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

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...

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Bibliographic Details
Published in:Structural chemistry 2020-02, Vol.31 (1), p.25-35
Main Authors: Alkorta, Ibon, Elguero, José
Format: Article
Language:English
Subjects:
Acid base equilibrium
Carbon dioxide
Cations
Chemistry
Chemistry and Materials Science
Computer Applications in Chemistry
Derivatives
Dimerization
Guanidines
Mathematical analysis
NMR
Nuclear magnetic resonance
Original Research
Physical Chemistry
Protonation
Tautomers
Theoretical and Computational Chemistry
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Summary: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.
ISSN:1040-0400
1572-9001
DOI:10.1007/s11224-019-01451-5