Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Structure Identification of 1,2-Disubstituted Chiral Calix[4]arene : X-Ray and NMR Analysis of 25-(3,5-Dinitrobenzoyloxy)-26-methoxy-27,28-dihydroxycalix[4]arene

  • Published : 1996.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

1,2-Disubstituted chiral calix[4]arene "25-(3,5-dinitrobenzoyloxy)-26-methoxy-27,28-dihydroxycalix[4]arene" was synthesized by the reaction of 25-(3,5-dinitrobenzoyloxy)-calix[4]arene with methyl iodide in the presence of K2CO3. Methylation was occurred at the 26-position of calix[4]arene. The partial cone conformation and 1,2-substitution were characterized based on the 1H NMR, 13C NMR and X-ray diffraction analysis. The crystal structure has been determined by X-ray diffraction method. The crystals are orthorhombic, Pbca, a=10.652(1), b=17.687(1), c=32.247(3) Å, Z=8, V=6075.4(9) Å3, Dc=1.38gcm-3. The intensity data were collected on an Enraf-Nonius CAD-4 Diffractometer with a graphite monochromated Cu-Kα radiation. The structure was solved by direct method and refined by full-matrix least-squares methods to a final R value of 0.050 for 2368 observed reflections. The molecule is in the partial cone conformation. It has two strong intramolecular hydrogen bonds of O(1D)-H…O(1C)-H…O(1B).

Keywords

References

  1. Acc. Chem. Res. v.16 Gutsche, C. D.
  2. J. Org. Chem. v.55 van Loon, J. D.;Arduini, A.;Coppi, L.;Verboom, W.;Pochini, A.;Ungaro, R.;Hakema, S.;Reinhoudt, D. N.
  3. Tetrahedron Lett. v.32 Groenen, L. C.;Ruel, B. H. M.;Casnati, A.;Timmerman, P.;Verboom, W.;Harkema, S.;Pochini, A.;Ungaro, R.;Reinhoudt, D. N.
  4. Tetrahedron v.42 Gutsche, C. D.;Lin, L. G.
  5. Tetrahedron v.47 Casnati, A.;Arduini, A.;Chidini, E.;Pochini, A.;Ungaro, R.
  6. Tetrahedron v.19 Gutsche, C. D.;Dhawan, B.;Levine, J. A.;No, K. H.;Bauer, L. J.
  7. Bull. Korean Chem. Soc. v.13 Nam, K. C.;Kim, D. S.;Yang, S. J.
  8. J. Org. Chem. v.57 Gutsche, C. D.;See, K. A.
  9. J. Am. Chem. Soc. v.115 Iwamoto, K.;Shimizu, H.;Araki, K.;Shinkai, S.
  10. Bull. Korean Chem. Soc. v.16 Nam, K. C.;Kim, J. M.;Kim, D. S.
  11. J. Org. Chem. v.56 Jaime, C.;Mandoza, J. D.;Parados, P.;Nieto, P. M.;Sanchez, C.
  12. Tetrahedron v.49 Shinkai, S.
  13. Shelxs-86 and Shelxl-93, Program for Crystal Structure Determination Shedrick, G. M.
  14. International Table for X-ray Crystallography v.Ⅳ Kynoch Press