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

  • Ibon AlkortaEmail author
  • José Elguero
Original Research
  • 32 Downloads

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.

Keywords

B3LYP Tautomerism IR NMR Acid-base equilibria N-Heterocyclic carbenes 

Notes

Acknowledgments

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

Funding information

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).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11224_2019_1451_MOESM1_ESM.doc (92 kb)
ESM 1 (DOC 92 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Instituto de Química MédicaCSICMadridSpain

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