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Theoretical studies of perimidine and its derivatives: structures, energies, and spectra

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Abstract

Theoretical calculations at the B3LYP/6-311++G(d,p) level plus GIAO calculations for NMR absolute shieldings have been carried out for the parent perimidine and several of its derivatives. These include its anion and cation and the acid-base equilibria and other examples of annular tautomerism, such as the 2-hydroxy (and their radical cations), 2-thiol, 2-amino, and 2-alkyl perimidines, and the functional tautomers, such as the benzologues of perimidone. The protonation of 2-aminoperimidines (cyclic guanidines) and the properties of perimidine carbene (dimerization and addition to carbon dioxide), biperimidine, dihydroperimidine, and spiro bidihydroperimidine were also studied.

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Acknowledgments

Thanks are given to the CTI (CSIC) for their continued computational support.

Funding

This work was carried out with financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (Projects PGC2018-094644-B-C2), and Dirección General de Investigación e Innovación de la Comunidad de Madrid (PS2018/EMT-4329 AIRTEC-CM).

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Authors and Affiliations

  1. Instituto de Química Médica, CSIC, Juan de la Cierva, 3, E-28006, Madrid, Spain

    Ibon Alkorta & José Elguero

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  1. Ibon Alkorta
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  2. José Elguero
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Correspondence to Ibon Alkorta.

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The authors declare that they have no conflict of interest.

Additional information

This research is dedicated to Professor Alexander F. Pozharskii of the Department of Organic Chemistry of the Southern Federal University (Rostov-on-Don), our friend and the main contributor of perimidine chemistry on the occasion of his 81th anniversary.

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Alkorta, I., Elguero, J. Theoretical studies of perimidine and its derivatives: structures, energies, and spectra. Struct Chem 31, 25–35 (2020). https://doi.org/10.1007/s11224-019-01451-5

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