CN113105359A - Schiff base compound and preparation method thereof - Google Patents
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- CN113105359A CN113105359A CN202110243971.9A CN202110243971A CN113105359A CN 113105359 A CN113105359 A CN 113105359A CN 202110243971 A CN202110243971 A CN 202110243971A CN 113105359 A CN113105359 A CN 113105359A
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 53
- -1 Schiff base compound Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 claims abstract description 20
- GRWMSCBKWMQPON-UHFFFAOYSA-N 2-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1N GRWMSCBKWMQPON-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
- 239000000843 powder Substances 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000011085 pressure filtration Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 150000004753 Schiff bases Chemical class 0.000 abstract description 16
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 3
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 5
- 230000005311 nuclear magnetism Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a Schiff base compound which has a structure shown in a formula I and is named as 5-methyl salicyl aldehyde condensed 2-amino-phenylhydrazide Schiff base. On the other hand, the invention provides a preparation method of the Schiff base compound, which takes 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide as raw materials, prepares the Schiff base of the 5-methyl salicylaldehyde-condensed 2-aminobenzoyl hydrazide in the presence of a solvent under mild conditions, simple process and low cost, has no toxicity in the raw materials, does not need to be limited in the aspects of reaction operation, post-treatment and environmental pollution prevention and control, and has high applicability.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a Schiff base compound and a preparation method thereof.
Background
Schiff bases are organic compounds containing imino and methylimino (-RC-N-) formed by addition elimination reaction of aldehyde and amine, have special coordination structures and good coordination performance, and are important organic ligands. In the specific structure of the Schiff base, various Schiff base ligands with different performances and variable structures from chain to ring and from monodentate to multidentate can be developed by various means such as changing the connected substituent, changing the electron donor atom and the position thereof and the like. The ligands have good coordination capability, can form complexes with different stabilities with most metal ions in the periodic table of elements through coordination bonds, can be applied to various fields of luminescence, magnetism, catalysis and the like, and have important performance and application prospects. Meanwhile, Schiff base compounds and metal complexes thereof also have important application in the fields of medicine, catalysis, corrosion, detection and photochromism.
In the prior art, Schiff bases are generally prepared by hydrazine hydrate with high toxicity, and due to the toxicity problem of hydrazine hydrate, the aspects of reaction operation, post-treatment and environmental pollution prevention and control are greatly limited, and the applicability is not high.
In view of the above, it is necessary to provide a technical solution to solve the above technical problems.
Disclosure of Invention
One of the objects of the present invention is: aiming at the defects of the prior art, the Schiff base compound is provided.
In order to achieve the purpose, the invention adopts the following technical scheme:
a schiff base compound having the structure of formula I:
the second purpose of the invention is: the preparation method of the Schiff base compound, which is described in the specification, is provided, does not need hydrazine hydrate, has simple reaction, mild conditions, easy satisfaction and environmental friendliness, and comprises the following operations: dissolving 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in a solvent for reaction to obtain the Schiff base compound with the structure shown in (I).
As an improvement of the preparation method of the Schiff base compound, the molar ratio of the 5-methyl salicylaldehyde to the 2-aminobenzoyl hydrazide is 1: 3-3: 1. Preferably, the molar ratio of 5-methyl salicylaldehyde to 2-aminobenzoyl hydrazide is 1.5:1 or 1:1.5 or 1:1. More preferably, the molar ratio of 5-methyl salicylaldehyde to 2-aminobenzoic hydrazide is 1:1.
As an improvement of the process for preparing the schiff base compound of the present invention, the solvent includes methanol or ethanol.
As an improvement of the preparation method of the Schiff base compound, the mass percentage concentration of the methanol solvent is 20-40%. Preferably, the methanol solvent has a concentration of 20%, 25%, 30%, 35% or 40% by mass
As an improvement of the preparation method of the Schiff base compound, the solvent also comprises an entrainer. Since the reaction is a reversible reaction, an entrainer is often added to the system to carry the water produced by the reaction out of the reaction system, thereby achieving the purpose of improving the yield.
As an improvement of the preparation method of the Schiff base compound, the preparation method comprises the following steps:
(1) respectively weighing 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in proportion;
(2) dissolving the 5-methyl salicylaldehyde and the 2-aminobenzoyl hydrazide weighed in the step (1) in a solvent, heating, stirring, reacting, refluxing, and performing vacuum filtration to obtain powder;
(3) and (3) dissolving the powder obtained in the step (2) in the solvent, heating, cooling and recrystallizing to obtain the compound.
As an improvement of the preparation method of the Schiff base compound, in the step (2), the stirring reaction time is 3-6 h. Preferably, the reaction time with stirring is 3h, 4h, 5h or 6 h.
In the step (2), after stirring, adding a pH value regulator to regulate the pH value to 5-6, wherein the pH value regulator comprises formic acid and/or acetic acid.
As an improvement of the preparation method of the Schiff base compound, the preparation method comprises the following operations: mixing 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in a molar ratio of 1:1 in absolute methanol, heating to 60-110 ℃ under the protection of nitrogen, stirring to react to obtain a yellow transparent solution, performing reflux reaction for 3-6 hours after the reaction is finished, cooling to room temperature, performing reduced pressure filtration to obtain milky solid powder, filtering, washing and precipitating with methanol, drying in an oven for a plurality of days, dissolving the milky solid powder in a minimum amount of methanol solution, heating to 60 ℃, stopping heating after one hour, standing and cooling overnight, and recrystallizing to obtain milky Schiff base needle crystals.
Compared with the prior art, the invention has at least the following beneficial effects:
the invention provides a Schiff base compound, which is named as 5-methyl salicylidene 2-aminobenzene hydrazide Schiff base and has the molecular formula as follows: c15H15O2N3The molecular weight is: 269.3g/mol, the Schiff base compound contains C-N functional group, has special conjugated structure, can provide abundant coordination mode, has strong metal coordination ability and good chemical coordination performance, and has strong scientific research value and industrial application potential.
On the other hand, the invention provides a preparation method of the Schiff base compound, which takes 5-methyl salicylaldehyde and 2-aminobenzene hydrazide as raw materials, prepares the Schiff base of the 5-methyl salicylaldehyde-condensed 2-aminobenzene hydrazide in the presence of a solvent under mild conditions, simple process and low cost, and has easily controlled chemical components, good repeatability and high yield. In addition, the preparation raw materials do not contain toxicity, the reaction operation, the post-treatment and the environmental pollution prevention and control are not limited, the applicability is high, and the green and environment-friendly prepared brand-new 5-methyl salicylaldehyde-condensed 2-aminobenzene hydrazide Schiff base has strong scientific research value and industrial application potential.
Drawings
FIG. 1 is a schematic diagram of the synthesis route of the Schiff base compound of the invention.
FIG. 2 is a nuclear magnetic representation of the Schiff base compounds of the invention.
Detailed Description
In order to illustrate the invention more clearly, the invention will be described in further detail below with reference to the attached drawings and specific examples, without limiting the scope of the invention thereto.
Example 1
The embodiment provides a preparation method of Schiff base, which comprises the following steps:
the first step is as follows: adding 3mmol (0.4085g) of 5-methyl salicylaldehyde into a 50mL three-neck flask, adding 10mL anhydrous methanol, stirring at 60 deg.C for 10min, and discharging from a constant pressure funnel for 10d min-1Dropping 10mL of methanol solution containing 3mmol (0.45351g) of 2-aminobenzoyl hydrazide, and stirring for 20min under the protection of nitrogen to obtain a yellow transparent solution; and (3) after the dropwise addition is finished, carrying out reflux reaction for 4h, cooling to room temperature, carrying out reduced pressure filtration, washing the precipitate with methanol to obtain milky white solid powder, and drying in an oven for several days.
The second step is that: adding the white powder obtained in the first step into a 50mL three-neck flask, dropwise adding an anhydrous methanol solution until the white powder is just dissolved to be about 5mL, stirring at the constant temperature of 60 ℃ for 2 hours, cooling to room temperature, pouring into an ice water bath, separating out solids, performing suction filtration to obtain nearly transparent Schiff base needle-shaped crystal solids, and performing vacuum drying to obtain 0.6649g, wherein the yield is 81.5%.
And characterizing the prepared product by using nuclear magnetism, wherein nuclear magnetism characterization parameters are as follows: 1H-NMR (500MHz, CDCl3):8.29(s,2H),7.30(t, J ═ 7.5Hz,2H),7.15(d, J ═ 7.5Hz,2H),6.99(d, J ═ 7.5Hz,2H),6.88(t, J ═ 7.5Hz,2H),3.97(s, 4H). The synthesis of the ligand synthesized by the method is 5-methyl salicyl aldehyde shrinkage 2-amino phenylhydrazine Schiff base.
Example 2
The embodiment provides a preparation method of Schiff base, which comprises the following steps:
the first step is as follows: adding 5mmol (0.6808g) 5-methyl salicylaldehyde into 50mL three-neck flask, adding 10mL anhydrous methanol, stirring at 60 deg.C for 10min, and discharging from constant pressure funnel for 10d min-1Dropping 10mL of methanol solution containing 5mmol (0.7559g) of 2-aminobenzoyl hydrazide, and stirring for 20min under the protection of nitrogen to obtain a yellow transparent solution; and (3) after the dropwise addition is finished, carrying out reflux reaction for 4h, cooling to room temperature, carrying out reduced pressure filtration, washing the precipitate with methanol to obtain milky white solid powder, and drying in an oven for several days.
The second step is that: adding the white powder obtained in the first step into a 50mL three-neck flask, dropwise adding an anhydrous methanol solution until the white powder is just dissolved to be about 10mL, stirring at the constant temperature of 60 ℃ for 2 hours, cooling to room temperature, pouring into an ice water bath, separating out solids, performing suction filtration to obtain nearly transparent Schiff base needle-shaped crystal solids, and performing vacuum drying to obtain 1.0947g, wherein the yield is 80.9%.
And characterizing the prepared product by using nuclear magnetism, wherein nuclear magnetism characterization parameters are as follows: 1H-NMR (500MHz, CDCl3):8.29(s,2H),7.30(t, J ═ 7.5Hz,2H),7.15(d, J ═ 7.5Hz,2H),6.99(d, J ═ 7.5Hz,2H),6.88(t, J ═ 7.5Hz,2H),3.97(s, 4H). The synthesis of the ligand synthesized by the method is 5-methyl salicyl aldehyde shrinkage 2-amino phenylhydrazine Schiff base.
Example 3
The embodiment provides a preparation method of Schiff base, which comprises the following steps:
the first step is as follows: adding 10mol (1.3615g) of 5-methyl salicylaldehyde into a 50mL three-neck flask, adding 10mL of anhydrous methanol, stirring at 60 deg.C for 10min, and discharging from a constant pressure funnel for 10d min-110mL of methanol solution containing 10mol (1.5117g) of 2-aminobenzoyl hydrazide is dripped into the mixture, and the mixture is stirred for 20min under the protection of nitrogen, so that the system becomes yellow transparent solution; and (3) after the dropwise addition is finished, carrying out reflux reaction for 4h, cooling to room temperature, carrying out reduced pressure filtration, washing the precipitate with methanol to obtain milky white solid powder, and drying in an oven for several days.
The second step is that: adding the white powder obtained in the first step into a 50mL three-neck flask, dropwise adding an anhydrous methanol solution until the white powder is just dissolved to be about 15mL, stirring at the constant temperature of 60 ℃ for 2 hours, cooling to room temperature, pouring into an ice water bath, separating out solids, performing suction filtration to obtain nearly transparent Schiff base needle-shaped crystal solids, and performing vacuum drying to obtain 1.9508g, wherein the yield is 80.5%.
The prepared product was characterized by nuclear magnetism, and the results are shown in fig. 2. The nuclear magnetic characterization parameters are as follows: 1H-NMR (500MHz, CDCl3) 11.85(s,1H),11.21(s,1H),8.52(s,2H),7.58(d,1H),7.29(s,1H),7.24(t,1H),7.22(d,1H),7.20(d,1H),7.20(d,1H),7.20(t, 1H).
As can be seen from nuclear magnetic spectrum, the ligand synthesized by the method is 5-methyl salicylidene-2-amino-phenylhydrazine Schiff base.
Variations and modifications to the above-described embodiments may also occur to those skilled in the art, which fall within the scope of the invention as disclosed and taught herein. Therefore, the present invention is not limited to the above-mentioned embodiments, and any obvious improvement, replacement or modification made by those skilled in the art based on the present invention is within the protection scope of the present invention. Furthermore, although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.
Claims (10)
1. A schiff base compound having the structure of formula I:
2. a process for the preparation of the schiff base compound of claim 1, comprising the following operations: dissolving 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in a solvent for reaction to obtain the Schiff base compound with the structure shown in (I).
3. The preparation method of the Schiff base compound according to claim 2, wherein the molar ratio of the 5-methyl salicylaldehyde to the 2-aminobenzoyl hydrazide is 1: 3-3: 1.
4. The process for preparing a schiff base compound according to claim 2, wherein the solvent comprises methanol or ethanol.
5. The method for preparing a Schiff base compound according to claim 4, wherein the methanol solvent is used in an amount of 20-40% by mass.
6. The process for preparing a schiff base compound according to claim 2, wherein the solvent further comprises an entrainer.
7. A process for preparing a Schiff base compound according to any one of claims 2 to 6, comprising the steps of:
(1) respectively weighing 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in proportion;
(2) dissolving the 5-methyl salicylaldehyde and the 2-aminobenzoyl hydrazide weighed in the step (1) in a solvent, heating, stirring, reacting, refluxing, and performing vacuum filtration to obtain powder;
(3) and (3) dissolving the powder obtained in the step (2) in the solvent, heating, cooling and recrystallizing to obtain the compound.
8. The method for preparing Schiff base compound according to claim 7, wherein in the step (2), the stirring reaction time is 3-6 h.
9. The preparation method of the Schiff base compound according to claim 7, wherein in the step (2), after the stirring, a pH value regulator is added to regulate the pH value to 5-6, wherein the pH value regulator comprises formic acid and/or acetic acid.
10. The process for the preparation of schiff base compounds according to claim 7, comprising the following operations: mixing 5-methyl salicylaldehyde and 2-aminobenzoyl hydrazide in anhydrous methanol, heating to 60-110 ℃ under the protection of nitrogen, carrying out reflux reaction for 3-6 hours after stirring reaction, cooling, and carrying out reduced pressure filtration to obtain solid powder; filtering the solid powder, washing the precipitate with methanol, drying, dissolving in methanol solution, heating to 60 deg.C, stopping heating, standing, cooling, and recrystallizing to obtain Schiff base compound.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305490A (en) * | 1998-06-26 | 2001-07-25 | 辉瑞产品公司 | Improved processing for preparing schift base adducts of amines with i(o)-hydroxy aldehydes and compositions of matter based thereon |
| CN104262206A (en) * | 2014-09-04 | 2015-01-07 | 王晓伟 | Preparation method of ethoxy salicylaldehyde bis-Schiff base |
-
2021
- 2021-03-05 CN CN202110243971.9A patent/CN113105359A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305490A (en) * | 1998-06-26 | 2001-07-25 | 辉瑞产品公司 | Improved processing for preparing schift base adducts of amines with i(o)-hydroxy aldehydes and compositions of matter based thereon |
| CN104262206A (en) * | 2014-09-04 | 2015-01-07 | 王晓伟 | Preparation method of ethoxy salicylaldehyde bis-Schiff base |
Non-Patent Citations (4)
| Title |
|---|
| GEETA H. CHIMMALAGI 等: "Mononuclear Co(III), Ni(II) and Cu(II) complexes of 2-(2,4-dichlorobenzamido)-N"‐(3,5-di-tert-butyl-2-hydroxybenzylidene) benzohydrazide", 《APPLIED ORGANOMETALLIC CHEMISTRY》 * |
| MANAS SUTRADHAR 等: "Oxidovanadium(V) Complexes Anchored on Carbon Materials as Catalysts for the Oxidation of 1-Phenylethanol", 《CHEM CAT CHEM》 * |
| NIRMALENDU BISWAS 等: "Simultaneous formation of non-oxidovanadium(IV) and oxidovanadium(V) complexes incorporating phenol-based hydrazone ligands in aerobic conditions", 《NEW JOURNAL OF CHEMISTRY》 * |
| NIRMALENDU BISWAS 等: "Synthesis, characterization, and cytotoxic and antimicrobial activities of mixed-ligand hydrazone complexes of variable valence VOz+ (z=2,3)", 《NEW JOURNAL OF CHEMISTRY》 * |
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