Hydrogen Bond Geometries from Electron Paramagnetic Resonance and Electron-Nuclear Double Resonance Parameters: Density Functional Study of Quinone Radical Anion-Solvent Interactions

Journal of the American Chemical Society

Volumn 126, Issue 10, 2004, Pages 3280-3290

  Sinnecker, Sebastian ^a   Reijerse, Eduard ^a   Neese, Frank ^a   Lubitz, Wolfgang ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; NEGATIVE IONS; PARAMAGNETIC RESONANCE; PROBABILITY DENSITY FUNCTION; TENSORS;

COUPLING CONSTANTS; QUADRUPOLE COUPLING;

HYDROGEN BONDS;

1,4 BENZOQUINONE; 4 BENZOSEMIQUINONE; ANION; CARBON 13; DEUTERIUM; HYDROGEN; OXYGEN DERIVATIVE; QUINONE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CORRELATION ANALYSIS; DENSITY FUNCTIONAL THEORY; ELECTRON SPIN RESONANCE; EMPIRICISM; GEOMETRY; HYDROGEN BOND; MATHEMATICAL MODEL; STRUCTURE ANALYSIS;

ALCOHOLS; ANISOTROPY; BENZOQUINONES; DEUTERIUM; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HYDROGEN BONDING; MODELS, MOLECULAR; WATER;

EID: 1642412610     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0392014     Document Type: Article

References (92)

1. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
2. Vinogradov, S. N.; Linnell, R. H. Hydrogen Bonding; Van Nostrand Reinhold Company: New York, 1971.
3. Scheiner, S. Hydrogen Bonding. A Theoretical Perspective; Oxford University Press: Oxford, U.K., 1997.
4. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, U.K., 1999.
5. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76.
6. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: New York, 1991.
7. Trumpower, B. L., Ed. Functions of Quinones in Energy Conserving Systems; Academic Press: New York, 1982.
8. Lenaz, G., Ed. Coenzyme Q. Biochemistry, Bioenergetics and Clinical Applications of Ubiquinone; John Wiley & Sons: Chichester, U.K., 1985.
9. Cramer, W. A.; Knaff, D. B. In Energy Transduction in Biological Membranes. A Textbook of Bioenergetics; Springer-Verlag: New York, 1990; pp 193-238.
10. Blankenship, R. E. Molecular Mechanisms of Photosynthesis; Blackwell Science: Cambridge, MA, 2001.
11. Klinman, J. P.; Mu, D. Annu. Rev. Biochem. 1994, 63, 299-344.
12. Weil, J. A.; Bolton, J. R.; Wertz, J. E. Electron Paramagnetic Resonance, Elementary Theory and Practical Applications; Wiley: New York, 1994.
13. Schweiger, A.; Jeschke, G. Principles of Pulse Electron Paramagnetic Resonance; Oxford University Press: Oxford, U.K., 2001.
14. O'Malley, P. J.; Chandrashekar, T. K.; Babcock, G. T. In Antennas and Reaction Centers of Photosynthetic Bacteria. Structure, Interactions, and Dynamics; Michel-Beyerle, M. E., Ed.; Springer-Verlag: Berlin, 1985; pp 339-344.
15. Feher, G.; Isaacson, R. A.; Okamura, M. Y.; Lubitz, W. In Antennas and Reaction Centers of Photosynthetic Bacteria. Structure, Interactions, and Dynamics; Michel-Beyerle, M. E., Ed.; Springer-Verlag: Berlin, 1985; pp 174-189.
16. O'Malley, P. J.; Babcock, G. T. J. Am. Chem. Soc. 1986, 108, 3995-4001.
17. MacMillan, F.; Lendzian, F.; Lubitz, W. Magn. Reson. Chem. 1995, 33, S81-S93.
18. Soda, G.; Chiba, T. J. Chem. Phys. 1969, 50, 439-455.
19. Soda, G.; Chiba, T. J. Phys. Soc. Jpn. 1969, 26, 249-261.
20. Hunt, M. J.; MacKay, A. L. J. Magn. Reson. 1974, 15, 402-414.
21. Hunt, M. J.; MacKay, A. L. J. Magn. Reson. 1976, 22, 295-301.
22. Force, D. A.; Randall, D. W.; Britt, R. D.; Tang, X. S.; Diner, B. A. J. Am. Chem. Soc. 1995, 117, 12643-12644.
23. Bennati, M.; Stubbe, J.; Griffin, R. G. Appl. Magn. Reson. 2001, 21, 389-410.
24. van Dam, P. J.; Willems, J. P.; Schmidt, P. P.; Pötsch, S.; Barra, A. L.; Hagen, W. R.; Hoffman, B. M.; Andersson, K. K.; Gräslund, A. J. Am. Chem. Soc. 1998, 120, 5080-5085.
25. Doan, P. E.; Fan, C. L.; Hoffman, B. M. J. Am. Chem. Soc. 1994, 116, 1033-1041.
26. Fan, C. L.; Kennedy, M. C.; Beinert, H.; Hoffman, B. M. J. Am. Chem. Soc. 1992, 114, 374-375.
27. Flores, M.; Abresch, E.; Lubitz, W.; Isaacson, R.; Feher, G. Biophys. J. 2002, 82, 2334.
28. Flores, M.; Isaacson, R. A.; Calvo, R.; Feher, G.; Lubitz, W. Chem. Phys. 2003, 294, 401-413.
29. Lubitz, W.; Isaacson, R.; Flores, M.; Sinnecker, S.; Lendzian, F.; Feher, G. Biophys. J. 2002, 82, 2333.
30. Gulick, W. M.; Geske, D. H. J. Am. Chem. Soc. 1966, 88, 4119-4124.
31. Burghaus, O. Ph.D. Thesis, Freie Universität Berlin, Germany, 1991.
32. Stone, E. W.; Maki, A. H. J. Am. Chem. Soc. 1965, 87, 454-458.
33. Das, M. R.; Venkataraman, B. J. Chem. Phys. 1961, 35, 2262-2263.
34. Das, M. R.; Fraenkel, G. K. J. Chem. Phys. 1965, 42, 1350-1360.
35. Strauss, H. L.; Fraenkel, G. K. J. Chem. Phys. 1961, 35, 1738-1750.
36. Hales, B. J. J. Am. Chem. Soc. 1975, 97, 5993-5997.
37. Burghaus, O.; Plato, M.; Rohrer, M.; Möbius, K.; MacMillan, F.; Lubitz, W. J. Phys. Chem. 1993, 97, 7639-7647.
38. Chipman, D. M. J. Phys. Chem. A 2000, 104, 11816-11821.
39. O'Malley, P. J. J. Phys. Chem. A 1997, 101, 6334-6338.
40. O'Malley, P. J.; Collins, S. J. Chem. Phys. Lett. 1996, 259, 296-300.
41. Knüpling, M.; Törring, J. T.; Un, S. Chem. Phys. 1997, 219, 291-304.
42. Törring, J. T.; Un, S.; Knüpling, M.; Plato, M.; Möbius, K. J. Chem. Phys. 1997, 107, 3905-3913.
43. Engström, M.; Vahtras, O.; Ågren, H. Chem. Phys. 1999, 243, 263-271.
44. Kaupp, M.; Remenyi, C.; Vaara, J.; Malkina, O. L.; Malkin, V. G. J. Am. Chem. Soc. 2002, 124, 2709-2722.
45. Neyman, K. M.; Ganyushin, D. I.; Rinkevicius, Z.; Rösch, N. Int. J. Quantum Chem. 2002, 90, 1404-1413.
46. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864.
47. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, 1133.
48. Koch, W.; Holthausen, M. C. A] Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, Germany, 2000.
49. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
51. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
52. O'Malley, P. J. Antioxid. Redox. Sign. 2001, 3, 825-838.
53. Dunning, T. H. J. Chem. Phys. 1970, 53, 2823-2833.
54. Dunning, T. H.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum: New York, 1976.
55. Barone, V. In Recent Advances in Density Functional Methods; Chong, D. P., Ed.; World Scientific Publishing Co.: Singapore, 1996.
56. 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.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; 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.; Gonzales, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzales, C.; Head-Gordon, M.; Reploge, E. S.; Pople, J. A. Gaussian 98, revision A.7, A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
57. Neese, F. ORCA, an ab initio, Density Functional and Semiempirical Program Package, Version 2.2; Max-Planck-Institut für Bioanorganische Chemie: Mülheim an der Ruhr, Germany, 2001.
58. Neese, F. J. Chem. Phys. 2001, 115, 11080-11096.
59. Koseki, S.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. 1992, 96, 10768-10772.
60. Koseki, S.; Gordon, M. S.; Schmidt, M. W.; Matsunaga, N. J. Phys. Chem. 1995, 99, 12764-12772.
61. Koseki, S.; Schmidt, M. W.; Gordon, M. S. J. Phys. Chem. A 1998, 102, 10430-10435.
62. Malkina, O. L.; Vaara, J.; Schimmelpfennig, B.; Munzarová, M.; Malkin, V. G.; Kaupp, M. J. Am. Chem. Soc. 2000, 122, 9206-9218.
63. Neese, F.; Solomon, E. I. In Magnetism: Molecules to Materials; Miller, J. S., Drillon, M., Eds.; Wiley-VCH: Weinheim, Germany, 2003; pp 345-466.
64. Weil, J. A.; Rao, P. S. Bruker EPR/ENDOR Frequency Table; Bruker: Karlsruhe, Germany, 1998.
65. Huber, H. J. Chem. Phys. 1985, 83, 4591-4598.
66. Chiba, T. J. Chem. Phys. 1964, 41, 1352-1358.
67. Sienkiewicz, A.; Smith, B. G.; Veselov, A.; Scholes, C. P. Rev. Sci. Instrum. 1996, 67, 2134-2138.
68. Muha, G. M. J. Magn. Reson. 1982, 49, 431-443.
69. Kaupp, M. Biochemistry 2002, 41, 2895-2900.
70. Nimz, O.; Lendzian, F.; Boullais, C.; Lubitz, W. Appl. Magn. Reson. 1998, 14, 255-274.
71. Teutloff, C.; Hofbauer, W.; Zech, S. G.; Stein, M.; Bittl, R.; Lubitz, W. Appl. Magn. Reson. 2001, 21, 363-379.
72. Schmidt, P. P.; Andersson, K. K.; Barra, A. L.; Thelander, L.; Gräslund, A. J. Biol. Chem. 1996, 271, 23615-23618.
73. Feher, G.; Allen, J. P.; Okamura, M. Y.; Rees, D. C. Nature 1989, 339, 111-116.
74. Lubitz, W.; Feher, G. Appl. Magn. Reson. 1999, 17, 1-48.
75. Löwdin, P.-O. Adv. Quantum Chem. 1970, 5, 185-199.
76. Mulliken, R. S. J. Chem. Phys. 1962, 36, 3428-3439.
77. Despite the rather satisfactory performance of the simple point-dipole approximation in the present case, it should be noted that the estimation of spin densities at a given nucleus from the population on the associated atom is of limited reliability. The spin population samples the whole region of space where the orbitals of the spin-carrying atom have nonzero amplitudes while the physical spin density samples a single point in space; see Neese, F. J. Phys. Chem. A 2001, 105, 4290-4299.
78. Grimaldi, S.; Ostermann, T.; Weiden, N.; Mogi, T.; Miyoshi, H.; Ludwig, B.; Michel, H.; Pfisner, T. F.; MacMillan, F. Biochemistry 2003, 42, 5632-5639.
79. Teutloff, C.; Bittl, R.; Lubitz, W. Appl. Magn. Reson. 2004, in press.
80. This effect can be traced back to a formation of H-bonds between the coordinating water molecules. It is only observed for large H-bond distances to the quinone in the model with four water molecules. The effect cannot appear in the calculations on the model systems with one or two water molecules (coordinated to different carbonyl oxygens of the quinone radical anion), where an almost perfect linear fitting was found.
81. Jordan, P.; Fromme, P.; Witt, H. T.; Klukas, O.; Saenger, W.; Krauss, N. Nature 2001, 411, 909-917.
82. Isaacson, R. A.; Lendzian, F.; Abresch, E. C.; Lubitz, W.; Feher, G. Biophys. J. 1995, 69, 311-322.
83. Bluyssen, H.; Verhoeve, J.; Dymanus, A. Phys. Lett. A 1967, A 25, 214.
84. Treacy, E. B.; Beers, Y. J. Chem. Phys. 1962, 36, 1473.
85. Thaddeus, P.; Loubser, J. H. N.; Krisher, L. C. J. Chem. Phys. 1964, 40, 257.
86. Feher, G. Appl. Magn. Reson. 1998, 15, 23-38.
87. Feher, G.; Okamura, M. Y. Appl. Magn. Reson. 1999, 16, 63-100.
88. Deligiannakis, Y.; Hanley, J.; Rutherford, A. W. J. Am. Chem. Soc. 1999, 121, 7653-7664.
89. Muhiuddin, I. P.; Rigby, S. E. J.; Evans, M. C. W.; Amesz, J.; Heathcote, P. Biochemistry 1999, 38, 7159-7167.
90. MacMillan, F.; Lendzian, F.; Renger, G.; Lubitz, W. Biochemistry 1995, 34, 8144-8156.
91. Rigby, S. E. J.; Evans, M. C. W.; Heathcote, P. Biochim. Biophys. Acta 2001, 1507, 247-259.
92. Rigby, S. E. J.; Evans, M. C. W.; Heathcote, P. Biochemistry 1996, 35, 6651-6656.