Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Photochemical Reaction of Nalidixic Acid in Methanol

  • Park, Hyoung-Ryun (Department of Chemistry, Chonnam National University) ;
  • Park, Ok-Hyun (Department of Chemistry, Chonnam National University) ;
  • Lee, Hong-Yune (Department of Chemistry, Chonnam National University) ;
  • Seo Jung-Ja (Department of Chemistry, Chonnam National University) ;
  • Bark, Ki-Min (Department of Chemical Education and Institute of Natural Sciences, Gyeongsang National University)
  • Published : 2003.11.20
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Abstract

The photochemical reactions of methanolic nalidixic acid (NAL) solution in the absence and in the presence of air have been investigated using 300 nm UV light. From the reactions, 1-ethyl-7-methyl-4-oxo-4-hydro-1,8-naphthyridine (EMDN),formic acid, and formaldehyde are produced. In the presence of air, hydrogen peroxide is also detected along with the products listed above. The presence of oxygen during the irradiation of methanolic NAL solution effects on the product yield. The initial quantum yields of the products and of the NAL decomposition are determined. Possible reaction pathways for the photochemical reaction are suggested on the basis of the products analysis.

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References

  1. Lesher, G.; Froelich, M.; Gruett, J. J. Med. Pharm. Chem. 1962, 5,1063. https://doi.org/10.1021/jm01240a021
  2. Kang, J. S.; Kim, T. H.; Park, K. B.; Chung, B. H.; Youn, J. I.Photodermal. Photoimmunol. Photome. 1993, 9, 159.
  3. Cho, Y. H.; Kim, T. H.; Park, H. B.; Park, C. K.; Park, K. M. Kor.J. Dermatol. 1995, 33, 1021.
  4. Detzer, N.; Huber, B. Tetrahedron 1975, 31, 1937. https://doi.org/10.1016/0040-4020(75)87055-4
  5. Moore, D. E.; Hemmens, V. J.; Yip, H. Photochem. Photobiol.1984, 39, 57. https://doi.org/10.1111/j.1751-1097.1984.tb03404.x
  6. Vermeersch, G.; Ronfard-Haret, J. C.; Bazin, M.; Carillet, V.;Moriere, P.; Santus, R. Photochem. and Photobiol. 1991, 54,661. https://doi.org/10.1111/j.1751-1097.1991.tb02072.x
  7. Fernandez, E.; Cardenas, A. M. J. Photochem. Photobiol., B:Photobiol. 1990, 4, 329. https://doi.org/10.1016/1011-1344(90)85038-X
  8. Park, H. R.; Chung, K. Y.; Lee, H. C.; Lee, J. K.; Bark, K. M. Bull.Korean Chem. Soc. 2000, 21, 849.
  9. Hatchard, C. G.; Parker, C. A. Proc. Roy. Soc. (London) 1956,A235, 518.
  10. Lee, J.; Seliger, H. H. J. Chem. Phys. 1968, 40, 519.
  11. Atkins, R. C. J. Chem. Ed. 1975, 52, 550. https://doi.org/10.1021/ed052p550
  12. Bark, K. M.; Force, R. K. Spectrochim. Acta 1993, 49A, 1605.
  13. Eaton, D. F. Reference Compounds for Fluorescence Measurements;IUPAC Organic Chemistry Division: Washington DC, USA,1987; pp 1-11.
  14. Demas, J. N.; Grosby, G. A. J. Phys. Chem. 1971, 75, 2463. https://doi.org/10.1021/j100685a009
  15. Nasch, T. Biochem. J. 1958, 55, 418.
  16. Wolfe, W. C. J. Anal. Chem. 1962, 34, 1328. https://doi.org/10.1021/ac60190a040
  17. Sonntag, C. Z. Phys. Chem. 1970, 69, 292.
  18. Wine, P. H.; Astalos, R. J.; Mauldin III, R. L. J. Phys. Chem. 1985,89, 2620. https://doi.org/10.1021/j100258a037

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