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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).

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Structure and Nomenclature of Epoxides

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...

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.

Preparation of Epoxides

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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Bis{bis-(azido-κN)bis-[bis-(pyridin-2-yl-κN)amine]cobalt(III)} sulfate dihydrate.

Acta crystallographica. Section E, Crystallographic communications·2016

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Crystal structure of di-μ-aqua-μ-(pyrazine N,N'-dioxide)-κ(2) O:O-bis-(di-aqua-sodium) tetra-phenyl-borate dihydrate pyrazine N,N'-dioxide monosolvate.

Acta crystallographica. Section E, Crystallographic communications·2016

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Crystal structures of [Ln(NO3)3(μ2-bpydo)2], where Ln = Ce, Pr or Nd, and bpydo = 4,4'-bi-pyridine N,N'-dioxide: layered coordination networks containing 4(4) grids.

Acta crystallographica. Section E, Crystallographic communications·2016

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Poly[[tetra-kis-(μ(2)-pyrazine N,N'-dioxide-κO:O')neodymium(III)] tris-(perchlorate)].

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Poly[[tetra-kis-(μ(2)-pyrazine N,N'-dioxide-κO:O')dysprosium(III)] tris-(perchlorate)].

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Related Experiment Video

Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

2-Methyl-pyrazine 1,4-dioxide.

Jessica L Gratton¹, Jacqueline M Knaust

¹Allegheny College, Chemistry Department, 520 North Main St., Meadville, PA 16335, USA.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

Researchers synthesized a novel compound, C(5)H(6)N(2)O(2), using 2-methyl-pyrazine. The crystal structure reveals significant π-π stacking and hydrogen bonding, forming one-dimensional ribbons.

Area of Science:

Crystal Engineering
Supramolecular Chemistry
Organic Synthesis

Background:

Understanding molecular interactions is crucial for designing new materials.
Pyrazine derivatives are versatile building blocks in supramolecular chemistry.

Purpose of the Study:

To synthesize and characterize a novel pyrazine derivative.
To investigate the crystal packing and intermolecular interactions of the synthesized compound.

Main Methods:

Organic synthesis involving 2-methyl-pyrazine, acetic acid, and hydrogen peroxide.
Single-crystal X-ray diffraction to analyze crystal structure.
Analysis of π-π stacking and C-H⋯O hydrogen bonding interactions.

Main Results:

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

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Last Updated: Jun 1, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

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

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

Published on: June 23, 2019

Successful synthesis of the title compound C(5)H(6)N(2)O(2).
Observed π-π stacking interactions with specific centroid-centroid (3.7370 Å), inter-planar (3.167 Å), and slippage (1.984 Å) distances.
Formation of one-dimensional ribbons via C-H⋯O hydrogen bonding linking each molecule to four neighbors.

Conclusions:

The synthesized compound exhibits unique crystal packing driven by π-π stacking and hydrogen bonding.
The observed one-dimensional ribbon structure offers potential for designing novel functional materials.