Variable temperature neutron diffraction analysis of a very short O-H;⋯O hydrogen bond in 2,3,5,6-pyrazinetetracarboxylic acid dihydrate: Synthon-assisted short Oacid-H⋯Owater hydrogen bonds in a multicenter array

Journal of Physical Chemistry A

Volumn 108, Issue 43, 2004, Pages 9406-9416

  Vishweshwar, Peddy ^a   Babu, N Jagadeesh ^a   Nangia, Ashwini ^a   Mason, Sax A ^b   Puschmann, Horst ^c   Mondal, Raju ^c   Howard, Judith A K ^c  

^a UNIVERSITY OF HYDERABAD   (India)

^b INSTITUT LAUE LANGEVIN   (France)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CRYSTAL STRUCTURE; DATABASE SYSTEMS; NEUTRON DIFFRACTION; PROTONS; WATER;

MULTICENTER ARRAY; PROTON MIGRATION; TAUTOMERS; X-RAY CRYSTAL STRUCTURE;

HYDROGEN BONDS;

EID: 8344270863     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0476848     Document Type: Article

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6. Reviews: (a) Speakman, J. C. Struct. Bonding 1972, 12, 141. (b) Huggins, M. L. Angew. Chem., Int. Ed. Engl. 1971, 10, 147. Emsley, J. Chem. Soc. Rev. 1980, 9, 91. Jeffrey, G. A. Cryst. Rev. 1995, 4, 213. (d) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
7. Reviews: (a) Speakman, J. C. Struct. Bonding 1972, 12, 141. (b) Huggins, M. L. Angew. Chem., Int. Ed. Engl. 1971, 10, 147. Emsley, J. Chem. Soc. Rev. 1980, 9, 91. Jeffrey, G. A. Cryst. Rev. 1995, 4, 213. (d) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
8. Reviews: (a) Speakman, J. C. Struct. Bonding 1972, 12, 141. (b) Huggins, M. L. Angew. Chem., Int. Ed. Engl. 1971, 10, 147. Emsley, J. Chem. Soc. Rev. 1980, 9, 91. Jeffrey, G. A. Cryst. Rev. 1995, 4, 213. (d) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
9. Reviews: (a) Speakman, J. C. Struct. Bonding 1972, 12, 141. (b) Huggins, M. L. Angew. Chem., Int. Ed. Engl. 1971, 10, 147. Emsley, J. Chem. Soc. Rev. 1980, 9, 91. Jeffrey, G. A. Cryst. Rev. 1995, 4, 213. (d) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
10. Reviews: (a) Speakman, J. C. Struct. Bonding 1972, 12, 141. (b) Huggins, M. L. Angew. Chem., Int. Ed. Engl. 1971, 10, 147. Emsley, J. Chem. Soc. Rev. 1980, 9, 91. Jeffrey, G. A. Cryst. Rev. 1995, 4, 213. (d) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1. (e) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
11. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
12. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
13. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
14. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
15. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
16. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
17. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
18. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
19. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
20. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
21. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
22. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
23. (6) Some selected recent papers: (a) Kuppers, H.; Takusagawa, F.; Koetzle, T. F. J. Chem. Phys. 1985, 82, 56360. (b) Madsen, G. K. H.; Wilson, C.; Nymand, C. T. M.; McIntyre, G. J.; Larsen, F. K. J. Phys. Chem. A 1999, 103, 8684. Steiner, T. Chem. Commun. 1999, 2299. Davidson, M. G.; Goeta, A. E.; Howard, J. A. K.; Lamb, V.; Mason, S. A. New J. Chem. 2000, 24, 477. (e) Macchi, P.; Iversen, B. B.; Sironi, A.; Chakoumakos, B. C.; Larsen, F. K. Angew. Chem., Int. Ed. 2000, 39, 2719. (f) Remer, L. C.; Jenses, J. H. J. Phys. Chem. A 2000, 104, 9266. (g) Steiner, T.; Schreurs, A. M. M.; Lutz, M.; Kroon, J. New J. Chem. 2001, 25, 174. (h) Olovsson, I.; Ptasiewiczbak, H.; Gustafsson, T.; Majerz, I. Acta Crystallogr. 2001, B57, 311. Rodrigues, B. L.; Tellgren, R.; Fernandes, N. G. Acta Crystallogr. 2001, B57, 353. (j) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4353. (k) Kumarswamy, K. C.; Kumarswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642. Wilson, C. C. New J. Chem. 2002, 26, 1733. Janiak, C.; Scharmann, T. G.; Mason, S. A. J. Am. Chem. Soc. 2002, 124, 14010.
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84. Details of neutron diffraction and X-ray diffraction experiments are given in the Supporting Information.
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91. 14c,21
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104. A useful concept in crystal engineering is the idea of networks, that is, to dissect a crystal structure in terms of nodes (molecules) and node connectors (hydrogen bonds). Pyrazine tetracarboxylic acid serves as a four-connected node to self-assemble square hydrogen-bond networks. Unpublished results. Recent reviews on networks: (a) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101, 1629. (b) Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460.
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109. X-ray diffraction: (a) Stevens, E. D.; Coppens, P. Acta Crystallogr. 1980, B36, 1864. (b) Wang, Y.; Tsai, C. J.; Liu, W. L.; Calvert, L. D. Acta Crystallogr. 1985, B41, 131. Zobel D.; Luger, P.; Dreissing, W.; Koritsanszky, T. Acta Crystallogr. 1992, B48, 837. Martin, A.; Pinkerton, A. A. Acta Crystallogr. 1998, B54, 471. Neutron diffraction: (e) Lehmann, A.; Luger, P.; Lehmann, C. W.; Ibberson, R. M. Acta Crystallogr. 1994, B50, 344.
110. X-ray diffraction: (a) Stevens, E. D.; Coppens, P. Acta Crystallogr. 1980, B36, 1864. (b) Wang, Y.; Tsai, C. J.; Liu, W. L.; Calvert, L. D. Acta Crystallogr. 1985, B41, 131. Zobel D.; Luger, P.; Dreissing, W.; Koritsanszky, T. Acta Crystallogr. 1992, B48, 837. Martin, A.; Pinkerton, A. A. Acta Crystallogr. 1998, B54, 471. Neutron diffraction: (e) Lehmann, A.; Luger, P.; Lehmann, C. W.; Ibberson, R. M. Acta Crystallogr. 1994, B50, 344.
111. X-ray diffraction: (a) Stevens, E. D.; Coppens, P. Acta Crystallogr. 1980, B36, 1864. (b) Wang, Y.; Tsai, C. J.; Liu, W. L.; Calvert, L. D. Acta Crystallogr. 1985, B41, 131. Zobel D.; Luger, P.; Dreissing, W.; Koritsanszky, T. Acta Crystallogr. 1992, B48, 837. Martin, A.; Pinkerton, A. A. Acta Crystallogr. 1998, B54, 471. Neutron diffraction: (e) Lehmann, A.; Luger, P.; Lehmann, C. W.; Ibberson, R. M. Acta Crystallogr. 1994, B50, 344.
112. X-ray diffraction: (a) Stevens, E. D.; Coppens, P. Acta Crystallogr. 1980, B36, 1864. (b) Wang, Y.; Tsai, C. J.; Liu, W. L.; Calvert, L. D. Acta Crystallogr. 1985, B41, 131. Zobel D.; Luger, P.; Dreissing, W.; Koritsanszky, T. Acta Crystallogr. 1992, B48, 837. Martin, A.; Pinkerton, A. A. Acta Crystallogr. 1998, B54, 471. Neutron diffraction: (e) Lehmann, A.; Luger, P.; Lehmann, C. W.; Ibberson, R. M. Acta Crystallogr. 1994, B50, 344.
113. See ref 2 (p 99) and ref 19c for π-bond cooperative H-bond shortening in carboxylic acids and amides.
114. We have plotted r and d distances in 1 to compare their scatter plot with the CAHB/RAHB data, in Figure 5 of ref 18c. The scatter of points in 1 along the solid curve is comparable to conventional short H-bonds.
115. Angyán, J. G.; Loos, M.; Mayer, I. J. Phys. Chem. 1994, 98, 5244. We thank one of the referees for bringing this method to our attention.
116. -1 (O⋯O = 2.70 and 2.80 Å).
117. HB is approximate. We mention these values to show that the numbers for tetraacid 1 are similar to strong RAHB systems.