CN108147998A - A kind of structure of imidazoles cyanophenyl nitrate and preparation method thereof - Google Patents
A kind of structure of imidazoles cyanophenyl nitrate and preparation method thereof Download PDFInfo
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- CN108147998A CN108147998A CN201810118184.XA CN201810118184A CN108147998A CN 108147998 A CN108147998 A CN 108147998A CN 201810118184 A CN201810118184 A CN 201810118184A CN 108147998 A CN108147998 A CN 108147998A
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- imidazoles
- cyanophenyl
- nitrate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The present invention provides a kind of structure of imidazoles cyanophenyl nitrate and preparation method thereof, molecular formula C11H10N4O3.The preparation of the compound is that the in the mixed solvent formed in first alcohol and water mixes a certain proportion of imidazoles cyanophenyl and nitric acid, is put into and is placed in baking oven with 50 150 DEG C of temperature heating 5 for 24 hours, white needle-like crystals being obtained after cold filtration in 15ML polytetrafluoroethylene (PTFE).Method therefor operation of the present invention is succinct, safe；Its product has many advantages, such as that stability is good, crystallinity is high.The compound has potential application prospect in fluorescent material etc..
Description
Technical field
The invention belongs to organic compound fields, are related to a kind of structure of imidazoles cyanophenyl nitrate and preparation method thereof.
Background technology
Imidazole and its derivants have good bioactivity, receive chemistry and pharmaceutical field research worker all the time
Favor.Many drugs are imdazole derivatives or its complex.Research finds that imidazoles is an interesting nitrogen heterocyclic, it
There are one the nitrogen-atoms comprising lone pair electrons for tool, can be bonded a proton and form protonation cation, and because contain two
A nitrogen-atoms, so be a kind of special construction that hydrogen bond can be formed with the enzyme in organism and receptor etc., in anticancer, anti-true
Bacterium, easing pain and diminishing inflammation etc. play a role.
Research history using imidazoles parent nucleus as activated centre can trace back to nineteen forties, pharmacy man at that time
Woolley speculates that imidazoles can play the function similar to some bioactivity that purine causes.Between subsequent several years, largely
Medical science authoritative expert such as inhibits to aoxidize, inhibits blood clotting, anti-by the multiple biological activities that constantly research discloses imidazoles
Diabetes etc.；By the optimization to different loci on benzimidazole parent nucleus, many good effects are also obtained and have still used
Drug such as mebendazol etc..At present, for for the development of new types of therapeutic agents, the knot using imidazoles parent nucleus as activated centre is designed
Structure has become a kind of important development approach.Imidazoles cyanophenyl is an important pharmaceutical intermediate.However, up to the present,
The synthesis of imidazoles cyanophenyl nitrate and crystal structure do not have document report.The present invention proposes a kind of imidazoles cyanophenyl for this problem
Nitric acid salt production process and its structural characterization.
Invention content
The present invention provides a kind of structures of imidazoles cyanophenyl nitrate and preparation method thereof.
The technical problems to be solved by the invention are achieved by the following technical programs：A kind of imidazoles cyanophenyl nitrate,
Its molecular formula is：C11H10N4O3, the mixture is monoclinic system,P21/cSpace group, cell parameter area=16.5428 (3),b=6.8402 (1),c=9.8154 (2),α=90o,β=98.947 (2) o,γ=90o,V=1097.16(3)Å3。
A kind of preparation method of imidazoles cyanophenyl nitrate is：A certain proportion of imidazoles cyanophenyl nitric acid is dissolved in water and methanol
In mixed solution, it is placed in polytetrafluoroethylene (PTFE).5-24h is heated at a temperature of 50 DEG C -150 DEG C, at room temperature natural cooling, knot
It is brilliant, until white needle-like crystals are precipitated.
Beneficial effects of the present invention：The imidazoles cyanophenyl nitrate of the present invention is to obtain being conducive to give birth under hydrothermal synthesizing condition
Long few defect, is orientated, and sample purity is high, and preparation method is simple, pollution-free.The compound has very good in terms of fluorescence
Potential application prospect.
Description of the drawings
Fig. 1, a kind of asymmetric cell figure of imidazoles cyanophenyl nitrate of the present invention.
Fig. 2, a kind of one-dimensional chain figure of imidazoles cyanophenyl nitrate of the present invention.
Fig. 3, a kind of two-dimensional structure figure of imidazoles cyanophenyl nitrate of the present invention.
Fig. 4, a kind of accumulation graph of imidazoles cyanophenyl nitrate of the present invention.
Specific embodiment
With reference to embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention,
It is not limitation of the invention.Embodiment 1
By 0.0183g imidazoles cyanophenyls（0.1mmol）, 0.0063g nitric acid（0.1mmol）It is dissolved in water（3ml）And methanol（3ml）It is mixed
It closes in solution.Reaction solution is transferred in polytetrafluoroethylene (PTFE), is heated at a temperature of 100 DEG C for 24 hours, cool down, filtering, crystallize,
Until white needle-like crystals are precipitated.
Above-mentioned imidazoles cyanophenyl nitrate compound is characterized
Crystal X-ray diffraction data is measured using Bruker Smart CCD single crystal diffractometers.MoKa radiation (λ=0.71073 Å
), graphite monochromator, withωScan mode collects data, and carries out Lp factor corrections and empirical absorption correction.It is first true with direct method
Determine the position of other non-hydrogen atoms of metallic atom and part, it is all non-that remaining then is obtained with difference function method and least square method
Hydrogen atom coordinates, and obtain hydrogen atom position with theoretical hydrogenation method or found from difference Fourier figure, with complete matrix minimum two
Multiplication is modified structure.
Fig. 1 is the asymmetric cell figure obtained by single crystal diffraction method.From figure 1 it appears that the compound is not right
Unit is claimed to include a nitrate anion, an imidazoles cyanophenyl cation.Bond distance's range of wherein N-O be 1.2437 (13)-
1.2753 (13), bond distance's range of N-C is 1.1506 (17) -1.4776 (15), and bond distance's range of C-C is 1.3510 (16)
Å-1.3977(16)Å。
Fig. 2 is the one-dimensional chain figure of imidazoles cyanophenyl nitrate of the present invention.One is formed by two kinds of hydrogen bond
Chain structure is tieed up, the bond distance of respectively N (1)-H (1) O (1) is 2.7904 (13), and bond angle is 164 °.C(1)-H(1A)
The bond distance of O (1) is 3.2123 (14), and bond angle is 144 °.
Fig. 3 is the two-dimensional structure figure of imidazoles cyanophenyl nitrate of the present invention.As shown in figure 3, by increasing C (2)-H
(2)∙∙∙O(2)（Bond distance 3.1962 (14), 138 ° of bond angle）Hydrogen bond action causes one-dimensional chain to extend to two-dimentional supramolecular structure.
Fig. 4 is the accumulation graph of imidazoles cyanophenyl nitrate of the present invention.Also exist other than there are above-mentioned hydrogen bond as follows
Hydrogen bond：The bond distance of C (3)-H (3) O (1) is 3.1167 (14), and bond angle is 122 °, the bond distance of C (3)-H (3) O (3)
For 3.2064 (14), bond angle is 156 °, and the bond distance of C (4)-H (4B) O (3) is 3.4260 (15), and bond angle is 147 °C
(7) bond distance of-H (7) N (3) is 3.4449 (16), and bond angle is 151 °, and the bond distance of C (9)-H (9) N (3) is
3.4253 (16), bond angle are 152 °；These supermolecular mechanism power make two-dimensional layer extend to Magnetic Properties of Three-Dimensional Supramolecular Complex structure.
The fluorescence spectrum of imidazoles cyanophenyl nitrate of the present invention research shows that, imidazoles cyanophenyl nitrate is in solid state fluorescence
Emission peak is 391nm.
Embodiment described above only expresses embodiments of the present invention, and description is more specific and detailed, but can not
Therefore the limitation to the scope of the claims of the present invention is interpreted as, as long as the skill obtained using the form of equivalent substitution or equivalent transformation
Art scheme should all be fallen within the scope and spirit of the invention.
Claims (4)
1. a kind of imidazoles cyanophenyl nitrate, it is characterised in that its molecular formula is C11H10N4O3。
2. the imidazoles cyanophenyl nitrate is monoclinic system,P21/cSpace group, cell parameter area=16.5428 (3),b=
6.8402 (1),c=9.8154 (2),α=90o,β=98.947 (2) o,γ=90o,V=1097.16(3)Å3, the compound is not
Symmetrical cell include a nitrate ion, an imidazoles cyanophenyl ion, wherein N-O keys bond distance range be 1.2437 (13)-
1.2753 (13), N-C key bond distance's ranges are 1.1506 (17) -1.4776 (15), and C-C key bond distance's ranges are 1.3510 (16)
Å-1.3977(16)Å。
3. the preparation method of imidazoles cyanophenyl nitrate according to claim 1, it is characterised in that：By molar ratio for 0.8 ~
1.2:0.8 ~ 1.2 imidazoles cyanophenyl, nitric acid are mixed to join in the mixed solvent of first alcohol and water composition, and it is molten to be placed in polytetrafluoroethylene (PTFE)
5-24h is heated with 50 DEG C -150 DEG C of temperature in agent, at room temperature natural cooling, crystallization, until precipitation white needle-like crystals.
4. the application of the imidazoles cyanophenyl nitrate according to claims 1, it is characterised in that the salt based on imidazoles cyanophenyl can
As fluorescent material.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810118184.XA CN108147998A (en) | 2018-02-06 | 2018-02-06 | A kind of structure of imidazoles cyanophenyl nitrate and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| CN107652240A (en) * | 2017-10-17 | 2018-02-02 | 齐鲁工业大学 | A kind of preparation, structure and the photoluminescent property of double imidazole nitrates |
-
2018
- 2018-02-06 CN CN201810118184.XA patent/CN108147998A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| CN107652240A (en) * | 2017-10-17 | 2018-02-02 | 齐鲁工业大学 | A kind of preparation, structure and the photoluminescent property of double imidazole nitrates |
Non-Patent Citations (1)
| Title |
|---|
| YAN-HONG XU ET AL.: "Self-assembly of zinc polymers based on a flexible linear ligand at different pH values: Syntheses, structures and fluorescent properties", 《SOLID STATE SCIENCES》 * |
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