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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.

Titration in Nonaqueous Solvents

Titration in Nonaqueous Solvents

Most acid-base titrations are performed in an aqueous medium. In aqueous titrations, water competes with weaker acids or bases for proton donation or acceptance, leading to ambiguous endpoints in the titration curve. Water also affects the partial ionization of weak acids or bases. For example, water accepts a proton from acetic acid to form hydronium and acetate ions. The hydronium ion formed is a stronger acid than acetic acid, and the acetate ion is a stronger base than water. As a result,...

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...

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.

Structure of Amines

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...

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(3-Pyrid-yl)methanaminium 4-nitro-phenolate 4-nitro-phenol solvate.

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Acta Crystallographica. Section E, Structure Reports Online

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Summary

The crystal structure reveals a three-dimensional network formed by hydrogen bonds between ions and molecules. This study details the specific hydrogen bonding interactions in the title compound.

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Area of Science:

Crystallography
Supramolecular Chemistry
Materials Science

Background:

Understanding the intermolecular interactions is crucial for designing novel materials.
Hydrogen bonding plays a significant role in the self-assembly of crystalline structures.
The title compound, C(6)H(9)N(2) (+)·C(6)H(4)NO(3) (-)·C(6)H(5)NO(3), presents an interesting case for studying hydrogen bond networks.

Purpose of the Study:

To elucidate the crystal structure of the title compound.
To identify and characterize the hydrogen bonding interactions present.
To describe the resulting three-dimensional network.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the crystal structure.
Analysis of the crystal structure involved identifying hydrogen bond donors and acceptors.
Intermolecular interactions were visualized and analyzed.

Main Results:

The crystal structure consists of ions and molecules, specifically C(6)H(9)N(2) (+), C(6)H(4)NO(3) (-), and C(6)H(5)NO(3).
Multiple types of intermolecular hydrogen bonds were observed: N-H⋯O, N-H⋯N, O-H⋯O, and C-H⋯O.
These hydrogen bonds connect the components into an extended three-dimensional network.

Conclusions:

The title compound forms a robust three-dimensional supramolecular network through a combination of hydrogen bonding interactions.
The specific arrangement of hydrogen bonds dictates the overall crystal packing and network architecture.
This structural information provides a foundation for further investigations into the compound's properties and potential applications.