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Related Concept Videos

Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

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...
NMR Spectroscopy Of Amines01:19

NMR Spectroscopy Of Amines

In proton NMR spectroscopy, primary amines and secondary amines showcase their N–H protons as a broad signal in the chemical shift range between δ 0.5 and 5 ppm. The exact position in this range depends on several factors, including sample concentration, hydrogen bonding, and the type of solvent used. Since amine protons undergo fast proton exchange in solution, the protons are labile and therefore do not participate in any splitting with adjacent protons. Thus, the observed peak is broad and...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
Mass Spectrometry of Amines01:15

Mass Spectrometry of Amines

In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule; a molecule with an odd number of nitrogen atoms produces a molecular ion with an odd molecular weight. Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit strong molecular ion peaks, but acyclic aliphatic amines show...
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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).

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Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones
06:06

Color Spot Test As a Presumptive Tool for the Rapid Detection of Synthetic Cathinones

Published on: February 5, 2018

A new colorimetric test for solid-phase amines and thiols.

Stijn Claerhout1, Denis S Ermolat'ev, Erik V Van der Eycken

  • 1Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.

Journal of Combinatorial Chemistry
|June 12, 2008
PubMed
Summary

A novel color test enables visual detection of resin-bound amines and thiols. This efficient method uses a specific reagent to generate a colored intermediate, allowing sensitive identification of primary amines even with secondary amines present.

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Materials Science

Background:

  • Resin-bound amines are crucial in various chemical applications, including solid-phase synthesis.
  • Accurate and sensitive detection methods for these functional groups are essential for quality control and reaction monitoring.
  • Existing methods for detecting resin-bound amines can be complex or lack specificity.

Purpose of the Study:

  • To develop a new, efficient, sensitive, and reliable color test for the visual detection of resin-bound primary and secondary amines.
  • To establish protocols for differentiating between primary and secondary amines on solid supports.
  • To explore the applicability of the test for detecting resin-bound thiols.

Main Methods:

  • A novel colorimetric assay utilizing 1-methyl-2-(4 omino)-imidazo[1,2-a]pyrimidinium perchlorate (DESC) as the chromogenic reagent.
  • Reaction of DESC with resin-bound amines to form a stable, colored azadiene intermediate directly on the resin bead.
  • Development of specific protocols for selective detection of primary amines in the presence of secondary amines.

Main Results:

  • The developed color test provides efficient, sensitive, and reliable visual detection of resin-bound primary and secondary amines.
  • The method successfully generates a colored, stable azadiene intermediate on the resin bead.
  • Protocols were established to allow for the detection of resin-bound primary amines even when secondary amines are present.
  • The test demonstrated utility for the detection of resin-bound thiols.

Conclusions:

  • A new, user-friendly color test has been established for the visual detection of resin-bound amines and thiols.
  • The assay offers high sensitivity and reliability, making it valuable for solid-phase chemistry applications.
  • The ability to distinguish between primary and secondary amines enhances its utility in complex synthetic procedures.