Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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...
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Naming Enantiomers02:21

Naming Enantiomers

The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
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...
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...

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Inverted metal-free active template synthesis of rotaxanes via axle‑mediated macrocyclization.

Nature chemistry·2026
Same author

Trefoil polymers from a knotted synthon.

Nature chemistry·2026
Same author

Conformationally Switchable Molecular Trefoil Knot Assembled From 2,6-Bis(1,2,3-triazol-4-yl)pyridine (btp) Building Blocks.

Journal of the American Chemical Society·2026
Same author

Coordination Chemistry of a Star of David [2]Catenand.

Journal of the American Chemical Society·2026
Same author

Breaking Metal-Organic Cage Symmetry Enhances Diels-Alder Catalytic Specificity and Proficiency.

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

Chiral catalysis-driven rotary molecular motors.

Nature chemistry·2026

Video Experimental Relacionado

Updated: Jun 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Isomerismo de secuencia en [3]rotaxanos.

Anne-Marie L Fuller1, David A Leigh, Paul J Lusby

  • 1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, EH9 3JJ United Kingdom.

Journal of the American Chemical Society
|March 17, 2010
PubMed
Resumen

Los investigadores desarrollaron un nuevo método para secuenciar con precisión los macrociclos en hilos de rotaxano. Esta técnica crea estereoisómeros distintos mediante el bloqueo mecánico del orden del macrociclo, lo que permite un ensamblaje molecular controlado.

Más Videos Relacionados

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Videos de Experimentos Relacionados

Last Updated: Jun 15, 2026

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Área de la Ciencia:

  • Química supramolecular de las moléculas.
  • Síntesis orgánica La síntesis orgánica.
  • Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

  • El ensamblaje secuencial preciso de los componentes moleculares es crucial para crear arquitecturas funcionales complejas.
  • Los rotaxanos, estructuras moleculares entrelazadas, ofrecen posibilidades únicas para el control mecánico y el almacenamiento de información.
  • El control de la secuencia de múltiples macrociclos en un solo hilo molecular sigue siendo un desafío sintético.

Objetivo del estudio:

  • Desarrollar una estrategia general para el ensamblaje secuencial y controlado de diferentes macrociclos en un hilo de rotaxano no simétrico.
  • Para demostrar la síntesis de diastereómeros de [3]rotaxano con secuencias de macrociclos dictadas mecánicamente.
  • Explorar el potencial para la creación de rotaxanos complejos, multi-anillo con arreglos estructurales predeterminados.

Principales métodos:

  • Coordinación iterativa de los complejos de palladio (((II) piridina-2,6-dicarboxamida a un ligando de piridina en un hilo de rotaxano.
  • Macrociclado a través de la metátesis de olefinas de cierre de anillo para asegurar cada macrociclo.
  • Eliminación secuencial de las plantillas de paladio (II) para permitir la complicación y macrociclación posteriores, asegurando una secuenciación precisa.

Principales resultados:

  • Síntesis exitosa de un par de diastereómeros de [3]rotaxano que sólo difieren en la secuencia de sus macrociclos.
  • Demostración del control mecánico sobre la disposición del macrociclo, lo que lleva al estereoisomerismo análogo al atropisomerismo.
  • Establecimiento de un método para la construcción de rotaxanos de múltiples anillos con una secuencia predeterminada de macrociclos.

Conclusiones:

  • La estrategia descrita proporciona un control secuencial preciso sobre el ensamblaje del macrociclo en hilos de rotaxano.
  • Este método permite la síntesis de arquitecturas complejas de rotaxano con estereoquímica mecánicamente forzada.
  • Los hallazgos abren vías para diseñar máquinas moleculares sofisticadas y materiales con propiedades a medida.