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.
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
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
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
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
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
Pedley JB (1994) Thermochemical data and structures of organic compounds. TRC data series, vol 1. TRC, College Station, TX
Liebman JF, Greenberg A (1974) The origin of rotational barriers in amides and esters. Biophys Chem 1:222–226
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
Gudmundsdottir AD, Liebman JF (2005) The energetics of N-acylimines. Struct Chem 16:155–157
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
Liebman JF, Greenberg A (2019) The resonance energy of amides and their radical cations. Struct Chem 30:1631–1634
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
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
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
Hunter EPL, Lias SG (1998) Evaluated gas phase basicities and proton affinities of molecules: an update. J Phys Chem Ref Data 27:413–656
Meot-Ner M (2012) Update 1 of strong ionic hydrogen bonds. Chem Rev 112:PR22–PR103
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
Traeger JC, McLoughlin RG, Nicholson AJC (1982) Heat of formation for acetyl cation in the gas phase. J Am Chem Soc 104:5318–5322
Bieri G (1977) Valence ionization energies of hydrocarbons. Helv Chim Acta 60:2213–2233
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
Dauletyarov Y, Wallace AA, Blackstone CC, Sanov A (2019) Photoelectron spectroscopy of biacetyl and its cluster anions. J Phys Chem A 123:4158–4167
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
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
Author information
Authors and Affiliations
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
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.
About this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11224-023-02155-7