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

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

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...
Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Prochirality02:05

Prochirality

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...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
Chirality02:25

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chirality in Nature02:30

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...

You might also read

Related Articles

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

Sort by
Same author

Comparisons and Contrasts in a Complete Set of Alkali Metal Cumyl Structures.

Inorganic chemistry·2026
Same author

Crystallographic and computational investigation of a bent-core Schiff base Ni(ii) complex with DNA and protein binding studies.

RSC advances·2026
Same author

Salt forms of a thioamide: protonation of 1-(2,6-dimethylphenyl)thiourea.

Acta crystallographica. Section C, Structural chemistry·2026
Same author

How Alkali Metal Alkoxides Initiate Organic Radical Reactions.

Journal of the American Chemical Society·2026
Same author

N‑Heterocyclic Carbene Stabilized Aluminum Alkyls and Their Reactivity toward NHC-Alanes.

Organometallics·2026
Same author

Strengthening school-university collaborations.

Nature reviews. Chemistry·2026
Same journal

Pyridines with adamantane fragments and their 1,2,4-triazine analogues as anti-quorum-sensing agents, synthesis and molecular docking.

Organic & biomolecular chemistry·2026
Same journal

Synthesis of polymethylene-linked bis(cyclobutane-fused chromanones) mediated by gold photocatalysis.

Organic & biomolecular chemistry·2026
Same journal

Palladium-catalyzed chelation-assisted C-H functionalization of quinoline aldehydes to esters with mechanistic insights.

Organic & biomolecular chemistry·2026
Same journal

One-pot metal-free access to uracil-benzofuran bis-heterocycles: synthesis and DFT insights.

Organic & biomolecular chemistry·2026
Same journal

Transition-metal-free three-component synthesis of α-tertiary trifluoromethyl phosphonates from CF<sub>3</sub> diazo compounds.

Organic & biomolecular chemistry·2026
Same journal

Synthesis of <i>meta</i>-substituted phenols and 1-estradiol conjugated analogues of suberoylanilide hydroxamic acid (SAHA).

Organic & biomolecular chemistry·2026
See all related articles

Related Experiment Video

Updated: May 14, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Readily accessible chiral at nitrogen cage structures.

Julian H Rowley1, Sze Chak Yau, Benson M Kariuki

  • 1WestCHEM, Department of Pure and Applied Chemistry, Thomas Graham Building, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, UK.

Organic & Biomolecular Chemistry
|February 14, 2013
PubMed
Summary
This summary is machine-generated.

Researchers created a novel chiral cage structure using glycine-N-methyl amide and paraformaldehyde. This rigid cage, synthesized with ytterbium triflate, offers diverse structural possibilities and stability under basic conditions.

More Related Videos

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Related Experiment Videos

Last Updated: May 14, 2026

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
04:38

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Published on: July 28, 2022

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Catalysis

Background:

  • Chiral amine synthesis is crucial for pharmaceuticals.
  • Developing novel synthetic methodologies for complex molecular architectures is an ongoing challenge.
  • Metal triflate catalysts offer unique reactivity in organic transformations.

Purpose of the Study:

  • To synthesize a novel chiral cage structure from readily available starting materials.
  • To investigate the stereochemical outcomes and stability of the synthesized cage.
  • To explore the potential for structural diversity through variations in starting materials.

Main Methods:

  • Reaction of glycine-N-methyl amide with paraformaldehyde catalyzed by ytterbium triflate.
  • Single crystal X-ray diffraction for structural elucidation.
  • Density Functional Theory (DFT) calculations for conformational analysis.
  • Separation of diastereoisomers via crystallization and column chromatography.

Main Results:

  • A novel, rigid chiral cage structure (6) was successfully synthesized.
  • The cage exhibits chirality at nitrogen and adopts a single low-energy conformation.
  • Diastereoisomers were formed from enantiomerically pure α-amino amides, separable under basic conditions.
  • Racemic and mixed cages were also synthesized, increasing structural diversity.

Conclusions:

  • The ytterbium triflate-catalyzed reaction provides a versatile route to novel chiral cage structures.
  • The synthesized cages demonstrate configurational stability under basic conditions, facilitating separation.
  • The methodology allows for the preparation of diverse cage architectures with potential applications in asymmetric synthesis.