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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

10.3K
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...
10.3K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.3K
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).
11.3K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

13.2K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
13.2K
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

3.2K
When disubstituted benzenes undergo electrophilic substitution, the product distribution depends on the directing effect of both substituents. When the directing effects of both substituents reinforce each other, a single product is obtained. For example, bromination of p-nitrotoluene occurs ortho to the methyl group and meta to the nitro group, which is the same position, resulting in a single product. However, if the directing effects of the two groups oppose each other, the...
3.2K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

8.6K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the...
8.6K
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

4.2K
The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
4.2K

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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What difference does a methyl group make: pentamethylbenzene?

Matthew Mudge1, Boon K Ng, Catherine Jessica Onie

  • 1School of Chemistry, University of New South Wales, Sydney, New South Wales 2052 (Australia).

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|September 13, 2014
PubMed
Summary
This summary is machine-generated.

The crystal structure of pentamethylbenzene was determined using synchrotron radiation. Its lattice dynamics, influenced by methyl group torsions, were studied via inelastic neutron scattering, revealing insights into symmetry and charge-transfer properties.

Keywords:
X-ray diffractionaromatic hydrocarbonscharge transfermolecular packingneutron scattering

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Area of Science:

  • Solid-state chemistry
  • Materials science
  • Molecular physics

Background:

  • Pentamethylbenzene and hexamethylbenzene are related aromatic compounds.
  • Understanding molecular structure and dynamics is crucial for predicting material properties.
  • Charge-transfer complexes are important in areas like organic electronics.

Purpose of the Study:

  • To determine the crystal structure of pentamethylbenzene.
  • To investigate the lattice dynamics and methyl group torsions.
  • To analyze the impact of reduced symmetry on charge-transfer complex formation.

Main Methods:

  • Synchrotron X-ray diffraction for crystal structure determination.
  • Inelastic neutron scattering for lattice dynamics and methyl group torsion analysis.
  • Formation of charge-transfer complexes with tetracyanoethylene for electronic property investigation.

Main Results:

  • The first crystal structure of pentamethylbenzene was successfully obtained.
  • Low-energy lattice dynamics, dominated by methyl group torsions, were characterized.
  • The study revealed how symmetry lowering in pentamethylbenzene affects charge-transfer complex behavior.

Conclusions:

  • The crystal structure and lattice dynamics of pentamethylbenzene provide fundamental insights into molecular behavior.
  • Symmetry reduction significantly influences the electronic properties of its charge-transfer complexes.
  • This research contributes to understanding structure-property relationships in organic molecular solids.