Controlled incorporation of water molecules into carboxy hydrogen-bond networks: A designed approach

Organic Letters

Volumn 5, Issue 5, 2003, Pages 641-644

  Pérez, Cirilo ^a   Rodríguez, Matías L ^a   Foces Foces, Concepción ^b   Pérez Hernández, Natalia ^c   Pérez, Ricardo ^c   Martín, Julio D ^c  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^c INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBROMAL; CYCLOPROPANE DERIVATIVE; DIMER; FUNCTIONAL GROUP; HYDROGEN; ORGANIC COMPOUND; WATER;

ARTICLE; CRYSTAL STRUCTURE; ENTROPY; HYDRATION; HYDROGEN BOND; HYDROPHOBICITY; MOLECULE; POLYMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0141629863     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027332o     Document Type: Article

References (21)

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6. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
7. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
8. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
9. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
10. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
11. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
12. For some representative examples, see: (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747-3754. (b) Zhao, X.; Chang, Y.; Fowler, F. W.; Lauher, J. W. J. Am. Chem. Soc. 1990, 112, 6627-6634. (c) Asthon, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 735-739. (d) Holy, P.; Zavada, J.; Cisarova, I.; Podlaha, J. Angew. Chem., Int. Ed. 1999, 38, 381-383. (e) Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441-3461. (f) Kobayashi, K.; Shikahara, T.; Horn, E.; Furukawa, N. Tetrahedron Lett. 2000, 41, 89-93. (g) Jetti, R. K. R.; Xue, F.; Mak, T. C. N.; Nangia, A. J. Chem. Soc., Perkin Trans. 2 2000, 1223-1232. (h) Thalladi, V. R.; Nüsse, M.; Boese, R. J. Am. Chem. Soc. 2000, 122, 9227-9236.
13. (a) ten Wolde, P. R.; Frenkel, D. Science 1997, 277, 1975-1978.
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16. (d) Lee, W. T.; Salje, E. K. H.; Dove, M. T. J. Phys.: Condens. Matter 1999, 11, 7385-7410.
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18. Because in a cyclic carboxylic acid dimer there is repulsion and destabilization from short O⋯H and H⋯H contact across the ring, increasing the ring size by incorporation of ordered water molecules maintaining the centrosymmetry of the H-bonding pattern will be a stabilizing factor in that structure.
19. Since in Scheme 1 we have considered the more favorable head-to-head/tail-to-tail arrangement, water can only be ordered with the participation of the oxolane oxygen in the head-to-head carboxy acid pattern. However, the head-to-tail arrangement cannot be excluded. In this latter case, hydration should occur by distribution of water molecules among both (head-to-tail and tail-to-head) carboxy dimer patterns.
20. Crystals of all compounds were grown under identical conditions using a previously water-saturated mixture of carbon tetrachloride/n-hexane as a solvent.
21. Another significant effect of carboxy group twisting that we ought to consider is that, since the two alternating carboxy dimers along the chain are in almost perpendicular planes, ordering water molecules along both dimers extends the H-bonding in two further directions, giving a three-dimensional array.