Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

Fully zwitterionic diaminobenzoquinonediimines promoted by cyanoaromatic N-substituents

Popis výsledku anglicky

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

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

<a href="/cs/project/GA20-08667S" target="_blank" >GA20-08667S: Chemie thiacalixarenů na bázi phenoxathiinu a příbuzných látek</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2022

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Dyes and Pigments

ISSN

0143-7208

e-ISSN

1873-3743

Svazek periodika

206

Číslo periodika v rámci svazku

Neuveden

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

8

Strana od-do

nestrankovano

Kód UT WoS článku

000850881300004

EID výsledku v databázi Scopus

2-s2.0-85138441461