CN109251225A - Pyrazoles -3- formic acid nickel complex and preparation method - Google Patents
Pyrazoles -3- formic acid nickel complex and preparation method Download PDFInfo
- Publication number
- CN109251225A CN109251225A CN201811303819.XA CN201811303819A CN109251225A CN 109251225 A CN109251225 A CN 109251225A CN 201811303819 A CN201811303819 A CN 201811303819A CN 109251225 A CN109251225 A CN 109251225A
- Authority
- CN
- China
- Prior art keywords
- pyrazoles
- formic acid
- complex
- nickel complex
- atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000010668 complexation reaction Methods 0.000 title abstract description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000019253 formic acid Nutrition 0.000 claims abstract description 11
- 150000002500 ions Chemical class 0.000 claims abstract description 9
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims abstract description 8
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims abstract description 8
- 230000036571 hydration Effects 0.000 claims abstract description 5
- 238000006703 hydration reaction Methods 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001455 metallic ions Chemical class 0.000 claims description 4
- 229910018553 Ni—O Inorganic materials 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000003927 aminopyridines Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 229910001220 stainless steel Inorganic materials 0.000 claims description 3
- 239000010935 stainless steel Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 229910052759 nickel Inorganic materials 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 2
- 238000001027 hydrothermal synthesis Methods 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000013110 organic ligand Substances 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a kind of pyrazoles -3- formic acid nickel complex and preparation methods.Pyrazoles -3- formic acid nickel complex belongs to anorthic system, and space group isPī.In the complex, pyrazoles -3- formic acid is with bidentate bridging, the form and metal ion Ni (II) ion coordination of chelating, 4-dimethylaminopyridine in the form of monodentate with metal ion Ni (II) ion coordination.The present invention is ligand and six hydration nickel sulfate by hydro-thermal method acquisition nickel complex using pyrazoles -3- formic acid, 4-dimethylaminopyridine, has many advantages, such as simple process, low in cost, reproducible, the complex for synthesis transition metal provides certain foundation.
Description
Technical field
The invention belongs to complex preparation technical field, in particular to a kind of pyrazoles -3- formic acid nickel complex and preparation side
Method.
Background technique
Pyrazole carboxylic acid class organic ligand has good coordination ability, can pass through monodentate, bidentate bridging, bidentate chelating etc.
A variety of coordination modes and central metallic ions are coordinated, and have very high bioactivity, are widely used in medicine, agriculture
Medicine, dyestuff etc., therefore it is played a very important role in Coordinative Chemistry, such as pyrazoles -3- formic acid.In addition, 4- diformazan
There is aminopyridine intramolecular to be conjugated big pi bond, and product can be measured as highly effective chromophore, and have good
Intramolecular electron transmission and energy transmission property, it is possible to as good assistant ligand.Transiting metal nickel, pyrazoles -3- first
There are rich and varied structures for the complex that acid is formed with 4-dimethylaminopyridine, for the complex of design synthesis object construction
Get a good eye meaning.
Summary of the invention
The object of the present invention is to provide a kind of pyrazoles -3- formic acid nickel complex and preparation methods.
Thinking of the invention: being that ligand and six hydration nickel sulfate pass through water using pyrazoles -3- formic acid, 4-dimethylaminopyridine
Thermal method obtains nickel complex.
The molecular structure of pyrazoles -3- formic acid nickel complex of the present invention is shown in attached drawing 1.It is tiltedly brilliant that the complex belongs to three
System, space group arePī, central metallic ions are Ni (II) ion.In the complex, minimum structural unit is by two Ni
(II) ion, two pyrazoles -3- formate anions, four 4-dimethylaminopyridine neutral molecules and four hydrone compositions.
Center Ni1 ion is respectively with the oxygen atom (N1, O2) on the nitrogen-atoms and carboxyl of a pyrazoles -3- formate anion with bidentate
The form of chelating is coordinated, and is coordinated in the form of monodentate with the nitrogen-atoms (N2A) of another pyrazoles -3- formate anion, with two
Two nitrogen-atoms (N3, N5) of a 4-dimethylaminopyridine neutral molecule are coordinated in the form of monodentate, and with a hydrone
(O3) it is coordinated, forms the distorted octahedron configuration of hexa-coordinate.Tetra- atoms of O2, O3, N1, N2A form equatorial plane, N3, N5
In axial distribution.Ni-O average bond length is that 2.106, Ni-N average bond length is 2.111.
Pyrazoles -3- formic acid the nickel complex the preparation method comprises the following steps:
(1) it weighs 0.2 ~ 0.5 mM of six hydration nickel sulfate to be dissolved in 3 ~ 5 milliliters of distilled water, it is molten that nickel sulfate is made
Liquid.
(2) it weighs 0.2 ~ 0.5 mM of pyrazoles -3- formic acid to be dissolved in 3 ~ 5 milliliters of distilled water, pyrazoles -3- is made
Formic acid solution.
(3) it weighs 0.2 ~ 0.5 mM of 4-dimethylaminopyridine to be dissolved in 2 ~ 5 milliliters of dehydrated alcohols, 4- is made
Dimethylamino naphthyridine solution.
(4) solution made from step (1), (2) and (3) is added in ptfe autoclave liner, dropwise addition 1 ~
2 drops analyze pure triethylamines, put on stainless steel cauldron housing and are put into 110 degrees Celsius and react 48 ~ 72 hours, after the reaction was completed with
10 degrees Celsius of gradients are down to room temperature per hour, open kettle after standing 12 ~ 24 hours, filter to obtain blue rhabdolith, as pyrazoles-
3- formic acid nickel complex.
The present invention has many advantages, such as simple process, low in cost, reproducible, has successfully synthesized pyrazoles -3- nickel formate
Complex provides certain foundation to synthesize the complex of transition metal.
Detailed description of the invention
Fig. 1 is pyrazoles -3- nickel formate complex molecule structure chart of the invention.
Specific embodiment
Embodiment:
(1) it weighs 0.2 mM of (0.0526 gram) six hydration nickel sulfate to be dissolved in 5 milliliters of distilled water, it is molten that nickel sulfate is made
Liquid.
(2) it weighs 0.2 mM of (0.0224 gram) pyrazoles -3- formic acid to be dissolved in 5 milliliters of distilled water, pyrazoles -3- is made
Formic acid solution.
(3) it weighs 0.5 mM of (0.0610 gram) 4-dimethylaminopyridine to be dissolved in 5 milliliters of dehydrated alcohols, 4- is made
Dimethylamino naphthyridine solution.
(4) solution made from step (1), (2) and (3) is added in ptfe autoclave liner, 1 drop is added dropwise
Pure triethylamine is analyzed, stainless steel cauldron housing is put on and is put into 110 degrees Celsius of reactions 72 hours, after the reaction was completed with per hour 10
Degree Celsius gradient is down to room temperature, opens kettle after standing 24 hours, filters to obtain blue rhabdolith, and as pyrazoles -3- nickel formate cooperates
Object.
The complex belongs to anorthic system, and space group isPī, central metallic ions are Ni (II) ion.In the complex
In, minimum structural unit is by two Ni (II) ions, two pyrazoles -3- formate anions, four 4-dimethylaminopyridine
Neutral molecule and four hydrone compositions.The center Ni1 ion nitrogen-atoms and carboxylic with a pyrazoles -3- formate anion respectively
The form coordination that oxygen atom (N1, O2) on base is chelated with bidentate, the nitrogen-atoms with another pyrazoles -3- formate anion
(N2A) it is coordinated in the form of monodentate, two nitrogen-atoms (N3, N5) with two 4-dimethylaminopyridine neutral molecules are with monodentate
Form coordination, and be coordinated with a hydrone (O3), form the distorted octahedron configuration of hexa-coordinate.O2, O3, N1, N2A tetra-
Atom forms equatorial plane, and N3, N5 are in axial distribution.Ni-O average bond length is that 2.106, Ni-N average bond length is 2.111
Å。
Claims (2)
1. a kind of pyrazoles -3- formic acid nickel complex, it is characterised in that pyrazoles -3- formic acid nickel complex belongs to anorthic system, space
Group bePī, central metallic ions are Ni (II) ion；In the complex, minimum structural unit by two Ni (II) ions,
Two pyrazoles -3- formate anions, four 4-dimethylaminopyridine neutral molecules and four hydrone compositions；Center Ni1 from
The shape that son is chelated respectively with oxygen atom, that is, N1, O2 on the nitrogen-atoms and carboxyl of a pyrazoles -3- formate anion with bidentate
Formula coordination, is coordinated, with two 4- diformazans in the form of monodentate with nitrogen-atoms, that is, N2A of another pyrazoles -3- formate anion
Two nitrogen-atoms, that is, N3, N5 of aminopyridine neutral molecule are coordinated in the form of monodentate, and are coordinated with a hydrone, that is, O3, shape
At the distorted octahedron configuration of hexa-coordinate；Tetra- atoms of O2, O3, N1, N2A form equatorial plane, and N3, N5 are in axial distribution；
Ni-O average bond length is that 2.106, Ni-N average bond length is 2.111.
2. the preparation method of pyrazoles -3- formic acid nickel complex according to claim 1, it is characterised in that its specific steps
Are as follows:
(1) it weighs 0.2 ~ 0.5 mM of six hydration nickel sulfate to be dissolved in 3 ~ 5 milliliters of distilled water, it is molten that nickel sulfate is made
Liquid；
(2) it weighs 0.2 ~ 0.5 mM of pyrazoles -3- formic acid to be dissolved in 3 ~ 5 milliliters of distilled water, pyrazoles -3- formic acid is made
Solution；
(3) it weighs 0.2 ~ 0.5 mM of 4-dimethylaminopyridine to be dissolved in 2 ~ 5 milliliters of dehydrated alcohols, 4- diformazan is made
Aminopyridine solution；
(4) solution made from step (1), (2) and (3) is added in ptfe autoclave liner, 1 ~ 2 drop is added dropwise
Pure triethylamine is analyzed, stainless steel cauldron housing is put on and is put into 110 degrees Celsius of reactions 48 ~ 72 hours, after the reaction was completed with every
Hour, 10 degrees Celsius of gradients were down to room temperature, opened kettle after standing 12 ~ 24 hours, filtered to obtain blue rhabdolith, as pyrazoles -3-
Formic acid nickel complex.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811303819.XA CN109251225A (en) | 2018-11-03 | 2018-11-03 | Pyrazoles -3- formic acid nickel complex and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811303819.XA CN109251225A (en) | 2018-11-03 | 2018-11-03 | Pyrazoles -3- formic acid nickel complex and preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109251225A true CN109251225A (en) | 2019-01-22 |
Family
ID=65044259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811303819.XA Withdrawn CN109251225A (en) | 2018-11-03 | 2018-11-03 | Pyrazoles -3- formic acid nickel complex and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109251225A (en) |
-
2018
- 2018-11-03 CN CN201811303819.XA patent/CN109251225A/en not_active Withdrawn
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| PB01 | Publication | ||
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Application publication date: 20190122 |