Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

4.2K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
4.2K
Preparation of Amides01:29

Preparation of Amides

4.5K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.5K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.9K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.9K
Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

5.7K
Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
5.7K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.8K
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...
5.8K
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.9K
The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.9K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

β-Sitosterol β-D-glucoside (BSSG) triggers intestinal inflammation in zebrafish and mouse models prior to neurodegeneration onset.

Journal of biomedical science·2026
Same author

Yeast Display Technology Enables Rapid Discovery of Low-Nanomolar Macrocyclic Peptide Inhibitors of Human Angiotensin-Converting Enzyme 2.

Journal of medicinal chemistry·2026
Same author

Self-Assembly of Unconventional Triphenylene-Based Frustrated Amphiphile in Solution.

Langmuir : the ACS journal of surfaces and colloids·2026
Same author

Screening macrocyclic peptide libraries by yeast display allows control of selection process and affinity ranking.

Nature communications·2025
Same author

Challenges and Achievements of Peptide Synthesis in Aqueous and Micellar Media.

Chembiochem : a European journal of chemical biology·2025
Same author

A deep learning framework for multiplet splitting classification in <sup>1</sup>H NMR.

Journal of magnetic resonance (San Diego, Calif. : 1997)·2025

Related Experiment Video

Updated: Apr 19, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
07:11

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

3.3K

Substrate selective amide coupling driven by encapsulation of a coupling agent within a self-assembled hexameric

Sonia Giust1, Giorgio La Sorella, Laura Sperni

  • 1Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca' Foscari di Venezia, Calle Larga S. Marta 2137, 30123, Venezia, Italy. alesca@unive.it.

Chemical Communications (Cambridge, England)
|December 16, 2014
PubMed
Summary

A novel capsule made of resorcin[4]arene units encapsulates a condensing agent, enhancing selectivity in amide synthesis. This nano-environment favors the formation of shorter amides from carboxylic acids and primary amines.

More Related Videos

Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
10:12

Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers

Published on: September 19, 2022

3.0K
Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

8.2K

Related Experiment Videos

Last Updated: Apr 19, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
07:11

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

3.3K
Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers
10:12

Construction of Cyclic Cell-Penetrating Peptides for Enhanced Penetration of Biological Barriers

Published on: September 19, 2022

3.0K
Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

8.2K

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Amide synthesis is a fundamental reaction in organic chemistry.
  • Controlling selectivity in reactions involving multiple similar substrates can be challenging.

Purpose of the Study:

  • To develop a nano-environment for enhancing substrate selectivity in amide synthesis.
  • To investigate the influence of encapsulation on the reaction between carboxylic acids and primary amines.

Main Methods:

  • Self-assembly of resorcin[4]arene units into a hexameric capsule.
  • Encapsulation of a cationic carbodiimide condensing agent within the capsule.
  • Studying the amide synthesis reaction between carboxylic acids and primary amines in the presence and absence of the capsule.

Main Results:

  • The hexameric capsule provides a confined nano-environment.
  • Encapsulation significantly steers substrate selectivity in amide synthesis.
  • The formation of shorter amides is greatly favored within the capsule compared to solution.

Conclusions:

  • Self-assembled capsules can effectively control reactivity and selectivity in chemical reactions.
  • This approach offers a novel strategy for designing selective synthetic methodologies.
  • The resorcin[4]arene capsule demonstrates potential for fine-tuning organic transformations at the nanoscale.