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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1509 - 1512

DOI: https://doi.org/10.6023/cjoc201204006

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Novel Naphthalene-Based Open Chain Crown Ether: Synthesis and Crystal Structure

  • 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 of Jiaxing City, Jiaxing 314001;
    c School of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058

Received date: 2012-04-05

  Revised date: 2012-04-25

  Online published: 2012-05-04

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 open-chain crown ether has been synthesized by the etherification of 2-bromo- N-phenylacetamide with 3,6-dibromo-2,7-dihydroxynaphthalene, followed by reduction with sodium borohydride and boron trifluoride ether solution, in 95% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic space group P-1 with a=9.588(3) Å, b=10.898(3) Å, c=13.060(4) Å, α=103.190(4)°, β=93.953(4)°, γ=115.622(5)°, V=1176.0(6) Å3, Z=2, Dc=1.571 g/cm3, λ=0.71075 Å, μ(Mo Kα)=3.472 mm-1, Mr=353.22 and F(000)=560. In the structure, one of the N—H groups forms bifurcated N—H…Br and N—H…O hydrogen bonds. These link the molecules into inversion related dimers. The centrosymmetric dimers are aggregated via pairs of C—H…π interactions into two-dimensional sheets parallel to (110).

Key words： open-chain crown ethers; synthesis; crystal structure

Cite this article

Zong Qianshou , Wu Jianyi . Novel Naphthalene-Based Open Chain Crown Ether: Synthesis and Crystal Structure[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1509 -1512 . DOI: 10.6023/cjoc201204006

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