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Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...

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Updated: Jun 5, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

Acetoguanamine N,N-dimethyl-formamide solvate.

Gustavo Portalone¹

¹Chemistry Department, "Sapienza" University of Rome, P. le A. Moro, 5, I-00185 Rome, Italy.

Acta Crystallographica. Section E, Structure Reports Online

|January 5, 2011

Summary

The crystal structure of acetoguanamine, a methyl-triazine compound, was determined as an N,N-dimethyl-formamide solvate. Molecular ribbons formed by hydrogen bonds stabilize the crystal structure.

Area of Science:

Crystallography
Materials Science
Organic Chemistry

Background:

Acetoguanamine (2,4-diamino-6-methyl-1,3,5-triazine) is a nitrogen-rich heterocyclic compound.
Understanding the crystal structure of solvates is crucial for predicting material properties and designing new compounds.

Purpose of the Study:

To determine the crystal structure of acetoguanamine when crystallized with N,N-dimethyl-formamide.
To elucidate the intermolecular interactions stabilizing the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction was employed to analyze the crystal structure.
Hydrogen bonding networks were identified and characterized.

Main Results:

The structure was determined as the N,N-dimethyl-formamide (DMF) solvate, C(4)H(7)N(5)·C(3)H(7)NO.

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Acetoguanamine molecules and DMF molecules associate to form extended ribbons.

The ribbons are stabilized by a network of three N-H⋯N and one N-H⋯O hydrogen bonds.

Conclusions:

The crystal packing of acetoguanamine is significantly influenced by hydrogen bonding with the DMF solvent.
The identified hydrogen bonding patterns provide insights into the solid-state behavior of acetoguanamine.