Abstract
The crystal and molecular structure of3 has been determined by X-ray analysis. Thecrystal data are: triclinic, space group P'1,a = 12.999(2),b = 14.114(3),c = 16.132(3) Å,α = 91.62(2),β = 97.71(1),γ = 91.38(2)°,V = 2930.6(9) Å3,Z = 2,Dm = 1.046 g cm-3.Rotational disorder has been seen in the t-butyl groups whichwere refined isotropically. Least-squares refinementbased on F2, using 4827 observedreflections with I > 2σ(I) and 18 restraints,led to R = 0.123. The calix is found in a coneconformation. The crown ether part of the molecule isnot in a fully extended conformation but has foldsin the chain. The calix[4]crown ether-ester exhibitsmolecular recognition properties toward alkylamines.
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C.D. Gutsche: in: J.F. Stoddart (ed.), Calixarenes: Monographs in Supramolecular Chemistry, Royal Society of Chemistry, (1989). (b) V. Böhmer: Angew. Chem. Int. Ed. Engl. 713 (1995).
J. Vicens and V. Böhmer (eds.): Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht (1991).
C.D. Gutsche and M. Iqbal: Org. Synth. 68 234 (1989).
Arnaud-Neu, E.M. Collins, M. Desay, G. Ferguson, S.J. Harris, B. Kainter, A.J. Lough, M.A. McKervey, E. Marques, B.L. Ruhe, M.J. Schwing-Weill and E. Seward: J. Am. Chem. Soc. 111, 8681 (1989).
M.A. McKervey, E.M. Seward, G. Ferguson, B.L. Ruhl and S.J. Harris: J. Chem. Soc., Chem. Commun. 388 (1985). (b) S.K. Chang and I. Cho: Chem. Lett. 477 (1984). (c) S.K. Chang and I. Cho: J. Chem. Soc., Perkin Trans. 1, 211 (1986). (d) A. Arduini, A. Pochini, S. Reverberi, R. Ungaro, C.D. Andreeti and F. Ugozzoli: Tetrahedron 42, 2089 (1986).
S.K. Chang, S.K. Kwon and I. Cho: Chem. Lett. 947 (1987). (b) A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, G.D. Andreeti, G. Calestani and F. Ugozzoli: J. Incl. Phenom. 6, 119 (1986). (c) F. Arnaud-Neu, M.J. Schwing-Weill, K. Ziat, S. Cremin, S.J. Harris and M.A. McKervey: New J. Chem. 15, 33 (1991).
M.A. McKervey, M. Owens, H.R. Schulten, W. Vogt and V. Böhmer: Angew. Chem. Int. Ed. Engl. 29, 280 (1990).
R. Ungaro, A. Pochini and G.D. Andreeti: J. Incl. Phenom. 2, 199 (1984).
C. Alfieri, E. Dradi, A. Pochini, R. Ungaro and G.D. Andreeti: J. Chem. Soc., Chem. Commun. 1075 (1983).
E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A.A. El-Fadl and D.N. Reinhoudt: J. Am. Chem. Soc. 112, 6979 (1990).
A. Arduini, A. Casnati, L. Dodi, A. Pochini and R. Ungaro: J. Chem. Soc., Chem. Commun. 1597 (1990).
D.N. Reinhoudt, P.J. Dijkstra, F.J.A. in't Veld, K.E. Brugge, S. Harkema, R. Ungaro and B. Ghidini: J. Am. Chem. Soc. 109, 4761 (1987).
P.D. Beer, A.D. Keefe, A.M.Z. Slawin and D.J. Williams: J. Chem. Soc., Dalton Trans. 3975 (1990).
J.D. Vanloon, D. Kraft, M.J.K. Ankone, W. Verboom, S. Harkema, W. Vogt, V. Böhmer and D.N. Reinhoudt: J. Org. Chem. 55, 5176 (1990).
D. Kraft, J.D. Vanloon, M. Owens, W. Verboom, W. Vogt, M.A. Mckervey, V. Böhmer and D.N. Reinhoudt: Tetrahedron Lett. 31, 4941 (1990).
V. Böhmer, G. Ferguson, J.F. Gallagher, A.J. Lough, M.A. Mckervey, E.Madigan,M.B.Moran, J. Philips and G. Williams: J. Chem. Soc., Perkin Trans. 1 1521 (1993).
Q-Y. Zheng, C-F. Chen and Z-T. Huang: Tetrahedron 53, 10345 (1997).
E.M. Collins,M.A.McKervey, E.Madigan,M.Moran,M. Owens, G. Ferguson and S.J. Harris: J. Chem. Soc., Perkin Trans. 1, 3137 (1991).
C. Almansa, A.Moyano, P. Prados, P.M. Nieto and C. Sanchez: J. Org. Chem. 56, 3373 (1991).
F. Ugozzoli and G.D. Andreeti: J. Incl. Phenom. 13, 337 (1992).
G.D. Andreeti, F. Ugozzoli, Y. Nakamoto and S.I. Ishida: J. Incl. Phenom. 10, 241 (1991).
F. Arnaud-Neu, V. Böhmer, L. Guerra, M.A. Mckervey, E.F. Paulus, A. Rodriguez, M-J. Schwing-Weill, M. Tabatabai and W. Vogt: J. Phys. Org. Chem. 5, 1992 (471).
G.D. Andreeti, R. Ungaro and A. Pochini: J. Chem. Soc. Chem. Commun. 1005 (1979).
R. Hilgenfeld and W. Saenger: Topics in Current Chemistry, F. Vögtle (ed.), Springer-Verlag, New York, 101, 38 (1982).
A. Arduini, A. Pochini, S. Reverberi and R. Ungaro: J. Chem. Soc., Chem. Commun. 981 (1984).
S. Kanamathareddy and C.D. Gutsche: J. Org. Chem. 57, 3160 (1992).
C. Jaime, J. de Mendoza, P. Prados, P.M. Nieto and C. Sanchez: J. Org. Chem. 56, 3372 (1991).
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Kumar, M., Hundal, G., Bhalla, V. et al. Crystal Structure of a Calix[4]crown Ether-Ester and Molecular Recognition of Alkyl- and Arylalkylamines. Journal of Inclusion Phenomena 36, 461–472 (2000). https://doi.org/10.1023/A:1008134703152
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DOI: https://doi.org/10.1023/A:1008134703152