메뉴 건너뛰기




Volumn , Issue 8, 2001, Pages 1519-1523

C-H⋯O interactions as isofunctional replacements for N-H⋯O interactions - Dimer formation of methyl 5-amidopyrrole-2-carboxylates in the solid state

Author keywords

Hydrogen bonds; Molecular recognition; Nitrogen heterocycles; Self assembly; Supramolecular chemistry

Indexed keywords

5 (GUANIDINIOCARBONYL)PYRROLE 2 CARBOXYLIC ACID; 5 AMIDOPYRIDINIUMPYRROLE 2 CARBOXYLATE; CARBON; CARBON MONOXIDE; CARBOXYLIC ACID DERIVATIVE; DIMER; HYDROGEN; METHYL 5 AMIDOPYRROLE 2 CARBOXYLATE DERIVATIVE; NITROGEN; OXYGEN; PYRIDINIUM DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0035049099     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200104)2001:8<1519::AID-EJOC1519>3.0.CO;2-2     Document Type: Article
Times cited : (36)

References (31)
  • 5
    • 0002285424 scopus 로고    scopus 로고
    • Design of Organic Solids
    • E. Weber, Ed. Design of Organic Solids, Top. Curr. Chem. 1998, 198.
    • (1998) Top. Curr. Chem. , pp. 198
    • Weber, E.1
  • 8
    • 0004217931 scopus 로고
    • Cambridge University Press, Cambridge
    • J. D. Wright, Molecular Crystals, Cambridge University Press, Cambridge, 1987.
    • (1987) Molecular Crystals
    • Wright, J.D.1
  • 13
    • 36949064021 scopus 로고
    • D. J. Sutor, Nature 1962, 195, 68-69.
    • (1962) Nature , vol.195 , pp. 68-69
    • Sutor, D.J.1
  • 18
    • 0003766353 scopus 로고
    • Springer Verlag, Berlin
    • Even as recently as 1991 it was still believed that CH-O bonds would not have a major influence on molecular conformations: G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer Verlag, Berlin, 1991.
    • (1991) Hydrogen Bonding in Biological Structures
    • Jeffrey, G.A.1    Saenger, W.2
  • 19
    • 0034678016 scopus 로고    scopus 로고
    • For example, in the last years Kool et al. have shown that synthetic nonpolar nucleoside isosteres can replace normal DNA bases without affecting base pairing or replication properties: E. T. Kool, J. C. Morales, K. M. Guckian, Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1009.
    • (2000) Angew. Chem. Int. Ed. Engl. , vol.39 , pp. 990-1009
    • Kool, E.T.1    Morales, J.C.2    Guckian, K.M.3
  • 20
    • 0001120760 scopus 로고    scopus 로고
    • For a review see: E. T. Kool, Chem. Rev. 1997, 97, 1473-1487.
    • (1997) Chem. Rev. , vol.97 , pp. 1473-1487
    • Kool, E.T.1
  • 23
    • 19544382154 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structure of 2·Cl have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-149249. 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.]
  • 25
    • 0031587446 scopus 로고    scopus 로고
    • For a CH-O bond to a negatively charged carboxylate oxygen even a C⋯H distance of only 2.107 Å (corresponding to a C⋯O distance of 3.193 A with a bond angle of 176°) was reported: P. R. Mallison, K. Wozniak, G. T. Smith, K. L. McCormack, J. Am. Chem. Soc. 1997, 119, 11502-11509.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11502-11509
    • Mallison, P.R.1    Wozniak, K.2    Smith, G.T.3    McCormack, K.L.4
  • 26
    • 0034640006 scopus 로고    scopus 로고
    • Recently, Gokel and co-workers showed that within a series of lariat ethers even CH-O hydrogen bonds with bond lengths of >3.5 A are important structure determining interactions: E. S. Meadow, S. L. DeWall, L. J. Barbour, F. R. Fronczek, M.-S. Kim, G. W. Gokel, J. Am. Chem. Soc. 2000, 122, 3325-3335.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3325-3335
    • Meadow, S.1    DeWall, S.L.2    Barbour, L.J.3    Fronczek, F.R.4    Kim, M.-S.5    Gokel, G.W.6
  • 31
    • 0033599295 scopus 로고    scopus 로고
    • A similar analysis was done recently to establish the relative contributions of π-π stacking and CH-O hydrogen bonds to the overall binding of bipyridinium guests by catenated hosts: K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 1479-1487.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1479-1487
    • Houk, K.N.1    Menzer, S.2    Newton, S.P.3    Raymo, F.M.4    Stoddart, J.F.5    Williams, D.J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.