DOI QR코드

DOI QR Code

Rotational Photoisomerization of Thioamide, N-5-Trifluoromethyl-6-methoxy-1-thionaphthoyl-N-methylglycine

  • Shim, Sang-Chul (Department of Chemistry, Korea Advanced Institute of Scinece and Technology) ;
  • Lee, Sang-Jin (Department of Chemistry, Korea Advanced Institute of Scinece and Technology)
  • Published : 1988.08.20

Abstract

A thioamide, N-5-trifluoromethyl-6-methoxy-1-thionaphthoyl-N-m ethylglycine, undergoes trans${\rightleftharpoons}$cis photoisomerization around C-N bound in solution. Azulene quenching studies showed the photoisomerization to proceed via both singlet and triplet excited states.The total quantum yield of the trans${\rightarrow}$cis photoisomerization is about 0.26, 0.14 from the singlet excited state and 0.12 from the triplet excited state. Intersystem crossing and internal conversion quantum yields were calculated from sensitized photostationary state and a plausible mechanism is proposed.

Keywords

References

  1. U. S. Patent. 4,439,617 Kazimir, Sestanj;Nedumparambil, A. Abraham;Francesco, Bellini;Adi, Treasurywala
  2. J. Med. Chem. v.27 Kazimir, Sestanj;Francesco, Bellini;Steven, Fung;Nedumparambil, Abraham;Adi, Treasurywala;Leslie, Humber
  3. Diabetes v.32 no.SUP.1 Dvornik, D.;Simard-Duquesne, N.;Greselin, E.;Dubuc J.;Hick, D.;kraml, M.
  4. Diabetes v.34 no.SUP.1 Rasdin, P.;Rosenstock, J.;Challis, P.;Ryder, S.;Mullane, J. F.;Gonalez, R.;Hicks, D.;Smith, T.;Dvornik, D.
  5. Diabetes v.34 no.SUP.1 Kogoin, L.;Clark, C.;Ryder, S.;Mullane, J. F.
  6. Diabetes v.36 Notvest, R. R.;Inserra, J. J.
  7. Proc. Soc. Exp. Biol. Med. v.178 Simard-Duquesne, N.;Greselin, E.;Gonzalez, R.;Dvornik D.
  8. Angew. Chem. Intern. Ed. v.4 Mannschreck, A.
  9. Tetrahedron Lett. v.19 Mannschreck, A.
  10. Phys. Chem. v.68 Loewenstein, A.;Melera, A.;Rigny P.;Walter W. J.
  11. J. Phys. Chem. v.69 Neuman, R. C. Jr.;Young, L. B.
  12. J. Phys. Chem. v.65 Rogers, M. T.;Woodberg, J. C.
  13. J. Phys. Chem. v.71 Sandstron, J.
  14. J. Am. Chem. Soc. v.89 Neuman, R. C. Jr.;Roark, D. N.;Jones, V.
  15. J. Pharm. Sci. v.74 Hyuk-Koo, Lee;Gloria, Querijero
  16. Metabolism v.28 Gabby, K. H.;Spack , N.;Loo, S.(et al.)
  17. Diabetes v.30 Handelsman, D. J.;Turtle, J. R.
  18. Diabetes v.32 Young, R. J.;Ewing, D. J.;Clark B. F.
  19. Diabetologia v.27 Lewin, I. G.;O'Brien, I. A. D.;Morgan, M. H.(et al.)
  20. Metabolism v.34 no.10 Simard-Duquesne, N.;Greselin, E.;Dubuc, J.;Dvornik, D.
  21. Molecular Pharmacology v.24 Kador, P. F.;Sharpless, N. E.
  22. Proc. Roy. Soc.(London) v.A235 Hatchard, C. G.;Parker, C. A.
  23. Creation and Detection of the Excited State Wagner, P. J.
  24. J. Am. Chem. Soc. v.86 Hammond, G. S.;Saltiel, J.;Lamola, A. A.;Turro N. J.;Bradshaw, J. S.;Cowan, D. O.;Counsell, R. C.;Vogt, V.;Dalton, C.
  25. J. Am. Chem. Soc. v.95 Campbell, R. O.;Lin, R. S. H.
  26. Purification of Laboratory Chemicals(2nd ed.) Perrin, D. D.;Armarego W. L. F.;Perrin, D. R.
  27. J. Am. Chem. Soc. v.69 Price, C. C.;Enos, H. I.;Kaplan W.
  28. Handbook of Photochemistry Steven, L. Murov
  29. Org. Photochem. Saltiel, J.;Joan, D'Agostino;Dennis, Megarity;Lewis, Metts;Kennedth, R. Neuberger;Mark, Wrighton;Zafiriou O. C.