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Salicylidenehydrazine receptor compound, preparation method and application thereof

A technology of salicylaldehyde hydrazide and compounds, which is applied in the preparation of hydrazone, the analysis of materials through chemical reactions, organic chemistry, etc., can solve the problems of long detection time, high cost, unfavorable copper element detection, etc., and achieve high yield High, simple process effect

Inactive Publication Date: 2012-12-12
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, atomic absorption spectrometry and atomic fluorescence spectrometry are mainly used for the determination of copper content. These detection methods not only require expensive equipment, but also take a long time and cost a lot, which is not conducive to the rapid detection of copper.

Method used

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  • Salicylidenehydrazine receptor compound, preparation method and application thereof
  • Salicylidenehydrazine receptor compound, preparation method and application thereof
  • Salicylidenehydrazine receptor compound, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Preparation of salicylaldehyde hydrazide receptor H1

[0037] Under the protection of nitrogen, add salicylaldehyde and hydrazine hydrate into a round bottom flask at a molar ratio of 2.5:1, add an appropriate amount of ethanol, reflux and stir for 4 hours, stop the reaction, filter, wash with ethanol, dry in vacuum, and recrystallize with ethanol to obtain salicylaldehyde hydrazide receptor.

[0038] Salicylaldehyde hydrazide receptor H1: khaki solid, m.p. 220.5-221.4℃; H1 yield: 83.3%; ESI-MS m / e 241.31, 1 H NMR (DMSO- d 6 ): δ 11.2 (s, 2H, Ar-OH), 9.01 (s, 2H, CH=N), 7.37-6.99 (m, Ar-CH). Elemental analysis: calcd for C 14 h 12 N 2 o 2 : C 69.99%, H 5.03%, N 11.66%; Found: C 69.80%, H 5.09%, N 11.59%.

Embodiment 2

[0040] Preparation of salicylaldehyde hydrazide receptor H2

[0041] Under argon protection, add p-nitrosalicylaldehyde and hydrazine hydrate at a molar ratio of 2.5:1 to a round bottom flask, add an appropriate amount of ethanol, stir at room temperature for 12 hours, stop the reaction, filter, wash with ethanol, dry in vacuum, and recrystallize with ethanol Salicylaldehyde hydrazide receptor.

[0042] Salicylaldehyde hydrazide receptor H2: yellow solid, m.p. 251.6-252.1℃; H2 yield: 89.12%; ESI-MS m / e 359.1, 1 H NMR (DMSO- d 6 ): δ 11.42 (s, 2H, Ar-OH), 9.23 (s, 2H, CH=N), 7.52-7.11 (m, Ar-CH). Elemental analysis: calcd for C 16 h 14 N 4 o 6 : C 53.63%, H 3.94%, N 15.64%; Found: C 53.58%, H 3.90, N 15.61%.

Embodiment 3

[0044] Preparation of salicylaldehyde hydrazide receptor H3

[0045] Under nitrogen protection, add 5-methoxy-p-nitrosalicylaldehyde and hydrazine hydrate into a round bottom flask at a molar ratio of 3:1, add an appropriate amount of ethanol, stir at room temperature for 18 hours, stop the reaction, filter, wash with ethanol, and dry in vacuo. Salicylaldehyde hydrazide acceptor was obtained by recrystallization from ethanol.

[0046] Salicylaldehyde hydrazide receptor H3: yellow solid, m.p. 253.5-254.1℃; ESI-MS m / e 391.12, 1 H NMR (CDCl 3 ): δ 11.11 (s, 2H, Ar-OH), 8.96 (s, 2H, CH=N), 7.36-6.33 (m, ArH), 3.83 (s, 6H, CH 3 ).Elemental analysis: calcd for C 18 h 20 N 2 o 4 : C 49.24%, H 3.62%, N 14.35%; Found: C 49.28%, H 3.56%, N 14.32%.

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Abstract

The invention discloses a novel compound used as Cu<2+> colorimetric identification reagent, a preparation method and application of the compound. The novel compound is salicylidenehydrazine receptor obtained by condensing salicylaldehyde and hydrazine hydrate. The inventive compound with good metal ion identification ability can selectively identify Cu<2+>. Photochemical colorimetric probe prepared by the receptor can be widely applied to the technical field of heavy metal ion identification and detection.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a salicylaldehyde hydrazide acceptor compound, in particular to a colorimetric probe for detecting copper ions and the application of the colorimetric probe in the identification and detection of heavy metal ions. Background technique [0002] As one of the essential trace elements in the physiological process of organisms, copper can be combined with proteins and participate in a series of electron transfer, oxidation-reduction processes and oxygen-carrying processes. Copper deficiency can also lead to growth and metabolic disorders, such as Wilson disease, Alzheimers disease and Menkes disease. In addition, excessive copper in the environment will cause it to accumulate in crops, resulting in poor growth of animals and plants, and it will also be passed on to humans through the food chain. Therefore, the detection of copper content is of great importance in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/88C07C249/16G01N21/78
Inventor 刘凯
Owner TIANJIN NORMAL UNIVERSITY
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