ニンヒドリンによるカルボン酸ヒドラジドの呈色反応

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書誌事項

タイトル別名
  • Studies on color reaction of hydrazides with ninhydrin
  • ニンヒドリン ニ ヨル カルボンサン ヒドラジド ノ テイショク ハンノウ

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説明

Hydrazides, as well as α-amino acids, react readily with ninhydrin at 100°C in the presence of ascorbic acid and pyridine to give a violet color (Ruhemann's Purple). The mechanism of this reaction was investigated. At the first step of this reaction, hydrazide condenses with ninhydrin to produce RCONHNH-_??_C6H4 (I), and then the elimination of H2O and the rearrangement of hydrogen take place by heating to yield an azo-type double bond, RCO-N=N-_??_C6H4 (II). The double bond, -N=N-, is cleavaged reductively with ascorbic acid to yield an amine (enolate form of 2-amino-1, 3-indandione) and an amide, then a further molecule of ninhydrin recondeses with the amine to produce Ruhemann's Purple.<BR>The intermediate compounds, (I) and (II), were obtained from m-nitrobenzoyl-, anisoyl- and iso-nicotinoyl - hydrazines. Their structures were determined from their IR and UV spectra. Amides were identified by isolating them from the color solution or by paper chromatography. Meanwhile, hydrazines and aromatic amines give no color under the same conditition.<BR>The color reaction was applied to the microdetection and the colorimetric determination of hydrazides. Isoniazide (III) and its derivatives in pharmaceutical preparations were determined and good results were obtained in the presence of diverse materials.<BR>Colorimetric procedure: Prepare the test solution containing ca. 40μg/ml of (III), take 2ml of this solution into a 30ml glass stoppered test tube, add each 1ml of 1% ninhydrin solution, 0.05% ascorbic acid solution and pyridine. and then heat the mixture for 25min. in boiling water. Cool rapidly in ice-water, shake vigorously for 2 min. and dilute with water to make 25ml. Measure the absorbancy Et, against the blank solution at 570mμ. At the same time, determine the absorbancy, Es, of the standard solution (40μg/ml) in the same manner with the same reagent, and calculate the per cent amount by Et/Es.

収録刊行物

  • 分析化学

    分析化学 11 (12), 1255-1262, 1962

    公益社団法人 日本分析化学会

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