-3577.
66. Lehn, J. M. Top. Curr. Chem. 1970, 15, 311-377.
67. Müller, K.; Eschenmoser, A. Helv. Chim. Acta 1969. 52, 1823-1830.
68. (a) Hassan, A.; Wazeer, M. I. M.; Perzanowski, H. P.; Ali, S. A. J. Chem. Soc., Perkin Trans. 2 1997. 411-418.
69. (b) Perrin, C. L.; Thoburn, J. D.; Elsheimer, S. J. Org. Chem. 1991, 56, 7034-7038.
70. Grünbein, W.; Fojtik, A.; Henglein, A. Monatsh. Chem. 1970; 101, 1243-1252.
71. Capon, B.; Nimmo, K.; Reid, G. L. J. Chem. Soc., Chem. Commun. 1976. 871-873.
72. McClelland, R. A.; Kangasabapathy, V. M.; Mathivanan, N. Can. J. Chem. 1991, 69, 2084-2093.
73. Corrie, J. E. T. J. Chem. Soc., Perkin Trans, 1 1993, 2161-2166.
74. Observation of a long-lived hemiacetal intermediate formed by photolysis of a 2-nitrobenzyl ether has been reported previously: Hirayama, Y.; Iwamura, M.; Furuta, T. Bioorg. Med. Chem. Lett. 2003, 13, 905-908. See also: Peyser, J. R.; Flechtner, T. W. J. Org. Chem. 1987, 52, 4645-4646.
75. Observation of a long-lived hemiacetal intermediate formed by photolysis of a 2-nitrobenzyl ether has been reported previously: Hirayama, Y.; Iwamura, M.; Furuta, T. Bioorg. Med. Chem. Lett. 2003, 13, 905-908. See also: Peyser, J. R.; Flechtner, T. W. J. Org. Chem. 1987, 52, 4645-4646.