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Nitrosation of Enols

Nitrosation of Enols

The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.

Acidity and Basicity of Alcohols and Phenols

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.

2° Amines to N-Nitrosamines: Reaction with NaNO2

2° Amines to N-Nitrosamines: Reaction with NaNO₂

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Overview

Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
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...

E2 Reaction: Kinetics and Mechanism

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...

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

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...

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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

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

(E)-2-[(2-Hydr-oxy-5-nitro-phen-yl)iminiometh-yl]-4-nitro-phenolate.

Yousef M Hijji, Belygona Barare, Ray J Butcher

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals a novel molecule with a zwitterionic effect, confirmed by its crystal structure and computational analysis. The molecule forms an infinite polymeric chain through intermolecular hydrogen bonding.

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Area of Science:

Crystal Engineering and Supramolecular Chemistry
Computational Chemistry
Organic Chemistry

Background:

Understanding molecular interactions is crucial for designing novel materials.
Zwitterionic compounds exhibit unique electronic and structural properties.
Intra- and intermolecular hydrogen bonding significantly influences crystal packing and material properties.

Purpose of the Study:

To characterize the crystal structure and electronic properties of a novel molecule C(13)H(9)N(3)O(6).
To investigate the role of intra- and intermolecular hydrogen bonding in the molecular assembly.
To provide computational support for the observed structural and electronic features.

Main Methods:

Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Analysis of bond lengths, dihedral angles, and hydrogen bonding interactions.
MOPAC AM1 calculations for theoretical support.

Main Results:

The molecule exhibits a zwitterionic character due to extended π-delocalization.
Intramolecular hydrogen bonding involves the amine group and nearby oxygen atoms.
Extensive intermolecular O-H⋯O hydrogen bonding leads to the formation of infinite polymeric chains in the crystal lattice.

Conclusions:

The studied molecule displays significant zwitterionic properties and a near-planar conformation.
Intermolecular hydrogen bonding dictates the formation of a 1D polymer structure.
Computational results support the experimental observations of electronic delocalization and hydrogen bonding.