Interplay of stereoelectronic and enviromental effects in tuning the structural and magnetic properties of a prototypical spin probe: Further insights from a first principle dynamical approach

Journal of the American Chemical Society

Volumn 128, Issue 13, 2006, Pages 4338-4347

  Pavone, Michele ^a   Cimino, Paola ^b   De Angelis, Filippo ^c   Barone, Vincenzo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR DYNAMICS; MOLECULAR VIBRATIONS; PARAMAGNETIC RESONANCE; QUANTUM THEORY; SOLUTIONS; TENSORS;

DISCRETE-CONTINUUM EMBEDDING; ENVIROMENTAL EFFECTS; FINITE-TEMPERATURE VIBRATIONAL AVERAGING; HYPERFINE COUPLING CONSTANT (HCC); PROTOTYPICAL SPIN PROBE;

ELECTRONIC STRUCTURE;

DI TERT BUTYL NITROXIDE; NITROXIDE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOTECHNOLOGY; COMPLEX FORMATION; EMBEDDING; ENVIRONMENTAL FACTOR; FINITE ELEMENT ANALYSIS; HYPERFINE COUPLING CONSTANT; MAGNETISM; MATHEMATICAL ANALYSIS; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; MOLECULAR PROBE; QUANTUM MECHANICS; RELIABILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; VALIDATION PROCESS; VIBRATION;

EID: 84962383032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0574872     Document Type: Article

References (101)

1. Keana, J. F. W. Chem. Rev. 1978, 78, 37.
2. Improta, R.; Barone, V. Chem. Rev. 2004, 104, 1231.
3. (a) Berliner, L. J., Ed. Spin Labelling, Theory and Applications; Academic Press: New York, 1976.
4. (b) Stone, T. J.; Buckman, T.; Nordio, P. L.; McConnel, H.; Proc. Natl. Acad. Sci. U.S.A. 1965, 54, 1010.
5. (a) Berliner, L. J. Ed. Biological Magnetic Resonance, Spin Labeling in the Next Millennium; Plenum Press: New York, 1998; Vol. 14.
6. (b) Engström, M.; Vaara, J.; Schimelpfennig, B.; Ågren, H. J. J. Phys. Chem. B 2002, 106, 12354.
7. (a) Baur, J. E.; Wang, S.; Brandt, M. C. Anal. Chem. 1996, 68, 3815.
8. (b) Krzyczmonik, P. H. S. J. Electroanal. Chem. 1992, 335, 233.
9. Brash, R. C.; London, D. A.; Wesbey, G. E.; Tozer, T. N.; Nirecki, D. E.; Williams, R. D.; Doemeny, J.; Tuck, L. d.; Lallemand, D. P. Radiology 1983, 147, 773.
10. (a) Hayes Griffith, O.; Waggoner, A. S. Acc. Chem. Res. 1969, 2, 17.
11. (b) Dugas, H. Acc. Chem. Res. 1977, 10, 47.
12. (c) Hanson, P.; Millhauser, G.; Formaggio, F.; Crisma, M.; Toniolo, C. J. Am. Chem. Soc. 1996, 118, 7618.
13. (d) Miller, T. R.; Alley, S. C.; Reese, A. W.; Solomon, M. S.; McCallister, W. V.; Mailer, C.; Robinson, B. H.; Hopkins, P. B. J. Am. Chem. Soc. 1995, 117, 9377.
14. (e) Pyter, R. A.; Ramachandran, C.; Mukerjee, P. J. Phys. Chem. 1982, 86, 3206.
15. (f) Greenspoon, N.; Wachet, E. J. Am. Chem. Soc. 1991, 113, 7233.
16. (g) Ionita, P.; Caragheorgheopol, A. J. Am. Chem. Soc. 2002, 124, 9048.
17. (h) Zhang, Z.; Berg, A.; Levanon, H.; Fessenden, R. W.; Meisel, D. J. Am. Chem. Soc. 2003, 125, 7959.
18. (i) Edwards, T. E.; Okonogi, T. M.; Robinson, B. H.; Sigurdsson, S. T. J. Am. Chem. Soc. 2001, 123, 1527.
19. (j) Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99.
20. (k) Kocherginsky, N., Swartz, H. M., Eds. Nitroxide Spin Labels, Reactions in Biology and Chemistry; CRC Press: Boca Raton, 1995.
21. Knauer, B. R.; Napier, Ji J. J. Am. Chem. Soc. 1976, 91, 4395.
22. Tedeschi, A. M.; D'Errico, G.; Busi, E.; Basosi, R.; Barone, V. Phys. Chem. Chem. Phys. 2002, 4, 2180.
23. Wu, D. G.; Malec, A. D.; Head-Gordon, M.; Majda, M. J. Am. Chem. Soc. 2005, 127, 4490.
24. (a) Garrett, B. C.; et al. Chem. Rev. 2005, 105, 355.
25. (b) Wernet, P.; et al. Science 2004, 304, 995.
26. (a) Goedecker, S.; Scuseria, G. E. Comput. Sci. Eng. 2003, 5, 14.
27. (b) Scuseria, G. E. J. Phys. Chem. A 1999, 103, 4782.
28. (c) Merchan, M.; Serrano-Andres, L.; Falscher, M. P.; Roos, B. O. Recent Adv. Comput. Chem. 1999, 4, 161.
29. (a) Roos, B. O. Acc. Chem. Res. 1999, 32, 137.
30. (b) Helgaker, T.; Jaszunski, M.; Ruud, K. Chem. Rev. 1999, 99, 293.
31. (a) Persico, M.; Tomasi, J. Chem. Rev. 1994, 94, 2027.
32. (b) Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
33. (c) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999.
34. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
35. Scalmani, G.; Barone, V.; Kudin, K. N.; Pomelli, C. S.; Scuseria, G. E.; Frisch, M. J. Theor. Chem. Acc. 2004, 111, 90.
36. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
37. (a) Adamo, C.; Cossi, M.; Rega, N.; Barone, V. Theoretical Biochemistry: Processes and Properties of Biological Systems; Eriksson, L. A., Ed.; Theoretical and Computational Chemistry, Vol. 9; Elsevier: New York, 1999.
38. (b) Cossi, M.; Barone, V. J. Chem. Phys. 2000, 112, 2427.
39. (c) Cossi, M.; Barone, V. J. Chem. Phys. 2001, 115, 4708.
40. (c) Adamo, C.; Barone, V. Chem. Phys. Lett. 2000, 320, 152.
41. (d) Aquilante, F.; Roos, B.; Barone, V. J. Chem. Phys. 2003, 119, 12323.
42. (e) Koch, A.; Thomas, S.; Kleinpeter, E. THEOCHEM 1997, 401, 1.
43. (f) Saracino, G. A.; Tedeschi, A.; D'Errico, G.; Improta, R.; Barone, V. J. Phys. Chem. A 2002, 106, 10700.
44. Car, R.; Parrinello, M. Phys. Rev. Lett. 1985, 55, 2471.
45. Crescenzi, O.; Pavone, M.; De Angelis, F.; Barone, V. J. Phys. Chem. B 2005, 109, 445.
46. (a) Kaupp, M.; Bühl, M.; Malkin, V. G. Calculation of NMR and EPR parameters: Wiley-VCH: Weinheim, 2004.
47. (b) Neugebauer, J.; Louwerse, M. J.; Belanzoni, P.; Wesolowski, T. A.; Baerends, E. J. J. Chem. Phys. 2005, 123, 114101.
48. (a) Kawamura, T.; Matsunami, S.; Yonezawa, T. Bull. Chem. Soc. Jpn. 1967, 40, 1111.
49. (b) Mukerjee, P.; Ramachandran, C.; Pyter, R. A. J. Phys. Chem. 1982, 86, 3189
50. (c) Owenius, R.; Engstrom, M.; Lindgren, M.; Huber, M. J. Phys. Chem. A 2001, 105, 10967.
51. Mattar, S. M.; Stephens, A. D. Chem. Phys. Lett. 2001, 347, 189.
52. Rinkevicius, Z.; Telyatnyk, L.; Vahtras, O.; Ruud, K. J. Chem. Phys. 2004, 121, 5051.
53. (a) Aschi, M.; Spezia, R.; Di Nola, A.; Amadei, A. Chem. Phys. Lett. 2001, 344, 374.
54. (b) R. Spezia, R.; Aschi, M.; Di Nola, A.; Amadei, A. Chem. Phys. Lett. 2002, 365, 450.
55. (c) Amadei, A.; Marinelli, F.; D'Abramo, M.; D'Alessandro, M.; Anselmi, M.; di Nola, A.; Aschi, M. J. Chem. Phys. 2005, 122, 124506.
56. (d) Sebastiani, D.; Parrinello, M. J. Phys. Chem. A 2001, 105, 1951.
57. (a) Bühl, M. J. Phys. Chem. A 2002, 106, 10505
58. (b) Asher, J. R.; Doltsinis, N. L.; Kaupp, M. J. Am. Chem. Soc. 2004, 126, 9854
59. (c) Bühl, M.; Parrinello, M. Chem. Eur. J. 2001, 7, 4487.
60. (d) Bühl, M. Inorg. Chem. 2005, 44, 6277.
61. (e) Aidas, K.; Kongsted, J.; Osted, A.; Mikkelsen, K. V.; Christiansen, O. J. Phys. Chem. A 2005, 109, 8001.
62. Pavone, M.; Benzi, C.; De Angelis, F.; Barone, V. Chem. Phys. Lett. 2004, 395, 120.
63. (a) Saracino, G. A. A.; Tedeschi, A.; D'Errico, G.; Improta, R.; Barone, V. J. Phys. Chem. A 2002, 106, 10700.
64. (b) Improta, R.; Barone, V. J. Am. Chem. Soc. 2004, 126, 14320.
65. (c) Cimino, P.; Barone, V. THEOCHEM 2005, 729, 1.
66. (a) Hohenberg, P.; W. Kohn, W. Phys. Rev. 1964, 136, B864.
67. (b) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133.
68. (a) Kanai, Y.; Cicero, G.; Selloni, A.; Car, R.; Galli, G. J. Phys. Chem. B 2005, 109, 13656
69. (b) Fischer, D.; Curioni, A.; Billeter, S. R.; Andreoni, W. Phys. Rev. Lett. 2004, 92, 236405.
70. (c) Gleich, D.; Hutter, J. Chem. Eur. J. 2004, 10, 2435.
71. (a) Andreoni, W.; Curioni, A. Parallel Comput. 2000, 26, 819.
72. (b) Hutter, J.; Curioni, A. ChemPhysChem 2005, 6, 1.
73. Giannozzi, P.; De Angelis, F.; Car, R. J. Chem. Phys. 2004, 120, 5903.
74. Pasquarello, A.; Laasonen, K.; Car, R.; Lee, C.; Vanderbilt, D. Phys. Rev. Lett. 1992, 69, 1982.
75. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
76. Vanderbilt, D. Phys. Rev. B 1990, 41, 7892.
77. Hetenyi, B.; De Angelis, F.; Giannozzi, P.; Car, R. J. Chem. Phys. 2004, 120, 8632.
78. Nosé, S. J. Chem. Phys. 1984, 81, 511.
79. Hura, G.; Sorenson, J. M.; Glaeser, R. M.; Head-Gordon, T. J. Chem. Phys. 2000, 113, 9140.
80. Soper, A. K. Chem. Phys. 2000, 258, 121.
81. Silvestrelli, P. L.; Parrinello, M. J. Chem. Phys. 1999, 111, 3572
82. Silvestrelli, P. L.; Parrinello, M. Phys. Rev. Lett. 1999, 82, 3308.
83. Frisch, M. J.; et al. Gaussian03, rev. C.02; Gaussian. Inc.: Philadelphia, PA, 2003.
84. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158.
85. Francl, M. M.; Petro, W. J.; Hehre, W. J. S.; Binkley, J.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
86. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
87. Adamo, C.; Barone, V.; Fortunelli, A. J. Chem. Phys. 1995, 102, 384.
88. Barone, V. Theor. Chim. Acta 1995, 91, 113.
89. Chipman, D. M. Theor. Chim. Acta 1992, 82, 93.
90. McWeeny, R. Methods of Molecular Quantum Mechanics; Academic Press: London, 1992.
91. Stone, A. J. Proc. R. Soc. London. Ser. A 1963, 271, 424.
92. Neese, F. J. Chem. Phys. 2001, 115, 11080.
93. (a) Ditchfield, R. Mol. Phys. 27, 789 1974.
94. (b) Cheesman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1998, 104, 5497.
95. Malkina, O. L.; Vaara, J.; Schimmelpfenning, B.; Munzarova, M. L.; Malkin, V. G.; Kaupp, M. J. Am. Chem. Soc. 2000, 122, 9206.
96. Koseki, S.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. 1992, 96, 10768.
97. (a) Ciofini, I.; Adamo, C.; Barone, V. J. Chem. Phys. 2004, 121, 6710.
98. (b) Barone, V.; Carbonniere, P.; Pouchan, C. J. Chem. Phys. 2005, 122, 224308.
99. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
100. Ferrario, M.; Haughney, M.; McDonald, I. R.; Klein, M. L. J. Chem. Phys 1990, 93, 5156.
101. Pavone, M.; Barone, V.; Ciofini, I.; Adamo, C. J. Chem. Phys. 2004, 120, 9167.