메뉴 건너뛰기




Volumn , Issue 9, 1999, Pages 2397-2403

Highly stable self-association of 5-(guanidiniocarbonyl)-1H-pyrrole- 2carboxylate in DMSO - The importance of electrostatic interactions

Author keywords

Guanidinium cations; Molecular recognition; Self assembly; Supramolecular chemistry

Indexed keywords

5 (GUANIDINIOCARBONYL) 1H PYRROLE 2 CARBOXYLIC ACID; AMPHOLYTE; DIMER; DIMETHYL SULFOXIDE; UNCLASSIFIED DRUG;

EID: 0032853750     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2397::aid-ejoc2397>3.0.co;2-3     Document Type: Article
Times cited : (77)

References (73)
  • 1
    • 0000633029 scopus 로고    scopus 로고
    • Recent key reviews: [1a] D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
    • (1996) Angew. Chem. , vol.108 , pp. 1242-1286
    • Philp, D.1    Stoddart, J.F.2
  • 2
    • 0029811409 scopus 로고    scopus 로고
    • Recent key reviews: [1a] D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1154-1196
  • 5
    • 0000731210 scopus 로고
    • For the tobacco virus, see: [2a] A. Klug, Angew. Chem. 1983, 95, 579-596; Angew. Chem. Int. Ed. Engl. 1983, 22, 565-582.
    • (1983) Angew. Chem. , vol.95 , pp. 579-596
    • Klug, A.1
  • 6
    • 84985631191 scopus 로고
    • For the tobacco virus, see: [2a] A. Klug, Angew. Chem. 1983, 95, 579-596; Angew. Chem. Int. Ed. Engl. 1983, 22, 565-582.
    • (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 565-582
  • 10
    • 0032342244 scopus 로고    scopus 로고
    • For recent review articles on metal-templated self-assembly, see: [4a] M. Fujita, Chem. Soc. Rev. 1998, 27, 417-426.
    • (1998) Chem. Soc. Rev. , vol.27 , pp. 417-426
    • Fujita, M.1
  • 16
    • 0031021123 scopus 로고    scopus 로고
    • For a sampling of hydrogen-bonded self-assembled structures: [6a] J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
    • (1997) Nature , vol.385 , pp. 50-52
    • Kang, J.1    Rebek J., Jr.2
  • 19
    • 4243322506 scopus 로고    scopus 로고
    • [6d] For a comprehensive review article, see: M. M. Conn. J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668.
    • (1997) Chem. Rev. , vol.97 , pp. 1647-1668
    • Conn, M.M.1    Rebek J., Jr.2
  • 23
    • 0000565497 scopus 로고    scopus 로고
    • For a ditopic sulfate receptor, it has recently been shown that in methanol entropie and not enthalpic effects are responsible for the binding. Due to the strong solvation of host and guest molecules in this solvent, the complexation is endothermic but entropically favored because of the release of solvent molecules: M. Berger, F. P. Schmidtchen, Angew. Chem. 1998, 110, 2840-2842; Angew. Chem. Int. Ed. Engl. 1998, 37, 2694-2696.
    • (1998) Angew. Chem. , vol.110 , pp. 2840-2842
    • Berger, M.1    Schmidtchen, F.P.2
  • 24
    • 0032538365 scopus 로고    scopus 로고
    • For a ditopic sulfate receptor, it has recently been shown that in methanol entropie and not enthalpic effects are responsible for the binding. Due to the strong solvation of host and guest molecules in this solvent, the complexation is endothermic but entropically favored because of the release of solvent molecules: M. Berger, F. P. Schmidtchen, Angew. Chem. 1998, 110, 2840-2842; Angew. Chem. Int. Ed. Engl. 1998, 37, 2694-2696.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 2694-2696
  • 25
    • 0000570064 scopus 로고    scopus 로고
    • A new example of solid-state hydrogen-bonded structures based on pyrrole-2,5-dicarboxylic acids can be found in: Q. Lin, S. J. Geib, A. D. Hamilton, J. Chem. Soc., Perkin Trans. 2 1998, 2109-2116; see also references therein.
    • (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 2109-2116
    • Lin, Q.1    Geib, S.J.2    Hamilton, A.D.3
  • 26
    • 0001537306 scopus 로고    scopus 로고
    • 3 has recently been reported by: J. L. Sessler, R. Wang, Angew. Chem. 1998, 110, 1818-1821; Angew. Chem. Int. Ed. Engl. 1998, 37, 1726-1729.
    • (1998) Angew. Chem. , vol.110 , pp. 1818-1821
    • Sessler, J.L.1    Wang, R.2
  • 27
    • 0032479404 scopus 로고    scopus 로고
    • 3 has recently been reported by: J. L. Sessler, R. Wang, Angew. Chem. 1998, 110, 1818-1821; Angew. Chem. Int. Ed. Engl. 1998, 37, 1726-1729.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1726-1729
  • 28
    • 0032483698 scopus 로고    scopus 로고
    • Some general examples, but not self-assembling structures, of artificial receptors that function in more polar solvents, can be found in: [11a] A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11208-11209.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11208-11209
    • Hossain, A.1    Schneider, H.-J.2
  • 41
    • 33748225866 scopus 로고
    • [12d] M. W. Göbel, J. W. Bats, G. Dürner, Angew. Chem. 1992, 104, 217-218; Angew. Chem. Int. Ed. Engl. 1992, 31, 207-208.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 207-208
  • 42
    • 0031192717 scopus 로고    scopus 로고
    • Recent review articles on the binding of carboxylates by artificial receptors including guanidinium-based systems: [13a] F. P. Schmidtchen, M. Berger, Chem. Rev. 1997, 97, 1609-1646.
    • (1997) Chem. Rev. , vol.97 , pp. 1609-1646
    • Schmidtchen, F.P.1    Berger, M.2
  • 50
    • 84961985321 scopus 로고    scopus 로고
    • For a representative theoretical study, see: Y-J. Zheng, R. L. Ornstein, J. Am. Chem. Soc. 1996, 118, 11237-11243; for an experimental study, see B. Dietrich, D. L. Fyles, T. M. Fyles, J.-M. Lehn, Helv. Chim. Acta 1979, 62, 2763-2787.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11237-11243
    • Zheng, Y.-J.1    Ornstein, R.L.2
  • 51
    • 21244468517 scopus 로고
    • For a representative theoretical study, see: Y-J. Zheng, R. L. Ornstein, J. Am. Chem. Soc. 1996, 118, 11237-11243; for an experimental study, see B. Dietrich, D. L. Fyles, T. M. Fyles, J.-M. Lehn, Helv. Chim. Acta 1979, 62, 2763-2787.
    • (1979) Helv. Chim. Acta , vol.62 , pp. 2763-2787
    • Dietrich, B.1    Fyles, D.L.2    Fyles, T.M.3    Lehn, J.-M.4
  • 52
    • 0002112707 scopus 로고    scopus 로고
    • Thermodynamics of anion complexation
    • (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, New York
    • A. Bianchi, E. García-España, Thermodynamics of Anion Complexation, in Supramolecular Chemistry of Anions (Eds.: A. Bianchi, K. Bowman-James, E. García-España), Wiley-VCH, New York, 1997, p. 217-276.
    • (1997) Supramolecular Chemistry of Anions , pp. 217-276
    • Bianchi, A.1    García-España, E.2
  • 54
    • 0000343019 scopus 로고
    • A similar zwitterion, forming much less stable dimers, has been used to realize a self-replicating system: A. Terfort, G. v. Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl.1992, 31, 654-656.
    • (1992) Angew. Chem. , vol.104 , pp. 626-628
    • Terfort, A.1    Kiedrowski, G.V.2
  • 55
    • 33748242422 scopus 로고
    • A similar zwitterion, forming much less stable dimers, has been used to realize a self-replicating system: A. Terfort, G. v. Kiedrowski, Angew. Chem. 1992, 104, 626-628; Angew. Chem. Int. Ed. Engl.1992, 31, 654-656.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 654-656
  • 57
    • 0032479772 scopus 로고    scopus 로고
    • For the self-organization of other heteroditopic molecules into oligomers rather than discrete dimers in non-polar solvents, see e.g.: [19a] P. R. Ashton, I. W. Parson, F. M. Raymo, J. F. Stoddart, A. J. P. White, D. J. Williams, R. Wolf, Angew. Chem. 1998, 110, 2016-2019; Angew. Chem. Int. Ed. Engl. 1998, 37, 1913-1916.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1913-1916
  • 59
    • 0032544461 scopus 로고    scopus 로고
    • [19b] N. Yamaguchi, D. S. Nagvekar, H. W. Gibson, Angew. Chem. 1998, 110, 2518-2520; Angew. Chem. Int. Ed. Engl. 1998, 37, 2361-2364.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 2361-2364
  • 64
    • 0344066037 scopus 로고
    • Other methods for guanidinylation can be found in: [24a] R. N. Prasad, A. F. McKay, Can. J. Chem. 1967, 45, 2247-2252.
    • (1967) Can. J. Chem. , vol.45 , pp. 2247-2252
    • Prasad, R.N.1    McKay, A.F.2
  • 72
    • 0345359653 scopus 로고    scopus 로고
    • note
    • The formation of higher aggregates can not be completely ruled out at this point. Though it seems rather unlikely that under the high-dilution conditions used in these studies oligomers of type B are formed, they could form at higher concentrations and be responsible for the low solubility of the zwitterion.
  • 73
    • 0344066033 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure of 1·HCl have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-111759. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.