Molecular Design of Calixarenes(VI)- Synthesis and Crystal Structure of a Novel Sulfonamino Calix[4]arene Derivative

Abstract

Abstract: A novel calix[4]arene derivative (2), 5,11,17, 23-tetra-tert-butyl--25, 26-dihydroxy-27, 28-[bis(p-toluenesulfonylaminoethoxy)]calix [4]arene was synthesized in a 90% yield by the reaction of 5,11, 17, 23-tetra-tert-butyl-25, 26-dihydroxy-27, 28- [bis (β-aminoethoxy)]-calix [4] arene (1) and p-tolue-nesulfonyl chloride in dry CH₂C₁₂ in the presence of NEt₃.compound 2 crystallizes in triclinic space group P1, with a = 1.20444(11) nm, b = 1.61735(14) nm, c = 1.77316(15) nm, a=80.050(2)°, β=76.644(2) °,γ = 82.084(2) °, V = 3.2929(5) nm³, D_c=1.135 g/cm³, Z=2, R = 0.0683.Theresult shows the flatted cone conformation with the distorted sulfonamido substituents attached to the low-er rim of compound 2 resulted from the dipole-dipole repulsive interaction.The structure of 2-acetonitrilecomplex shows that the acetonitrile lies on the pseudo crystallgraphic fourfold axis with the nitrogen atomdirecting exo and the methyl pointing inside the intramolecular cavity, which is attributed to the specificCH-π interaction between the acetonitrile CH₃ group and the aromatic nuclei of host 2.

Key words: Calixarene, Sulfonamino derivative, Crystal structure, CH-&pi, interaction

CLC Number:

O641.4

TrendMD:

ZHAO Bang-Tun, ZHANG Ning, LIU Yu, CHEN Qi-Fa. Molecular Design of Calixarenes(VI)- Synthesis and Crystal Structure of a Novel Sulfonamino Calix[4]arene Derivative[J]. Chem. J. Chinese Universities, 2002, 23(4): 617.

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Molecular Design of Calixarenes(VI)- Synthesis and Crystal Structure of a Novel Sulfonamino Calix[4]arene Derivative

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