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Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

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.

Ions as Acids and Bases

Ions as Acids and Bases

Salts with Acidic Ions
Salts are ionic compounds composed of cations and anions, either of which may be capable of undergoing an acid or base ionization reaction with water. Aqueous salt solutions, therefore, may be acidic, basic, or neutral, depending on the relative acid-base strengths of the salt’s constituent ions. For example, dissolving the ammonium chloride in water results in its dissociation, as described by the equation:

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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Updated: Jun 1, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

2-Phenyl-imidazolium acetate.

Dao-Cheng Xia¹, Ji-Huan Yao

¹Yuncheng University, College of Chemistry, Yuncheng 044000, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study details the molecular structure of a 2-phenyl-imidazole and acetate salt. Crystal structure analysis reveals hydrogen bonding interactions stabilizing the molecular salt into chains.

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Area of Science:

Crystallography
Chemical Physics
Materials Science

Background:

Molecular salts composed of heterocyclic cations and carboxylate anions are of interest for their diverse structural and electronic properties.
Understanding the crystal packing and intermolecular interactions is crucial for designing materials with specific functionalities.

Purpose of the Study:

To elucidate the crystal structure of the molecular salt formed between 2-phenyl-imidazole and acetate.
To investigate the nature and role of intermolecular interactions in stabilizing the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the title compound.
Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
Intermolecular interactions, including hydrogen bonding, were identified and analyzed.

Main Results:

The asymmetric unit contains two 2-phenyl-imidazole cations and two acetate anions.
The dihedral angles between the phenyl and imidazole rings in the two cation units are 5.50(2)° and 6.90(2)°.
The crystal structure is stabilized by N-H⋯O and weak C-H⋯O hydrogen bonds, forming chains propagating along the [110] direction.

Conclusions:

The study provides a detailed structural characterization of the 2-phenyl-imidazole acetate molecular salt.
Hydrogen bonding plays a significant role in the self-assembly and stabilization of the crystal structure.
The observed chain-like structure may influence the bulk properties of the material.