The self-assembly and spontaneous resolution of a hydrogen-bonded helix

Chemical Communications

Volumn , Issue 8, 1999, Pages 719-720

  Norsten, Tyler B ^a   McDonald, Robert ^a   Branda, Neil R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE; THIOKETONE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND;

EID: 0033590998     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808638i     Document Type: Article

References (17)

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4. For examples of supramolecular helices, see: S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 163; S. Geib, C. Vincent, E. Fan and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1993, 32, 119; S. Sun, J. F. Britten, C. N. Cow, C. F. Matta and P. H. M. Harrison, Can. J. Chem., 1998, 76, 301; A. E. Rowan and R. J. M. Nolte, Angew. Chem., Int. Ed., 1998, 37, 63.
5. For examples of supramolecular helices, see: S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 163; S. Geib, C. Vincent, E. Fan and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1993, 32, 119; S. Sun, J. F. Britten, C. N. Cow, C. F. Matta and P. H. M. Harrison, Can. J. Chem., 1998, 76, 301; A. E. Rowan and R. J. M. Nolte, Angew. Chem., Int. Ed., 1998, 37, 63.
6. For examples of supramolecular helices, see: S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 163; S. Geib, C. Vincent, E. Fan and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1993, 32, 119; S. Sun, J. F. Britten, C. N. Cow, C. F. Matta and P. H. M. Harrison, Can. J. Chem., 1998, 76, 301; A. E. Rowan and R. J. M. Nolte, Angew. Chem., Int. Ed., 1998, 37, 63.
7. For examples of supramolecular helices, see: S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 163; S. Geib, C. Vincent, E. Fan and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1993, 32, 119; S. Sun, J. F. Britten, C. N. Cow, C. F. Matta and P. H. M. Harrison, Can. J. Chem., 1998, 76, 301; A. E. Rowan and R. J. M. Nolte, Angew. Chem., Int. Ed., 1998, 37, 63.
8. For examples of supramolecular helices, see: S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630; T. Gulik-Krzywicki, C. Fouquey and J.-M. Lehn, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 163; S. Geib, C. Vincent, E. Fan and A. D. Hamilton, Angew. Chem., Int. Ed. Engl., 1993, 32, 119; S. Sun, J. F. Britten, C. N. Cow, C. F. Matta and P. H. M. Harrison, Can. J. Chem., 1998, 76, 301; A. E. Rowan and R. J. M. Nolte, Angew. Chem., Int. Ed., 1998, 37, 63.
9. H. Lumbroso, C. Liegeois, G. C. Pappalardo and C. G. Andrieu, J. Mol. Struct., 1984, 112, 85; for an example of the solid state structure of a monopyrrolyl ketone, see: W. S. Sheldrick and W. Becker, Acta Crystallogr., Sect. B, 1978, 34, 2929.
10. H. Lumbroso, C. Liegeois, G. C. Pappalardo and C. G. Andrieu, J. Mol. Struct., 1984, 112, 85; for an example of the solid state structure of a monopyrrolyl ketone, see: W. S. Sheldrick and W. Becker, Acta Crystallogr., Sect. B, 1978, 34, 2929.
11. M. Suárez, N. Branda, J.-M. Lehn, A. Decian and J. Fischer, Helv. Chim. Acta, 1998, 81,1; for a general discussion of non-chiral molecules packing into chiral crystals, see: J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolution, Wiley Interscience, New York, 1981; for other examples of hydrogen bond directed resolution in the solid state, see: H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato and M. Kiguchi, Tetrahedron Lett., 1997, 38, 5009; L. Leiserowitz and M. Weinstein, Acta Crystallogr., Sect. B, 1975, 31, 1463 and references cited therein.
12. M. Suárez, N. Branda, J.-M. Lehn, A. Decian and J. Fischer, Helv. Chim. Acta, 1998, 81,1; for a general discussion of non-chiral molecules packing into chiral crystals, see: J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolution, Wiley Interscience, New York, 1981; for other examples of hydrogen bond directed resolution in the solid state, see: H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato and M. Kiguchi, Tetrahedron Lett., 1997, 38, 5009; L. Leiserowitz and M. Weinstein, Acta Crystallogr., Sect. B, 1975, 31, 1463 and references cited therein.
13. M. Suárez, N. Branda, J.-M. Lehn, A. Decian and J. Fischer, Helv. Chim. Acta, 1998, 81,1; for a general discussion of non-chiral molecules packing into chiral crystals, see: J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolution, Wiley Interscience, New York, 1981; for other examples of hydrogen bond directed resolution in the solid state, see: H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato and M. Kiguchi, Tetrahedron Lett., 1997, 38, 5009; L. Leiserowitz and M. Weinstein, Acta Crystallogr., Sect. B, 1975, 31, 1463 and references cited therein.
14. M. Suárez, N. Branda, J.-M. Lehn, A. Decian and J. Fischer, Helv. Chim. Acta, 1998, 81,1; for a general discussion of non-chiral molecules packing into chiral crystals, see: J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolution, Wiley Interscience, New York, 1981; for other examples of hydrogen bond directed resolution in the solid state, see: H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato and M. Kiguchi, Tetrahedron Lett., 1997, 38, 5009; L. Leiserowitz and M. Weinstein, Acta Crystallogr., Sect. B, 1975, 31, 1463 and references cited therein.
15. V. R. Pedireddi, S. Chatterjee, A. Ranganathan and C. N. R. Rao, J. Am. Chem. Soc., 1997, 119, 10867; C. E. Bugg and U. Thewalt, J. Am. Chem. Soc., 1970, 92, 7441.
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17. For a similar comparison of urea and thiourea, see: D. Mullen, Acta Crystallogr., Sect. B, 1982, 38, 2620 and refs. therein.