Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

MO Theory and Covalent Bonding

MO Theory and Covalent Bonding

The molecular orbital theory describes the distribution of electrons in molecules in a manner similar to the distribution of electrons in atomic orbitals. The region of space in which a valence electron in a molecule is likely to be found is called a molecular orbital. Mathematically, the linear combination of atomic orbitals (LCAO) generates molecular orbitals. Combinations of in-phase atomic orbital wave functions result in regions with a high probability of electron density, while...

Molecular Orbital Theory II

Molecular Orbital Theory II

Molecular Orbital Energy Diagrams

Basicity of Heterocyclic Aromatic Amines

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).

Basicity of Aromatic Amines

Basicity of Aromatic Amines

The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...

Introduction to Electrophilic Addition Reactions of Alkenes

Introduction to Electrophilic Addition Reactions of Alkenes

The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...

You might also read

Related Articles

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

Sort by

Same author

Management of odontogenic sinusitis related to dental implants and maxillary sinus grafting: a retrospective single-center study.

Frontiers in surgery·2026

Same author

Boronate-crosslinked hyaluronic acid hydrogels with grafting-dependent mechano-redox properties.

Biomaterials advances·2026

Same author

Temporally Controlled Supramolecular Catalysts with pH-Dependent Activity.

ACS omega·2026

Same author

Transient Salt-Bridge-Based Supramolecular Polymers: Experiments and Theory.

Journal of the American Chemical Society·2026

Same author

The dynamic chemistry of the boron-nitrogen bond.

Chemical science·2025

Same author

Concentration-Dependent Evolution of the Belousov-Zhabotinsky Reaction as Determined by X-ray Absorption and UV-Vis Spectroscopies.

The journal of physical chemistry. B·2025

Search research articles

Related Experiment Video

Updated: Jun 25, 2025

Molecular Entanglement and Electrospinnability of Biopolymers

Molecular Entanglement and Electrospinnability of Biopolymers

Published on: September 3, 2014

Molecular entanglement can strongly increase basicity.

Giorgio Capocasa¹, Federico Frateloreto¹, Matteo Valentini¹

¹Department of Chemistry Università di Roma La Sapienza and ISB-CNR Sede Secondaria di Roma - Meccanismi di Reazione P.le A. Moro 5, I-00185, Roma, Italy.

Communications Chemistry

|May 28, 2024

Summary

This summary is machine-generated.

Mechanically interlocked molecules like catenanes and rotaxanes exhibit exceptionally high Brønsted basicity. This unique entanglement creates superbases by bringing multiple basic sites together, enhancing proton affinity.

More Related Videos

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Determination of the Gas-phase Acidities of Oligopeptides

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Related Experiment Videos

Last Updated: Jun 25, 2025

Molecular Entanglement and Electrospinnability of Biopolymers

Molecular Entanglement and Electrospinnability of Biopolymers

Published on: September 3, 2014

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Determination of the Gas-phase Acidities of Oligopeptides

Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

Area of Science:

Supramolecular Chemistry
Organic Chemistry
Physical Chemistry

Background:

Brønsted basicity is a key chemical property of many compounds.
Mechanical entanglement in molecules can significantly alter their properties.
Previous research has explored basicity in various molecular architectures.

Purpose of the Study:

To review the development of superbases based on mechanical entanglement.
To highlight the role of catenanes and rotaxanes in achieving high basicity.
To discuss the rational design of mechanically interlocked superbases.

Main Methods:

Historical review of findings related to mechanically interlocked superbases.
Analysis of structure-property relationships in catenanes and rotaxanes.
Discussion of experimental and computational studies on proton affinity.

Main Results:

Mechanical entanglement in catenanes and rotaxanes leads to exceptionally high Brønsted basicity.
Proton affinity is significantly increased due to the proximity of multiple basic sites.
Mechanically interlocked superbases outperform their non-entangled counterparts.

Conclusions:

Mechanically interlocked molecules represent a promising platform for designing potent superbases.
Rational design strategies are emerging for creating tailored mechanically interlocked superbases.
This field has evolved from serendipitous discoveries to targeted molecular design.