Search research articles

ACERCA DE JoVE

Visión General Liderazgo Blog Centro de Ayuda JoVE

AUTORES

Proceso de Publicación Consejo Editorial Alcance y Políticas Revisión por Pares Preguntas Frecuentes Enviar

BIBLIOTECARIOS

Testimonios Suscripciones Acceso Recursos Consejo Asesor de Bibliotecas Preguntas Frecuentes

INVESTIGACIÓN

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archivo

EDUCACIÓN

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Centro de Recursos para Profesores Sitio de Profesores

Términos y Condiciones de Uso

Política de Privacidad

Videos de Conceptos Relacionados

Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

SN2 Reaction: Transition State

S_N2 Reaction: Transition State

An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...

SN1 Reaction: Stereochemistry

S_N1 Reaction: Stereochemistry

This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.

También podría leer

Artículos Relacionados

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

Ordenar por

Same author

Toward the Synthesis of Pestalustaine A: Structural Revision and Formation of Original Strained Tricyclic Architectures.

Angewandte Chemie (International ed. in English)·2026

Same author

Strain-Release Pentafluorosulfanylation of Carbonyl-Containing Disubstituted Bicyclobutanes: A Fortuitous Path to SF<sub>5</sub>-Containing Oxa[2.1.1]bicyclohexanes.

Angewandte Chemie (International ed. in English)·2026

Same author

Reinvestigation of the mechanism and selectivity of 1,8-cineole synthase using <i>TerDockin</i>.

Chemical science·2026

Same author

The One Ring: A Monocycle Producing Class II Diterpene Cyclase from <i>Isodon leucophyllus</i>.

Journal of the American Chemical Society·2026

Same author

Investigations toward a unified reaction pathway of thermal and TBSOTf-mediated oxidopyrylium-alkene (5 + 2) cycloadditions.

Organic & biomolecular chemistry·2026

Same author

High-fat diet-driven gut microbial sphingolipid metabolic reprogramming is associated with stress susceptibility in CUMS rats.

Frontiers in microbiology·2026

Search research articles

Video Experimental Relacionado

Updated: Nov 23, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Efectos dinámicos en las aptitudes migratorias en las reacciones de carbocatión

Zhitao Feng¹, Dean J Tantillo¹

¹Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.

Journal of the American Chemical Society

|January 5, 2021

Resumen

Las reacciones de reordenamiento de carbocationes son vitales en la química. Los efectos dinámicos, no solo los factores estáticos, influyen significativamente en la forma en que los carbocationes migran, afectando las vías sintéticas y biosintéticas.

Más Videos Relacionados

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Videos de Experimentos Relacionados

Last Updated: Nov 23, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Área de la Ciencia:

Química orgánica
Química computacional

Sus antecedentes:

Las reorganizaciones de carbocationes son fundamentales en la síntesis orgánica y la biosíntesis.
Comprender la aptitud migratoria es crucial para predecir los resultados de la reacción.

Objetivo del estudio:

Desarrollar una escala de la aptitud migratoria inherente teniendo en cuenta los efectos dinámicos.
Investigar los eventos de migración en competencia en un sistema de carbocatión modelo.

Principales métodos:

Utilizó simulaciones de dinámica molecular (AIMD) en cuesta arriba y cuesta abajo.
Analizó la topografía de la superficie de energía potencial.
Empleó cálculos de la teoría del estado de transición variacional.

Principales resultados:

Se ha identificado el papel significativo de los efectos dinámicos no estadísticos en la aptitud migratoria.
Demostró que los factores dinámicos más allá de los sesgos estáticos son críticos para comprender el comportamiento del carbocatión.

Conclusiones:

La aptitud migratoria está influenciada por efectos dinámicos más allá de las consideraciones estéricas y electrónicas tradicionales.
Los métodos computacionales como el AIMD proporcionan información crucial sobre los mecanismos de reacción.