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Efficient synthesis of new 17-, 18-, 19- and 20-membered N2O2-donor macrocycles by NaBH4 reduction and metal picrate extraction studies
Journal of Inclusion Phenomena and Macrocyclic Chemistry ( IF 2.3 ) Pub Date : 2020-03-19 , DOI: 10.1007/s10847-020-00987-y
Marija Paurević , Andrea Dandić , Martina Šrajer Gajdošik , Barbara Vidović , Franc Perdih , Tomislav Balić

Four new N2O2-donor macrocycles mDo4R, mDo5R, mDo6R, mDo7R (mDo4R = 1,5-diaza-2,4:7,8:15,16- tribenzo-9,14-dioxa-cycloheptadecane, mDo5R = 1,5-diaza-2,4:7,8:16,17-tribenzo-9,15-dioxa-cyclooctadecane, mDo6R = 1,5-diaza-2,4:7,8:17,18-tribenzo-9,16-dioxa-cyclononadecane; mDo7R = 1,5-diaza-2,4:7,8:18,19-tribenzo-9,17-dioxa-cycloeicosane) were prepared by NaBH4 reduction of appropriate macrocyclic Schiff bases in high yields. The compounds were characterized by means of FT-IR and NMR spectroscopy and elemental analysis. The crystal and molecular structure was determined for mDo5R and mDo7R. The molecular structure of mDo5R indicate large deviation from planarity, relatively large inner macrocyclic hole size (1.542–3.048 Å) and exodentante orientation of one nitrogen atom (N2) due to presence of intramolecular N–H⋯O hydrogen bond. In mDo7R both nitrogen atoms are exodentante and involved in intramolecular N–H⋯O hydrogen bond. The mDo7R molecules are quite planar with small values of puckering amplitude (1.329(2) Å, 1.355(2) Å and 1.433(2) Å). In the crystal structure of both compounds, molecules are primarily linked by weak C–H⋯π, C–H⋯N and C–H⋯O interactions. The metal cation extractability was determined for all compounds by UV–Vis spectrophotometry and all of compounds show affinity towards extraction of iron (III) and mercury (II) cations. Synthesis and characterisation of secondary amine macrocycles derived from macrocyclic Schiff base analouges and metal picrate extraction studies

中文翻译:

通过 NaBH4 还原和金属苦味酸盐提取研究有效合成新的 17-、18-、19- 和 20-元 N2O2 供体大环

四种新的 N2O2 供体大环 mDo4R、mDo5R、mDo6R、mDo7R(mDo4R = 1,5-二氮杂-2,4:7,8:15,16-三苯并-9,14-二氧杂环庚烷,mDo5R = 1,5- diaza-2,4:7,8:16,17-tribenzo-9,15-dioxa-cyclooctadecane, mDo6R = 1,5-diaza-2,4:7,8:17,18-tribenzo-9,16-二恶杂-环十九烷;mDo7R = 1,5-二氮杂-2,4:7,8:18,19-三苯并-9,17-二恶杂-环二十烷)是通过 NaBH4 还原适当的大环席夫碱以高产率制备的。通过FT-IR和NMR光谱以及元素分析对化合物进行表征。确定了 mDo5R 和 mDo7R 的晶体和分子结构。由于分子内 N-H⋯O 氢键的存在,mDo5R 的分子结构表明与平面性的较大偏差、相对较大的内部大环孔尺寸 (1.542-3.048 Å) 和一个氮原子 (N2) 的外齿状取向。在 mDo7R 中,两个氮原子都是外齿并参与分子内 N-H⋯O 氢键。mDo7R 分子非常平坦,褶皱幅度很小(1.329(2) Å、1.355(2) Å 和 1.433(2) Å)。在这两种化合物的晶体结构中,分子主要通过弱 C–H⋯π、C–H⋯N 和 C–H⋯O 相互作用连接起来。通过紫外-可见分光光度法测定所有化合物的金属阳离子可萃取性,并且所有化合物都显示出对铁 (III) 和汞 (II) 阳离子的萃取亲和性。来自大环席夫碱类似物的仲胺大环化合物的合成和表征和金属苦味酸盐提取研究 433(2)埃)。在这两种化合物的晶体结构中,分子主要通过弱 C–H⋯π、C–H⋯N 和 C–H⋯O 相互作用连接起来。通过紫外-可见分光光度法测定所有化合物的金属阳离子可萃取性,并且所有化合物都显示出对铁 (III) 和汞 (II) 阳离子的萃取亲和性。来自大环席夫碱类似物的仲胺大环化合物的合成和表征和金属苦味酸盐提取研究 433(2)埃)。在这两种化合物的晶体结构中,分子主要通过弱的 C–H⋯π、C–H⋯N 和 C–H⋯O 相互作用连接起来。通过紫外-可见分光光度法测定所有化合物的金属阳离子可萃取性,并且所有化合物都显示出对铁 (III) 和汞 (II) 阳离子的萃取亲和性。来自大环席夫碱类似物的仲胺大环化合物的合成和表征和金属苦味酸盐提取研究
更新日期:2020-03-19
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