Preference of intra- and intermolecular cation-π interaction: cis-trans geometrical effects of amide bond on the interaction mode

Tetrahedron Letters

Volumn 46, Issue 34, 2005, Pages 5673-5676

  Yamada, Shinji ^a   Morimoto, Yuka ^a   Misono, Tomoko ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Amide bond; Cation interaction; cis trans effect; Pyridinium interaction

Indexed keywords

AMIDE; CATION;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CONFORMATION; GEOMETRY;

EID: 22544453873     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.088     Document Type: Article

References (19)

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16. Irradiation of N-Me protons of 4a resulted in 0.9% NOE for the m- and p-protons of the phenyl group. Similarly, irradiation of m- and p-protons of the phenyl group resulted in 2.8%, 3.6% and 3.1% NOEs for the 2, 4 and 5-protons of the pyridinium ring, respectively.
17. int = 0.1223). R1 and wR2 are 0.0502 [I > 2σ(I)] and 0.1898 (all data), respectively. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 267263 and 267264. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.jp].
18. A. Bondi J. Phys. Chem. 68 1964 441
19. -1 lower than that of the conformer having a same interaction face as that of X-ray structure.