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Videos de Conceptos Relacionados

Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

9.2K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
9.2K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

9.1K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
9.1K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.4K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
8.4K
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

2.7K
The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
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Resonance02:52

Resonance

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The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N-O and N=O bonds. 
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Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.6K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
10.6K

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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Estructura de equilibrio exacta del benceno

Brian J Esselman1, Maria A Zdanovskaia1, Andrew N Owen1

  • 1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, United States.

Journal of the American Chemical Society
|September 29, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio determinó con precisión la estructura de equilibrio del benceno utilizando métodos computacionales avanzados y datos experimentales. Los resultados muestran una excelente concordancia entre los valores teóricos y experimentales, estableciendo nuevos puntos de referencia para la geometría molecular.

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Área de la Ciencia:

  • Química Cuántica
  • Espectroscopia
  • Determinación de la estructura molecular

Sus antecedentes:

  • Las estructuras de equilibrio semi-experimentales (rSE) muestran una excelente concordancia con las mejores estimaciones teóricas (BTE) para los heterociclos aromáticos.
  • Estudios anteriores han demostrado una alta precisión para las estructuras de pirimidina y piridazina.

Objetivo del estudio:

  • Extender el análisis de la determinación de la estructura de la fase gaseosa a la molécula aromática fundamental, el benceno.
  • Lograr una estructura de equilibrio (rSE) de alta precisión y exactitud para el benceno.
  • Validar los métodos teóricos con datos experimentales para el benceno.

Principales métodos:

  • Se utilizaron datos espectroscópicos experimentales publicados de 11 isotopólogos del benceno.
  • Cluster acoplado aplicado con cálculos individuales, dobles y triples perturbadores (CCSD(T)) con conjuntos de bases grandes (cc-pCV5Z).
  • Incorporó correcciones para la interacción vibración-rotación, distribución de masa de electrones, conjuntos de bases finitos, correlación de electrones, efectos relativistas y desglose de Born-Oppenheimer.

Principales resultados:

  • Se alcanzó un acuerdo pendiente (0.0001 Å) entre rSE y BTE para el benceno.
  • Se determina la geometría D6h del benceno con una precisión sin precedentes: R_C-C = 1,3913 (1) Å y R_C-H = 1,0809 (1) Å.
  • Superó los niveles acordados previamente reportados para la pirimidina y la piridazina.

Conclusiones:

  • La alta precisión y exactitud de la estructura del benceno ahora están establecidas.
  • El excelente acuerdo entre la teoría y el experimento valida ambos enfoques.
  • Las discrepancias entre las estructuras semiexperimentales y teóricas en la literatura se resuelven sustancialmente.