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Probing the aromaticity of unsaturated N-heterocyclic carbenes and their heavy analogues with the EDDB criterion

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Abstract

Three series of N-heterocyclic carbene analogues including Arduengo-type systems (HCNBut)2E (1; E = C, Si, Ge, Sn), their benzannulated derivatives C6H4(NCH2But)2E (2; E = C, Si, Ge, Sn, Pb), and amidophenolates C6H2But2(O)NButE (3; E = Ge, Sn, Pb) were studied by the electron density of delocalized bonds (EDDB) method. The results obtained confirmed the π-aromaticity of systems 1–3. The aromaticity series were obtained. The degree of aromaticity of heavy carbene analogues increases on going down Group 14 of the periodic system.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    R. R. Aysin & S. S. Bukalov

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  1. R. R. Aysin
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  2. S. S. Bukalov
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Correspondence to R. R. Aysin.

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Dedicated to the blessed memory of L. A. Leites.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 706–714, April, 2021.

This work was financially supported by the Ministry of Science and Education of the Russian Federation.

This paper does not contain description of studies on animals or humans.

The authors declare no competing interests.

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Aysin, R.R., Bukalov, S.S. Probing the aromaticity of unsaturated N-heterocyclic carbenes and their heavy analogues with the EDDB criterion. Russ Chem Bull 70, 706–714 (2021). https://doi.org/10.1007/s11172-021-3140-4

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  • DOI: https://doi.org/10.1007/s11172-021-3140-4

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