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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...

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.

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

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

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

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.

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...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates

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Published on: January 15, 2018

3-Carb-oxy-pyridinium nitrate.

Khalid Al-Farhan¹, Miftahul Khair, Mohamed Ghazzali

¹Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia.

Acta Crystallographica. Section E, Structure Reports Online

|July 17, 2012

Summary

This study details the crystal structure of a protonated compound, revealing how its cations and anions form chains through hydrogen bonds. The research highlights specific molecular arrangements and interactions within the crystal lattice.

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Area of Science:

Crystallography
Molecular Structure
Hydrogen Bonding

Background:

Understanding the intermolecular forces governing crystal structures is crucial for materials science.
Protonated organic compounds often exhibit unique packing arrangements due to ionic interactions.
Hydrogen bonding plays a significant role in dictating the three-dimensional architecture of crystalline solids.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(6)H(6)NO(2) (+)·NO(3) (-).
To investigate the hydrogen bonding network and other intermolecular interactions present in the crystal lattice.
To determine the spatial relationship between the aromatic ring and the carboxylate group within the cation.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors.
Geometric parameters, including dihedral angles, were calculated from the diffraction data.

Main Results:

The crystal structure consists of protonated cations (C(6)H(6)NO(2) (+)) and nitrate anions (NO(3) (-)).
N-H⋯O hydrogen bonds link the protonated cations into chains along the b axis.
Additional N-H⋯O and O-H⋯O hydrogen bonds, along with C-H⋯O interactions, connect cations and anions.
A dihedral angle of 10.1(3)° was observed between the ring and the carboxylate group in the cation.

Conclusions:

The crystal packing is dominated by a network of hydrogen bonds involving both cation-cation and cation-anion interactions.
The observed dihedral angle provides insight into the conformation of the protonated cation.
The study contributes to the understanding of supramolecular assembly in organic salts.