Related Experiment Video
Updated: Jul 3, 2026

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
Nitrated isomers of 2-(trichloromethyl)quinoline
Jana Sopková-de Oliveira Santos1, Pierre Verhaeghe, Jean François Lohier
1Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen, 5 rue Vaubénard, 14032 Caen, France. jana.sopkova@unicaen.fr
Abstract:
In the closely related quinoline compounds 8-nitro-2-(trichloromethyl)quinoline, (I), 6-nitro-2-(trichloromethyl)quinoline, (II), and 5-nitro-2-(trichloromethyl)quinoline, (III), all C(10)H(5)Cl(3)N(2)O(2), which are of both reactivity and pharmacological interest, and for which the biological activity and cytotoxicity appear to be based on the positions of the CCl(3) and nitro substituents, the nitro group is only coplanar with its aromatic substrate in (II). The deviation of the nitro group from coplanarity is concluded to be a function of both its position with respect to the trichloromethyl group and the intermolecular contacts in which it participates. The discrepancies between the crystal structures and the molecular shapes predicted by ab initio calculations are also explained in these terms. The quinoline ring is not rigorously planar in any of the structures, which may be explained by stress produced by the CCl(3) substituent.
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
Preparation of Nitriles
Diazonium Group Substitution: –OH and –H
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by water loss...
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

