CN104788363B - 一种三氮烯‑钴(iii)单核配合物及其制备方法 - Google Patents

一种三氮烯‑钴(iii)单核配合物及其制备方法 Download PDF

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CN104788363B
CN104788363B CN201510124059.6A CN201510124059A CN104788363B CN 104788363 B CN104788363 B CN 104788363B CN 201510124059 A CN201510124059 A CN 201510124059A CN 104788363 B CN104788363 B CN 104788363B
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程发良
张燕
张敏
柳鹏
陈妹琼
蔡志泉
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City College Dongguan University of Technology
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Abstract

2‑氨基吡啶基三氮烯为配体，合成出了未见报道的三氮烯‑钴(III)单核配合物Co(C13H11N4O2)3，并通过X‑ray单晶衍射对配合物晶体结构进行了表征，配合物属三斜晶系，P1空间群，晶胞参数：a=15.929(2)Å，b=15.929(2)Å，c=63.589(13)Å，α=90o，β=90o，γ=120o；分子式：C39H33N12CoO6，Mr=823.26，V=1397.3(4)Å3，Z=2，Dc=1.320 Mgm‑3，F(000)=577，I>2σ(I)的数据：最终偏离因子R 1=0.0697，wR 2=0.1593；全部数据：R 1=0.0756，wR 2=0.1566。

Description

一种三氮烯-钴(III)单核配合物及其制备方法
技术领域
本发明属三氮烯金属配合物制备领域，尤其涉及一种三氮烯-钴(III)单核配合物及其制备方法。
背景技术
三氮烯是指含有重氮化氨基基团(-N=N-N<)的化合物，三氮烯类化合物因其含有重氮化氨基基团(-N=N-N<)，具有较好的热力学稳定性及可修饰性，进而容易与金属离子形成三氮烯-金属配合物，因此，三氮烯类化合物在药物学、全合成、聚合物技术、构建异环体系等领域具有广阔的应用前景。自Meldola首次合成出三氮烯类配体并将其应用于三氮烯过渡金属配合物后，大量的过渡金属三氮烯配合物已经被人们研究。由于三氮烯与金属潜在的多种配位模式，所以对其的研究逐渐增多，它可以作为单齿配体；螯合配体或者是两个金属中心之间的桥联配体与金属配位。目前为止包括 K, Ca, Mg, Al, Cu, Pt, Pd, Ag,Co, Ru, Os 等大量三氮烯类金属配合物都已经成功合成。本发明以2-氨基吡啶基三氮烯为配体，合成出了未见报道的三氮烯-钴(III)单核配合物Co(C13H11N4O2)3，并通过X-ray单晶衍射对配合物晶体结构进行了表征。
发明内容
本发明的目的是为了提供了一种新的三氮烯-钴(III)单核配合物及其制备方法，为今后研究三氮烯-钴(III)单核配合物的性质及应用打下基础。
本发明的目的可以通过以下技术方案来实现：
一种新的三氮烯-钴(III)单核配合物的制备方法，其特征在于，包括以下步骤：
(1) 将2.997 g邻氨基苯甲酸甲酯(19.3 mmol)溶解于55 mL(1 mol/L)的盐酸中，在0-5℃搅拌下，缓慢滴加0.2 g/mL的亚硝酸钠水溶液10 mL，滴加完毕后，使重氮化完全，得到澄清的重氮盐溶液；
(2) 与2-氨基吡啶偶联
将1.816 g 2-氨基吡啶(19.3 mmol)溶于10 mL的乙醇溶液中，在0-5℃搅拌下缓慢加入上述重氮盐溶液中，搅拌45 min之后用饱和醋酸钠调节混合液的pH值为7左右，再反应6 h，静置，抽滤，干燥后的粗产品用乙酸乙酯和正己烷按照9：1 的比例-4℃下重结晶1天后，得到2.62g黄色柱状单晶（C13H12N4O2），即，1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯；元素分析实测值(%，理论值)：C 60.91(60.94)，H 4.66(4.68)，N 21.85(21.87)，产率：53.03%；
(3) 金属与2-氨基吡啶三氮烯单核配合物[Co(C13H11N4O2)3]的合成
称取0.0768g(0.3mmol)的1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯，将其溶解于含有5mLCH3CN和5mL乙酸乙酯的混合溶液中，加入3滴三乙胺，在搅拌条件下，加入0.0238g(0.1mmol) CoCl2·6H2O，在常温下磁力搅拌20min，过滤，得到黄色的澄清溶液，将所得黄色的澄清液静置5天，得到棕色块状晶体，即为三氮烯-钴(III)单核配合物[Co(C13H11N4O2)3]，产量：0.036g，产率：43.7% (以金属Co计算)，元素分析实测值（%，理论值）：C56.88(56.86)，H4.02(4.03)，N20.38(20.40)。
其中，2-氨基吡啶基三氮烯的合成原理为：在低温条件下，用盐酸和亚硝酸钠溶液将邻氨基苯甲酸甲酯重氮化完全，得到澄清重氮盐溶液，然后，在 0-5℃直接将上述重氮盐溶液与2-氨基吡啶的乙醇溶液偶合，之后再调节 pH值，最后合成目标产物1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯。
金属配合物[Co(C13H11N4O2)3] (尺寸约为0.4 x 0.3 x 0.25 mm)的单晶数据是在113 K下测定，用Bruker Smart 1000 CCD 单晶衍射仪，采用经石墨单色器单色化的MO-Ka射线，辐射波长λ = 0.71073 Å，全部吸收强度数据经SADABS校正。晶体结构通过直接法解出，计算方法采用SHELXTL-97程序，用差值Fourier合成确定所有非氢原子的坐标，所有非氢原子的坐标及各向异性参数采用Shelxl 97程序以小二乘法对F2进行结构精修，分子结构由ORTEP-3作出。
表1配合物[Co(C13H11N4O2)3]晶体数据和结构精修参数
Crystall data complex 1
Empirical formula Co(C13H11N4O2)3
Formula weight 823.62
λ(Å) 0.71073
Crystal system triclinic
Space group P1
Unit cell dimension (Å,°)
a 15.929(2)
b 15.929(2)
c 63.589(13)
α 90
β 90
γ 120
V(Å3) 1397.3(4)
Z 2
Dc(Mgm-3) 1.320
F(000) 577
θ range for data collection 1.51 to 27.01
Reflections collected/unique 7860 / 3221
Data/restraints/parameters 1203 / 0 / 83
Goodness-of-fit on F2 1.063
Final R indices [I>2σ(I)] R 1= 0.0697
wR 2= 0.1593
R indices(all data) R 1= 0.0756
wR 2=0.1566
_____________________________________________________________________
表2 配合物[Co(C13H11N4O2)3]的部分键长和键角
_____________________________________________________________________
Bond distances
Co(2)-N(2) 1.906(3) Co(2)-N(2)#3 1.906(3)
Co(2)-N(2)#4 1.906(3) Co(2)-N(4)#4 1.924(3)
Co(2)-N(4)#3 1.924(3) N(2)-N(1) 1.266(5)
N(2)-N(3) 1.337(5) N(4)-C(11) 1.351(5)
N(4)-C(15) 1.362(6) O(2)-C(7) 1.338(6)
O(2)-C(8) 1.461(6) N(1)-C(1) 1.436(5)
N(3)-C(15)#4 1.359(6) C(1)-C(2) 1.390(6)
C(1)-C(6) 1.390(7) C(14)-C(13) 1.368(7)
Bond angles
N(2)-Co(2)-N(2)#3 92.85(13) N(2)-Co(2)-N(2)#4 92.85(13)
N(2)#3-Co(2)-N(2)#4 92.85(13) N(2)-Co(2)-N(4) 90.95(14)
N(2)#3-Co(2)-N(4) 81.45(14) N(2)#4-Co(2)-N(4) 173.31(14)
N(2)-Co(2)-N(4)#4 81.45(14) N(2)#3-Co(2)-N(4)#4 173.31(14)
N(2)#4-Co(2)-N(4)#4 90.95(14) N(4)-Co(2)-N(4)#4 95.07(14)
N(2)-Co(2)-N(4)#3 173.31(15) N(2)#3-Co(2)-N(4)#3 90.95(14)
N(2)#4-Co(2)-N(4)#3 81.45(14) N(4)-Co(2)-N(4)#3 95.07(14)
N(4)#4-Co(2)-N(4)#3 95.07(14) N(1)-N(2)-N(3) 121.1(3)
N(1)-N(2)-Co(2) 121.1(3) N(3)-N(2)-Co(2) 117.7(3)
C(11)-N(4)-C(15) 120.2(4) C(11)-N(4)-Co(2) 129.1(3)
N(2)-N(1)-C(1) 117.0(3) N(2)-N(3)-C(15)#4 110.1(3)
_____________________________________________________________________
配合物[Co(C13H11N4O2)3]属于三斜晶系，P1空间群，单晶 X-射线衍射分析结果表明配合物中包含一个单核钴的[Co(C13H11N4O2)3]的结构，该结构由三个去质子化的1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯配体与一个钴配位连接组成，Co与三氮烯上的N及来自吡啶结构中杂环上的 N进行配位，是典型的六配位对称结构，其ORTEP图及原子编号见说明书附图图2。
钴原子配位数为六，分别与配体吡啶环上三个氮原子和三氮烯上三个氮原子相连，其中Co(2)-N(2)、Co(2)-N(2)#3和Co(2)-N(2)#4的键长为1.906(3)Å，Co(2)-N(4)#4和Co(2)-N(4)#3的键长为1.924(3)Å，Co(2)-N(2)#4的键长为1.906(3)Å，N(2)-N(1)的键长为1.351(5)Å，N(2)-N(3)的键长为1.337(5)Å；N(2)-Co(2)-N(2)#3、N(2)-Co(2)-N(2)#4和N(2)#3-Co(2)-N(2)#4的键角为92.85(13)o，N(2)-Co(2)-N(4)、N (2)#4-Co(2)-N(4)#4、N(2)#3-Co(2)-N(4)#3、N(4)#4-Co(2)-N(4)#3的键角为90.95(14)o，N(2)#3-Co(2)-N(4)、N(2)-Co(2)-N(4)#4、N(2)#4-Co(2)-N(4)#3的键角为81.45(14)o，N(2)#3-Co(2)-N(4)#4、N(2)-Co(2)-N(4)#3、N(2)#3-Co(2)-N(4)#4的键角为173.31(14)o。
附图说明
图1为本发明1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯的合成步骤；
图2为采用ORTEP作出的配合物[Co(C13H11N4O2)3]的晶体结构图。
具体实施方式
实施例1
(1) 将2.997 g邻氨基苯甲酸甲酯(19.3 mmol)溶解于55 mL(1 mol/L)的盐酸中，在0-5℃搅拌下，缓慢滴加0.2 g/mL的亚硝酸钠水溶液10 mL，滴加完毕后，使重氮化完全，得到澄清的重氮盐溶液；
(2) 与2-氨基吡啶偶联
将1.816 g 2-氨基吡啶(19.3 mmol)溶于10 mL的乙醇溶液中，在0-5℃搅拌下缓慢加入上述重氮盐溶液中，搅拌45 min之后用饱和醋酸钠调节混合液的pH值为7左右，再反应6 h，静置，抽滤，干燥后的粗产品用乙酸乙酯和正己烷按照9：1 的比例-4℃下重结晶1天后，得到2.62g黄色柱状单晶（C13H12N4O2），即，1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯；元素分析实测值(%，理论值)：C 60.91(60.94)，H 4.66(4.68)，N 21.85(21.87)，产率：53.03%；
(3) 金属与2-氨基吡啶三氮烯单核配合物[Co(C13H11N4O2)3]的合成
称取0.0768g(0.3mmol)的1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯，将其溶解于含有5mLCH3CN和5mL乙酸乙酯的混合溶液中，加入3滴三乙胺，在搅拌条件下，加入0.0238g(0.1mmol) CoCl2·6H2O，在常温下磁力搅拌20min，过滤，得到黄色的澄清溶液，将所得黄色的澄清液静置5天，得到棕色块状晶体，即为三氮烯-钴(III)单核配合物[Co(C13H11N4O2)3]，产量：0.036g，产率：43.7% (以金属Co计算)，元素分析实测值（%，理论值）：C56.88(56.86)，H4.02(4.03)，N20.38(20.40)。

Claims (1)

1.一种三氮烯-钴(III)单核配合物制备方法，其特征在于，包括以下步骤：
(1) 将2.997 g邻氨基苯甲酸甲酯溶解于55 mL 1 mol/L的盐酸中，在0-5℃搅拌下，缓慢滴加0.2 g/mL的亚硝酸钠水溶液10 mL，滴加完毕后，使重氮化完全，得到澄清的重氮盐溶液；
(2) 与2-氨基吡啶偶联
将1.816 g 2-氨基吡啶溶于10 mL的乙醇溶液中，在0-5℃搅拌下缓慢加入上述重氮盐溶液中，搅拌45 min之后用饱和醋酸钠调节混合液的pH值为7，再反应6 h，静置，抽滤，干燥后的粗产品用乙酸乙酯和正己烷按照9：1 的比例-4℃下重结晶1天后，得到2.62g黄色柱状单晶C13H11N4O2，即，1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯；元素分析实测值(%，理论值)：C 60.91(60.94)，H 4.66(4.68)，N 21.85(21.87)，产率：53.03%；
(3) 三氮烯单核配合物[Co(C13H11N4O2)3]的合成
称取0.0768g的1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯，将其溶解于含有5mL CH3CN和5mL乙酸乙酯的混合溶液中，加入3滴三乙胺，在搅拌条件下，加入0.0238g CoCl2·6H2O，在常温下磁力搅拌20min，过滤，得到黄色的澄清溶液，将所得黄色的澄清液静置5天，得到棕色块状晶体，即为三氮烯-钴(III)单核配合物[Co(C13H11N4O2)3]，产量：0.036g，以金属Co计算，产率43.7% ，元素分析实测值（%，理论值）：C56.88(56.86)，H4.02(4.03)，N20.38(20.40)；其中，配合物中包含一个单核钴的[Co(C13H11N4O2)3]的结构，该结构由三个去质子化的1-[(2-羧甲基)苯]-3-[2-(吡啶)]三氮烯配体与一个钴配位连接组成，Co与三氮烯上的N及来自吡啶结构中杂环上的 N进行配位，钴原子配位数为六，分别与配体吡啶环上三个氮原子和三氮烯上三个氮原子相连，配合物[Co(C13H11N4O2)3]属于三斜晶系，P1空间群，晶胞参数为：a = 15.929(2)Å，b = 15.929(2) Å，c = 63.589(13)Å，α = 90o，β = 90o，γ =120o，V = 1397.3(4) Å3，Z = 2，Dc = 1.320 Mgm-3，F(000) = 577，I >2σ(I)的数据：最终偏离因子R 1= 0.0697，wR 2 = 0.1593；全部数据：R 1 = 0.0756，wR 2 = 0.1566。
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