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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...

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...

Carboxylic Acids to Acid Chlorides

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.

α-Halogenation of Carboxylic Acid Derivatives: Overview

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...

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Related Experiment Video

Updated: May 9, 2026

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

5-Amino-levulinic acid hydro-chloride.

Jean Guillaume Ducreux¹, James A Kaduk¹, Anja Dosen²

¹North Central College, Department of Chemistry 131 S Loomis St Naperville IL 60540 USA.

|May 8, 2026

Summary

The crystal structure of 5-amino-levulinic acid hydro-chloride was determined using X-ray powder diffraction and DFT. This study reveals layered structures with prominent hydrogen bonding, enhancing understanding of this important compound.

Keywords:

Rietveld refinement aminolevulinic acid density functional theory powder diffraction

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Last Updated: May 9, 2026

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Area of Science:

Crystallography
Solid-state chemistry
Materials science

Background:

5-Amino-levulinic acid hydro-chloride is a compound with potential biological and chemical applications.
Understanding its crystal structure is crucial for predicting its properties and reactivity.

Purpose of the Study:

To determine and refine the crystal structure of 5-amino-levulinic acid hydro-chloride.
To compare the findings with previous single-crystal data.
To elucidate the hydrogen bonding network and structural characteristics.

Main Methods:

Synchrotron X-ray powder diffraction data collection and refinement.
Density Functional Theory (DFT) optimization.
Comparison with existing single-crystal structure data.

Main Results:

The crystal structure was solved in the space group Pbca.
A layered structure parallel to the ab plane was identified, with hydrophilic and hydrophobic regions.
Extensive hydrogen bonding networks involving ammonium, chloride, and carboxyl groups were observed.

Conclusions:

The crystal structure of 5-amino-levulinic acid hydro-chloride has been successfully determined.
The layered arrangement and hydrogen bonding significantly influence the compound's solid-state properties.
The powder diffraction data has been submitted for inclusion in the Powder Diffraction File (PDF).