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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.9K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
11.9K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.1K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.1K
Prochirality02:05

Prochirality

5.1K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
5.1K
SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.5K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.5K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

8.5K
Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
8.5K
Ligand Binding and Linkage00:49

Ligand Binding and Linkage

5.7K
Allosteric proteins have more than one ligand binding site; the binding of a ligand to any of these sites influences the binding of ligands to the other sites. When a protein is allosteric, its binding sites are called coupled or linked.  In the case of enzymes, the site that binds to the substrate is known as the active site and the other site is known as the regulatory site. When a ligand binds to the regulatory site, this leads to conformational changes in the protein that can influence...
5.7K

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Related Experiment Video

Updated: Feb 17, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

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

Published on: April 27, 2017

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C(5) Site-Selective Functionalization of (S)-Cotinine.

Hugo Rego Campello1, Timothy Gallagher1

  • 1School of Chemistry, University of Bristol , Bristol BS8 1TS, United Kingdom.

The Journal of Organic Chemistry
|December 6, 2017
PubMed
Summary

(S)-(-)-Cotinine was directly borylated using iridium catalysis. This provides a flexible method for creating new C(5)-substituted cotinine compounds for further research.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Cotinine is a major metabolite of nicotine.
  • Developing efficient synthetic routes to cotinine derivatives is important for pharmacological studies.
  • Site-selective functionalization of cotinine remains a synthetic challenge.

Purpose of the Study:

  • To develop a direct and site-selective method for functionalizing cotinine.
  • To synthesize novel C(5)-substituted cotinine variants.
  • To establish a versatile platform for cotinine derivative synthesis.

Main Methods:

  • Iridium-catalyzed direct borylation of (S)-(-)-cotinine.
  • Synthesis of boronate ester and bromide intermediates.
  • Characterization of the synthesized compounds.

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Targeting Cysteine Thiols for in Vitro Site-specific Glycosylation of Recombinant Proteins

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Related Experiment Videos

Last Updated: Feb 17, 2026

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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Main Results:

  • Successful direct and site-selective iridium-catalyzed borylation of (S)-(-)-cotinine was achieved.
  • Boronate ester and bromide derivatives at the C(5) position were synthesized.
  • These intermediates provide flexible access to various C(5)-substituted cotinine analogs.

Conclusions:

  • The developed iridium-catalyzed borylation offers an efficient and site-selective route to functionalized cotinine.
  • The synthesized intermediates serve as valuable building blocks for exploring cotinine's chemical space.
  • This methodology facilitates the discovery of new cotinine-based compounds with potential biological activities.