Photochemical analysis studies—III A fluorimetric and ultraviolet spectrophotometric study of the photolysis of chloroquine on silica-gel thin layers, and its analytical application

Aaron, Jean‐Jacques; Fidanza, Joëlle

doi:10.1016/0039-9140(82)80173-2

Cited by 18 publications

(1 citation statement)

References 9 publications

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“…Therefore, following our recent study on the photoisomerization of carvone (13) , we have determined, in the present paper, the kinetics and quantum yields of the photolysis of three novel carvone hydrazone derivatives, that is carvone-dimethyl hydrazone (CDMH), carvone phenyl hydrazone (CPH) r and carvone-hydrazone-benzoic acid (CHBA). Also, we have evaluated the usefulness of this photoreaction for the analytical determination of carvone, using the photochemical-fluorimetric approach (14)(15)(16)(17). The latter approach is based on the measurement of the fluorescence of the photoproduct of the analyte under study or of its derivative.…”

Section: Introductionmentioning

confidence: 99%

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1

Ndiaye¹,

Aaron

1993

Bulletin des Soc Chimique

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The photolysis of carvone dimethylhydrazone (CDMH) carvone‐ Phenylhydrazone (CPH), and carvone hydrazono‐orthobenzoic acid (CHBA), was studied at room‐temperature (293K) in several solvents (cyclohexane, dioxane, formamide, acetonitrile, ethanol, propanol). The photolysis overall first‐order rate constants (k1) and quantum yields (φp) were found to depend Markedly of the structure of the carvone hydrazone derivative and of the solvent, k1 values varied in the range 1.3 × 10‐3, 2.4 × 10‐3 min‐1 for CDMH ‐ 4.0 × 10‐2 ‐ 2 × 10‐1 min‐1 for CPH, and 8 × 10‐3 ‐ 4.6 × 10‐2 min‐1 for CHBA, and φp values between 0.0009 and 0.0012 for CDMH, 0.07 and 0.19 for CPH, and 0.004 and 0.0085 for CHBA, according to the solvent. The structure of the photoproducts was investigated by mass spectrometry and fluorescence spectroscopy. Mechanisms are proposed for the photolysis of these carvone hydrazone derivatives. A photochemical‐fluorimetric method is presented for the analysis of carvone, following derivatization. Limits of detection of carvone are in the ng range.

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Section: Introductionmentioning

confidence: 99%

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1

Ndiaye¹,

Aaron

1993

Bulletin des Soc Chimique

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Chromatographische Artefakte bei Arzneistoffen der 3,5‐Pyrazolidindion‐Gruppe, 2. Mitt. „Post‐Photoeffekt”︁ bei bestrahlten Kieselgel‐Fertigplatten

Takacs

Kertész

Wiener

et al. 1985

Archiv der Pharmazie

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Takdcs, Kertksz, Wiener und ReischArch. Pharm. b) aus Formamid: Ein aus 24,Og (0,l mol) 2b und 80ml Formamid bestehendes Gemisch wird 3 h zum Sieden erhitzt. Durch Konzentrieren der Usung i. Vak. wird eine Festsubstanz erhalten, die beim Umkristallisieren aus Benzol farblose Plattchen vom Schmp. 129-130' liefert. Ausb. 18,3 g (68 % d. Th.). Die Eigenschaften der mit Formamid gewonnenen Substanz sind mit denjenigen einer nach a) dargestellten Substanz identisch.

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Photochemical Reactivity and Fluorescence Analysis of 6‐Methoxyquinoline, 6‐Methoxyquinaldine, and 4,7‐Dichloroquinoline

Fidanza

Aaron

1985

Bulletin des Soc Chimique

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The photochemical reactivity of 6-methoxyquinoline, 6-methoxyquinaldine, and 4,7-dichloroquinoline has been investigated by W spectrophotometry and spectrophotofluorimetry, in liquid solution and on silica-gel thin layers. Ultraviolet irradiation decreases the fluorescence intensity of 6-methoxyquinoline and 6-methoxyquinaldine, with apparent first-order rate constants of photolysis. A highly fluorescent photoproduct is formed upon irradiation of 4,7-dichloroquinoline, and a photochemical scheme is proposed. The effect of solvent composition, pH, and irradiation timeon fluorescence intensity, and the effect of medium on the photochemical enhancement or quenching of fluorescence have been studied for the three compounds. Fluorimetric pKa values are found to be in good agreement with the ground-state dissociation constants. Linear calibration plots are obtained over a concentration range of two to three orders of magnitude. Very low fluorimetric detection limits, at the piconole (or ng) level are determined for the methoxyquinolines. Photochemical-fluorimetry is a useful method for the analysis of 4,7-dichloroquinoline. INTRODUCTIONBecause of their considerable importance as analytical reagents, especially for the complexation with metal ions, and of their uoefulness in the biomedical field, substituted quinolines have already been assayed by several analytical methods (1-7). The luminescence properties of some quinoline derivatives have been studied extensively in relation with the pH of the medium (8-13), and several, sensitive fluorimetric (4,7), and phosphorimetric procedures (5-7) have been proposed for their quantitative determination. However, in spite of the large interest generated by the excited-state properties of quinolines, very few reports have been published concerning their photochemical behaviour (14,15,28).Recently, in the framework of photochemical analysis studies of organic compounds (16-22), we have shown that antimalarial quinoline derivatives containing an alcoyldiamino side-chain, such as chloroquine, primaquine, and plasmocid, were reactive photochemically, and that the sensitivity of their fluorescence detection could be increased significantly upon ultraviolet irradiation (17-21). Photochemical enhancements Factors were found to range between 1.3 and 19, according to molecular structure of the alcoyldiamino substituted quinolines and to experimental conditions of the photoreaction (18-20).Therefore, it was of interest to study also the photochemical behaviour of the model compounds, i.e. quinolines with methoxy or chloro groups, in the absence of the

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Photochemical analysis studies—III A fluorimetric and ultraviolet spectrophotometric study of the photolysis of chloroquine on silica-gel thin layers, and its analytical application

Cited by 18 publications

References 9 publications

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1

Chromatographische Artefakte bei Arzneistoffen der 3,5‐Pyrazolidindion‐Gruppe, 2. Mitt. „Post‐Photoeffekt”︁ bei bestrahlten Kieselgel‐Fertigplatten

Photochemical Reactivity and Fluorescence Analysis of 6‐Methoxyquinoline, 6‐Methoxyquinaldine, and 4,7‐Dichloroquinoline

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Photochemical analysis studies—III A fluorimetric and ultraviolet spectrophotometric study of the photolysis of chloroquine on silica-gel thin layers, and its analytical application

Cited by 18 publications

References 9 publications

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE*1

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE*1

Chromatographische Artefakte bei Arzneistoffen der 3,5‐Pyrazolidindion‐Gruppe, 2. Mitt. „Post‐Photoeffekt”︁ bei bestrahlten Kieselgel‐Fertigplatten

Photochemical Reactivity and Fluorescence Analysis of 6‐Methoxyquinoline, 6‐Methoxyquinaldine, and 4,7‐Dichloroquinoline

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KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1

KINETIC STUDY OF THE PHOTOLYSIS OF NOVEL CARVONE HYDRA20NE DERIVATIVES. ANALYTICAL APPLICATION TO THE DETERMINATION OF CARVONE^*1