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Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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Based on their attached substituent groups, ethers can be classified into two...
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated benzene...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Structures of Aldehydes and Ketones01:04

Structures of Aldehydes and Ketones

Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the carbonyl...

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1,2-Diedehidro[10]anulenos: estructuras, aromaticidad y ciclizaciones.

Armando Navarro-Vázquez1, Peter R Schreiner

  • 1Institute of Organic Chemistry, Justus-Liebig-University, Heinrich-Buff-Ring 58, 35392 Giessen, Germany.

Journal of the American Chemical Society
|June 2, 2005
PubMed
Resumen

Los estudios computacionales revelan que los C(10)H(8) 1,2-didehidro[10]anulenos favorecen una estructura aromática plana de "corazón" sobre una forma retorcida. Este hallazgo tiene un impacto en la comprensión de su conversión en isonaftalenos y en las reacciones de deshidratación Diels-Alder.

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Área de la Ciencia:

  • Química computacional es la química computacional.
  • Química orgánica es la química orgánica.
  • Química teórica es la química teórica.

Sus antecedentes:

  • Comprender las preferencias conformacionales y la reactividad de los sistemas de anilenos es crucial en la química orgánica.
  • Estudios previos sobre sistemas relacionados como el C(10) H(10) [10]annuleno proporcionan el contexto para la investigación actual.
  • Se sabe que las reacciones de deshidratación Diels-Alder que involucran fenilacetilenos producen mezclas isoméricas complejas.

Objetivo del estudio:

  • Para investigar por medio de la computación el paisaje conformacional de C(10) H(8) 1,2-didehydro[10]annulenes.
  • Para dilucidar la vía de conversión unimolecular de estos annulenes a isonaftalenes (alenos cíclicos).
  • Determinar el mecanismo subyacente a las isomerizaciones observadas en las reacciones de Diels-Alder de deshidro de fenilacetilenos.

Principales métodos:

  • Teoría Funcional de Densidad (DFT) utilizando el funcional B3LYP.
  • Cluster acoplado de referencia única con cálculos individuales, dobles y triples perturbadores [CCSD(T) ].
  • Cluster acoplado cuadrático promediado por multireferencia con métodos individuales y dobles y corrección de Davidson (MCQDPT2) después de Hartree-Fock.

Principales resultados:

  • La introducción de una fracción alquinila lineal en C(10) H(8) 1,2-didehidro[10]anulenos estabiliza un conformador aromático plano de "corazón" en más de 6 kcal/mol (a nivel de CCSD(T) en comparación con una estructura localizada de "torsión" C(2).
  • Esta preferencia conformacional difiere significativamente del estrechamente relacionado sistema de C(10) H(10) [10]anuleno.
  • El análisis computacional indica que los isonaftalenos se someten a una apertura de anillo electrocíclico al "corazón" C(10) H(8) annuleno a través de una barrera de baja energía (aprox. 15 kcal/mol). es decir, tiene 15 kcal/mol.

Conclusiones:

  • El conformador aromático del "corazón" plano es la estructura preferida para los C(10)H(8) 1,2-didehidro[10]anulenos debido a la reducción de la tensión angular del grupo alquinile.
  • La apertura de anillos electrocíclicos de baja barrera de los isonaftalenos proporciona un mecanismo viable para las isomerizaciones observadas en las reacciones de deshidro Diels-Alder de los fenilacetilenos.
  • Estos hallazgos computacionales ofrecen información valiosa sobre la estructura, la estabilidad y los mecanismos de reacción de los deshidroanulenos y los allenos cíclicos relacionados.