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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.

Structure and Nomenclature of Alcohols and Phenols

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...

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...

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.

Diazonium Group Substitution: –OH and –H

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.

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.

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Optimized Procedure for Determining the Adsorption of Phosphonates onto Granular Ferric Hydroxide using a Miniaturized Phosphorus Determination Method

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2-Amino-4-nitro-phenol monohydrate.

Hasan Tanak, Ferda Erşahin, Metin Yavuz

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a nitro compound hydrate. Molecules exhibit near-planarity, with nitro groups slightly twisted, forming a 3D network via various intermolecular interactions.

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Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
Nitroaromatic compounds are important in various fields, including pharmaceuticals and energetic materials.
Hydrated crystalline structures can exhibit unique packing arrangements and intermolecular interactions.

Purpose of the Study:

To elucidate the crystal structure of the title compound, C(6)H(6)N(2)O(3)·H(2)O.
To analyze the molecular geometry, including planarity and torsion angles of the nitro groups.
To investigate the intermolecular interactions responsible for the crystal packing.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of bond lengths, bond angles, and torsion angles provided insights into molecular geometry.
Identification and analysis of intermolecular interactions (N-H⋯O, C-H⋯O, O-H⋯O, O-H⋯N) were performed.

Main Results:

The title compound crystallizes with two formula units in the asymmetric unit.
Molecules are largely planar, with slight twists in the nitro groups (maximum deviations of 0.13(2) and 0.22(2) Å).
A three-dimensional network is formed through extensive intermolecular hydrogen bonding and other interactions.

Conclusions:

The crystal structure reveals a specific arrangement of nitroaromatic molecules and water in the solid state.
The observed molecular planarity and nitro group torsion angles are characteristic of this compound.
Intermolecular interactions play a significant role in stabilizing the observed three-dimensional crystal network.