Skip to main content
Log in

Paradigms and paradoxes: stabilization, destabilization and resonance energy of α-diketones, dienes and derived radical ions

  • Research
  • Published:
Structural Chemistry Aims and scope Submit manuscript

Abstract

By analogy to the understanding of the energetics of amides, the current study discusses the stabilization/destabilization energy of α-diketones, dienes and derived radical ions.

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

Data and material availability

Not applicable. There are no data sets associated with the current paper except for those cited and already in the chemical literature. As no experiments were done for this publication, no compound samples were used nor any apparatus employed.

Code availability

Not applicable.

References

  1. Pauling L, Sherman J (1933) The nature of the chemical bond. VI. The calculation from thermochemical data of the energy of resonance of molecules among several electronic structures. J Chem Phys 1:606–617

    Article  CAS  Google Scholar 

  2. George P, Bock CW, Trachtman M (1987) In: Liebman JF, Greenberg A (eds) Molecular structure and energetics: Biophysical aspects, (Vol. 4) VCH, Deerfield Beach, FL, pp 163–187

  3. Wiberg KB, Hadad CM, Rablen PR, Cioslowski J (1992) Substituent effects. 4. Nature of substituent effects at carbonyl groups. J Am Chem Soc 114:8644–8654

    Article  CAS  Google Scholar 

  4. Hadad CM, Rablen PR, Wiberg KB (1998) C-O and C-S bonds: Stability, bond dissociation energies, and resonance stabilization. J Org Chem 63:8668–8681

    Article  CAS  Google Scholar 

  5. Pedley JB (1994) Thermochemical data and structures of organic compounds. TRC data series, vol 1. TRC, College Station, TX

  6. Liebman JF, Greenberg A (1974) The origin of rotational barriers in amides and esters. Biophys Chem 1:222–226

    Article  CAS  PubMed  Google Scholar 

  7. Greenberg A, Chiu Y-Y, Johnson JL, Liebman JF (1991) The resonance energy of amides, the structure of aziridinone and its relationship to other strained lactams. Struct Chem 2:117–126

    Article  CAS  Google Scholar 

  8. Gudmundsdottir AD, Liebman JF (2005) The energetics of N-acylimines. Struct Chem 16:155–157

    Article  CAS  Google Scholar 

  9. Morgan J, Greenberg A, Liebman JF (2012) Paradigms and paradoxes: O- and N-protonated amides, stabilization energy and resonance energy. Struct Chem 23:197–199

    Article  CAS  Google Scholar 

  10. Liebman JF, Greenberg A (2019) The resonance energy of amides and their radical cations. Struct Chem 30:1631–1634

    Article  CAS  Google Scholar 

  11. Ponikvar-Svet M, Liebman JF (2023) Paradoxes and paradigms: the stabilization/resonance energy of some –C(O)– species: acetyl derivatives, metal carbonyls and amides alike. Struct Chem 34:51–54

    Article  Google Scholar 

  12. Kercher JP, Fogleman EA, Koizumi H, Sztaráy B, Baer T (2005) Heats of formation of the propionyl ion and radical and 2,3-pentanedione by threshold photoelectron photoion coincidence spectroscopy. J Phys Chem A 109:939–946

    Article  CAS  PubMed  Google Scholar 

  13. Temprado M, Roux MV, Umnahanant P, Zhao H, Chickos JS (2005) The thermochemistry of 2,4-pentanedione revisited: observance of a nonzero enthalpy of mixing between tautomers and its effects on enthalpies of formation. J Phys Chem B 109:12590–12595

    Article  CAS  PubMed  Google Scholar 

  14. Hunter EPL, Lias SG (1998) Evaluated gas phase basicities and proton affinities of molecules: an update. J Phys Chem Ref Data 27:413–656

    Article  CAS  Google Scholar 

  15. Meot-Ner M (2012) Update 1 of strong ionic hydrogen bonds. Chem Rev 112:PR22–PR103

    Article  CAS  Google Scholar 

  16. Yamabe S, Hirao K, Wasada H (1992) A correlation between proton affinities and intramolecular hydrogen bonds in bifunctional organic compounds. J Phys Chem 96:10261–10264

    Article  CAS  Google Scholar 

  17. Traeger JC, McLoughlin RG, Nicholson AJC (1982) Heat of formation for acetyl cation in the gas phase. J Am Chem Soc 104:5318–5322

    Article  CAS  Google Scholar 

  18. Bieri G (1977) Valence ionization energies of hydrocarbons. Helv Chim Acta 60:2213–2233

    Article  CAS  Google Scholar 

  19. Hammer NI, Diri K, Jordan KD, Desfrancois C, Compton RN (2003) Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules. J Chem Phys 119:3650–3660

    Article  CAS  Google Scholar 

  20. Dauletyarov Y, Wallace AA, Blackstone CC, Sanov A (2019) Photoelectron spectroscopy of biacetyl and its cluster anions. J Phys Chem A 123:4158–4167

    Article  CAS  PubMed  Google Scholar 

  21. Jordan KD, Burrow PD (1980) Temporary negative ions of methyl-substituted ethylenes: trends in the electron affinities, ionization potentials, and excitation energies. J Am Chem Soc 102:6882–6883

    Article  CAS  Google Scholar 

  22. Staley SW, Strnad JT (1994) Calculation of the energies of π* negative ion resonance states by the use of Koopmans’ theorem. J Phys Chem 98:116–121

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Contributions

Not applicable in this single-authored study. All parts of this paper were by J.F.L and he takes total responsibility for its contents.

Corresponding author

Correspondence to Joel Fredric Liebman.

Ethics declarations

Ethical approval

Not applicable, as there were no human nor animal studies, and so, neither ethics reviews nor informed consent were necessary.

Competing interests

The author declares there are no competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liebman, J.F. Paradigms and paradoxes: stabilization, destabilization and resonance energy of α-diketones, dienes and derived radical ions. Struct Chem 34, 729–732 (2023). https://doi.org/10.1007/s11224-023-02155-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11224-023-02155-7

Keywords

Navigation