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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.

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

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...

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,...

Electrophilic Aromatic Substitution: Nitration of Benzene

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.

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).

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A Nitrilium-Type N-Heterocyclic Aryne.

Marisol Alvarado¹, Lauren Tran¹, Christina Tönshoff²

¹Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.

Journal of the American Chemical Society

|June 2, 2025

Summary

Researchers report the first synthesis of a nitrilium-type N-hetaryne, a 1,6-BN-aryne, enabling new reactions and access to novel 1,2-azaborine structures.

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Area of Science:

Organic Chemistry
Heterocyclic Chemistry
Synthetic Methodology

Background:

N-hetarynes are reactive intermediates crucial for synthesizing heterocyclic compounds.
Previous syntheses of N-hetarynes were limited, hindering access to diverse structures.

Purpose of the Study:

To achieve the first solution-phase synthesis of a nitrilium-type N-hetaryne.
To explore the reactivity and synthetic utility of this novel intermediate.

Main Methods:

Solution-phase synthesis of 1,2-azaborine-derived 1,6-BN-aryne.
Characterization of the 1,6-BN-aryne under matrix isolation conditions.
Density Functional Theory (DFT) calculations to elucidate electronic structure.

Main Results:

The 1,6-BN-aryne (2) was successfully synthesized and characterized.
It demonstrated reactivity in [4+2], [3+2], and [2+2] cycloadditions and electrophilic aromatic substitution (EAS).
Regio- and diastereoselectivities were consistent with a polarized aryne/nitrilium species.

Conclusions:

The 1,6-BN-aryne exists in resonance between ketenimine and nitrilium forms.
This versatile building block provides access to previously inaccessible functionalized 1,2-azaborines.