Abstract
Two new calix[4]arene derivatives, 5,17-dinitro-26,28-dimethyoxy-25,27-dipropoxycalix[4]arene (4) and 5,17-diamino-26,28-dimethyoxy-25,27-dipropoxycalix[4]arene (5), have been synthesized and fully characterized. The 1H NMR spectra measured in different solvents and temperatures indicated that the dominant conformer is partial cone for 4 and cone for 5, though there are some variations in relative ratio of partial cone to cone conformers. The structures of partial cone 4 and cone 5 are determined by X-ray crystallography. The different conformational behavior in compounds 4 and 5 is governed by the two substituents at the upper rim. The repulsion of the dipole due to the p-nitro substituents and weak interaction between methoxy group and the inverted anisole ring in the 4 may be responsible for stabilizing the partial cone conformation.
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Yang, G., Jin, C., Li, Y. et al. Conformations and Structures of Two Novel Upper Rim Disubstituted Derivatives of Tetra-O-alkylcalix[4]arene: The Effect of Substituents. J Incl Phenom Macrocycl Chem 52, 119–127 (2005). https://doi.org/10.1007/s10847-004-6331-3
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DOI: https://doi.org/10.1007/s10847-004-6331-3