CN108191914A - A kind of manganese complex crystal - Google Patents
A kind of manganese complex crystal Download PDFInfo
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- CN108191914A CN108191914A CN201810018591.3A CN201810018591A CN108191914A CN 108191914 A CN108191914 A CN 108191914A CN 201810018591 A CN201810018591 A CN 201810018591A CN 108191914 A CN108191914 A CN 108191914A
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- complex crystal
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- manganese complex
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- 239000013078 crystal Substances 0.000 title claims abstract description 19
- 229910052748 manganese Inorganic materials 0.000 title claims abstract description 13
- 239000011572 manganese Substances 0.000 title claims abstract description 12
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 12
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 6
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940071125 manganese acetate Drugs 0.000 claims abstract description 5
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000010189 synthetic method Methods 0.000 claims abstract description 5
- 241000272525 Anas platyrhynchos Species 0.000 claims abstract description 4
- 238000003556 assay Methods 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 230000036571 hydration Effects 0.000 claims abstract 2
- 238000006703 hydration reaction Methods 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000002447 crystallographic data Methods 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 abstract description 3
- 230000002335 preservative effect Effects 0.000 abstract description 3
- -1 tetracyanoethylene manganese Chemical compound 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003446 ligand Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- UHIJLWIHCPPKOP-UHFFFAOYSA-N [N].[Zn] Chemical compound [N].[Zn] UHIJLWIHCPPKOP-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GBSYTTRCFYEGDV-UHFFFAOYSA-N 2,2-bis(3,5-dimethylpyrazol-1-yl)propanoic acid Chemical group N1=C(C)C=C(C)N1C(C)(C(O)=O)N1C(C)=CC(C)=N1 GBSYTTRCFYEGDV-UHFFFAOYSA-N 0.000 description 1
- BPFVHHLYBQRNKE-UHFFFAOYSA-N 2-(2,5-dicarboxyphenyl)terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C=2C(=CC=C(C=2)C(O)=O)C(O)=O)=C1 BPFVHHLYBQRNKE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical class [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 229910018648 Mn—N Inorganic materials 0.000 description 1
- 241000238370 Sepia Species 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- MSBWDNNCBOLXGS-UHFFFAOYSA-L manganese(2+);diacetate;hydrate Chemical compound O.[Mn+2].CC([O-])=O.CC([O-])=O MSBWDNNCBOLXGS-UHFFFAOYSA-L 0.000 description 1
- MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VFIJOUHBZUMVCW-UHFFFAOYSA-N n-[benzamido(phenyl)methyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1C=CC=CC=1)NC(=O)C1=CC=CC=C1 VFIJOUHBZUMVCW-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- XYBUIQUQPGBKAR-UHFFFAOYSA-N tripotassium;chromium(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Cr+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XYBUIQUQPGBKAR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
-
- 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
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
A kind of manganese complex crystal, chemical formula are as follows：The synthetic method of the complex crystal (I), tetracyanoethylene is weighed with assay balance and four hydration manganese acetate 1.2807g, 0.4907g are poured into round-bottomed flask respectively, make solvent with absolute methanol (about 40ml), it is placed in round-bottomed flask and is reacted, back flow reaction is after 48 hours, heat filtering, it is sealed with preservative film, several duck eyes are pricked, is recrystallized again after a few days, there is tan crystals appearance；The purposes of the complex crystal (I) is that preferable catalytic performance is shown in the reacting of benzaldehyde and benzamide, and conversion ratio is up to 99%.
Description
First, technical field
The present invention relates to a kind of noval chemical compound and preparation method thereof, more particularly to a kind of manganese complex and preparation method thereof,
It is exactly preparation and the synthetic method of a kind of chiral tetracyanoethylene manganese complex.
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.Change
The important content for learning catalysis dissymmetric synthesis is chiral ligand and the design containing metallic catalyst, so as to which reaction be made to have height
Effect and high enantioselectivity.Chiral manganese nitrogen metal complex achieves preferable catalysis effect in asymmetric catalysis field in recent years
Fruit.
Bibliography：
1.Syntheses of Group 7 Metal Carbonyl Complexes with a Stable N-
Heterocyclic Chlorosilylene.Azhakar,Ramachandran；Sarish,Sankaranarayana
Pillai；Roesky,Herbert W.；Hey,Jakob；Stalke,Inorganic Chemistry.
2.Synthesis,characterization and spectral studies of noble
heterobinuclear complexes of transition metal ions and their biological
activity.Singh,Netra Pal；Srivastava,Abhay Nanda.E-Journal of Chemistry(2011),
8(2),809-814.
3.Transition metal complexes bearing a 2,2-bis(3,5-dimethylpyrazol-1-
yl)propionate ligand:one methyl more matters.Tuerkoglu,Gazi；Heinemann,Frank
W.；Burzlaff,Nicolai.Inorganic Chemistry,Dalton Transactions(2011),40(17),
4678-4686.
4.A general and modular synthesis of monoimidouranium(IV)
dihalides.Jilek,Robert.E.；Spencer,Liam P.；Kuiper,David L.；Scott,Brian L.；
Williams,Ursula J.；Kikkawa,James M.；Schelter,Eric J.；Boncella,James M.(2011),
50(10),4235-4237.
5.Syntheses,crystal structures,and magnetic properties of two new
manganese(II)complexes based on biphenyl-2,5,2',5'-tetracarboxylic acid.Tian,
Dan；Pang,Yu；Guo,Shengqi；Zhu,Xiaofei；Zhang,Hong.Journal of Coordination
Chemistry(2011),64(6),1006-101
6.Two dinuclear Schiff-base complexes:synthesis,characterization,and
biological activity.Chen,Yun-Feng；Wei,Lai；Bai,Jun-Lin；Zhou,Hong；Huang,Qi-Mao；
Li,Jun-Bo；Pan,Zhi-Quan.Journal of Coordination Chemistry(2011),64(7),1153-
1164.
7.Two Novel Cyanide-Bridged Bimetallic Magnetic Chains Derived from
Manganese(III)Schiff Bases and Hexacyanochromate(III)Building Blocks.Yang,
Chun；Wang,Qing-Lun；Qi,Jing；Ma,Yue；Yan,Shi-Ping；Yang,Guang-Ming；Cheng,Peng；
Liao,Dai-Zheng.Inorganic Chemistry(Washington,DC,United States)(2011),50(9),
4006-4015.
3rd, invention content
The present invention is intended to provide a kind of Mn-N metal organic complexes, to be applied to catalytic field, technology to be solved is asked
Topic selects neighbour as ligand and synthesis of chiral zinc-nitrogen coordination compound.
The so-called zinc-nitrogen coordination compound of the present invention be by tetracyanoethylene and four acetate hydrate manganese prepare by below formula institute
The complex shown：
Chemical name：Tetracyanoethylene manganese complex, abbreviation complex (I).The complex is in benzaldehyde and benzamide
Show preferable catalytic performance in reaction, conversion ratio is up to 99%.
This synthetic method includes synthesis and separation, and the synthesis is to weigh tetracyanoethylene with four water with assay balance respectively
Conjunction manganese acetate 1.2807g (about 0.01mol), 0.4907g (about 0.002mol) are poured into round-bottomed flask, using absolute methanol (about
40ml) make solvent, be placed in round-bottomed flask and reacted, after 48 hours, heat filtering is sealed back flow reaction with preservative film, is pricked several
A duck eye is recrystallized, there is tan crystals appearance again after a few days.
Synthetic reaction is as follows：
One step of this synthetic method obtains target product, simple for process, easy to operate.
The reaction mechanism that the complex is formed can be speculated as under the action of a large amount of lewis acid zinc chloride, tetracyanoethylene
One cyano is replaced by the hydroxyl in moisture in air, two cyano in two molecule tetracyanoethylenes respectively with metal manganese atom
Coordination, and two acetate ions in manganese acetate act on two hydrogen atoms on carbon in two tetracyanoethylenes and release 2
Molecule acetic acid forms target product.
4th, it illustrates
Fig. 1 is the X- diffraction analysis figures of tetracyanoethylene manganese complex.
5th, specific embodiment
1. the preparation of multinuclear tetracyanoethylene manganese complex：
Tetracyanoethylene is weighed with assay balance be hydrated manganese acetate 1.2807g (about 0.01mol), 0.4907g (about with four respectively
It 0.002mol) pours into round-bottomed flask, makees solvent using absolute methanol (about 40ml), be placed in round-bottomed flask and reacted, return
After stream reaction 48 hours, heat filtering is sealed with preservative film, pricks several duck eyes, is recrystallized again after a few days, there is sepia crystalline substance
Body occurs；Fusing point:>220℃；Elemental analysis data, actual value：N：18.05%, C 39.58%, H 3.81%；Theory is N
17.86%, C 39.81%, H 3.85%, ir data (KBr, cm-1)：615,665,744,953,1028,1092,
1115,1194,1232,1284,1342,1413,1437,1558,1645,1720,2139,2212,2956,3018；MS(ESI-
TOF)(m/z):calculated for C13H15N5O6Mn,[M+H]+:393.2300；found:393.2289；
The crystal data of complex：
The typical bond distance's data of crystal：
The typical bond angle data of crystal:
The preparation of N, N '-(phenylmethylene) dibenzamide
In 25mL two-mouth bottles, add in 0.0659g complexs I, 2mLTHF and chlorobenzene 2mL, 0.05mL benzaldehyde and
0.1302g benzamides, back flow reaction have crystal appearance after 24 hours：It is detected with nuclear-magnetism, conversion ratio：99%；1HNMR
(500MHz,CDCl3, 27 DEG C), δ (ppm)=9.02 (d, J=7.77Hz, 2H), 7.91 (d, J=7.42Hz, 4H), 7.54 (t,
J=7.4Hz, 2H), 7.47 (t, J=7.7Hz, 6H), 7.37 (t, J=7.7Hz, 2H), 7.30 (t, J=7.3Hz, 1H), 7.03
(t, J=7.9Hz, 1H).
Meanwhile under parallel condition, inventor has done reacting for similar complex zinc (II) catalysis benzaldehyde and benzamide,
Its result is as follows：
Benzaldehyde is reacted with benzamide：Yield：II:68%III:62%.
Claims (4)
1. a kind of manganese complex crystal, chemical formula are as follows：
2. manganese complex crystal (I) described in claim 1, at a temperature of 100.01 (10) K, in Oxford X-ray single crystal diffraction
On instrument, with the CuK alpha rays through graphite monochromator monochromatizationDiffraction data is collected with ω-θ scan modes,
It is characterized in that crystal category orthorhombic system, space group P n m a, α=90 °；β=
90°；γ=90 °.
3. the synthetic method of manganese complex crystal (I) described in claim 1, including synthesizing and detaching, described in the synthesis
Synthesis respectively with assay balance weigh tetracyanoethylene and four hydration manganese acetate 1.2807g, 0.4907g pour into round-bottomed flask,
Make solvent with absolute methanol (about 40ml), be placed in round-bottomed flask and reacted, back flow reaction is after 48 hours, heat filtering, with guarantor
Fresh film seals, and pricks several duck eyes, is recrystallized again after a few days, there is tan crystals appearance.
4. the purposes of manganese complex crystal (I) described in claim 1：The complex is in the reacting of benzaldehyde and benzamide
Show preferable catalytic performance, conversion ratio is up to 99%.
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| CN201810018591.3A CN108191914A (en) | 2018-01-09 | 2018-01-09 | A kind of manganese complex crystal |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622646A (en) * | 2015-12-31 | 2016-06-01 | 合肥工业大学 | Zinic complex crystal |
| CN107337652A (en) * | 2017-07-05 | 2017-11-10 | 合肥祥晨化工有限公司 | A kind of Chiral oxazoline cobalt complex and purposes |
-
2018
- 2018-01-09 CN CN201810018591.3A patent/CN108191914A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622646A (en) * | 2015-12-31 | 2016-06-01 | 合肥工业大学 | Zinic complex crystal |
| CN107337652A (en) * | 2017-07-05 | 2017-11-10 | 合肥祥晨化工有限公司 | A kind of Chiral oxazoline cobalt complex and purposes |
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Application publication date: 20180622 |