Deprotonation yields, pKa, and aci-nitro decay rates in some substituted o-nitrobenzaldehydes

Photochemical and Photobiological Sciences

Volumn 2, Issue 7, 2003, Pages 796-800

  Abbruzzetti, Stefania ^a   Carcelli, Mauro ^a   Rogolino, Dominga ^a   Viappiani, Cristiano ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; EXCITATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 12944281323     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b301818k     Document Type: Article

References (36)

1. J. A. McCray and D. R. Trentham, Properties and use of photoreactive caged compounds, Annu. Rev. Biophys. Biophys. Chem., 1989, 18, 239-270.
2. Caged compounds, in Methods in Enzymology, ed. G. Marriott, Academic Press, New York, London, 1998, vol. 291.
3. R. W. Yip, D. K. Sharma, R. Giasson and D. Gravel, Picosecond excited-state absorption of alkyl nitrobenzenes in solution, J. Phys. Chem., 1984, 88, 5770-5772.
4. R. W. Yip, D. K. Sharma, R. Giasson and D. Gravel, Photochemistry of the o-nitrobenzyl system in solution: Evidence for singlet state intramolecular hydrogen abstraction, J. Phys. Chem., 1985, 89, 5328-5330.
5. R. W. Yip, Y. X. Wen, D. Gravel, R. Giasson and D. K. Sharma, Photochemistry of the o-nitrobenzyl system in solution: identification of the biradical intermediate in the intramolecular rearrangement, J. Phys. Chem., 1991, 95, 6078-6081.
6. M. V. George and J. C. Scaiano, Photochemistry of o-nitrobenzaldehyde and related studies, J. Phys. Chem., 1980, 84, 492-495.
7. R. A. McClelland and S. Steenken, Pronounced solvent effect on the absorption spectra of the photochemically produced 2,4-dinitrobenzyl carbanion, Can. J. Chem., 1987, 65, 353-356.
8. S. J. Atherton and B. B. Craig, laser photolysis of 2,6-dinitrotoluene in solution, Chem. Phys. Lett., 1986, 127, 7-12.
9. M. Schwörer and J. Wirz, Photochemical reaction mechanisms of 2-nitrobenzyl compounds in solution 1. 2-nitrotoluene: thermod ynamic and kinetic parameters of the aci-nitro tautomer, Helv. Chim. Acta, 2001, 84, 1441-1458.
10. M. Gutman and E. Nachliel, The dynamic aspects of proton transfer processes, Biochim. Biophys. Acta, 1990, 1015, 391-414.
11. a of the aci-nitro intermediate in o-nitrobenzyl systems, Isr. J. Chem., 1998, 38, 213-221.
12. G. Bonetti, A. Vecli and C. Viappiani, Reaction volume of water formation detected by time resolved photoacoustics: photoinduced proton transfer between o-nitrobenzaldehyde and hydroxyls in water, Chem. Phys. Lett., 1997, 269, 268-273.
13. C. Viappiani, S. Abbruzzetti, J. R. Small, L. J. Libertini and E. W. Small, An experimental methodology for measuring volume changes in proton transfer reactions in aqueous solutions, Biophys. Chem., 1998, 73, 13-22.
14. C. Viappiani, G. Bonetti, M. Carcelli, F. Ferrari and A. Sternieri, Study of proton transfer processes in solution using the laser induced pH-jump: a new experimental setup and an improved data analysis based on genetic algorithms, Rev. Sci. Instrum., 1998, 69, 270-276.
15. A. Barth and J. E. T. Corrie, Characterization of a new caged proton capable of inducing large pH jumps, Biophys. J., 2002, 83, 2864-2871.
16. G. C. R. Ellis-Davies and J. H. Kaplan, A new class of of photo-labile chelators for the rapid release of divalent cations: generation of caged Ca and caged Mg, J. Org. Chem., 1988, 53, 1966-1969.
17. G. C. R. Ellis-Davies, J. H. Kaplan and R. J. Barsotti, Laser photolysis of caged calcium: rates of calcium release by nitrophenyl-EGTA and DM-Nitrophen, Biophys. J., 1996, 70, 1006-1016.
18. G. C. R. Ellis-Davies, Synthesis of photosensitive EGTA derivatives, Tetrahedron Lett., 1998, 39, 953-956.
19. C. P. Holmes, Model studies for new o-nitrobenzyl photolabile linkers: substituent effects on the rates of photochemical cleavage, J. Org. Chem., 1997, 62, 2370-2380.
20. E. B. Brown, J. B. Shear, S. R. Adams, R. Y. Tsien and W. W. Webb, Photolysis of caged calcium in femtoliter volumes using two-photon excitation, Biophys. J., 1999, 76, 489-499.
21. K. Janko and J. Reichert, Proton concentration jumps and generation of transmembrane pH-gradients by photolysis of 4-formyl-6-methoxy-3- nitrophenoxyacetic acid, Biochim. Biophys. Acta, 1987, 905, 409-116.
22. S. Abbruzzetti, C. Viappiani, D. H. Murgida, R. Erra-Balsells and G. M. Bilmes, Non toxic, water soluble photocalorimetric reference compounds for UV and visible excitation, Chem. Phys. Lett., 1999, 304, 167-172.
23. S. Abbruzzetti, C. Viappiani, J. R. Small, L. J. Libertini and E. W. Small, Kinetics of histidine deligation from the heme in GuHCl unfolded Fe(III) cytochrome c studied by a laser induced pH-jump technique, J. Am. Chem. Soc., 2001, 123, 6649-6653.
24. S. Abbruzzetti, E. Crema, L. Masino, A. Vecli, C. Viappiani, J. R. Small, L. J. Libertini and E. W. Small, Fast events in protein folding. Structural volume changes accompanying the early events in the N->I transition of apomyoalobin induced by ultrafast pH jump, Biophys. J., 2000, 78, 405-115.
25. S. Abbruzzetti, C. Viappiani, J. R. Small, L. J. Libertini and E. W. Small, Kinetics of local helix formation in poly-L-glutamic acid studied by time-resolved photoacoustics: neutralization reactions of carboxylates in aqueous solutions and their relevance to the problem of protein folding, Biophys. J., 2000, 79, 2714-2721.
26. T. Gensch, C. Viappiani and S. E. Braslavsky, Laser-induced time-resolved optoacoustic spectroscopy in solution, in Encyclopedia of spectroscopy and spectrometry, ed. J. C. Lindon, G. E. Tranter and J. L. Holmes, Academic Press Ltd, London, 1999.
27. J. R. Small, Deconvolution analysis for pulsed-laser photoacoustics, in Numerical computer methods, ed. L. Brand and M. L. Johnson, Academic Press, Inc., San Diego, CA, 1992, pp. 505-521.
28. J. E. Rudzki, J. L. Goodman and K. S. Peters, Simultaneous determination of photoreaction dynamics and energetics using pulsed, time-resolved photoacoustic calorimetry, J. Am. Chem. Soc., 1985, 107, 7849-7854.
29. T. Gensch and S. E. Braslavsky, Volume changes related to triplet formation of water-soluble porphyrins. A laser-induced optoacoustic spectroscopy (LIOAS) study, J. Phys. Chem., 1997, 101, 101-108.
30. CRC Handbook of Chemistry and Physics, ed. R. C. Weast, CRC Press, Boca Raton, FL, 52nd edn, 1971.
31. S. E. Braslavsky and G. E. Heibel, Time-resolved photothermal and photoacoustics methods applied to photoinduced processes in solution, Chem. Rev., 1992, 92, 1381-1410.
32. Y. V. Il'ichev and J. Wirz, Rearrangements of 2-nitrobenzyl compounds. 1. Potential energy surface of 2-nitrotoluene and its isomers explored with ab initio and density functional theory methods, J. Phys. Chem. A, 2000, 104, 7856-7870.
33. T. Asano and W. J. Le Noble, Activation and reaction volumes in solution, Chem. Rev., 1978, 78, 407-489.
34. R. Van Eldik, T. Asano and W. J. Le Noble, Activation and reaction volumes in solution. 2, Chem. Rev., 1989, 89, 549-688.
35. A. Drljaca, C. D. Hubbard, R. van Eldik, T. Asano, M. V. Basilevsky and W. J. le Noble, Activation and reaction volumes in solution. 3, Chem. Rev., 1998, 98, 2167-2289.
36. C. D. Borsarelli and S. E. Braslavsky, The partial molar volume of the proton in water determined by laser-induced optoacoustic studies, J. Photochem. Photobiol., B: Biol., 1998, 43, 222-228.