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

Conformations of Cyclohexane02:11

Conformations of Cyclohexane

Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal tetrahedral value,...
Molecular Models02:00

Molecular Models

Physical models representing molecular architectures of chemical compounds play essential roles in understanding chemistry. The use of molecular models makes it easier to visualize the structures and shapes of atoms and molecules.
Hydrogen Bonds00:26

Hydrogen Bonds

Hydrogen BondsHydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.Hydrogen Bonds Control the World!Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are...
Hydrogen Bonds01:04

Hydrogen Bonds

A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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...
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...

You might also read

Related Articles

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

Sort by
Same author

Modeling Binding Selectivity of Xylene Isomers in Resorcin[4]arene-Based Organo- and Metallo-Cavitands.

The Journal of organic chemistry·2025
Same author

Selective Aliphatic Aldimine Formation and Stabilization by a Hydrophobic Capsule in Water.

Journal of the American Chemical Society·2025
Same author

Recent Applications of Pillararene-Inspired Water-Soluble Hosts.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Recent progress using novel tetraphenylethylene-based macrocyclic hosts in water.

Chemical communications (Cambridge, England)·2024
Same author

Modeling Amine Methylation in Methyl Ester Cavitand.

Chemistry (Weinheim an der Bergstrasse, Germany)·2024
Same author

Control of reactivity and selectivity in isomerization and rearrangement reactions inside confined spaces.

Chemical communications (Cambridge, England)·2023
Same journal

Ethanol's Dual Role as a Mediator and Green Solvent in Photocatalytic Hydrogen Atom Transfer-Enabled Formal Ring-Closing Metathesis toward 2-Quinolinones.

The Journal of organic chemistry·2026
Same journal

Scalable Syntheses of Pseudouridine and <i>N</i><sup>1</sup>-Methylpseudouridine.

The Journal of organic chemistry·2026
Same journal

Silyl Radical Formation from Silanethiols via Sulfur Atom Transfer with Phosphinites.

The Journal of organic chemistry·2026
Same journal

Chiral Benzimidazole Manganese Catalysts for Asymmetric Transfer Hydrogenation of 3-Substituted 2<i>H</i>-1,4-Benzoxazines.

The Journal of organic chemistry·2026
Same journal

Thia-Michael Stapling of Allenamide-Incorporated α-Helical Antimicrobial Peptides.

The Journal of organic chemistry·2026
Same journal

Ru(II)-Catalyzed Hydrodefluorination of Monofluoroalkenes.

The Journal of organic chemistry·2026
See all related articles

Related Experiment Video

Updated: Jun 21, 2026

Alginate Encapsulation of Pluripotent Stem Cells Using a Co-axial Nozzle
07:13

Alginate Encapsulation of Pluripotent Stem Cells Using a Co-axial Nozzle

Published on: July 2, 2015

Multicomponent, hydrogen-bonded cylindrical capsules.

Dariush Ajami1, Julius Rebek

  • 1The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

The Journal of Organic Chemistry
|August 7, 2009
PubMed
Summary
This summary is machine-generated.

Synthetic capsules formed from resorcinarene cavitands and glycolurils encapsulate various molecules. Their chiral structure influences guest behavior and racemization dynamics, offering insights into molecular interactions within confined spaces.

More Related Videos

Microfluidic Fabrication of Core-Shell Microcapsules carrying Human Pluripotent Stem Cell Spheroids
10:51

Microfluidic Fabrication of Core-Shell Microcapsules carrying Human Pluripotent Stem Cell Spheroids

Published on: October 13, 2021

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

Related Experiment Videos

Last Updated: Jun 21, 2026

Alginate Encapsulation of Pluripotent Stem Cells Using a Co-axial Nozzle
07:13

Alginate Encapsulation of Pluripotent Stem Cells Using a Co-axial Nozzle

Published on: July 2, 2015

Microfluidic Fabrication of Core-Shell Microcapsules carrying Human Pluripotent Stem Cell Spheroids
10:51

Microfluidic Fabrication of Core-Shell Microcapsules carrying Human Pluripotent Stem Cell Spheroids

Published on: October 13, 2021

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers
11:42

Synthesis of Monodisperse Cylindrical Nanoparticles via Crystallization-driven Self-assembly of Biodegradable Block Copolymers

Published on: June 20, 2019

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Chemical Physics

Background:

  • Self-assembled capsules are formed through hydrogen bonding between synthetic resorcinarene-derived cavitands and soluble glycolurils.
  • These capsules require specific guest molecules to initiate the self-assembly process.

Purpose of the Study:

  • To characterize the structure and properties of self-assembled cavitand-glycoluril capsules.
  • To investigate the encapsulation of various guest molecules, including alkanes, aromatic compounds, and gases.
  • To explore the chiral environment within the capsule and its influence on guest behavior and racemization.

Main Methods:

  • Capsule formation using resorcinarene cavitands and glycolurils with guest molecules.
  • Nuclear Magnetic Resonance (NMR) spectroscopy to determine guest positions and dynamics.
  • Computational methods, including nucleus-independent chemical shift (NICS) calculations, to map magnetic shielding.
  • Analysis of racemization kinetics influenced by guest properties and interactions.

Main Results:

  • The self-assembled capsules possess a chiral structure with a cavity volume of approximately 620 ų.
  • They accommodate linear n-alkanes (C14-C19), capsaicin, and combinations of molecules up to 22 Å in length.
  • NMR chemical shifts reveal distinct shielding near cavitand ends and deshielding near glycolurils, indicating a defined internal magnetic environment.
  • Encapsulated alkanes exhibit diastereotopic proton signals due to the chiral environment, and racemization is influenced by guest pressure and hydrogen bonding.
  • Flexible guests like hexane have a tumbling activation barrier of 16.2 kcal/mol, while aromatic groups and gases can also be encapsulated.

Conclusions:

  • The chiral cavitand-glycoluril capsules provide a well-defined environment for studying guest molecule encapsulation and dynamics.
  • The internal steric and magnetic asymmetry influences guest behavior, leading to phenomena like diastereotopic signals and controlled racemization.
  • The capsule's properties can be tuned by guest molecules, affecting assembly, stability, and internal dynamics, with potential applications in molecular recognition and encapsulation.