Theoretical study of NH and CH acidities of toluidine isomers – dependence on their oxidation states

  1. Vladimir Lukes and
  2. Horst HartmannORCID Logo

Submitting author affiliation: Technische Universität Dresden, Dresden, Germany

Beilstein Arch. 2020, 2020113. https://doi.org/10.3762/bxiv.2020.113.v1

Published 05 Oct 2020

  • Preprint

Abstract

For the toluidine isomers, the amino group acidity represents a characteristic feature of these compounds in their electric neutral state. The CH acidity of methyl group is hidden under NH acidity. As demonstrated by theoretical calculations based on the quantum chemistry composite method G4 and Density functional theory, the transformation of toluidines into their mono- and bi-oxidised states significantly increases the acidity of methyl group. This study indicates that the presence or absence of these deprotonated species in reaction mixture will determine the CN or CC coupling toluidine products

Keywords: Acidity of Oxidized States; Isodesmic Reaction; pKa; Anilinium Ion; M062X

Supporting Information

Format: DOCX Size: 314.4 KB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Lukes, V.; Hartmann, H. Beilstein Arch. 2020, 2020113. doi:10.3762/bxiv.2020.113.v1

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2020 Lukes and Hartmann; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia