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Paradoxes and paradigms: the stabilization/resonance energy of some –C(O)– species: acetyl derivatives, metal carbonyls, and amides alike

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Abstract

Decarbonylation reactions of acetyl metal carbonyls, in particular of organocobalt compounds, and of amides are discussed in view of stabilization/resonance energies. It is found that the archetypal acetylcobalt tetracarbonyl, CH3C(O)Co(CO)4, has ca. 25 kJ mol−1 stabilization, while the corresponding phthalimido- and phenoxy-substituted species have inexplicable destabilization of ca. 8 kJ mol−1. By comparison, the archetypal N,N-dimethylacetamide, CH3C(O)N(CH3)2, has a resonance energy of 71 kJ mol−1.

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Funding

MPS received financial support from Slovenian Research Agency (ARRS Grant P1-0045, Inorganic Chemistry and Technology).

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Authors and Affiliations

  1. Department of Inorganic Chemistry and Technology, Jožef Stefan Institute, Jamova 39, Ljubljana, Slovenia

    Maja Ponikar-Svet

  2. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD, 21250, USA

    Maja Ponikar-Svet & Joel Fredric Liebman

Authors
  1. Maja Ponikar-Svet
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  2. Joel Fredric Liebman
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Contributions

MP-S: conceptualization, writing. JFL: conceptualization, writing.

Corresponding author

Correspondence to Joel Fredric Liebman.

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We did not perform any experiments when preparing this article, so neither ethics reviews nor informed consent were necessary.

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The authors declare no competing interests.

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Dedication

The current study is dedicated to the memory of the recently deceased Professor László Markó (1928–2022). From his many papers on organocobalt carbonyl species, we have learned much fine science. From his colleagues, we have learned how fine a person he was.

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Ponikar-Svet, M., Liebman, J.F. Paradoxes and paradigms: the stabilization/resonance energy of some –C(O)– species: acetyl derivatives, metal carbonyls, and amides alike. Struct Chem 34, 51–54 (2023). https://doi.org/10.1007/s11224-022-02023-w

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  • DOI: https://doi.org/10.1007/s11224-022-02023-w

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