Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F22%3A43924478" target="_blank" >RIV/60461373:22310/22:43924478 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0143720822006039?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0143720822006039?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.dyepig.2022.110681" target="_blank" >10.1016/j.dyepig.2022.110681</a>

Result language
angličtina
Original language name
Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents
Original language description
2,5-Diamino-1,4-benzoquinonediimine (DABQDI) derivatives possessing two electron-withdrawing aromatic N-substituents can potentially exhibit a zwitterionic ground state in lieu of the expected canonical structure. It was previously shown that the use of nitroaromatics electron-withdrawing groups (EWG) could yield the quantitative formation of zwitterionic tautomer of DABQDI in polar solvents, while a mixture of canonical and zwitterionic forms was present in low polarity solvents. In this work, we report that the replacement of nitro-containing EWG by weaker nitrile ones prevents the formation of canonical species in apolar solvents for the benefit of the zwitterionic tautomer. This counterintuitive observation is rationalized with theoretical calculations, which points out that the fully zwitterionic electronic structure of the nitrile-containing DABQDI arises from the absence of possible intramolecular hydrogen bonding between the cyanoaromatic N-substituent and the N–H proton of the bridge in the canonical form. © 2022 Elsevier Ltd
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GA20-08667S" target="_blank" >GA20-08667S: Chemistry of phenoxathiin-based thicalixarenes and related compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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