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Related Concept Videos

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).
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for the...
Preparation of Nitriles01:12

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...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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...
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.

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Related Experiment Video

Updated: May 26, 2026

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

2-Chloro-5-methyl-3-nitro-pyridine.

Da-Tong Zhang1, Ling-Yan Huo

  • 1School of Chemistry and Pharmaceutical Engineering, Shandong Polytechnic University, Jinan 250353, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|January 6, 2012
PubMed
Summary
This summary is machine-generated.

This study details the crystal structure of a specific organic compound, C(6)H(5)ClN(2)O(2). The research found that intermolecular hydrogen bonds play a key role in stabilizing its crystal lattice.

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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

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Last Updated: May 26, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
07:49

On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes

Published on: August 5, 2016

Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding the crystalline structure of organic compounds is crucial for predicting their physical and chemical properties.
  • The specific compound C(6)H(5)ClN(2)O(2) has potential applications that necessitate a detailed structural analysis.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound, C(6)H(5)ClN(2)O(2).
  • To identify and characterize the intermolecular interactions responsible for crystal stabilization.

Main Methods:

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

Main Results:

  • The title compound, C(6)H(5)ClN(2)O(2), crystallizes with two independent molecules in the asymmetric unit.
  • Intermolecular C-H⋯O hydrogen bonds were identified as the primary stabilizing forces within the crystal structure.

Conclusions:

  • The crystal structure of C(6)H(5)ClN(2)O(2) is characterized by the presence of two independent molecules and stabilized by C-H⋯O hydrogen bonds.
  • This detailed structural information provides a foundation for further research into the compound's properties and potential applications.