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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 03: 568 - 572

DOI: https://doi.org/10.6023/cjoc201211037

Articles

Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives

  • Zong Qianshou ,
  • Wu Jianyi
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  • a Department of Biology and Chemical Engineering, Jiaxing University, Jiaxing 314001;
    b Key Laboratory of Chemical Cleaning Technology, Jiaxing City, Jiaxing 314001;
    c School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058

Received date: 2012-11-20

  Revised date: 2012-12-04

  Online published: 2012-12-10

Supported by

Project supported by the China Postdoctoral Science Foundation (No. 2011M500989) and the Excellent Yong Teachers Program of Zhejiang Province (No. 00511024).

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Abstract

A Novel naphthalene-based crown ether has been synthesized by the etherification of 2,7-dihydroxynaphthalene with 8-tosyloxy-3,6-dioxaoctanol in the presence of K2CO3, followed by reaction with p-toluenesufonyl chloride to give 7. Compound 7 was further reacted with 2,7-dihydroxynaphthalene in the presence of cesium carbonate to give 1 in 38% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic, space group P-1 with a＝ 8.165(3) Å, b＝13.435(4) Å, c＝14.083(3) Å, α＝64.11(2)°, β＝80.40(3)°, γ＝88.19(3)°, V＝1368.9(7) Å3, Z＝2, Dc＝1.331 g/cm3, λ＝0.071070 nm, μ(Mo Kα)＝1.331 mm-1, Mr＝353.22, F(000)＝584. The crystal structure of 1 shows that two napthalene units are linked two tri(ethylene glycol) bridges to form dinapthalzo[30]crown-8 cavity and one Z-like central cavity with size of ca. 8.2 Å×12.0 Å. The host 4 was proved to be a efficient host for the complexation with paraquat derivatives in solution by 1H NMR.

Key words： crown ethers; synthesis; crystal structure; complexation; paraquat derivatives

Cite this article

Zong Qianshou , Wu Jianyi . Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 568 -572 . DOI: 10.6023/cjoc201211037

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