Skip to main content
Log in

Paradigms and paradoxes: Energetics of the oxidative cleavage of indigo and of other olefins

  • Original Paper
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

Indigo is a unique organic compound in terms of its blue color and its multiple conjugated functional groups contained therein. We ask whether the enthalpy of its cleavage reaction into two isatin molecules reflects the novelty of either this color and/or the conjugated functionalities contained therein.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Gandra N, Frank AT, Le Gendre O, Sawwan N, Aebisher D, Liebman JF, Houk KN, Greer A, Gao R (2006) Tetrahedron 62:10771

    Google Scholar 

  2. Liebman JF, Pollack RM (1989) In: Patai S, Rappoport Z (ed) The chemistry of the enone functional group. Wiley, Chichester

  3. Liebman JF, Perks HM (1994) In: Rappoport Z (ed) The chemistry of enamines. Wiley, Chichester

  4. Gao HX, Zhao FQ, Hu RZ, Pan Q, Wang BZ, Yang XW, Gao Y, Gao SL, Shi QZ (2006) Chin J Chem 24:177

    Article  CAS  Google Scholar 

  5. Steele WV, Chirico RD, Knipmeyer SE, Nguyen A, Smith NK (1997) J Chem Eng Data 42:1037

    Article  CAS  Google Scholar 

  6. Van-chin-syan YY, KochubeiVV, Sergeev VV, Raevskii YA, Gerasimchuk SI, Kotovich KZ (1996) Russ J Chem Phys (Engl Transl) 70:1789

    Google Scholar 

  7. Steele WV, Chirico RD, Cowell AB, Knipmeyer SE, Nguyen A (2002) J Chem Eng Data 47:700

    Article  CAS  Google Scholar 

  8. Rogers DW, Zhao Y, Trætteberg M, Hulce M, Liebman J (1998) J Chem Thermodyn 30:1393

    Article  CAS  Google Scholar 

  9. Pedley JB (1994) Thermochemical data and structures of organic compounds, vol 1: TRC data series. Thermodynamics Research Center, College Station, TX

  10. Chickos JS, Acree Jr WE, Liebman JF (1999) J Phys Chem Ref Data 28:1535

    CAS  Google Scholar 

  11. Chickos JS, Acree Jr WE (2002) J Phys Chem Ref Data 31:537

    Article  CAS  Google Scholar 

  12. Chickos JS, Acree Jr WE (2003) J Phys Chem Ref Data 32:519

    Article  CAS  Google Scholar 

  13. Manion JA (2002) J Phys Chem Ref Data 31:123

    Article  CAS  Google Scholar 

  14. Asher RL, Appelman EH, Ruscic B (1996) J Chem Phys 105:9781

    Article  CAS  Google Scholar 

  15. Glukhovtsev MN, Bach RD (1997) J Phys Chem A 101:3574

    Article  CAS  Google Scholar 

  16. Turecek F, Havlas Z (1986) J Org Chem 51:4066

    Article  CAS  Google Scholar 

  17. Born M, Ingemann S, Nibbering NMM (1996) J Phys Chem 100:17662

    Article  CAS  Google Scholar 

  18. Kim IB, Chin CS (1985) Bull Kor Chem Soc 6:176

    CAS  Google Scholar 

  19. Fang W, Rogers DW (1972) J Org Chem 57:2294

    Article  Google Scholar 

  20. Li Y, Baer T (2002) Int J Mass Spectrom 218:37

    Article  CAS  Google Scholar 

  21. Roth WR, Adamczak O, Breuckmann R, Lennartz HW, Boese R (1991) Chem Ber 124:2499

    CAS  Google Scholar 

  22. (a) Traeger JC (2000) Int J Mass Spectrom 194: 261; (b) Aubrey C, Holmes JL, Terlouw JK (1997) J Phys Chem A 101:5958; (c) Bouchoux G, Salpin J-Y. (1996) J Phys Chem 100:16555

  23. Wiberg KB, Wasserman, DJ (1981) J Am Chem Soc 103:6563

    Article  CAS  Google Scholar 

  24. Rogers DW, Dejroongruang K, Samuel SD, Fang W, Zhao Y (1992) J Chem Thermodyn 24:561

    Article  CAS  Google Scholar 

  25. Kabo GY, Miroshnichenko EA, Frenkel ML, Kozyro AA. Simirskii VV, Krasulin AP, Vorob’eva V, Lebedev YA (1990) Bull Acad Sci USSR, Div Chem Sci 662

  26. Fattahi A, Kass SR, Liebman JF, Matos MAR, Miranda MS, Morais VMF (2005) J Am Chem Soc 127:6116

    Article  CAS  Google Scholar 

  27. Guthrie JP (1978) J Am Chem Soc 100:6892

    Article  Google Scholar 

  28. Verevkin SP (1997) J Chem Thermodyn 29:1495

    Article  CAS  Google Scholar 

  29. Liebman JF (1997) In: Rappoport Z (ed) The chemistry of functional groups supplement A2: The chemistry of dienes and polyenes, vol 1. Wiley, Chichester

  30. Berthelot M (1893) Ann Chim Phys 28:126; Bertholet M, Matignon C (1893) Ann Chim Phys 139, as reported in Domalski ES (1972) J Phys Chem Ref Data 1:221

  31. Wiberg KB, Morgan KM, Maltz H (1994) J Am Chem Soc 116:11067

    Article  CAS  Google Scholar 

  32. Kreysig VD, Friebe R, Aparowsky H, Schirmer J (1968) J Prakt Chem 37:329

    Article  CAS  Google Scholar 

  33. Moureu C, Boutaric A (1920) J Chim Phys 18:348

    CAS  Google Scholar 

  34. d’Aladern R (1893) Compt Rend 116:1457 reported in Domalski, ES (1972) J Phys Chem Ref Data 1:221

  35. Matos MAR, Miranda MS, Morais VMF, Liebman JF (2003) J Org Biomol Chem 1:2566

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Joel F. Liebman.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Frank, A.T., Adenike, A., Aebisher, D. et al. Paradigms and paradoxes: Energetics of the oxidative cleavage of indigo and of other olefins. Struct Chem 18, 71–74 (2007). https://doi.org/10.1007/s11224-006-9126-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-006-9126-x

Keywords

Navigation