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Nomenclature of Aryl and Heterocyclic Amines

Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.

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).

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.

Physical Properties of Amines

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Five-Membered Heterocyclic Aromatic Compounds: Overview

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines

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Published on: June 23, 2019

5-Iodo-pyrimidin-2-amine.

Yen-Hsun Chiang¹, Chia-Jun Wu, Pei-Chi Cheng

¹Department of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study reveals the crystal structure of a C(4)H(4)IN(3) compound, highlighting its mirror plane symmetry. Molecules form polymeric tapes via N-H⋯N hydrogen bonds, characteristic of 2-aminopyrimidines.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Published on: September 12, 2018

Area of Science:

Crystallography
Materials Science
Organic Chemistry

Background:

2-aminopyrimidines are known to form specific hydrogen-bonded structures in crystals.
Understanding the supramolecular assembly of such compounds is crucial for materials design.

Purpose of the Study:

To elucidate the crystal structure and hydrogen bonding patterns of the title compound, C(4)H(4)IN(3).
To analyze the role of hydrogen bonding in the supramolecular architecture of this 2-aminopyrimidine derivative.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
Analysis of intermolecular interactions, specifically hydrogen bonds, was performed.

Main Results:

The title compound C(4)H(4)IN(3) crystallizes with crystallographic mirror plane symmetry.
Molecules self-assemble into polymeric tapes along the a axis through N-H⋯N hydrogen bonds.
Each molecule functions as both a hydrogen bond donor and acceptor, facilitating tape formation.

Conclusions:

The observed hydrogen bonding pattern is typical for 2-aminopyrimidine derivatives, leading to extended polymeric structures.
The crystal structure provides insights into the intermolecular forces governing the assembly of this specific compound.