一些手性氨基酸衍生物和几个四唑配合物的合成与表征
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摘要
基于以手性配体为构筑块,与金属离子自组装获得手性配位聚合物,我们以L-酪氨酸(L-tyrosine),二羟基苯丙氨酸(多巴),天门冬氨酸,谷氨酸为原料,合成出一些未见报道的含有氰基和乙烯基的氨基酸衍生物。
通过溶液培养法,我们得到两个既含四唑基又含氰基的配体晶体2-(1H-tetrazol- 5-yl)benzonitrile和4-((2H-tetrazol-2-yl)methyl)benzonitrile;利用四唑基中氮原子和羧基中氧原子的配位能力,通过水热合成法,由配体2-(1H-tetrazol-5-yl)benzoic acid得到四唑金属配合物1和2,由配体5-(1H-tetrazol-5-yl)isophthalic acid得到金属配合物3、4、5。配合物1:C2 / c,a = 1.9886 (4) nm,b = 0.7352 (15) nm,c = 1.5409 (3) nm,β= 115.97 (3) o;配合物2:C2,a = 1.9696 (8) nm,b = 0.7134 (18) nm,c = 1.4932 (6) nm,β= 114.39 (2) o;配合物3:P-1,a = 0.7909 (16) nm,b = 0.8448 (17) nm,c = 1.0994 (2) nm,α= 102.65 (3) o,β= 124.319 (17) o,γ= 96.28 (3) o;配合物4:P21 / c,a = 0.8020 (24) nm,b = 1.0358 (25) nm,c = 1.7901 (41) nm,β= 92.422 (18) o;配合物5:C2 / c,a = 1.9593 (9) nm,b = 1.1034 (17) nm,c = 1.3330 (6) nm,β= 124.319 (17) o。我们对配合物3和4进行了荧光和紫外光性质的测试,结果显示稀土金属配合物对比原四唑基配体有明显的荧光增强变化和轻微的紫外光谱蓝移现象。
实验所得到的产物用红外光谱、紫外光谱、元素分析、质谱、荧光光谱、核磁共振氢谱、X-射线单晶衍射进行表征和分析。
Basing on using chiral organic ligand as building block to self-assemble chiral metal organic coordination polymers with metal ion, several unreported aminophenol derivatives with cyanogens and ethylene were synthesized by L-tyrosine, dihydroxyphenylalanine (DOPA), aspartic acid and glutamic acid.
Through the way of hydroponic reaction, we gained two crystal structures of 2-(1H- tetrazol-5-yl)benzonitrile and 4-((2H-tetrazol-2-yl)methyl)benzonitrile with tetrazolyl and cyanogen group. Through the way of hydrothermal reaction, we gained two tetrazole metal coordination compounds (1, 2) with the ligand 2-(1H-tetrazol-5-yl)benzoic acid and three tetrazole metal coordination compounds (3, 4 and 5) with the ligand 5-(1H-tetrazol-5-yl) isophthalic acid using the coordination ability of the N atoms in tetrazole and the O atoms in carboxyl. Compound 1: C2 / c, a = 1.9886 (4) nm; b = 0.7352 (15) nm; c = 1.5409 (3) nm;β= 115.97 (3) o; compound 2: C2, a = 1.9696 (8) nm; b = 0.7134 (18) nm; c = 1.4932 (6) nm;β= 114.39 (2) o; compound 3: P-1, a = 0.7909 (16) nm; b = 0.8448 (17) nm; c = 1.0994 (2) nm;α= 102.65 (3) o;β= 124.319 (17) o;γ= 96.28 (3) o; compound 4: P21 / c, a = 0.8020 (24) nm; b = 1.0358 (25) nm; c = 1.7901 (41) nm;β= 92.422 (18) o; compound 5: C2 / c, a = 1.9593 (9) nm; b = 1.1034 (17) nm; c = 1.3330 (6) nm;β= 124.319 (17) o. We also tested the fluorescent and ultraviolet characters of the two compounds 3 and 4. Enhanced luminescence efficiency and slightly blue shift of the absorption peaks in ultraviolet spectrum of the lanthanon coordination compounds were obvious contrast to the original tetrazolyl ligands.
Structures of the productions were characterized by IR spectroscopy, UV spectroscopy, elemental analyses, mass spectrum, fluorescent spectroscopy, 1H NMR spectroscopy and X-ray single crystal diffraction.
通过溶液培养法,我们得到两个既含四唑基又含氰基的配体晶体2-(1H-tetrazol- 5-yl)benzonitrile和4-((2H-tetrazol-2-yl)methyl)benzonitrile;利用四唑基中氮原子和羧基中氧原子的配位能力,通过水热合成法,由配体2-(1H-tetrazol-5-yl)benzoic acid得到四唑金属配合物1和2,由配体5-(1H-tetrazol-5-yl)isophthalic acid得到金属配合物3、4、5。配合物1:C2 / c,a = 1.9886 (4) nm,b = 0.7352 (15) nm,c = 1.5409 (3) nm,β= 115.97 (3) o;配合物2:C2,a = 1.9696 (8) nm,b = 0.7134 (18) nm,c = 1.4932 (6) nm,β= 114.39 (2) o;配合物3:P-1,a = 0.7909 (16) nm,b = 0.8448 (17) nm,c = 1.0994 (2) nm,α= 102.65 (3) o,β= 124.319 (17) o,γ= 96.28 (3) o;配合物4:P21 / c,a = 0.8020 (24) nm,b = 1.0358 (25) nm,c = 1.7901 (41) nm,β= 92.422 (18) o;配合物5:C2 / c,a = 1.9593 (9) nm,b = 1.1034 (17) nm,c = 1.3330 (6) nm,β= 124.319 (17) o。我们对配合物3和4进行了荧光和紫外光性质的测试,结果显示稀土金属配合物对比原四唑基配体有明显的荧光增强变化和轻微的紫外光谱蓝移现象。
实验所得到的产物用红外光谱、紫外光谱、元素分析、质谱、荧光光谱、核磁共振氢谱、X-射线单晶衍射进行表征和分析。
Basing on using chiral organic ligand as building block to self-assemble chiral metal organic coordination polymers with metal ion, several unreported aminophenol derivatives with cyanogens and ethylene were synthesized by L-tyrosine, dihydroxyphenylalanine (DOPA), aspartic acid and glutamic acid.
Through the way of hydroponic reaction, we gained two crystal structures of 2-(1H- tetrazol-5-yl)benzonitrile and 4-((2H-tetrazol-2-yl)methyl)benzonitrile with tetrazolyl and cyanogen group. Through the way of hydrothermal reaction, we gained two tetrazole metal coordination compounds (1, 2) with the ligand 2-(1H-tetrazol-5-yl)benzoic acid and three tetrazole metal coordination compounds (3, 4 and 5) with the ligand 5-(1H-tetrazol-5-yl) isophthalic acid using the coordination ability of the N atoms in tetrazole and the O atoms in carboxyl. Compound 1: C2 / c, a = 1.9886 (4) nm; b = 0.7352 (15) nm; c = 1.5409 (3) nm;β= 115.97 (3) o; compound 2: C2, a = 1.9696 (8) nm; b = 0.7134 (18) nm; c = 1.4932 (6) nm;β= 114.39 (2) o; compound 3: P-1, a = 0.7909 (16) nm; b = 0.8448 (17) nm; c = 1.0994 (2) nm;α= 102.65 (3) o;β= 124.319 (17) o;γ= 96.28 (3) o; compound 4: P21 / c, a = 0.8020 (24) nm; b = 1.0358 (25) nm; c = 1.7901 (41) nm;β= 92.422 (18) o; compound 5: C2 / c, a = 1.9593 (9) nm; b = 1.1034 (17) nm; c = 1.3330 (6) nm;β= 124.319 (17) o. We also tested the fluorescent and ultraviolet characters of the two compounds 3 and 4. Enhanced luminescence efficiency and slightly blue shift of the absorption peaks in ultraviolet spectrum of the lanthanon coordination compounds were obvious contrast to the original tetrazolyl ligands.
Structures of the productions were characterized by IR spectroscopy, UV spectroscopy, elemental analyses, mass spectrum, fluorescent spectroscopy, 1H NMR spectroscopy and X-ray single crystal diffraction.
引文
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[3] (a) F. R. Benson. Tetrazoles, tetrazines and purines and related ring systems [J]. Heterocycl. Compd., 1967, 8, 1-12. (b) R. N. Butler. Recent advances in tetrazole chemistry [J]. Adv. Heterocycl. Chem., 1977, 21, 323-435.
[4] G. I. Koldobskii, V. A. Ostrovskii. Tetrazoles [J]. Russ. Chem. Rev., 1994, 63, 797-814.
[5] R. Stolle. Zur Kenntnis des amino-5-tetrazols [J]. Chem. Ber., 1929, 62, 1118-1127.
[6] G. Gazz. 2-Methyl-4, 5-benzoindandione [J]. Chim. Ital., 1911, 41, 190-196.
[7] J. V. Dunica, M. E. Pierce, J. B. Santella. 6-Methyl-5-(2-propynyl)-2-thio-4(lH, 3H)pyrimidinone [J]. J. Org. Chem., 1991, 56, 2395-2400.
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[9] D. P. Curra, S. Hadida, S. Y. Kim. Tris(2-perfluorohexylethyl)tin azide: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous / organic liquid-liquid extraction [J]. Tetrahedron, 1999, 55, 8997-9001.
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