Solution and solid-state study of the structure of azo-coupling products from isomeric enaminones possessing tert-butyl group: An unprecedented observation of pure hydrazo form in azo coupled N-alkyl-enaminones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F14%3A39897771" target="_blank" >RIV/00216275:25310/14:39897771 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.molstruc.2014.06.069" target="_blank" >http://dx.doi.org/10.1016/j.molstruc.2014.06.069</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2014.06.069" target="_blank" >10.1016/j.molstruc.2014.06.069</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Solution and solid-state study of the structure of azo-coupling products from isomeric enaminones possessing tert-butyl group: An unprecedented observation of pure hydrazo form in azo coupled N-alkyl-enaminones

Popis výsledku v původním jazyce

The structure of the azo-coupling products from enaminones derived from 4,4-dimethyl-1-phenylpentane-1,3-dione has been studied by means of solution-state 1H, 13C and 15N NMR spectroscopy and X-ray diffractometry. The presence of bulky tert-butyl group hinders or even prevents from the formation of planar conjugated heterodiene system H-N-C=C-N=N with an intramolecular hydrogen bond N-H???N= which is the prerequisite for fast tautomeric exchange imino-hydrazo - enamino-azo. The minor amount of azo compounds is formed by a proton exchange through a hydrogen bond N-H???N, which is either intramolecular (in solution) or intermolecular (solid state). The intermolecular exchange proceeds via the dimers of the azo coupling products. This is unprecedented result among the similar molecules hitherto studied.

Název v anglickém jazyce

Solution and solid-state study of the structure of azo-coupling products from isomeric enaminones possessing tert-butyl group: An unprecedented observation of pure hydrazo form in azo coupled N-alkyl-enaminones

Popis výsledku anglicky

The structure of the azo-coupling products from enaminones derived from 4,4-dimethyl-1-phenylpentane-1,3-dione has been studied by means of solution-state 1H, 13C and 15N NMR spectroscopy and X-ray diffractometry. The presence of bulky tert-butyl group hinders or even prevents from the formation of planar conjugated heterodiene system H-N-C=C-N=N with an intramolecular hydrogen bond N-H???N= which is the prerequisite for fast tautomeric exchange imino-hydrazo - enamino-azo. The minor amount of azo compounds is formed by a proton exchange through a hydrogen bond N-H???N, which is either intramolecular (in solution) or intermolecular (solid state). The intermolecular exchange proceeds via the dimers of the azo coupling products. This is unprecedented result among the similar molecules hitherto studied.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

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Svazek periodika

1075

Číslo periodika v rámci svazku

October

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

187-195

Kód UT WoS článku

000342254500024

EID výsledku v databázi Scopus

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