Oziminski, WP and Ramsden, CA (2021) Valence tautomerism and recyclisation of type B mesoionic tetrazoles: a computational study. Structural Chemistry. ISSN 1040-0400

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The energy profiles for ring opening of representative type B mesoionic 2,3-diphenyl-1,2,3,4-tetrazolium-5-olates, -thiolates, -aminides and -methylides and for alternative recyclisation pathways are investigated using ab initio MP2 calculations. The energetics of initial ring opening are found to be comparable for all systems, but the tetrazolium-5-olates are anomalous in that no alternative reaction pathway is accessible. The influence of solvent is explored using the polarised continuum model (PCM) method to simulate aqueous solvation. The only significant solvent effect is found to be solvation of the mesoionic precursors. This solvent effect correlates with dipole moment and disfavours initial valence tautomerism both kinetically and thermodynamically.

Item Type: Article
Additional Information: Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/.
Uncontrolled Keywords: Mesoionic · MP2 Calculations · Valence tautomerism · Tetrazoles · Solvation · Recyclisation
Subjects: R Medicine > R Medicine (General)
Divisions: Faculty of Medicine and Health Sciences > School of Medicine
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Depositing User: Symplectic
Date Deposited: 06 Oct 2021 16:09
Last Modified: 30 Nov 2021 10:41
URI: https://eprints.keele.ac.uk/id/eprint/10099

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