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Related Concept Videos

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

Electrophilic Aromatic Substitution: Nitration of Benzene

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.
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.
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...

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A Method for Selecting Structure-switching Aptamers Applied to a Colorimetric Gold Nanoparticle Assay
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Published on: February 28, 2015

Target-driven selection in a dynamic nitrone library.

Simon M Turega1, Christiane Lorenz, Jan W Sadownik

  • 1EaStCHEM and Centre for Biomolecular Sciences, School of Chemistry, University of St Andrews, St Andrews, Fife, UK KY16 9ST.

Chemical Communications (Cambridge, England)
|September 2, 2008
PubMed
Summary
This summary is machine-generated.

Nitrones dynamically exchange in chloroform via hydrolysis or hydroxylamine addition. This property was used to select a specific nitrone receptor for diacids by targeting glutaric acid.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Nitrones exhibit dynamic covalent exchange in solution.
  • This dynamic behavior can be influenced by reaction mechanisms like hydrolysis and hydroxylamine addition/elimination.

Purpose of the Study:

  • To exploit the dynamic exchange of nitrones for molecular recognition.
  • To select a specific nitrone-based bis(amidopyridine) receptor for diacids.

Main Methods:

  • Investigated dynamic exchange mechanisms of nitrones in chloroform at room temperature.
  • Utilized a glutaric acid-based target to selectively bind a nitrone receptor.
  • Screened a library of four nitrones based on their binding affinity.

Main Results:

  • Confirmed dynamic exchange in nitrones occurs through hydrolysis and hydroxylamine addition/elimination pathways.
  • Successfully selected a specific nitrone-based bis(amidopyridine) receptor through selective binding to the glutaric acid target.
  • Demonstrated the utility of dynamic exchange in designing selective molecular receptors.

Conclusions:

  • Dynamic exchange of nitrones is a viable strategy for developing selective molecular recognition systems.
  • The bis(amidopyridine) receptor demonstrated high affinity and selectivity for diacids, exemplified by glutaric acid binding.
  • This work provides a novel approach for the rational design of functional supramolecular receptors.