Skip to main content
Log in

Structure of red and orange fluorescein

  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

The structures of colorless, red, and yellow-orange fluorescein have been investigated by a combination of solution and solid state13C NMR. It is demonstrated that the three forms have lactonic, zwitterionic, and quinoid structures, respectively. Conflicting X-ray, NMR, and IR structural evidence is discussed for samples of red fluorescein which cannot readily be obtained in definite crystalline form. It is concluded that solid-state13C NMR spectroscopy is superior by revealing primarily the molecular structure but being fairly insensitive toward lattice variations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Baeyer, A.Ber. 1871,4, 555.

    Google Scholar 

  2. Osborn, R. S.; Rogers, D.Acta Crystallogr. Sec. B 1975,31, 359.

    Google Scholar 

  3. Polyakova, I. N.; Starikova, Z. A.; Parusnikov, B. V.; Krasavin, I. A.; Dobryakova, G. M.; Zhadanov, B. V.Zh. Strukt. Khim. 1984,25, 98 (Engl. transl.)

    Google Scholar 

  4. Markuszewski, R.; Diehl, H.Talanta 1980,27, 937.

    Google Scholar 

  5. Abrams, M. J.; Picker, D. H.; Fackler, P. H.; Lock, C. J. L.; Howard-Lock, H. E.; Faggiani, R.; Teicher, B. A.; Richmond, R. C.Inorg. Chem. 1986,25, 3980.

    Google Scholar 

  6. Thorn, D. L.; Fultz, W. C.J. Phys. Chem. 1989,93, 1234.

    Google Scholar 

  7. Amat-Guerri, F.; López-González, M. M. C.; Martinez-Utrilla, R.; Sastre, R.Dyes and Pigments 1990,12, 249 and Ref. 9.

    Google Scholar 

  8. Breitmaier, E.; Voelter, W.Carbon-13 NMR Spectroscopy, 3rd ed.; VCH: Weinheim, Germany, 1987.

    Google Scholar 

  9. Fompeydie, D.; Levillain, P.Bull. Soc. Chim. Fr. 1980, I-459.

  10. Dubost, J.-P.; Léger, J.-M.; Colleter, J.-C.; Levillain, P.; Fompeydie, D. C.R. Acad. Sci. Paris Ser. II 1981,292, 965.

    Google Scholar 

  11. Feuerstein, W.; Dutoit, M.Ber. 1901,34, 2637.

    Google Scholar 

  12. Liebig, H. v.J. Prakt. Chem. 1913, [it2]88, 26 (18).

    Google Scholar 

  13. Fischer, O.; Hepp, E.Ber. 1895,28, 396.

    Google Scholar 

  14. Bernstein, J.; Cohen, M. D.; Leiserowitz, L. InThe Chemistry of the Quinoid Compounds, Part 1; Patai, S., Ed.; Wiley-Interscience: New York, 1974, Chap 2.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

The Editors regret the long delay in having this paper printed due to an unfortunate administrative error.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Anthoni, U., Christophersen, C., Nielsen, P.H. et al. Structure of red and orange fluorescein. Struct Chem 6, 161–165 (1995). https://doi.org/10.1007/BF02286443

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02286443

Key words

Navigation