CN107417709A - A kind of preparation of Zn complex crystal and its synthetic method - Google Patents
A kind of preparation of Zn complex crystal and its synthetic method Download PDFInfo
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- CN107417709A CN107417709A CN201710645428.5A CN201710645428A CN107417709A CN 107417709 A CN107417709 A CN 107417709A CN 201710645428 A CN201710645428 A CN 201710645428A CN 107417709 A CN107417709 A CN 107417709A
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- 239000013078 crystal Substances 0.000 title claims abstract description 13
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000011701 zinc Substances 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 238000001556 precipitation Methods 0.000 claims abstract description 3
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 3
- 239000011592 zinc chloride Substances 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 241000254173 Coleoptera Species 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002447 crystallographic data Methods 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- GWSPYCNFOQMBGF-UHFFFAOYSA-L O.[Cl-].[Cl-].Cl.[Zn+2] Chemical compound O.[Cl-].[Cl-].Cl.[Zn+2] GWSPYCNFOQMBGF-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- OTMYLOBWDNFTLO-UHFFFAOYSA-N 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine Chemical compound C1=CC=CC=C1C1=NN=C(C=2N=CC=CC=2)N=C1C1=CC=CC=C1 OTMYLOBWDNFTLO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical class Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- -1 Zinc nitrogen metal complex Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical class C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
-
- 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
- C07B2200/07—Optical isomers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
Abstract
A kind of Zn complex, its chemical formula are as follows：The synthetic method of the Zn complex (I), it is to weigh the triazine of 5,6 xenyls 3 (2 pyridine radicals) of 0.0798g 1,2,4 to be put into 100mL round-bottomed flasks, adding 50mL absolute methanols and stirring makes its dissolving；0.0702g zinc chloride are added into above-mentioned solution, are heated to reflux 48h；Reaction terminate after while hot filtering reacting solution, filtrate volatilize naturally, have crystal precipitation after a couple of days.
Description
First, technical field
The present invention relates to a kind of organometallic complex (complex) and preparation method thereof, more particularly to nitrogenous gold
Belong to organic coordination compound and preparation method thereof, be exactly one kind 5,6- xenyls -3- (2- pyridine radicals) -1,2,4- tri- azine zinc
Complex crystal and its synthetic method.
2nd, background technology
With the development of organic chemistry, application of the metallo-organic compound in organic synthesis is more and more wide, be now with
One of extremely active field, has been widely used in organic synthesis in chemical machine.Later stage the 1960s occurs
The asymmetric catalysis synthesis being catalyzed using chiral ligand and transition metal complex greatly accelerated the research of chiral drug.Closely
Zinc nitrogen metal complex achieves preferable catalytic effect in catalytic field over year：
Bibliography：
1.Michaels,Heather A.；Murphy,Christopher S.；Clark,Ronald J.；Davidson,
Michael W.；Zhu,Lei.Inorganic Chemistry(2010),49(9),4278-4287；
2..Mei,Luo；Ming,Tang Hai；Rong,Li Qian；Jie,Sun；Zhong,Yang Shan；Liang,
Li Xue.Journal of Chemical Sciences(Bangalore,India)(2009),121(4),435-440；
3.Dong,Qingchen；Ma,Xiaping；Guo,Jianping；Wei,Xuehong；Zhou,Meisu；Liu,
Diansheng.Inorganic Chemistry Communications(2008),11(6),608-611；Similar 5,6- connection
The existing document report of the azine Zn complex crystal of phenyl -3- (2- pyridine radicals) -1,2,4- three：
4.Coordination studies of 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine
towards Zn2+cation.Synthesis and characterization by X-ray diffraction and
Spectroscopic methods, Bereau, Virginie and Marrot, Jerome, Comptes Rendus
Chimie,8(6-7),1087-1092；2005.
3rd, the content of the invention
The present invention is intended to provide a kind of Zn-N metal organic complexes applied to catalytic field, technology to be solved to ask
Topic selects the azines of 5,6- xenyls -3- (2- pyridine radicals) -1,2,4- three as part and synthesis of chiral Zn complex.Institute of the present invention
Manganese complex one kind of title be by the azines of 5,6- xenyls -3- (2- pyridine radicals) -1,2,4- three and zinc chloride prepare by following
Complex shown in chemical formula：
Chemical name：One trichloride hydrate zinc [azines of 5,6- xenyls -3- (2- pyridine radicals) -1,2,4- three] protochloride zinc
Complex
The complex shows preferable catalytic performance in the Henle reaction and nitrile silicification reaction 1 of benzaldehyde, and it is converted
Rate is respectively 70% and 32%.
This synthetic method includes synthesis and separation, and described synthesis is to weigh 0.0798g5,6- xenyls -3- (2- pyridines
Base) -1,2,4- triazines are put into 100mL round-bottomed flasks, and adding 50mL absolute methanols and stirring makes its dissolving；By 0.0702g chlorine
Change zinc and add above-mentioned solution, be heated to reflux 48h；Filtering reacting solution, filtrate are volatilized, had after a couple of days naturally while hot after reaction terminates
Crystal separates out.
Synthetic reaction is as follows：
The step of this synthetic method one obtains target product, and technique is simple, easy to operate.
4th, illustrate
The trichloride hydrate zinc of Fig. 1 mono- [azines of 5,6- xenyls -3- (2- pyridine radicals) -1,2,4- three] protochloride Zn complex
X- diffraction analysis figures.
5th, embodiment
0.3006g5 is weighed, 6- xenyls -3- (2- pyridine radicals) -1,2,4- triazines are put into 100mL round-bottomed flasks, are added
50mL absolute methanols and stir make its dissolving；0.3880g manganese chlorides are added into above-mentioned solution, are heated to reflux 48h；After reaction terminates
Filtering reacting solution while hot, filtrate are volatilized naturally, there is crystal precipitation after a couple of days；Crystal petroleum ether and n-hexane are rinsed 3 times,
30min is dried in vacuo, obtains target product, yield 65%, 232-234 DEG C of fusing point.Elemental analysis data
(C40H30Cl4N8OZn2) theoretical value：C：62.84%；H：3.96%；N：14.66%；Measured value：C：62.55%；H：
3.66%；N：14.24%；Ir data (KBr, cm-1)：3455；3053；1652；1596；1512；1446；1409；
1371；1300；1260；1225；1185；1107；1011；883；799；768；696；597；535；516.
Match crystal volume data is as follows：
The typical bond distance's data of crystal：
The typical bond angle data of crystal：
Henle reaction application
0.0453g (0.075mmol) complex is weighed, is placed in 25mL small flask, adds 1mL DMSO, then to solution
Middle addition 0.05mL benzaldehydes and 0.25mL nitromethanes, stirring reaction is carried out after 24 hours under normal temperature1HNMR detection conversions
Rate：70%；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)。
Nitrile silicification reaction application
The preparation of 2- phenyl -2- (three silyloxies) acetonitrile
0.15mmol compound I, benzaldehyde 0.1mL, TMSCN 0.3ml (3.3mmol) are added at 20~30 DEG C in succession,
After 72h, add water quenching and go out after post layer (petroleum ether/dichloromethane：5/1) colourless oil liquid, conversion ratio, are obtained：32%,1HNMR(300MHz,CDCl3)7.56–7.59(m,0.9Hz,2H),7.31–7.34(m,3H),5.43(s,1H),0.16(s,
9H).13C NMR(75MHz,CDCl3)136.1,128.8(x2),126.2(x2),119.1,63.5,-0.39(x3)。
Claims (3)
1. a kind of Zn complex, its chemical formula is as follows：
2. the Zn complex (I) described in claim 1, at a temperature of 296K, on the X-ray single crystal diffractometer of Oxford, with through stone
The CuK alpha rays of black monochromator monochromatization,Diffraction data is collected with ω-θ scan modes, it is characterised in thatIt is single
Oblique system, the 21/c 1 of P 1；Cell parameter α=90 °；β=110.102 (2) °；γ=90 °.
3. the synthetic method of the Zn complex (I) described in claim 1, including synthesize and separate, described synthesis is to weigh
0.0798g 5,6- xenyl -3- (2- pyridine radicals) -1,2,4- triazines are put into 100mL round-bottomed flasks, add 50mL without water beetle
Alcohol and stir make its dissolving；0.0702g zinc chloride are added into above-mentioned solution, are heated to reflux 48h；Filtering while hot is anti-after reaction terminates
Solution is answered, filtrate is volatilized naturally, there is crystal precipitation after a couple of days.
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| CN201710645428.5A CN107417709B (en) | 2017-08-01 | 2017-08-01 | A kind of preparation and its synthetic method of Zn complex crystal |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438420A (en) * | 2018-11-08 | 2019-03-08 | 南京工业大学 | A kind of imines zinc s-triazine complex |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432293A (en) * | 2016-10-05 | 2017-02-22 | 合肥祥晨化工有限公司 | Chiral zinc complex |
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2017
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106432293A (en) * | 2016-10-05 | 2017-02-22 | 合肥祥晨化工有限公司 | Chiral zinc complex |
Non-Patent Citations (1)
| Title |
|---|
| FARZIN MARANDI等: ""Zinc(II) and Cadmium(II) Complexes of the 3-(2-Pyridyl)-5,6-diphenyl-1,2,4-triazine (PDPT) Ligand, Structural Studies of [Zn(PDPT)2Cl(ClO4)] and [Cd(PDPT)2(NO3)(ClO4)]"", 《Z.ANORG.ALLG.CHEM.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438420A (en) * | 2018-11-08 | 2019-03-08 | 南京工业大学 | A kind of imines zinc s-triazine complex |
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