The nature of solid-state N-H⋯O/O-H⋯N tautomeric competition in resonant systems. Intramolecular proton transfer in low-barrier hydrogen bonds formed by the ⋯O=C-C=N-NH⋯⇄⋯HO-C=C-N=N⋯ ketohydrazone-azoenol system. A variable-temperature x-ray crystallographic and DFT computational study

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13554-13567

  Gilli, Paola ^a   Bertolasi, Valerio ^a   Pretto, Loretta ^a   Lyčka, Antonín ^b   Gilli, Gastrone ^a  

^a UNIVERSITY OF FERRARA   (Italy)

^b Vyzkumny ustav organickych syntez as   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

TAUTOMERS;

CRYSTAL STRUCTURE; HYDROGEN BONDS; PROTONS; RESONANCE; X RAY CRYSTALLOGRAPHY;

CHEMICAL ANALYSIS;

AZOENOL; HYDRAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CORRELATION ANALYSIS; ENTHALPY; GEOMETRY; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON TRANSPORT; SOLID STATE; TEMPERATURE DEPENDENCE; X RAY CRYSTALLOGRAPHY;

EID: 0037073237     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020589x     Document Type: Article

References (111)

1. (a) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1.
2. (b) Gilli, P.; Bertolasi, V.; Forretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405.
3. (a) Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 106, 1257.
4. (b) Meot-Ner (Mautner), M. In Molecular Structure and Energetics; Liebman, J. F., Greenberg, A., Eds.; VCH: Weinheim, 1987; Vol. IV, Chapter 3.
5. (c) Zeegers-Huyskens, T. J. Mol. Struct. 1986, 135, 93.
6. (d) Zeegers-Huyskens, T.; Huyskens, P. L. In Intermolecular Forces; Huyskens, P. L., Luck, W. A., Zeegers-Huyskens, T., Eds.; Springer-Verlag: Berlin, 1991; Chapter 1.
7. (e) Zeegers-Huyskens, T. In Intermolecular Forces; Huyskens, P. L., Luck, W. A., Zeegers-Huyskens, T., Eds.; Springer-Verlag: Berlin, 1991; Chapter 6.
8. (f) Malarski, Z.; Rospenk, M.; Sobczyk, L.; Grech. E. J. Phys. Chem. 1982, 86, 401.
9. (g) Sobczyk, L. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 377.
10. (h) Pan, Y.; McAllister, M. A. J. Org. Chem. 1997, 62, 8171.
11. (a) Cleland, W. W. Biochemistry 1992, 31, 317.
12. (b) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
13. (c) Frey, P. A.; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927.
14. (d) Cleland, W. W.; Frey, P. A.; Gerlt, J. A. J. Biol. Chem. 1998, 273, 25529.
15. e) Harris, T. K.; Mildvan, A. S. Proteins 1999, 35, 275.
16. (f) Frey, P. A. Magn. Reson. Chem. 2001, 39, S190.
17. (g) Perrin, C. L.; Ohta, B. K. J, Am. Chem. Soc. 2001, 123, 6520.
18. (a) Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V. J. Am. Chem. Soc. 1989, 111, 1023.
19. (b) Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1991, 113, 4917.
20. (c) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
21. (d) Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Chem. Eur. J. 1996, 2, 925.
22. (a) Gilli, G.; Bertolasi, V.; Ferretti, V.; Gilli, P. Acta Crystallogr. 1993, B49, 564.
23. (b) Gilli, P.; Ferretti, V.; Bertolasi, V.; Gilli, G. In Advances in Molecular Structure Research: Hargittai, I., Hargittai, M., Eds.; JAI Press Inc.: Greenwich, CT, 1996; Vol. 2, p 67.
24. (c) Gilli, P.; Ferretti, V.; Gilli, G. In Fundamental Principles of Molecular Modeling: Gans. W., Amann, A., Boeyens, J. C. A., Eds.: Plenum Press: New York, 1996.
25. (a) Bertolasi, V.; Ferretti, V.; Gilli, P.; Gilli, G.; Issa, Y. M.; Sherif, O. E. J. Chem. Soc., Perkin Trans. 2 1993, 2223.
26. (b) Bertolasi, V.; Nanni, L.; Gilli, G.; Ferretti, V.; Gilli, P.; Issa, Y. M.; Sherif, O. E. New. J. Chem. 1994, 18, 251.
27. (c) Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G.; Vaughan, K. New J. Chem. 1999, 23, 1261.
28. (d) Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G. Acta Crystallogr. 1998, B54, 50.
29. (a) Krygowski, T. M.; Wozniak, K.; Anulewicz, R.; Pawlak, D.; Kolodziejski, W.; Grech, E.; Szady, A. J. Phys. Chem. A 1997, 101, 9399.
30. (b) Filarowski, A.; Koll, A.; Glowiak, T.; Majewski, E.; Dziembowska, T. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 393.
31. (c) Filarowski, A.; Glowiak, T.; Koll, A. J. Mol. Struct. 1999, 484, 75.
32. (a) Olivieri, A. C.; Wilson R. B.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1989, 111, 5525.
33. (b) Kurahashi, M. Bull. Chem. Soc. Jpn. 1976, 49, 2927.
34. (a) Lyčka, A. Dyes Pigm. 1990, 12, 179.
35. (b) Lyčka, A.; Jirman, J.; Nečas, M. Dyes Pigm. 1991, 15, 23.
36. (c) Hansen, P. E.; Bolvig, S.; Buvari-Barcza, A.; Lyčka, A. Acta Chem. Scand. 1997, 51, 881.
37. (d) Hansen, P. E.; Sitkowski, J.; Rozwadowski, Z.; Dziembowska, T. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 410.
38. (e) Benedict, C.; Langer, U.; Limbach, H.-H.; Ogata, H.; Takeda, S. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 335.
39. (f) Takeda, S.; Inabe, T.; Benedict, C.; Langer, U.; Limbach, H.-H. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 1358.
40. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J.; Watson, D. G. Acta Crystallogr. 1979, B35, 2331.
41. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
42. (b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
43. (c) Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd Ed.; Wiley-VCH: Weinheim, 2001.
44. (a) Destro, R. Chem. Phys. Lett. 1991, 118, 232.
45. (b) Poupko, R.; Luz, Z.; Destro, R. J. Phys. Chem. A 1997, 101, 5097.
46. (c) Inabe, T.; Hoshino, N.; Mitani, T.; Maruyama, Y. Bull. Chem. Soc. Jpn. 1989, 62, 2245.
47. (d) Inabe, T. New J. Chem. 1991, 15, 129.
48. (e) Inabe, T.; Luneau, I.; Mitani, T.; Maruyama, Y.; Takeda, S. Bull. Chem. Soc. Jpn. 1994, 67, 612.
49. (f) Ogawa, K.; Kasahara, Y.; Ohtani, Y.; Harada, J. J. Am. Chem. Soc. 1998, 120, 7107.
50. Johnson, C. K. ORTEPII; Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
51. Ayala P. Y.; Schlegel H. B. J. Chem. Phys. 1997, 107, 375.
52. Bader. R. F. W. Atoms in Molecules - A Quantum Theory; Oxford University Press: Oxford, 1990.
53. (a) Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
54. (b) Marcus, R. A. Discuss. Faraday Soc. 1960, 29, 21.
55. (c) Marcus, R. A. J. Phys. Chem. 1968, 72, 891.
56. (d) Murdoch, J. R. J. Am. Chem. Soc. 1972, 94, 4410.
57. (e) More O'Ferral, R. A. J. Chem. Soc. B 1970, 274.
58. (f) Grunwald, E. J. Am. Chem. Soc. 1985, 107, 125.
59. N2 Mechanism; John Wiley: New York, 1992.
60. (h) Wolfe, S.; Mitchell, D. J.; Schlegel, H. B. J. Am. Chem. Soc. 1981, 103, 7694.
61. (a) Bent, H. A. Chem. Rev. 1968, 68, 587.
62. (b) Bürgi, H.-B. Inorg. Chem. 1973, 12, 2321.
63. (c) Bürgi, H.-B.; Dunitz, J. D.; Shelter, E. J. Am. Chem. Soc. 1973, 95, 5065.
64. (d) Murray-Rust, P.; Bürgi, H.-B.; Dunitz, J. D. J. Am. Chem. Soc. 1975, 97, 921.
65. (e) Bürgi, H.-B.; Dunitz. J. D. Acc. Chem. Res. 1983, 16. 253.
66. (f) Dunitz, J. D. X-Ray Analysis and the Structure of Orgasmic Molecules; Cornell University Press: Ithaca, NY, 1979.
67. (g) Structure Correlations; Bürgi, H.-B., Dunitz, J. D., Eds.; VCH: Weinheim, 1994.
68. (h) Ferretti, V.; Gilli, P.; Bertolasi, V.; Gilli, G. Cryst. Rev. 1996, 5, 3-104.
69. (a) Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
70. (b) Pauling, L. The Nature of the Chemical Bond, 3rd Ed.; Cornell University Press: Ithaca, NY, 1960.
71. (c) Bürgi, H.-B.; Dunitz, J. D. J. Am. Chem. Soc. 1987, 109, 2924.
72. i/5] - 1 when the ketohydrazone is fused with an aromatic ring (VI and VII).
73. -1 for test molecules 1-5, respectively, and apparently they are continuously decreasing while the thermodynamic stability of the corresponding O-H⋯N bonds is increasing (Figure 5).
74. a matching. It concerns concems the intermolecular acid-base complex between pentachlorophenol and 4-methylpyridine for which a nearly symmetric bond with d(N⋯O) = 2.513(3) Å was measured by neutron diffraction at 100 K by (a) Steiner, Th.; Majers, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651. (b) Steiner, Th. J. Phys. Chem. 1998, 102, 7041.
75. a matching. It concerns concems the intermolecular acid-base complex between pentachlorophenol and 4-methylpyridine for which a nearly symmetric bond with d(N⋯O) = 2.513(3) Å was measured by neutron diffraction at 100 K by (a) Steiner, Th.; Majers, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651. (b) Steiner, Th. J. Phys. Chem. 1998, 102, 7041.
76. a matching. It concerns concems the intermolecular acid-base complex between pentachlorophenol and 4-methylpyridine for which a nearly symmetric bond with d(N⋯O) = 2.513(3) Å was measured by neutron diffraction at 100 K by (a) Steiner, Th.; Majers, I.; Wilson, C. C. Angew. Chem., Int. Ed. 2001, 40, 2651. (b) Steiner, Th. J. Phys. Chem. 1998, 102, 7041.
77. ± = 0.06. Application of this simple method to all stationary-point geometries of Table 3 leads to the final results summarized in Table 4.
78. (a) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 239.
79. (b) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 245.
80. (c) Pimentel, G. C. J. Chem. Phys. 1951, 19, 446.
81. (d) Reid, C. J. Chem. Phys. 1959, 30, 182.
82. (e) Kollman, P. A.; Allen, L. C. J. Am. Chem. Soc. 1970, 92, 6101.
83. (f) Stevens, E. D.; Lehmann, M. S.; Coppens, P. J. Am. Chem. Soc. 1977, 99, 2829.
84. (g) Desmeules, P. J.; Allen, L. C. J. Chem. Phys. 1980, 72, 4731.
85. (a) Flensburg, C.; Larsen, S.; Stewart, R. F. J. Phys. Chem. 1995, 99, 10130.
86. (b) Madsen, D.; Flensburg, C.; Larsen, S. J. Phys. Chem. A 1998, 102, 2177.
87. (c) Mallinson, P. R.; Wozniak, K.; Smith, G. T.; McCormack, K. L. J. Am. Chem. Soc. 1997, 119, 11502.
88. (d) Madsen, G. K. H.; Iversen, B. B.; Larsen, F. K.; Kapon, M.; Reisner, G. M.; Herbstein, F. H. J. Am. Chem. Soc. 1998, 120, 10040.
89. (e) Schiott, B.; Iversen, B. B.; Madsen, G. H. K.; Bruice, T. C. J. Am. Chem. Soc. 1998, 120, 12117.
90. (f) Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101, 1583.
91. (a) Page 292 of ref 15.
92. (b) The present classification of strong H-bonds essentially agree with that recently proposed by P. A. Frey (ref 3f).
93. (a) Otwinowski, Z.; Minor, W. In Methods Enzymol.: Carter, C. W., Jr., Sweets, R. M., Eds.; Macromolecular Crystallography, Vol. 276, Part A; Academic Press: San Diego, CA, 1997: p 307.
94. (b) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
95. (c) Sheldrick, G. M. SHELXL97, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1997.
96. (a) Frisch, M. J.; Scheiner, A. C.; Schaefer, H. F., III; Binkley, J. S. J. Chem. Phys. 1985, 82, 4194.
97. (b) Dannenberg, J. J. Rios, R. J. Phys. Chem. 1994. 98, 6714.
98. (c) Barone, V.; Adamo, C. J. Chem. Phys. 1996, 105, 11007.
99. (d) Buemi, G.; Zuccarello, F. J. Chem. Soc., Faraday Trans. 1996, 92, 347.
100. (e) Buemi, G.; Zuccarello, F. Electron. J. Theor. Chem. 1997, 2, 302.
101. (f) Chung, G.; Kwon, O.; Kwon, Y. J. Phys Chem. A 1997, 101, 4628.
102. (g) Kobko. N.; Paraskevas, L.; del Rio, E.; Dannenberg, J. J. J. Am. Chem. Soc. 2001, 123, 4348.
103. (a) Here, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986: see also references therein.
104. (b) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
105. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
106. (d) Lee, C.; Yang, Y.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
107. (a) Pan, Y.; McAllister, M. A. J. Mol. Struct. (THEOCHEM) 1998, 427, 221.
108. (b) McAllister, M. A. J. Mol. Struct. (THEOCHEM) 1998, 427, 39.
109. (c) Smallwood, C. J.; McAllister, M. A. Can. J. Chem. 1997, 75, 1195.
110. (a) 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.; 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.; Gonzalez, C.; 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.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
111. (b) Stefanov, B. B.; Cioslowski, J. Mol. Phys. 1995, 84, 707.