Related Experiment Video

Updated: Jun 1, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

2-{(E)-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vin-yl}-6-hydroxy-meth-yl-4-nitro-phenolate dihydrate

Mark A Rodriguez, Greg O'Bryan, William J Andrzejewski

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed

    More Related Videos

    Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate06:46

    Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

    Published on: June 21, 2017

    A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species08:12

    A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

    Published on: August 16, 2018

    Related Concept Videos

    Acidity and Basicity of Alcohols and Phenols02:36

    Acidity and Basicity of Alcohols and Phenols

    Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
    Structure and Nomenclature of Alcohols and Phenols02:23

    Structure and Nomenclature of Alcohols and Phenols

    Overview
    Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
    As with other organic compounds, alcohols and phenols...
    Diazonium Group Substitution: –OH and –H01:19

    Diazonium Group Substitution: –OH and –H

    Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
    ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

    ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

    All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...