CN106117178A - 一种钴配合物 - Google Patents

一种钴配合物 Download PDF

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CN106117178A
CN106117178A CN201610423976.9A CN201610423976A CN106117178A CN 106117178 A CN106117178 A CN 106117178A CN 201610423976 A CN201610423976 A CN 201610423976A CN 106117178 A CN106117178 A CN 106117178A
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cobalt complex
cobalt
synthetic method
crystal
benzimidazole
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罗梅
李亚周
徐佳
郭晨晨
张竞成
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Hefei University of Technology
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Hefei University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

一种钴配合物（I），其化学式如下： （Ⅰ）。一种钴配合物（I）的合成方法，本合成方法包括合成和分离；称取0.9762g2‑（2‑吡啶基）苯并咪唑放入100mL圆底烧瓶中，加入40mL无水乙醇并搅拌使其溶解；将0.6225g四水乙酸钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有红色晶体析出；将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物。

Description

一种钴配合物
技术领域
本发明涉及一种新化合物及其制备方法，特别涉及一种钴化合物及其制备方法，确切地说是一种苯并咪唑钴配合物的制备及合成方法。
背景技术
钴配合物是重要的催化剂和医药化工产品，其作为催化剂在二乙基锌与苯甲醛对映选择性加成反应等反应中有较好的催化效果。【1-5】
参考文献：
1.Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt(II)-achiral base complex and chiral amino alcohol conjugated systems.Oxidoreductase model with enantioselectivity ，Ohgo, Yoshiaki; Natori,Yukikazu; Takeuchi, Seiji; Yoshimura, Juji , Chemistry Letters (1974), (11),1327-30.
Synthesis, structure and acid-base properties of cobalt(III) complexeswith aminoalcohols tepanenko, O. N.; Reiter, 2. L. G. Ukrainskii KhimicheskiiZhurnal (Russian Edition), (1992), 58(12), 1047-54.
3. Cobalt(III) mono- and trinuclear complexes with O,N-chelatingaminoalcohols apanadze, T. Sh.; Gulya, A. P.; Novotortsev, V. M.; Ellert, O.G.; Shcherbakov, V. M.; Kokunov, Yu. V.; Bushaev, Yu. A. KoordinatsionnayaKhimiya (1991), 17(7), 934-40.
4. Magnetic properties of cobalt complexes with amino alcohols, Evreev,V. N.; Bogdanov, A. P. 13 Vses. Chugaev. Soveshch. po Khimii Kompleks.Soedin., 1978 (1978), 137.
5.Synthesis, stereochemistry, and reactions of cobalt(III) complexes withamino alcohol ligands
Okamoto, Martha S. No Corporate Source data available | (1974), 146 pp.
6.Synthesis and properties of isomeric tris(N-[2-hydroxyethyl]ethylenediamine)cobalt(III) and tris(N-[2-hydroxypropyl]ethylenediamine)cobalt(III) chlorides, arpeiskaya, E. I.; Kukushkin, Yu. N.; Trofimov, V. A.;Yakovlev, I. P. , Zhurnal Neorganicheskoi Khimii (1971), 16(7), 1960-4。
发明内容
本发明旨在提供含一分子甲醇的三苯并咪唑钴配合物，所要解决的技术问题是一步合成得到目标产物。
本发明所称的钴配合物是由与苯并咪唑及四水乙酸钴制备的由以下化学式所示的化合物：
(I)。
化学名称：含一分子甲醇的三苯并咪唑钴配合物,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47%。
本合成方法包括合成和分离,其合成方法是称取0.9762g 2-（2-吡啶基）苯并咪唑放入100mL圆底烧瓶中，加入40mL无水甲醇并搅拌使其溶解；将0.6225g四水乙酸钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有红色晶体析出；将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物。
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是含一分子甲醇的三苯并咪唑钴配合物的单晶X-衍射图。
具体实施方式
含一分子甲醇的三苯并咪唑钴配合物的制备：
称取0.9762g2-（2-吡啶基）苯并咪唑放入100mL圆底烧瓶中，加入40mL无水甲醇并搅拌使其溶解；将0.6225g四水乙酸钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有红色晶体析出。
将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物，产率为42%，熔点98°C-100°C。元素分析数据C37H31CoN9O，理论值：C： 65.68%； H：4.62%；N：18.63%； 实测值：C：65.69%； H：4.45%；N：18.60%；红外光谱数据(KBr, cm-1)：3043；2815；1610；1562；1525；1448；1382；1278；1103；1031；784；763；736；698；657；
化合物的晶体数据：
经验式 C37H28N9O1Co
分子量 673.61’
温度 293(2) K
波长 0.71073 Å
晶系， 空间群 单斜晶系, P2(1)/n
晶胞参数 a = 10.948(4) Å alpha = 90°.
b = 14.377 (6) Å beta = 99.345(9)°.
c = 20.141(8) Å gamma = 90°.
体积 3128(2) Å^3
电荷密度 4, 1.430g/m^3
吸收 校正参数 0.596mm^-1
单胞内的电子数目 1392
晶体大小 0.180x 0.130x 0.100 mm
Theta 角的范围 1.748 to 24.995°
HKL的指标收集范围 -13<=h<=12, -15<=k<17, -23<=l<=18
收集/独立衍射数据 16257/ 5496 [R(int) = 0.1510]
theta = 30.5的数据完整度 97.1 %
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 5496/0/435
精修使用的方法 0.993
衍射点的一致性因子 R1 = 0.0752，wR2= 0.1662
可观察衍射的吻合因子 R1 = 0.1218, wR2 = 0.1870
差值傅里叶图上的最大峰顶和峰谷 0.748 and -0.622e.A^-3
晶体典型的键长数据：
Co(1)-N(1) 1.912(4)
Co(1)-N(7) 1.919(4)
Co(1)-N(4) 1.919(4)
Co(1)-N(6) 1.943(4)
Co(1)-N(9) 1.944(4)
Co(1)-N(3) 1.963(4)
N(1)-C(7) 1.356(6)
N(1)-C(6) 1.374(6)
N(2)-C(7) 1.315(6)
N(2)-C(1) 1.375(6)
N(3)-C(12) 1.339(6)
N(3)-C(8) 1.358(6)
N(4)-C(19) 1.353(6)
N(4)-C(13) 1.394(6)
N(5)-C(19) 1.312(6)
N(5)-C(18) 1.365(6)
N(6)-C(24) 1.323(6)
N(6)-C(20) 1.352(6)
N(7)-C(31) 1.358(6)
N(7)-C(25) 1.376(6)
N(8)-C(31) 1.323(6)
N(8)-C(30) 1.371(7)
N(9)-C(36) 1.345(6)
N(9)-C(32) 1.354(6)
O(1)-C(37) 1.377(7)
O(1)-H(1) 0.8200
C(1)-C(2) 1.399(7)
C(1)-C(6) 1.403(7)
C(2)-C(3) 1.353(8)
C(2)-H(2) 0.9300
C(3)-C(4) 1.409(9)
C(3)-H(3) 0.9300
C(4)-C(5) 1.369(8)
C(4)-H(4) 0.9300
C(5)-C(6) 1.386(7)
C(5)-H(5) 0.9300
C(7)-C(8) 1.438(6)
C(8)-C(9) 1.384(7)
C(9)-C(10) 1.366(7)
C(9)-H(9) 0.9300
C(10)-C(11) 1.359(7)
C(10)-H(10) 0.9300
C(11)-C(12) 1.366(7)
C(11)-H(11) 0.9300
C(12)-H(12) 0.9300
C(13)-C(14) 1.385(7)
C(13)-C(18) 1.396(7)
C(14)-C(15) 1.364(7)
C(14)-H(14) 0.9300
C(15)-C(16) 1.391(9)
C(15)-H(15) 0.9300
C(16)-C(17) 1.354(8)
C(16)-H(16) 0.9300
C(17)-C(18) 1.395(7)
C(17)-H(17) 0.9300
C(19)-C(20) 1.440(7)
C(20)-C(21) 1.393(7)
C(21)-C(22) 1.373(7)
C(21)-H(21) 0.9300
C(22)-C(23) 1.363(8)
C(22)-H(22) 0.9300
C(23)-C(24) 1.379(7)
C(23)-H(23) 0.9300
C(24)-H(24) 0.9300
C(25)-C(26) 1.393(7)
C(25)-C(30) 1.404(7)
C(26)-C(27) 1.357(8)
C(26)-H(26) 0.9300
C(27)-C(28) 1.388(9)
C(27)-H(27) 0.9300
C(28)-C(29) 1.369(8)
C(28)-H(28) 0.9300
C(29)-C(30) 1.395(7)
C(29)-H(29) 0.9300
C(31)-C(32) 1.430(7)
C(32)-C(33) 1.386(7)
C(33)-C(34) 1.367(8)
C(33)-H(33) 0.9300
C(34)-C(35) 1.381(8)
C(34)-H(34) 0.9300
C(35)-C(36) 1.367(7)
C(35)-H(35) 0.9300
C(36)-H(36) 0.9300
C(37)-H(37A) 0.9600
C(37)-H(37B) 0.9600
C(37)-H(37C) 0.9600
晶体典型的键角数据
N(1)-Co(1)-N(7) 94.97(16)
N(1)-Co(1)-N(4) 174.79(17)
N(7)-Co(1)-N(4) 89.30(16)
N(1)-Co(1)-N(6) 93.87(17)
N(7)-Co(1)-N(6) 93.42(17)
N(4)-Co(1)-N(6) 82.86(17)
N(1)-Co(1)-N(9) 89.86(16)
N(7)-Co(1)-N(9) 83.22(17)
N(4)-Co(1)-N(9) 93.63(17)
N(6)-Co(1)-N(9) 175.19(16)
N(1)-Co(1)-N(3) 82.51(16)
N(7)-Co(1)-N(3) 175.34(17)
N(4)-Co(1)-N(3) 93.44(16)
N(6)-Co(1)-N(3) 90.66(17)
N(9)-Co(1)-N(3) 92.83(16)
C(7)-N(1)-C(6) 104.3(4)
C(7)-N(1)-Co(1) 114.0(3)
C(6)-N(1)-Co(1) 141.4(3)
C(7)-N(2)-C(1) 102.1(4)
C(12)-N(3)-C(8) 117.9(4)
C(12)-N(3)-Co(1) 127.6(3)
C(8)-N(3)-Co(1) 114.2(3)
C(19)-N(4)-C(13) 104.1(4)
C(19)-N(4)-Co(1) 114.0(3)
C(13)-N(4)-Co(1) 141.9(3)
C(19)-N(5)-C(18) 102.7(4)
C(24)-N(6)-C(20) 118.6(5)
C(24)-N(6)-Co(1) 127.0(4)
C(20)-N(6)-Co(1) 114.3(3)
C(31)-N(7)-C(25) 103.8(4)
C(31)-N(7)-Co(1) 113.2(3)
C(25)-N(7)-Co(1) 142.2(3)
C(31)-N(8)-C(30) 102.7(4)
C(36)-N(9)-C(32) 118.2(4)
C(36)-N(9)-Co(1) 128.0(3)
C(32)-N(9)-Co(1) 113.8(3)
C(37)-O(1)-H(1) 109.5
N(2)-C(1)-C(2) 128.3(5)
N(2)-C(1)-C(6) 111.0(5)
C(2)-C(1)-C(6) 120.7(5)
C(3)-C(2)-C(1) 117.2(6)
C(3)-C(2)-H(2) 121.4
C(1)-C(2)-H(2) 121.4
C(2)-C(3)-C(4) 122.1(6)
C(2)-C(3)-H(3) 118.9
C(4)-C(3)-H(3) 118.9
C(5)-C(4)-C(3) 121.3(6)
C(5)-C(4)-H(4) 119.3
C(3)-C(4)-H(4) 119.3
C(4)-C(5)-C(6) 117.1(6)
C(4)-C(5)-H(5) 121.5
C(6)-C(5)-H(5) 121.5
N(1)-C(6)-C(5) 132.5(5)
N(1)-C(6)-C(1) 105.9(4)
C(5)-C(6)-C(1) 121.5(5)
N(2)-C(7)-N(1) 116.7(4)
N(2)-C(7)-C(8) 127.1(4)
N(1)-C(7)-C(8) 116.2(4)
N(3)-C(8)-C(9) 121.6(5)
N(3)-C(8)-C(7) 112.5(4)
C(9)-C(8)-C(7) 125.9(4)
C(10)-C(9)-C(8) 119.1(5)
C(10)-C(9)-H(9) 120.5
C(8)-C(9)-H(9) 120.5
C(11)-C(10)-C(9) 119.1(5)
C(11)-C(10)-H(10) 120.4
C(9)-C(10)-H(10) 120.4
C(10)-C(11)-C(12) 120.1(5)
C(10)-C(11)-H(11) 119.9
C(12)-C(11)-H(11) 119.9
N(3)-C(12)-C(11) 122.1(5)
N(3)-C(12)-H(12) 119.0
C(11)-C(12)-H(12) 119.0
C(14)-C(13)-N(4) 132.3(5)
C(14)-C(13)-C(18) 122.3(5)
N(4)-C(13)-C(18) 105.3(4)
C(15)-C(14)-C(13) 116.5(5)
C(15)-C(14)-H(14) 121.8
C(13)-C(14)-H(14) 121.8
C(14)-C(15)-C(16) 122.0(6)
C(14)-C(15)-H(15) 119.0
C(16)-C(15)-H(15) 119.0
C(17)-C(16)-C(15) 121.6(6)
C(17)-C(16)-H(16) 119.2
C(15)-C(16)-H(16) 119.2
C(16)-C(17)-C(18) 118.1(6)
C(16)-C(17)-H(17) 121.0
C(18)-C(17)-H(17) 121.0
N(5)-C(18)-C(17) 129.1(5)
N(5)-C(18)-C(13) 111.5(4)
C(17)-C(18)-C(13) 119.4(5)
N(5)-C(19)-N(4) 116.4(5)
N(5)-C(19)-C(20) 128.3(5)
N(4)-C(19)-C(20) 115.3(5)
N(6)-C(20)-C(21) 121.3(5)
N(6)-C(20)-C(19) 113.3(5)
C(21)-C(20)-C(19) 125.3(5)
C(22)-C(21)-C(20) 118.8(5)
C(22)-C(21)-H(21) 120.6
C(20)-C(21)-H(21) 120.6
C(23)-C(22)-C(21) 119.5(6)
C(23)-C(22)-H(22) 120.3
C(21)-C(22)-H(22) 120.3
C(22)-C(23)-C(24) 119.1(5)
C(22)-C(23)-H(23) 120.5
C(24)-C(23)-H(23) 120.5
N(6)-C(24)-C(23) 122.7(5)
N(6)-C(24)-H(24) 118.6
C(23)-C(24)-H(24) 118.6
N(7)-C(25)-C(26) 133.6(5)
N(7)-C(25)-C(30) 106.7(5)
C(26)-C(25)-C(30) 119.7(5)
C(27)-C(26)-C(25) 118.3(6)
C(27)-C(26)-H(26) 120.8
C(25)-C(26)-H(26) 120.8
C(26)-C(27)-C(28) 122.0(6)
C(26)-C(27)-H(27) 119.0
C(28)-C(27)-H(27) 119.0
C(29)-C(28)-C(27) 121.2(6)
C(29)-C(28)-H(28) 119.4
C(27)-C(28)-H(28) 119.4
C(28)-C(29)-C(30) 117.4(6)
C(28)-C(29)-H(29) 121.3
C(30)-C(29)-H(29) 121.3
N(8)-C(30)-C(29) 128.3(5)
N(8)-C(30)-C(25) 110.4(5)
C(29)-C(30)-C(25) 121.2(5)
N(8)-C(31)-N(7) 116.3(5)
N(8)-C(31)-C(32) 127.9(5)
N(7)-C(31)-C(32) 115.7(4)
N(9)-C(32)-C(33) 122.0(5)
N(9)-C(32)-C(31) 113.7(4)
C(33)-C(32)-C(31) 124.3(5)
C(34)-C(33)-C(32) 118.6(5)
C(34)-C(33)-H(33) 120.7
C(32)-C(33)-H(33) 120.7
C(33)-C(34)-C(35) 119.8(5)
C(33)-C(34)-H(34) 120.1
C(35)-C(34)-H(34) 120.1
C(36)-C(35)-C(34) 119.0(5)
C(36)-C(35)-H(35) 120.5
C(34)-C(35)-H(35) 120.5
N(9)-C(36)-C(35) 122.4(5)
N(9)-C(36)-H(36) 118.8
C(35)-C(36)-H(36) 118.8
O(1)-C(37)-H(37A) 109.5
O(1)-C(37)-H(37B) 109.5
H(37A)-C(37)-H(37B) 109.5
O(1)-C(37)-H(37C) 109.5
H(37A)-C(37)-H(37C) 109.5
H(37B)-C(37)-H(37C) 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24小时后，进行1HNMR检测。1HNMR (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)。

Claims (3)

1.一种钴配合物（I），其化学式如下：
（Ⅰ）。
2.权利要求1所述的钴配合物（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，其特征在于晶体属斜方晶系,空间群单斜晶系,P2(1)/n 晶胞参数 a = 10.948(4) Å alpha = 90°;b = 14.377 (6) Å beta = 99.345(9)°;c = 20.141(8) Å gamma = 90°。
3.权利要求1所述的钴配合物（I）的合成方法，本合成方法包括合成和分离，其特征在于：称取0.9762g2-（2-吡啶基）苯并咪唑放入100mL圆底烧瓶中，加入40mL无水乙醇并搅拌使其溶解；将0.6225g四水乙酸钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有红色晶体析出；将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物。
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