Cubanecarboxylic acids. Crystal engineering considerations and the role of C-H···O hydrogen bonds in determining O-H···O networks

Journal of the American Chemical Society

Volumn 121, Issue 9, 1999, Pages 1936-1944

  Kuduva, Srinivasan S ^a   Craig, Donald C ^b   Nangia, Ashwini ^a   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; CUBANE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DIMERIZATION; HYDROGEN BOND; STEREOCHEMISTRY;

EID: 0033541118     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981967u     Document Type: Article

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10. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.- C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
11. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.- C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
12. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.- C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
13. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.- C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
14. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.- C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
15. Selected examples on the use of strong and weak hydrogen bonding in crystal engineering strategies: (a) Schwiebert, K. E.; Chin, D. N.; MacDonald J. C.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 4018 (b) Lewis, F. D.; Yang, J.; Charlotte, L. S. J. Am. Chem. Soc. 1996, 118, 12029. (c) Coe, S.; Kane, J. J.; Nguyen, T. L.; Toledo, L. M.; Wininger, E.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1997, 119, 86. (d) Bhyrappa, P.; Wilson, S. R.; Suslick, K. S. J. Am. Chem. Soc. 1997, 119, 8492. (e) MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469. (f) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 499. (g) Karle, I. L.; Ranganathan, D.; Haridas, V. J. Am. Chem. Soc. 1997, 119, 2777. (h) Thalladi, V. R.; Brasselet, S.; Weiss, H.-C.; Bläser, D.; Katz, A. K.; Carrell, H. L.; Boese, R.; Zyss, J.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 2563.
16. Selected recent reviews on hydrogen bonding in crystal engineering: (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (b) Desiraju, G. R. Chem. Commun. 1997, 1475. (c) Aakeröy, C. B. Acta Crystallogr. 1997, B53, 569. (d) Hosseini, M. W.; Cian, A. D. Chem. Commun. 1998, 727. (e) Nangia, A.; Desiraju, G. R. Acta Crystallogr. 1998, A54, 934.
17. Selected recent reviews on hydrogen bonding in crystal engineering: (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (b) Desiraju, G. R. Chem. Commun. 1997, 1475. (c) Aakeröy, C. B. Acta Crystallogr. 1997, B53, 569. (d) Hosseini, M. W.; Cian, A. D. Chem. Commun. 1998, 727. (e) Nangia, A.; Desiraju, G. R. Acta Crystallogr. 1998, A54, 934.
18. Selected recent reviews on hydrogen bonding in crystal engineering: (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (b) Desiraju, G. R. Chem. Commun. 1997, 1475. (c) Aakeröy, C. B. Acta Crystallogr. 1997, B53, 569. (d) Hosseini, M. W.; Cian, A. D. Chem. Commun. 1998, 727. (e) Nangia, A.; Desiraju, G. R. Acta Crystallogr. 1998, A54, 934.
19. Selected recent reviews on hydrogen bonding in crystal engineering: (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (b) Desiraju, G. R. Chem. Commun. 1997, 1475. (c) Aakeröy, C. B. Acta Crystallogr. 1997, B53, 569. (d) Hosseini, M. W.; Cian, A. D. Chem. Commun. 1998, 727. (e) Nangia, A.; Desiraju, G. R. Acta Crystallogr. 1998, A54, 934.
20. Selected recent reviews on hydrogen bonding in crystal engineering: (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393. (b) Desiraju, G. R. Chem. Commun. 1997, 1475. (c) Aakeröy, C. B. Acta Crystallogr. 1997, B53, 569. (d) Hosseini, M. W.; Cian, A. D. Chem. Commun. 1998, 727. (e) Nangia, A.; Desiraju, G. R. Acta Crystallogr. 1998, A54, 934.
21. Selected reviews on hydrogen bonding: (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. (d) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (e) Steiner, T. Chem. Commun. 1997, 727. (f) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
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24. Selected reviews on hydrogen bonding: (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. (d) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (e) Steiner, T. Chem. Commun. 1997, 727. (f) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
25. Selected reviews on hydrogen bonding: (a) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397. (c) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383. (d) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441. (e) Steiner, T. Chem. Commun. 1997, 727. (f) Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
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71. In the type-I centrosymmetric geometry, it is possible that the inversion-related halogen atoms merely close pack rather than participate in specific polarization-driven interactions. (a) Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353. (b) Navon, O.; Bernstein, J.; Khodorkovsky, V. Angew. Chem., Int. Ed. Eng. 1997, 36, 601.
72. In the type-I centrosymmetric geometry, it is possible that the inversion-related halogen atoms merely close pack rather than participate in specific polarization-driven interactions. (a) Pedireddi, V. R.; Reddy, D. S.; Goud, B. S.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1994, 2353. (b) Navon, O.; Bernstein, J.; Khodorkovsky, V. Angew. Chem., Int. Ed. Eng. 1997, 36, 601.
73. (a) Diederich, D. A.; Paul, I. C.; Curtin, D. Y. J. Am. Chem. Soc. 1974, 96, 6372.
74. (b) Goud, B. S.; Pathaneni, S. S.; Desiraju, G. R. Acta Crystallogr. 1993, C49, 1107.
75. 2). Pairs of catemers were constructed with opposite senses, for the ordered and disordered acids. The difference in hydrogen bond energy between the two alternative catemer pair arrangements (parallel versus antiparallel) is large (∼10 kcal/mol) for the ordered acids, while it is very small for the disordered acids (<0.1 kcal/mol).
76. (a) Desiraju, G. R.; Murty, B. N.; Kishan, K. V. R. Chem. Mater. 1990, 2, 447.
77. (b) Goud, B. S.; Desiraju, G. R. Acta Crystallogr. 1993, C49, 292.
78. The packing features in acid 14 show some resemblance to those found in 1,4-dicubyl-1,3-butadiyne. Eaton, P. E.; Galoppini, E.; Gilardi, R. J. Am. Chem. Soc. 1994, 116, 7588.
79. Madhavi, N. N. L.; Katz, A. K.; Carrell, H. L.; Nangia, A.; Desiraju, G. R. Chem. Commun. 1997, 1953.
80. 2), the unobserved catemer structure was not generated for either 14 or 15. This computation provides some corroboration for the occurrence of dimer structure in 14 and 15. For details on generating structures using the Polymorph Predictor, see: (a) Leusen, F. J. J. J. Cryst. Growth 1996, 166, 900. (b) Payne, R. S., Roberts, R. J., Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1. (c) Mooij, W. T. M.; van Eijck, B. P.; Price, S. L.; Verwer, P.; Kroon, J. J. Comput. Chem. 1998, 19, 459. For an early computational study on the "nonexistence" of a proposed structure, see: Hagler, A. T.; Bernstein, J. J. Am. Chem. Soc. 1978, 100, 6349.
81. 2), the unobserved catemer structure was not generated for either 14 or 15. This computation provides some corroboration for the occurrence of dimer structure in 14 and 15. For details on generating structures using the Polymorph Predictor, see: (a) Leusen, F. J. J. J. Cryst. Growth 1996, 166, 900. (b) Payne, R. S., Roberts, R. J., Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1. (c) Mooij, W. T. M.; van Eijck, B. P.; Price, S. L.; Verwer, P.; Kroon, J. J. Comput. Chem. 1998, 19, 459. For an early computational study on the "nonexistence" of a proposed structure, see: Hagler, A. T.; Bernstein, J. J. Am. Chem. Soc. 1978, 100, 6349.
82. 2), the unobserved catemer structure was not generated for either 14 or 15. This computation provides some corroboration for the occurrence of dimer structure in 14 and 15. For details on generating structures using the Polymorph Predictor, see: (a) Leusen, F. J. J. J. Cryst. Growth 1996, 166, 900. (b) Payne, R. S., Roberts, R. J., Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1. (c) Mooij, W. T. M.; van Eijck, B. P.; Price, S. L.; Verwer, P.; Kroon, J. J. Comput. Chem. 1998, 19, 459. For an early computational study on the "nonexistence" of a proposed structure, see: Hagler, A. T.; Bernstein, J. J. Am. Chem. Soc. 1978, 100, 6349.
83. 2), the unobserved catemer structure was not generated for either 14 or 15. This computation provides some corroboration for the occurrence of dimer structure in 14 and 15. For details on generating structures using the Polymorph Predictor, see: (a) Leusen, F. J. J. J. Cryst. Growth 1996, 166, 900. (b) Payne, R. S., Roberts, R. J., Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1. (c) Mooij, W. T. M.; van Eijck, B. P.; Price, S. L.; Verwer, P.; Kroon, J. J. Comput. Chem. 1998, 19, 459. For an early computational study on the "nonexistence" of a proposed structure, see: Hagler, A. T.; Bernstein, J. J. Am. Chem. Soc. 1978, 100, 6349.
84. (a) Leiserowitz, L.; Nader, F. Acta Crystallogr. 1977, B33, 2719.
85. (b) Chang, Y.-L.; West, M.-A.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1993, 115, 5991.
86. (c) Wash, P. L.; Maverick, E.; Chiefari, J.; Lightner, D. A. J. Am. Chem. Soc. 1997, 119, 3802.
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89. For the crystal structure of N,N′-dibenzyl-1,4-cubanedicarboxamide, see ref 2b.
90. 1(7).
91. Wells, A. F. Structural Inorganic Chemistry, 4th ed.; Clarendon Press: Oxford, U.K., 1975.
92. (a) Power, K. N.; Hennigar, T. L.; Zaworotko, M. J. Chem. Commun. 1998, 595.
93. (b) Carlucci, L.; Ciano, G.; Macchi, P.; Proserpio, D. M. Chem. Commun. 1998, 1837.