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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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The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Conformations of Cyclohexane02:11

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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Chair Conformation of Cyclohexane02:02

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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.
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Towards 2D Borane Chemistry in Hexagonal Cyclic Compounds.

Rubén López-Sánchez1, Maxime Ferrer2,3, Josep M Oliva-Enrich1

  • 1Instituto de Química-Física "Blas Cabrera", CSIC, E-28006, Madrid, Spain.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|January 26, 2024
PubMed
Summary
This summary is machine-generated.

This study compares benzene and unknown borane molecules, analyzing their structures and electronic properties. Findings offer insights for synthesizing novel 2D borane compounds.

Keywords:
11B NMR spectroscopy2D boronaryl compoundschemical bondquantum chemistry

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Area of Science:

  • Computational chemistry
  • Inorganic chemistry
  • Materials science

Background:

  • Benzene derivatives (R-Ph) are well-characterized aromatic systems.
  • Isoelectronic R-cyclohexaborane(12) molecules are largely unexplored.
  • Understanding structure-property relationships is key for novel material design.

Purpose of the Study:

  • To conduct a comprehensive geometric and electronic structure comparison between known R-Ph compounds and unknown isoelectronic R-cyclohexaborane(12) molecules.
  • To propose novel chemical nomenclature for 2D borane compounds.
  • To predict properties that could guide synthetic efforts.

Main Methods:

  • Density Functional Theory (DFT) calculations.
  • Analysis of Highest Occupied Molecular Orbital-Lowest Unoccupied Molecular Orbital (HOMO-LUMO) energy gaps.
  • Examination of bonding schemes and electron density topological properties.
  • Prediction of Nuclear Magnetic Resonance (NMR) chemical shifts.

Main Results:

  • Detailed geometric and electronic structure comparisons between carbon-based benzene and boron-based cyclohexaborane systems.
  • Identification of key differences and similarities in bonding and electronic distributions.
  • Predicted NMR chemical shifts provide a benchmark for experimental verification.
  • Novel nomenclature proposed for the studied 2D borane compounds.

Conclusions:

  • The study provides a theoretical foundation for understanding the properties of isoelectronic R-cyclohexaborane(12) systems.
  • Predicted properties can aid in the rational design and synthesis of these novel 2D borane compounds.
  • This work bridges the gap between known aromatic systems and potential new boron-based materials.