CN105968144A - 一种镍配合物 - Google Patents

一种镍配合物 Download PDF

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CN105968144A
CN105968144A CN201610508614.XA CN201610508614A CN105968144A CN 105968144 A CN105968144 A CN 105968144A CN 201610508614 A CN201610508614 A CN 201610508614A CN 105968144 A CN105968144 A CN 105968144A
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罗梅
齐磊
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Hefei Xiangchen Chemical Engineering Co Ltd
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Abstract

一种镍配合物（I），其化学式如下：该镍配合物（I）的合成方法：称取1.8318g(15mmol)2-吡啶甲醛肟放入100mL圆底烧瓶中，加入40ml无水甲醇，搅拌使其溶解；再称取1.4974g(7.5mmol) Cu(OAc)2·H2O加入上述溶液中，控制温度在75℃左右，加热回流36h；趁热过滤反应溶液，将溶液用旋转蒸发仪旋至一半溶液，在剩余溶液中加入5ml左右正己烷，静置挥发，2周后，有墨绿色晶体析出；滤出晶体，将晶体用30～60℃石油醚冲洗3次，真空干燥30分钟，得到目标产物；该配合物在苯甲醛的亨利反应中显示了一定的催化性能，其转化率达80%。

Description

一种镍配合物
技术领域
本发明涉及一种新化合物及其制备方法，特别涉及一种铜化合物及其制备方法，确切地说是一种配合物的制备及合成方法。
背景技术
镍金属配合物在很多方面都有重要的应用，而且发展迅速。通过修饰配体的结构来提高催化剂的催化效率，因此镍金属配合物催化的反应种类也越来越多，近年来镍配合物的合成方法已有许多文献报道，参考文献如下：
参考文献：
1. Zeolite-Y Encapsulated Metal Picolinato Complexes as Catalyst forOxidation of Phenol with Hydrogen Peroxide，Bania, Kusum K. and Deka, RameshC.， Journal of Physical Chemistry C, 117(22), 11663-11678; 2013.
2. Coordination behavior of 3,4-bis(2-pyridylmethylthio)toluene withcopper(II) ions: Synthesis, structural characterization and reactivity, andDNA binding study of the dinuclear copper(II) complex, Sarkar, Sandipan etal, Polyhedron, 29(17), 3157-3163; 2010.
3. Two-dimensional assembly of [MnIII2MnII2] single-molecule magnets and[Cu(pic)2] linking units (Hpic = picolinic acid), Jeon, Ie-Rang et al, DaltonTransactions, 39(20), 4744-4746; 2010.
4. Relationship between coordination structure and biological activity ofcopper(II) nicotinate,Chen, Qiang et al,Chinese Journal of StructuralChemistry, 25(9), 1141-1147; 2006.
5. Preparation of three-dimensional porous metal complexes foradsorbents, separating materials, gas adsorbents, and hydrogen adsorbents,Ikura, Ami et al, Jpn. Kokai Tokkyo Koho, 2007277106, 25 Oct 2007
6. 1-D Hydrogen bonded water in Cu(II)-picolinate coordination polymer:synthesis, crystal structure, and thermogravimetric analysis, Siddiqui,Kafeel Ahmad, Journal of Coordination Chemistry, 65(23), 4168-4176; 2012。
发明内容
本发明旨在提供含双[2-吡啶甲醛肟]乙酸镍配合物，所要解决的技术问题是一步合成得到目标产物。
本发明所称的铜配合物是由2-吡啶甲醛肟与四水合乙酸镍制备的由以下化学式所示的配合物：
(I)。
化学名称：双[2-吡啶甲醛肟]乙酸镍,简称配合物(I)。
该配合物在苯甲醛的亨利反应中显示了一定的催化性能，其转化率达80%。
本合成方法包括合成和分离,其合成方法是称取1.2134g(0.01mol)2-吡啶甲醛肟放入100mL圆底烧瓶中，加入40ml无水甲醇，搅拌使其溶解；在称取2.4818g(0.01mol)Ni(OAc)2·4H2O加入上述溶液中，控制温度在75℃左右，加热回流36h；趁热过滤反应溶液，将溶液用旋转蒸发仪旋至一半溶液，在剩余溶液中加入5ml左右正己烷，静置挥发。2天后，有黄色晶体析出。滤出晶体，将晶体用30～60℃石油醚冲洗3次，真空干燥30分钟，得到目标产物。
合成反应如下：
本合成方法一步得到目标产物，工艺简单，操作方便。
附图说明
图1是双[2-吡啶甲醛肟]乙酸镍配合物的单晶X-衍射图。
具体实施方式
双[2-吡啶甲醛肟]乙酸镍,的制备：
称取1.2134g(0.01mol)2-吡啶甲醛肟放入100mL圆底烧瓶中，加入40ml无水甲醇，搅拌使其溶解；在称取2.4818g(0.01mol)Ni(OAc)2·4H2O加入上述溶液中，控制温度在75℃左右，加热回流36h；趁热过滤反应溶液，将溶液用旋转蒸发仪旋至一半溶液，在剩余溶液中加入5ml左右正己烷，静置挥发。2天后，有黄色晶体析出。滤出晶体，将晶体用30～60℃石油醚冲洗3次，真空干燥30分钟，得到目标产物0.64g，产率：30.5％，熔点：188℃~191℃。理论值：C：45.64 %； H：4.31 %；N：13.31%； 实测值：C：27.56%； H：5.39%；N：5.52%；红外光谱数据(KBr, cm-1):463，524，643，663，680,752,780,890，918,1020,1073,1221,1341,1418,1478,1553,1606,3402.
化合物的晶体数据：
经验式 C16H18N4O6Ni
分子量 421.05
温度 293(2) K
波长 0.71073 Å
晶系， 空间群 单斜晶系,P21/n
晶胞参数 a = 8.6207(10) Å alpha = 90°.
b = 13.6728 (16) Å beta = 90.086（2）°.
c = 15.5060(17) Å gamma = 120°.
体积 1827.7 (4) Å^3
电荷密度 4,1.530g/m^3
吸收 校正参数 1.103 mm^-1
单胞内的电子数目 872
晶体大小 0.190x 0.150x 0.110 mm
Theta 角的范围 1.986 to 25.998°
HKL的指标收集范围 -10<=h<=10, -14<=k<16, -15<=l<=19
收集/独立衍射数据 10757/3584 [R(int) = 0.0363]
theta = 30.5的数据完整度 99.9 %
吸收校正的方法 多层扫描
精修使用的方法 F^2 的矩阵最小二乘法
数据数目/使用限制的数目/参数数目 6662/12/393
精修使用的方法 1.014
衍射点的一致性因子 R1 = 0.0387，wR2= 0.0955
可观察衍射的吻合因子 R1 = 0.0520, wR2 = 0.1020
差值傅里叶图上的最大峰顶和峰谷 0.386 and -0.219e.Å^-3
晶体典型的键长数据：
Ni(1)-O(2) 2.0535(18)
Ni(1)-O(5) 2.0551(18)
Ni(1)-N(3) 2.074(2)
Ni(1)-N(1) 2.077(2)
Ni(1)-N(4) 2.096(2)
Ni(1)-N(2) 2.121(2)
O(1)-N(1) 1.356(3)
O(1)-H(1) 0.8200
O(2)-C(13) 1.239(3)
O(3)-C(13) 1.237(3)
O(4)-N(3) 1.356(3)
O(4)-H(4) 0.8200
O(5)-C(15) 1.251(3)
O(6)-C(15) 1.250(3)
N(1)-C(1) 1.266(3)
N(2)-C(6) 1.328(3)
N(2)-C(2) 1.350(3)
N(3)-C(7) 1.268(3)
N(4)-C(12) 1.334(3)
N(4)-C(8) 1.339(3)
C(1)-C(2) 1.448(4)
C(1)-H(1A) 0.9300
C(2)-C(3) 1.379(4)
C(3)-C(4) 1.378(4)
C(3)-H(3) 0.9300
C(4)-C(5) 1.366(4)
C(4)-H(4A) 0.9300
C(5)-C(6) 1.369(4)
C(5)-H(5) 0.9300
C(6)-H(6) 0.9300
C(7)-C(8) 1.463(4)
C(7)-H(7) 0.9300
C(8)-C(9) 1.380(4)
C(9)-C(10) 1.383(4)
C(9)-H(9) 0.9300
C(10)-C(11) 1.360(4)
C(10)-H(10) 0.9300
C(11)-C(12) 1.379(4)
C(11)-H(11) 0.9300
C(12)-H(12) 0.9300
C(13)-C(14) 1.507(4)
C(14)-H(14A) 0.9600
C(14)-H(14B) 0.9600
C(14)-H(14C) 0.9600
C(15)-C(16) 1.501(4)
C(16)-H(16A) 0.9600
C(16)-H(16B) 0.9600
C(16)-H(16C) 0.9600
晶体典型的键角数据
O(2)-Ni(1)-O(5) 89.56(8)
O(2)-Ni(1)-N(3) 101.52(8)
O(5)-Ni(1)-N(3) 88.79(7)
O(2)-Ni(1)-N(1) 87.08(7)
O(5)-Ni(1)-N(1) 101.70(8)
N(3)-Ni(1)-N(1) 166.56(8)
O(2)-Ni(1)-N(4) 178.95(7)
O(5)-Ni(1)-N(4) 89.98(7)
N(3)-Ni(1)-N(4) 77.53(8)
N(1)-Ni(1)-N(4) 93.93(8)
O(2)-Ni(1)-N(2) 90.23(8)
O(5)-Ni(1)-N(2) 178.98(7)
N(3)-Ni(1)-N(2) 92.23(8)
N(1)-Ni(1)-N(2) 77.29(8)
N(4)-Ni(1)-N(2) 90.25(8)
N(1)-O(1)-H(1) 109.5
C(13)-O(2)-Ni(1) 134.98(18)
N(3)-O(4)-H(4) 109.5
C(15)-O(5)-Ni(1) 131.64(18)
C(1)-N(1)-O(1) 115.7(2)
C(1)-N(1)-Ni(1) 116.17(18)
O(1)-N(1)-Ni(1) 127.99(15)
C(6)-N(2)-C(2) 117.9(2)
C(6)-N(2)-Ni(1) 129.29(18)
C(2)-N(2)-Ni(1) 112.83(16)
C(7)-N(3)-O(4) 115.1(2)
C(7)-N(3)-Ni(1) 116.29(17)
O(4)-N(3)-Ni(1) 128.55(16)
C(12)-N(4)-C(8) 118.2(2)
C(12)-N(4)-Ni(1) 127.93(18)
C(8)-N(4)-Ni(1) 113.87(16)
N(1)-C(1)-C(2) 117.8(2)
N(1)-C(1)-H(1A) 121.1
C(2)-C(1)-H(1A) 121.1
N(2)-C(2)-C(3) 121.7(2)
N(2)-C(2)-C(1) 115.5(2)
C(3)-C(2)-C(1) 122.8(2)
C(4)-C(3)-C(2) 119.1(3)
C(4)-C(3)-H(3) 120.4
C(2)-C(3)-H(3) 120.4
C(5)-C(4)-C(3) 119.2(3)
C(5)-C(4)-H(4A) 120.4
C(3)-C(4)-H(4A) 120.4
C(4)-C(5)-C(6) 118.7(3)
C(4)-C(5)-H(5) 120.7
C(6)-C(5)-H(5) 120.7
N(2)-C(6)-C(5) 123.5(2)
N(2)-C(6)-H(6) 118.3
C(5)-C(6)-H(6) 118.3
N(3)-C(7)-C(8) 117.1(2)
N(3)-C(7)-H(7) 121.5
C(8)-C(7)-H(7) 121.5
N(4)-C(8)-C(9) 122.7(2)
N(4)-C(8)-C(7) 115.1(2)
C(9)-C(8)-C(7) 122.2(2)
C(8)-C(9)-C(10) 118.3(3)
C(8)-C(9)-H(9) 120.9
C(10)-C(9)-H(9) 120.9
C(11)-C(10)-C(9) 119.3(3)
C(11)-C(10)-H(10) 120.4
C(9)-C(10)-H(10) 120.4
C(10)-C(11)-C(12) 119.4(3)
C(10)-C(11)-H(11) 120.3
C(12)-C(11)-H(11) 120.3
N(4)-C(12)-C(11) 122.2(3)
N(4)-C(12)-H(12) 118.9
C(11)-C(12)-H(12) 118.9
O(3)-C(13)-O(2) 125.8(3)
O(3)-C(13)-C(14) 116.5(2)
O(2)-C(13)-C(14) 117.6(3)
C(13)-C(14)-H(14A) 109.5
C(13)-C(14)-H(14B) 109.5
H(14A)-C(14)-H(14B) 109.5
C(13)-C(14)-H(14C) 109.5
H(14A)-C(14)-H(14C) 109.5
H(14B)-C(14)-H(14C) 109.5
O(6)-C(15)-O(5) 124.9(3)
O(6)-C(15)-C(16) 117.0(2)
O(5)-C(15)-C(16) 118.1(3)
C(15)-C(16)-H(16A) 109.5
C(15)-C(16)-H(16B) 109.5
H(16A)-C(16)-H(16B) 109.5
C(15)-C(16)-H(16C) 109.5
H(16A)-C(16)-H(16C) 109.5
H(16B)-C(16)-H(16C) 109.5
亨利反应应用
2-硝基-1-苯基乙醇
称取0.0483g（0.075mmol）配合物，置于25mL 的小烧瓶中，加入1mL 无水甲醇，再向溶液中加入0.05mL苯甲醛和0.25mL硝基甲烷，常温下搅拌反应6小时后，转化率：80%；进行1HNMR检测；1H NMR (300MHz, CDCl3) 7.28～7.32 (m, 5H, Ar-H), 5.32～5.35(d, J=9.18Hz, 1H, -CH), 4.38～4.56 (m, 2H, -CH2), 3.89(br, 1H, -OH)。
硅腈化反应
硅腈化反应也是一种常用的有机合成反应，是合成手性腈醇一种重要方法。在有机医药中间体方面也有广泛的应用。
实验的反应方程式：
称取0.0548g（0.1mmol）配合物，置于25mL小烧瓶中，加入2mLDMSO，再向溶液中加入0.1mL苯甲醛和0.3mL三甲基硅腈，常温下搅拌24h，进行1HNMR检测。催化转化率为65%；1HNMR (300MHz, CDCl3) 7.56–7.59 (m, 0.9 Hz, 2H), 7.31–7.34 (m, 3H), 5.43 (s,1H), 0.16 (s, 9H). 13C NMR (75 MHz, CDCl3) 136.1, 128.8(x2), 126.2(x2), 119.1,63.5, -0.39(x3)。

Claims (3)

1.一种镍配合物（I），其化学式如下：
（Ⅰ）。
2.权利要求1所述的镍配合物（I），在293（2）k温度下，在牛津 X-射线单晶衍射仪上，用经石墨单色器单色化的MoKα射线λ=0.71073 Å，以ω-θ 扫描方式收集衍射数据，其特征在于晶体属单斜晶系,P21/；晶胞参数 ：a = 8.6207(10) Å alpha = 90°；b = 13.6728 (16)Å beta = 90.086（2）°；c = 15.5060(17) Å gamma = 120°。
3.权利要求1所述的镍配合物（I）的合成方法，本合成方法包括合成和分离，其特征在于：所属的合成称取1.2134g(0.01mol)2-吡啶甲醛肟放入100mL圆底烧瓶中，加入40ml无水甲醇，搅拌使其溶解；在称取2.4818g(0.01mol)Ni(OAc)2·4H2O加入上述溶液中，控制温度在75℃左右，加热回流36h；趁热过滤反应溶液，将溶液用旋转蒸发仪旋至一半溶液，在剩余溶液中加入5ml左右正己烷，静置挥发；2天后，有黄色晶体析出；滤出晶体，将晶体用30～60℃石油醚冲洗3次，真空干燥30分钟，得到目标产物。
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CN105669772A (zh) * 2016-02-23 2016-06-15 合肥祥晨化工有限公司 一种镍配合物的制备及其合成方法

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GIUSEPPE D’ASCENZO: "THERMAL PROPERTIES OF SOME COMPLEXE-OF NICKEL(II) WITH PYRIDINE-2-ALDOXYME", 《THERMOCHLMICA ACTA》 *
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Application publication date: 20160928