INFLUENCE OF POSITIVE CHARGE ON THE NMR PARAMETERS OF MONO- AND DIPROTONATED FORMS OF 4-DIMETHYLAMINOPYRIDINE

Authors

  • Александр M. Генаев N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Георгий E. Сальников N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Константин Ю. Колтунов Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090 Boreskov Institute of Catalysis, 5 Akademika Lavrentieva Ave., Novosibirsk 630090

DOI:

https://doi.org/10.1007/5745

Keywords:

DMAP, super acids, NMR, N-protonation, quantum-chemical calculations, simulation of NMR spectra

Abstract

By the example of 4-dimethylaminopyridine and some of its derivatives taken as model nitrogen heterocycles with several basic centers, the correlation of the parameters of the NMR spectra with the direction (regioselectivity) and multiplicity of protonation of these compounds in CF3COOH-CD2Cl2, TfOH-CD2Cl2 и FSO3H-SbF5 acid systems was studied. The established dependence of the spectral characteristics on the value of the introduced positive charge will be useful in studying the reactivity of similar heterocyclic systems in the presence of acidic agents.

Authors: Alexander M. Genaev, George E. Salnikov, Konstantin Yu. Koltunov*

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Published

2020-08-19

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers