A multi-step procedure for evaluating the EPR parameters of indolinonic aromatic aminoxyls: A combined DFT and spectroscopic study

Chemical Physics

Volumn 323, Issue 2-3, 2006, Pages 501-510

  Stipa, Pierluigi ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Aromatic aminoxyls; DFT; EPR; Hyperfine coupling constants

Indexed keywords

EID: 33646074518     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphys.2005.10.016     Document Type: Article

References (92)

1. Spin Probe: usually a stable organic free radical introduced in various systems (e.g., biological) to be studied, by means of EPR spectroscopy, from the modifications occurring in the spectral lines:. In: Berliner L.J., and Reuben J. (Eds). Biological Magnetic Resonance vol. 8 (1989), Plenum Press, New York
2. Engström M., Vaara J., Schimmelpfennig B., and Ågren H.J. J. Phys. Chem. B 106 (2002) 12354
3. Ranby B., and Rabek J.F. ESR Spectroscopy in Polymer Research (1971), Springer Verlag, Berlin
4. Spin Label: usually a stable organic free radical that can be bonded to another molecule (e.g., biomolecule) to eventually act as a "probe" in different systems studied by means of EPR spectroscopy:. In: Berliner L.J. (Ed). Molecular Biology Series: Spin Labeling. Theory and Applications vol. 2 (1979), Academic Press, New York
5. Haering G., Luisi P.L., and Hauser H. J. Phys. Chem. 92 (1988) 3574
6. Subezynski W.K., Antholine W.E., Hyde J.S., and Kusumi A. Biochemistry 29 (1990) 736
7. Marsh D., Watts A., and Knowles P.F. Biochemistry 15 (1976) 3570
8. In: Berliner L.J. (Ed). Biological Magnetic Resonance. Spin Labeling the Next Millenium vol. 14 (1998), Plenum Press, New York
9. Strube T., Schiemann O., MacMillan F., Prisner T.F., and Engels J.W. Nucleoside Nucleotide Nucl. Acids 20 (2001) 1271
10. Edwards T.E., Okonogi T.M., Robinson B.H., and Sigurdsson S.T. J. Am. Chem. Soc. 123 (2001) 1527
11. Verma S., and Eckstein F. Annu. Rev. Biochem. 67 (1998) 99
12. Brash R.C., London D.A., Wesbey G.E., Tozer T.N., Nirecki D.E., Williams R.D., Doemeny J., Tuck L.D., and Lallemand D.P. Radiology 147 (1983) 773
13. Caneschi A., Gatteschi D., and Rey P. Progr. Inorg. Chem 39 (1991) 331
14. Klemchuk P.P., and Gande M.E. Polym. Degrad. Stab. 22 (1988) 241 and references cited therein
15. Kocherginsky N., and Swartz H.M. Nitroxide Spin Labels, Reactions in Biology and Chemistry (1995), CRC Press, Boca Raton, FL
16. Greci L., Damiani E., Carloni P., and Stipa P. In: Minisci F. (Ed). Free Radicals in Biology and Environment (1997), Kluwer Academic Publishers, The Netherlands 223
17. Samuni A., and Krishna M.C. In: Packer L., and Cadenas E. (Eds). Handbook of Synthetic Antioxidants (1997), Marcel Dekker Inc., New York 351
18. Krishna M.C., and Samuni A. Meth. Enzymol. 234 (1994) 580
19. Howard J.A., and Tait J.C. J. Org. Chem. 43 (1978) 4279
20. Grattan D.W., Carlsson D.J., Howard J.A., and Wiles D.M. Can. J. Chem. 57 (1979) 2834
21. Chateauneuf J., Lusztyk J., and Ingold K.U. J. Org. Chem. 53 (1988) 1629
22. Beckwith A.L.J., and Bowry V.W. J. Org. Chem. 53 (1988) 1632
23. Khote T., Marque S., Martschke R., Popov M., and Fisher H. J. Chem. Soc. Perkin 2 (1998) 1553
24. Stipa P., Greci L., Carloni P., and Damiani E. Polym. Degrad. Stab. 55 (1997) 323
25. Barton D.H.R., Le Gloahec V.N., and Smith J. Tetrahedron 39 (1998) 7483
26. Stipa P. J. Chem. Soc. Perkin 2 (2001) 1793
27. Howard J.A. Advan. Free Radical Chem. 4 (1971) 161
28. Khloplyankina M.A., Buchachenko A.L., Neiman M.B., and Vasil'eva A.G. Kinetika Kataliz. 6 (1965) 465
29. Berti C., Colonna M., Greci L., and Marchetti L. Tetrahedron 33 (1977) 2321
30. Berti C., Colonna M., Greci L., and Marchetti L. Tetrahedron 33 (1977) 3149
31. Greci L. Tetrahedron 38 (1982) 2435
32. Cardellini L., Carloni P., Greci L., and Stipa P. Gazz. Chim. Ital. 119 (1989) 621
33. Damiani E., Carloni P., Stipa P., and Greci L. Free Rad. Res. 31 (1999) 113
34. Carloni P., Damiani E., Scattolini M., Stipa P., and Greci L. J. Chem. Soc. Perkin 2 (2000) 447
35. Janzen E.G. Acc. Chem. Res. 4 (1971) 31
36. Pou S., Halpern H.J., Tsai P., and Rosen G.M. Acc. Chem. Res. 32 (1999) 155
37. Janzen E.G., and Liu J.I.-P. J. Magn. Reson. 9 (1973) 510
38. Janzen E.G., Evans C.A., and Liu J.I.-P. J. Magn. Reson. 9 (1973) 513
39. Buettner G.R. Free Rad. Biol. Med. 3 (1987) 259
40. Halliwell B., and Gutteridge J.M.C. Free Radicals in Biology and Medicine. second ed. (1989), Clarendon Press, Oxford 422
41. Korthuis D., Carden D.L., and Granger D.N. In: Spatz L., and Bloom D. (Eds). Biological Consequences of Oxidative Stress (1992), Oxford Press, London 50
42. Schulz J.B., Henshaw D.R., Siwek D., Jenkins B.G., Ferrante R.J., Cipolloni P.B., Kowall N.W., Rosen B.R., and Beal M.F. J. Neurochem. 64 (1995) 2239
43. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecule (1998), Oxford University Press, New York
44. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional Theory (2000), Wiley-VCH, Weinheim
45. Model Chemistry: combination of theoretical procedure (method) and basis set;. Foresman J.B., and Frisch A. Exploring Chemistry with Electronic Structure Methods (1996), Gaussian Inc., Pittsburgh, PA Chapter 1
46. Improta R., and Barone V. Chem. Rev. 104 (2004) 1231
47. Barone V. In: Chong D.P. (Ed). Recent Advances in Density Functional Methods (1995), World Scientific, Singapore 287
48. Adamo C., Barone V., and Fortunelli A. J. Chem. Phys. 102 (1995) 384
49. Adamo C., and Barone V. J. Chem. Phys. 110 (1999) 6158
50. Adamo C., and Barone V. J. Chem. Phys. 116 (2002) 593
51. Malkin V.G., Malkina O.L., Eriksson L.A., and Salahub D.R. In: Seminario J.M., and Politzer P. (Eds). Modern Density Functional Theory, A Tool for Chemistry (1995), Elsevier, New York
52. Engels B., Eriksson L.A., and Lunell S. Adv. Quantum Chem. 27 (1997) 297
53. Batra R., Giese B., Spichty M., Gescheidt G., and Houk K.N. J. Phys. Chem. 100 (1996) 18371
54. Chipman D.M. Theor. Chim. Acta 76 (1989) 73
55. Improta R., Scalmani G., and Barone V. Chem. Phys. Lett. 336 (2001) 349
56. Ban F., Gauld J.W., Wetmore S.D., and Boyd R.J. In: Lund A. (Ed). EPR of Free Radicals in Solids: Trends in Methods and Applications (2003), Kluwer Academic, Dordrecht 239
57. Di Matteo A., Adamo C., Cossi M., Barone V., and Rey P. Chem. Phys. Lett. 310 (1999) 159
58. Di Matteo A., Adamo C., Barone V., and Rey P. J. Phys. Chem. 103 (1999) 3481
59. Di Matteo A., Bencini A., Cossi M., Barone V., Mattesini M., and Totti F. J. Am. Chem. Soc. 120 (1998) 7069
60. Barone V., Grand A., Luneau D., Rey P., Minichino C., and Subra R. New. J. Chem. 17 (1993) 545
61. Cirujeda J., Vidal-Gancedo J., Jürgens O., Mota F., Novoa J.J., Rovira C., and Veciana J. J. Am. Chem. Soc. 122 (2000) 11393
62. Zheludev A., Barone V., Bonnet M., Delley B., Grand A., Ressouche E., Rey P., Subra R., and Schweizer J. J. Am. Chem. Soc. 116 (1994) 2019
63. Mattar S.M., and Stephens A.L. Chem. Phys. Lett. 319 (2000) 601
64. Beyer M., Fritscher J., Feresin E., and Schiemann O. J. Org. Chem. 68 (2003) 2209
65. See for example: http://www.esr.ethz.ch/links.html; http://www.ieprs.org/; http://epr.niehs.nih.gov/pest.html.
66. Berti C., Colonna M., Greci L., and Marchetti L. Tetrahedron 31 (1975) 1745
67. Damiani E., Kalinska B., Canapa A., Canestrai S., Wozniak M., Olmo E., and Greci L. Free Radic. Biol. Med. 28 (2000) 330
68. Damiani E., Belaid C., Carloni P., and Greci L. Free Rad. Res. 37 (2003) 731
69. Fedeli D., Damiani E., Greci L., Littarru G.P., and Falcioni G. Mutat. Res. 535 (2003) 117
70. Eur. Pat. 01400193.7-2109, 2001; US Patent 6,531,556, 2003; US Patent 6,706,832, 2004.
71. Benassi R., Taddei F., Greci L., Marchetti L., Andreetti G.D., Bocelli G., and Sgarabotto P. J. Chem. Soc. Perkin 2 (1980) 786
72. Jaszewski A.R., Jezierska J., and Jezierski A. Chem. Phys. Lett. 319 (2000) 611
73. Tabaka K., and Jezierska J. Chem. Phys. Lett. 394 (2004) 298
74. Weltner W. Magnetic Atoms and Molecules (1989), Dover, New York
75. Caciuffo R., Francescangeli O., Greci L., Melone S., Gillon B., Brustolon M., Maniero A.L., Amoretti G., and Sgarabotto P. Mol. Phys. 74 (1991) 905
76. Maniero A.L., Brustolon M., Ottaviani M.F., Rizzoli C., Sgarabotto P., Uguzzoli F., Carloni P., and Greci L. Mol. Phys. 73 (1991) 1
77. Weil J.A., Bolton J.R., and Wertz J.E. Electron Paramagnetic Resonance. Elementary Theory and Practical Applications (1994), Wiley-Interscience, New York 248
78. Gauld J.W., Eriksson L.A., and Radom L. J. Phys. Chem. A 101 (1997) 1352
79. Kirkwood J.G. J. Chem. Phys. 2 (1934) 351
80. Onsager L. J. Am. Chem. Soc. 58 (1936) 1486
81. Wong M.W., Frisch M.J., and Wiberg K.B. J. Am. Chem. Soc. 113 (1991) 4776
82. Wong M.W., Wiberg K.B., and Frisch M.J. J. Chem. Phys. 95 (1991) 8991
83. Wong M.W., Wiberg K.B., and Frisch M.J. J. Am. Chem. Soc. 114 (1992) 523
84. Wong M.W., Wiberg K.B., and Frisch M.J. J. Am. Chem. Soc. 114 (1992) 1645
85. Cancès M.T., Mennucci B., and Tomasi J. J. Chem. Phys. 107 (1997) 3032
86. Cossi M., Barone V., Mennucci B., and Tomasi J. J. Chem. Phys. Lett. 286 (1998) 253
87. Mennucci B., and Tomasi J. J. Chem. Phys. 106 (1997) 5151
88. Cossi M., Scalmani G., Rega N., and Barone V. J. Chem. Phys. 117 (2002) 43
89. MAD: average difference between the computed and experimental values ignoring the sign;. Foresman J.B., and Frisch A. Exploring Chemistry with Electronic Structure Methods (1996), Gaussian Inc., Pittsburgh, PA 145
90. Rizzoli C., Sgarabotto P., Ugozzoli F., Carloni P., Damiani E., Greci L., and Stipa P. J. Heterocyc. Chem. 30 (1993) 637
91. Duling D. PEST Winsim Ver. 0.96 (1996), National Institute of Environmental Health Sciences, Triangle Park, NC
92. Frisch M.J., et al. Gaussian 03, Revision B.05 (2003), Gaussian Inc., Pittsburgh, PA