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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

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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...
4.0K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

5.6K
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.
5.6K
Nitrosation of Enols01:19

Nitrosation of Enols

10.1K
The nitrosation reaction is one of the methods of preparing 1,2-diketones. The enol tautomer of the starting ketone reacts with sodium nitrite in hydrochloric acid, generating the 1,2-diketone after hydrolysis.
10.1K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

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

5.1K
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.
5.1K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

6.9K
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...
6.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

7.8K
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...
7.8K

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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2-Nitro-1,3-dinitro-oxypropane.

Megan M Breiner1, David E Chavez, Damon A Parrish

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Acta Crystallographica. Section E, Structure Reports Online
|March 12, 2013
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Summary
This summary is machine-generated.

Researchers synthesized a new compound, C3H5N3O8, using 2-nitro-propane-1,3-diol and acetyl nitrate. The crystal structure reveals ribbon-like packing and stabilization through C-H⋯O contacts.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • Nitrated organic compounds are important in various chemical applications.
  • Understanding crystal packing influences material properties.
  • 2-nitro-propane-1,3-diol is a precursor for synthesizing novel molecules.

Purpose of the Study:

  • To synthesize and characterize a novel nitrated organic compound.
  • To elucidate the crystal structure and packing of the title compound.
  • To investigate the intermolecular interactions stabilizing the crystal.

Main Methods:

  • Synthesis of the title compound (C3H5N3O8) via reaction of 2-nitro-propane-1,3-diol with acetyl nitrate.
  • Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.
  • Analysis of intermolecular interactions, including C-H⋯O contacts.

Main Results:

  • Successful synthesis of the compound C3H5N3O8.
  • The molecule possesses a crystallographic mirror plane.
  • Crystal packing exhibits a ribbon-like arrangement along the c-axis with nitro groups aligned.
  • C-H⋯O contacts were identified as contributing to crystal stabilization.

Conclusions:

  • The study presents the synthesis and crystal structure of a novel nitrated compound.
  • The observed ribbon-like packing and C-H⋯O interactions provide insights into crystal engineering.
  • This work contributes to the understanding of structure-property relationships in organic nitrates.