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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

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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).
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Structure of Benzene: Kekulé Model01:07

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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.
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NMR Spectroscopy of Benzene Derivatives01:34

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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...
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Molecular Orbital Energy Diagrams
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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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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Benzene and Borazine, so Different, yet so Similar: Insight from Experimental Charge Density Analysis.

María Del Rosario Merino-García1, Luis Antonio Soriano-Agueda2, Juan de Dios Guzmán-Hernández1

  • 1Centro Conjunto de Investigación en Química Sustentable UAEM-UNAM, Carretera Toluca-Atlacomulco, km. 14.5, Toluca, Estado de México C.P. 50200, México.

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Borazines exhibit weak aromaticity due to nitrogen-atom electronic delocalization, unlike benzene. This study uses charge density analysis to reveal their unique electronic structure and aromatic character.

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Area of Science:

  • Inorganic Chemistry
  • Physical Chemistry
  • Crystallography

Background:

  • Benzene and borazine are isoelectronic and isostructural but differ in electronic structure due to polar B-N bonds.
  • Understanding the electronic delocalization in borazine is crucial for characterizing its aromaticity.

Purpose of the Study:

  • To experimentally investigate the charge density distribution in borazine and trichloroborazine crystals.
  • To compare the electronic structure and aromaticity of borazines with benzene and its chlorinated derivatives.
  • To identify reliable indicators for assessing the degree of aromaticity in borazine systems.

Main Methods:

  • High-resolution X-ray diffraction data collection.
  • Multipole model formalism and Hirshfeld atom refinement (HAR) for charge density analysis.
  • Density functional theory (DFT) calculations for gas-phase electronic structure.

Main Results:

  • Borazines display weak aromaticity with electronic delocalization primarily localized on nitrogen atoms, contrasting with benzene's aromaticity.
  • Delocalization indices and interacting quantum atom energy effectively explain discrepancies in common aromaticity index evaluations for chlorinated borazines.
  • Crystal packing analysis reveals similarities between borazine and benzene, and between trichloroborazines and trichlorobenzene, supporting the weak aromatic character of borazines.

Conclusions:

  • Borazines possess a weakly aromatic character, with electronic delocalization confined to the nitrogen atoms within the B3N3 ring.
  • The study provides robust experimental and computational evidence for the distinct electronic nature of borazines compared to benzene.
  • Delocalization indices and quantum atom interactions offer valuable insights into the nuances of aromaticity in heterocyclic compounds.