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Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

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.
Basicity of Heterocyclic Aromatic Amines01:25

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).
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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 Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

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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.

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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.

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

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Related Experiment Video

Updated: Jun 1, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

2,5-Dimethyl-pyrazine 1,4-dioxide.

Carlton J Brown1, 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
PubMed
Summary

Researchers synthesized 2,5-dimethyl-pyrazine 1,4-dioxide, revealing its crystal structure. The compound forms 2D layers through π-π stacking and C-H⋯O hydrogen bonds, highlighting molecular interactions.

Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Pyrazine derivatives are important in various chemical applications.
  • Understanding molecular packing and interactions is crucial for materials science.
  • Hydrogen bonding and π-π stacking are key non-covalent interactions in crystal engineering.

Purpose of the Study:

  • To synthesize and characterize the crystal structure of 2,5-dimethyl-pyrazine 1,4-dioxide.
  • To investigate the intermolecular interactions governing the crystal packing.
  • To explore the formation of layered structures in organic N-oxides.

Main Methods:

  • Chemical synthesis involving 2,5-dimethyl-pyrazine, acetic acid, and hydrogen peroxide.
  • Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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

Published on: April 24, 2018

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Last Updated: Jun 1, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

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

Published on: February 7, 2019

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

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

Published on: April 24, 2018

  • Analysis of intermolecular interactions, including π-π stacking and hydrogen bonding.

    • Main Results:

    • The title compound, C(6)H(8)N(2)O(2), was successfully synthesized.
    • The 2,5-dimethyl-pyrazine 1,4-dioxide molecule resides on an inversion center.
    • Observed π-π interactions between molecules with an inter-planar distance of 3.191 Å.
    • Formation of two-dimensional layers via C-H⋯O hydrogen bonding between N-oxide moieties.

    Conclusions:

    • The crystal structure of 2,5-dimethyl-pyrazine 1,4-dioxide is elucidated.
    • The compound exhibits a layered structure driven by π-π stacking and hydrogen bonding.
    • This study provides insights into the supramolecular assembly of pyrazine N-oxide derivatives.