A Complex in Which the Carbonyl Oxygen Atom of a Simple Ketone Accepts Two Intermolecular Hydrogen Bonds

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3756-3757

  Saied, Okba ^a   Simard, Michel ^a   Wuest, James D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001604466     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9719113     Document Type: Article

References (36)

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15. For discussions of the double protonation of carbonyl compounds, see: Saito, S.; Ohwada, T.; Shudo, K. J. Org. Chem. 1996, 61, 8089. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767. Gold, V.; Mah, T. J. Chem. Soc., Perkin Trans. 2 1981, 812.
16. For discussions of the double protonation of carbonyl compounds, see: Saito, S.; Ohwada, T.; Shudo, K. J. Org. Chem. 1996, 61, 8089. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767. Gold, V.; Mah, T. J. Chem. Soc., Perkin Trans. 2 1981, 812.
17. For discussions of the double protonation of carbonyl compounds, see: Saito, S.; Ohwada, T.; Shudo, K. J. Org. Chem. 1996, 61, 8089. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211. Saito, S.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 11081. Olah, G. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 767. Gold, V.; Mah, T. J. Chem. Soc., Perkin Trans. 2 1981, 812.
18. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
19. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
20. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
21. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
22. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
23. For elegant studies of double intermolecular hydrogen bonding and its consequences, see: Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. Acta Crystallogr. 1990, C46, 2136. Hine, J.; Ahn, K. J. Org. Chem. 1987, 52, 2083. Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Org. Chem. 1985, 50, 5096. Hine, J.; Linden, S.-M.; Kanagasabapathy, V. M. J. Am. Chem. Soc. 1985, 107, 1082. Hine, J.; Ahn, K.; Gallucci, J. C.; Linden, S.-M. J. Am. Chem. Soc. 1984, 106, 7980.
24. Hamada, K.; Oh-hira, M.; Fujiwara, T.; Toda, F. Acta Crystallogr. 1992, C48, 1969. Clerk, M. D.; Zaworotko, M. J. Chem. Commun. 1991, 1607. Toda, F.; Tanaka, K.; Fujiwara, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 662. Tel, R. M.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 1976, 483.
25. Hamada, K.; Oh-hira, M.; Fujiwara, T.; Toda, F. Acta Crystallogr. 1992, C48, 1969. Clerk, M. D.; Zaworotko, M. J. Chem. Commun. 1991, 1607. Toda, F.; Tanaka, K.; Fujiwara, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 662. Tel, R. M.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 1976, 483.
26. Hamada, K.; Oh-hira, M.; Fujiwara, T.; Toda, F. Acta Crystallogr. 1992, C48, 1969. Clerk, M. D.; Zaworotko, M. J. Chem. Commun. 1991, 1607. Toda, F.; Tanaka, K.; Fujiwara, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 662. Tel, R. M.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 1976, 483.
27. Hamada, K.; Oh-hira, M.; Fujiwara, T.; Toda, F. Acta Crystallogr. 1992, C48, 1969. Clerk, M. D.; Zaworotko, M. J. Chem. Commun. 1991, 1607. Toda, F.; Tanaka, K.; Fujiwara, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 662. Tel, R. M.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 1976, 483.
28. Brock, C. P.; Morelan, G. L. J. Phys. Chem. 1986, 90, 5631.
29. Saied, O.; Simard, M.; Wuest, J. D. Organometallics 1996, 15, 2345.
30. For discussions of convergent functional groups, see: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. Rebek, J., Jr.; Marshall, L.; Wolak, R.; Parris, K.; Killoran, M.; Askew, B.; Nemeth, D.; Islam, N. J. Am. Chem. Soc. 1985, 107, 7476.
31. For discussions of convergent functional groups, see: Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F.-T. J. Am. Chem. Soc. 1987, 109, 2426. Rebek, J., Jr.; Marshall, L.; Wolak, R.; Parris, K.; Killoran, M.; Askew, B.; Nemeth, D.; Islam, N. J. Am. Chem. Soc. 1985, 107, 7476.
32. Ibragimov, B. T.; Gdaniec, M.; Dadabaev, B. N. J. Inclusion Phenom. 1990, 8, 333. Ouahab, L.; Mousser, A.; Boultif, A.; Grandjean, D.; Jolibois, H. Acta Crystallogr. 1989, C45, 1397. Osborn, R. S.; Rogers, D. Acta Crystallogr. 1975, B31, 359. These three examples provide suitable models because, in all cases, a simple aliphatic ketone (acetone or cyclohexanone) accepts a single intermolecular hydrogen bond from a phenolic OH group that does not participate in any other hydrogen bonds.
33. Ibragimov, B. T.; Gdaniec, M.; Dadabaev, B. N. J. Inclusion Phenom. 1990, 8, 333. Ouahab, L.; Mousser, A.; Boultif, A.; Grandjean, D.; Jolibois, H. Acta Crystallogr. 1989, C45, 1397. Osborn, R. S.; Rogers, D. Acta Crystallogr. 1975, B31, 359. These three examples provide suitable models because, in all cases, a simple aliphatic ketone (acetone or cyclohexanone) accepts a single intermolecular hydrogen bond from a phenolic OH group that does not participate in any other hydrogen bonds.
34. Ibragimov, B. T.; Gdaniec, M.; Dadabaev, B. N. J. Inclusion Phenom. 1990, 8, 333. Ouahab, L.; Mousser, A.; Boultif, A.; Grandjean, D.; Jolibois, H. Acta Crystallogr. 1989, C45, 1397. Osborn, R. S.; Rogers, D. Acta Crystallogr. 1975, B31, 359. These three examples provide suitable models because, in all cases, a simple aliphatic ketone (acetone or cyclohexanone) accepts a single intermolecular hydrogen bond from a phenolic OH group that does not participate in any other hydrogen bonds.
35. For a discussion of the geometry of hydrogen bonds in organic crystals, see: Taylor, R.; Kennard, O. Acc. Chem. Res. 1984, 17, 320.
36. The authors have deposited X-ray crystallographic data, a description of the structure determination, and tables of atomic coordinates and isotropic thermal parameters, bond lengths and angles, anisotropic thermal parameters, and refined and calculated hydrogen atom coordinates with the Cambridge Crystallographic Data Centre. The data can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.