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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
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.
2.8K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.0K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.0K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

5.6K
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...
5.6K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.2K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K

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Updated: Jul 4, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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(R)-(+)-3,5-Dinitro-N-(1-phenylethyl)benzothioamide.

Matthew G Donahue1, Emily Crull1

  • 1Department of Chemistry and Biochemistry, University of Southern Mississippi, Hattiesburg, MS 39406, USA.

Molbank
|January 26, 2024
PubMed
Summary
This summary is machine-generated.

A new chiral solvating agent, (R)-(+)-3,5-dinitro-N-(1-phenylethyl)benzothioamide, was synthesized. This compound shows potential for resolving enantiomers using proton NMR spectroscopy.

Keywords:
benzylaminechiral solvating agentthioamide

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry

Background:

  • Chiral compounds exist as enantiomers, which can have different biological activities.
  • Separating enantiomers is crucial in pharmaceutical and chemical industries.
  • Proton NMR spectroscopy is a common technique for chemical analysis.

Purpose of the Study:

  • To synthesize a single enantiomer of a novel chiral solvating agent.
  • To evaluate its utility in the spectral resolution of enantiomers via proton NMR spectroscopy.

Main Methods:

  • Synthesis of (R)-(+)-3,5-dinitro-N-(1-phenylethyl)benzothioamide from (R)-(+)-a-methylbenzylamine.
  • Utilizing proton NMR spectroscopy for enantiomeric analysis.

Main Results:

  • The target chiral solvating agent was synthesized in two steps with an 85% yield.
  • The compound demonstrated potential as a chiral solvating agent for enantiomer resolution.

Conclusions:

  • The developed synthetic route provides an efficient method for obtaining the chiral solvating agent.
  • The agent is a promising tool for enantiomeric separation using NMR spectroscopy.