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Volumn 51, Issue 11, 1996, Pages 1649-1654

Structural Assembly of Rigid Hydroxycarboxylic Acid Frameworks - Solid State Structures of Two Substituted 6-Hydroxy-trans-3-hexenoic Acids

Author keywords

Crystal Engineering; Hydrogen Bonding; Staple Structures; Structural Networks; Template Synthesis

Indexed keywords

CHEMISTRY; CRYSTAL ENGINEERING;

EID: 0347245267     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-1996-1120     Document Type: Article
Times cited : (5)

References (41)
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    • J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 107, 1689 (1995); Angew. Chem., Int. Ed. Engl. 34, 1545 (1995); G. R. Desiraju, Angew. Chem. 107, 2541 (1995); Angew. Chem., Int. Ed. Engl. 34, 2328 (1995).
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    • H. Nakamura, Y. Matsui, J. Am. Chem. Soc. 117, 2651 (1995). For general information about catalyzed sol-gel-processes see e.g.: D. Avnir, Acc. Chem. Res. 28, 328 (1995); C. J. Brinker, G. W. Scherer, "Sol-Gel-Science", Academic Press, New York (1990); H. Reuter, M. T. Brandherm, Angew. Chem. 117, 1712 (1995); Angew. Chem., Int. Ed. Engl. 34, 1578 (1995) and references cited therein.
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    • H. Nakamura, Y. Matsui, J. Am. Chem. Soc. 117, 2651 (1995). For general information about catalyzed sol-gel-processes see e.g.: D. Avnir, Acc. Chem. Res. 28, 328 (1995); C. J. Brinker, G. W. Scherer, "Sol-Gel-Science", Academic Press, New York (1990); H. Reuter, M. T. Brandherm, Angew. Chem. 117, 1712 (1995); Angew. Chem., Int. Ed. Engl. 34, 1578 (1995) and references cited therein.
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    • 0029639168 scopus 로고
    • H. Nakamura, Y. Matsui, J. Am. Chem. Soc. 117, 2651 (1995). For general information about catalyzed sol-gel-processes see e.g.: D. Avnir, Acc. Chem. Res. 28, 328 (1995); C. J. Brinker, G. W. Scherer, "Sol-Gel-Science", Academic Press, New York (1990); H. Reuter, M. T. Brandherm, Angew. Chem. 117, 1712 (1995); Angew. Chem., Int. Ed. Engl. 34, 1578 (1995) and references cited therein.
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    • Reuter, H.1    Brandherm, M.T.2
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    • 33745337483 scopus 로고
    • and references cited therein
    • H. Nakamura, Y. Matsui, J. Am. Chem. Soc. 117, 2651 (1995). For general information about catalyzed sol-gel-processes see e.g.: D. Avnir, Acc. Chem. Res. 28, 328 (1995); C. J. Brinker, G. W. Scherer, "Sol-Gel-Science", Academic Press, New York (1990); H. Reuter, M. T. Brandherm, Angew. Chem. 117, 1712 (1995); Angew. Chem., Int. Ed. Engl. 34, 1578 (1995) and references cited therein.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 1578
  • 13
    • 0000393544 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
    • (1965) Acta Crystallogr. , vol.18 , pp. 1053
    • Sundaralingam, M.1    Jensen, L.H.2
  • 14
    • 0000393544 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
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    • Van Eijck, B.P.1    Kanters, J.A.2    Kroon, J.3
  • 15
    • 0000393544 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
    • (1966) Acta Crystallogr. , vol.21 , pp. 237
    • Okaya, Y.1    Stemple, N.R.2    Kay, M.I.3
  • 16
    • 0014677813 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
    • (1969) Acta Crystallogr. Sect. b , vol.25 , pp. 1066
    • Glusker, J.P.1    Minkin, J.A.2    Patterson, A.L.3
  • 17
    • 0000393544 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
    • (1971) Acta Crystallogr. Sect. b , vol.27 , pp. 333
    • Ellison, R.D.1    Johnson, C.K.2    Levy, H.A.3
  • 18
    • 0000970872 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2778
    • Huang, C.-Y.1    Cabell, L.A.2    Anslyn, E.V.3
  • 19
    • 0342876316 scopus 로고
    • For other hydroxycarboxylic acid structures see e.g. M. Sundaralingam, L. H. Jensen, Acta Crystallogr. 18, 1053(1965); B. P. van Eijck, J. A. Kanters, J. Kroon, Acta Crystallogr. 19, 435 (1965); Y. Okaya, N. R. Stemple, M. I. Kay, Acta Crystallogr. 21, 237 (1966); J. P. Glusker, J. A. Minkin, A. L. Patterson, Acta Crystallogr. Sect. B 25, 1066 (1969); R. D. Ellison, C. K. Johnson, H. A. Levy, Acta Crystallogr. Sect. B 27, 333 (1971); C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 116, 2778 (1994); L. Turi, J. J. Dannenberg, J. Am. Chem. Soc. 116, 8714 (1994).
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    • Turi, L.1    Dannenberg, J.J.2
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
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    • Sharma, C.V.K.1    Panneerselvam, K.2    Pilati, T.3    Desiraju, G.R.4
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12055
    • Golubev, N.S.1    Smirnow, S.2    Gindin, V.A.3    Denisov, G.S.4    Benedict, H.5    Limbach, H.-H.6
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
    • (1994) Chem. Ber. , vol.127 , pp. 743
    • Güther, R.1    Nieger, M.2    Rissanen, K.3    Vögtle, F.4
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
    • (1995) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2213
    • Caira, M.R.1    Nassimbeni, L.S.2    Wildervanck, A.F.3
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
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    • For selected recent examples see e.g.: C. V. K. Sharma, K. Panneerselvam, T. Pilati, G. R. Desiraju, J. Chem. Soc., Perkin Trans 2, 2209 (1993); N. S. Golubev, S. Smirnow, V. A. Gindin, G. S. Denisov, H. Benedict, H.-H. Limbach, J. Am. Chem. Soc. 116, 12055 (1994); R. Güther, M. Nieger, K. Rissanen, F. Vögtle, Chem. Ber. 127, 743 (1994); M. R. Caira, L. S. Nassimbeni, A. F. Wildervanck, J. Chem. Soc., Perkin Trans. 2, 2213 (1995); Y. Kim, J. Am. Chem. Soc 118, 1522 (1996). See also: O. Ermer, J. Lex, Angew. Chem. 99, 455 (1987), Angew. Chem., Int. Ed. Engl. 26, 446 (1987).
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    • S. P. Weinbach, D. Jaquemain, F. Leveiller, K. Kjaer, J. Als-Nielsen, L. Leiserowitz, J. Am. Chem. Soc. 115, 11110 (1993); S. Kolotuchin, E. E. Fenlon, S. R. Wilson, C. J. Loweth, S. C. Zimmermann, Angew. Chem. 107, 2873 (1995); Angew. Chem., Int. Ed. Engl. 34, 2873 (1995); K. Kinbara, Y. Hashimoto, M. Sukegawa, H. Nohira, K. Saigo, J. Am. Chem. Soc. 118, 3441 (1996), and references cited in these articles.
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    • S. P. Weinbach, D. Jaquemain, F. Leveiller, K. Kjaer, J. Als-Nielsen, L. Leiserowitz, J. Am. Chem. Soc. 115, 11110 (1993); S. Kolotuchin, E. E. Fenlon, S. R. Wilson, C. J. Loweth, S. C. Zimmermann, Angew. Chem. 107, 2873 (1995); Angew. Chem., Int. Ed. Engl. 34, 2873 (1995); K. Kinbara, Y. Hashimoto, M. Sukegawa, H. Nohira, K. Saigo, J. Am. Chem. Soc. 118, 3441 (1996), and references cited in these articles.
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    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3441
    • Kinbara, K.1    Hashimoto, Y.2    Sukegawa, M.3    Nohira, H.4    Saigo, K.5


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