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

Zong, Qian‐Shou; Jian-yi, WU

doi:10.6023/cjoc201204006

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“…们 [11] ,报道了基于萘基块新型开链冠醚的合成及晶体结构研究由于这个开链冠醚结构的侧链较短对联吡啶盐没有络合作用. 因此, 我们基于富电子的 2, 7 位萘基块设计并合成了具有更大空腔的新型冠醚二萘并[30]-冠-8 (4) (Scheme 1), 并研究了其晶体结构及其对联吡啶盐的络合性能(图 1).…”

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

Zong¹,

Jian-yi²

2013

Chin. J. Org. Chem.

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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 K 2 CO 3 , 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) Å 3 , Z＝2, D c ＝1.331 g/cm 3 , λ＝0.071070 nm, μ(Mo Kα)＝1.331 mm -1 , M r ＝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 1 H NMR.

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