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Related Concept Videos

Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

4.6K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.6K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

3.3K
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.
3.3K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

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

4.0K
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
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.9K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.9K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.4K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.4K
Structure of Amines01:19

Structure of Amines

3.4K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
3.4K

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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Simplest N-Sulfonylamine HNSO2.

Guohai Deng1, Zhuang Wu1, Dingqing Li1

  • 1College of Chemistry, Chemical Engineering and Materials Science, Soochow University , Suzhou 215123, China.

Journal of the American Chemical Society
|August 31, 2016
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Researchers synthesized the simplest N-sulfonylamine (HNSO2) using flash vacuum pyrolysis. This novel compound was identified using matrix-isolation IR spectroscopy and quantum chemical calculations, revealing its decomposition pathway.

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Area of Science:

  • Inorganic Chemistry
  • Computational Chemistry
  • Spectroscopy

Background:

  • N-sulfonylamines are a class of compounds with diverse chemical properties.
  • Understanding the synthesis and decomposition of simple sulfonylamines provides fundamental insights into sulfur-nitrogen chemistry.

Purpose of the Study:

  • To synthesize and characterize the simplest N-sulfonylamine, HNSO2, in the gas phase.
  • To elucidate the decomposition mechanism of methoxysulfonyl azide.
  • To investigate the isomerization of HNSO2.

Main Methods:

  • Flash vacuum pyrolysis of methoxysulfonyl azide.
  • Matrix-isolation infrared (IR) spectroscopy.
  • Quantum chemical calculations.
  • 193 nm laser photolysis.

Main Results:

  • Successful generation and identification of the simplest N-sulfonylamine (HNSO2) in the gas phase.
  • Evidence for a stepwise decomposition of methoxysulfonyl azide via methoxysulfonyl nitrene.
  • Observation of concerted fragmentation into formaldehyde (CH2O) and HNSO2.
  • Discovery of HNSO2 isomerization to the novel N-hydroxysulfinylamine (HONSO) upon laser irradiation.

Conclusions:

  • The study provides the first experimental evidence for the simplest N-sulfonylamine.
  • The decomposition pathway of methoxysulfonyl azide has been clarified.
  • A novel isomer, N-hydroxysulfinylamine (HONSO), has been identified.