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

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.

You might also read

Related Articles

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

Sort by
Same author

Stereospecific Assembly of Triply Chiral Pseudopeptidic Cages Through Dynamic Dual Chirality Transfer.

Angewandte Chemie (International ed. in English)·2026
Same author

Efficient Small-Molecule Reversal Agents for Anticoagulant Fondaparinux.

ACS pharmacology & translational science·2025
Same author

Supramolecular chemical biology: designed receptors and dynamic chemical systems.

Chemical communications (Cambridge, England)·2024
Same author

Discovery of selective monosaccharide receptors <i>via</i> dynamic combinatorial chemistry.

Organic & biomolecular chemistry·2024
Same author

Molecular Recognition of Tyrosine-Containing Polypeptides with Pseudopeptidic Cages Unraveled by Fluorescence and NMR Spectroscopies.

Bioconjugate chemistry·2023
Same author

Pseudopeptidic host adaptation in peptide recognition unveiled by ion mobility mass spectrometry.

The Analyst·2022

Related Experiment Video

Updated: Jun 10, 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

Structurally disfavoured pseudopeptidic macrocycles through anion templation.

Miriam Bru1, Ignacio Alfonso, Michael Bolte

  • 1Departamento de Química Inorgánica y Orgánica, Universidad Jaume I, Avenida Sos Baynat s/n, E-12071, Castellón, Spain.

Chemical Communications (Cambridge, England)
|August 24, 2010
PubMed
Summary

An anionic dicarboxylate templates the creation of difficult-to-form macrocycles. This discovery advances supramolecular chemistry by enabling the synthesis of complex molecular architectures.

More Related Videos

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
08:48

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Published on: January 26, 2016

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

Related Experiment Videos

Last Updated: Jun 10, 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

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
08:48

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Published on: January 26, 2016

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

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Chemical Engineering

Background:

  • Dynamic covalent chemistry (DCvC) allows for the construction of complex molecular architectures.
  • Template-directed synthesis is a powerful strategy for controlling molecular assembly.
  • Oligoimines offer versatile building blocks for macrocycle formation.

Purpose of the Study:

  • To investigate the templating effect of an anionic dicarboxylate on macrocycle formation.
  • To explore the synthesis of geometrically disfavoured macrocycles using dynamic covalent mixtures.
  • To demonstrate a novel approach for controlling supramolecular assembly.

Main Methods:

  • Utilized a dynamic covalent mixture of open-chain oligoimines.
  • Employed an anionic dicarboxylate as a template.
  • Characterized the resulting macrocyclic products using spectroscopic and analytical techniques.

Main Results:

  • The anionic dicarboxylate successfully templated the formation of macrocycles.
  • Geometrically disfavoured macrocycles were selectively synthesized.
  • The templating effect enhanced the efficiency and selectivity of the macrocyclization process.

Conclusions:

  • Anionic dicarboxylates can effectively template the formation of challenging macrocycles.
  • This method provides a new route to complex molecular structures.
  • The findings have implications for the design of novel host-guest systems and functional materials.