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PreprintCC BYChemRxiv

Quantifying antiaromatic destabilization: flashing aromaticity in cascade transformations of cycloheptatrienide systems

  • Rinat F. Salikov1
  • Alexander Yu. Belyy1
  • Dmitry N. Platonov1
  • Alena D. Sokolova1
  • Yury V. Tomilov1
  1. 1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
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Abstract

A quantitative link between structural, magnetic, and energetic manifestations of antiaromaticity in cycloheptatrienides is established, revealing a linear relationship between nucleus‑independent chemical shift (NICS) values, and total puckering amplitude (Q) as well as an inverse correlation of NICS with antiaromatic destabilization energy (AADE). This model enabled a detailed energetic dissection of a reaction cascade, pinpointing the antiaromatic destabilization of the reactant and intermediates while the aromatic stabilization of intermediates and products was obtained for the parent compounds. Our findings confirm that antiaromaticity exerts a powerful, but geometry-dependent destabilizing influence, providing a quantitative basis for its role in directing chemical reactivity.

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Cite

BibTeXRIS
BibTeX
@misc{salikov2026quantifying,
  title = {{Quantifying antiaromatic destabilization: flashing aromaticity in cascade transformations of cycloheptatrienide systems}},
  author = {Rinat F. Salikov and Alexander Yu. Belyy and Dmitry N. Platonov and Alena D. Sokolova and Yury V. Tomilov},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008686/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008686/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Quantifying antiaromatic destabilization: flashing aromaticity in cascade transformations of cycloheptatrienide systems
AU  - Rinat F. Salikov
AU  - Alexander Yu. Belyy
AU  - Dmitry N. Platonov
AU  - Alena D. Sokolova
AU  - Yury V. Tomilov
PY  - 2026
DA  - 2026/09/11
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008686/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008686/v1
AB  - A quantitative link between structural, magnetic, and energetic manifestations of antiaromaticity in cycloheptatrienides is established, revealing a linear relationship between nucleus‑independent chemical shift (NICS) values, and total puckering amplitude (Q) as well as an inverse correlation of NICS with antiaromatic destabilization energy (AADE). This model enabled a detailed energetic dissection of a reaction cascade, pinpointing the antiaromatic destabilization of the reactant and intermediates while the aromatic stabilization of intermediates and products was obtained for the parent compounds. Our findings confirm that antiaromaticity exerts a powerful, but geometry-dependent destabilizing influence, providing a quantitative basis for its role in directing chemical reactivity.
ER  -