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Related Concept Videos

Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

8.8K
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.
8.8K
Nomenclature of Aromatic Compounds with a Single Substituent01:23

Nomenclature of Aromatic Compounds with a Single Substituent

8.1K
Benzene is the simplest aromatic hydrocarbon or arene. The IUPAC names for simple monosubstituted benzene derivatives are derived by adding the substituent's name as a prefix to the parent benzene. For example, halobenzene, where the halogen could be fluoro (F), chloro (Cl), bromo (Br), and iodo (I).
8.1K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

9.0K
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).
9.0K
NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

8.0K
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...
8.0K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.2K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.5K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
4.5K

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Updated: Jun 21, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

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Benzene-1,2,4,5-tetrol.

Benjamin L Weare1, Sean Hoggett2, William J Cull2

  • 1Nanoscale and Microscale Research Centre, University of Nottingham, Nottingham, NG7 2RD, United Kingdom.

Iucrdata
|July 8, 2024
PubMed
Summary
This summary is machine-generated.

This study determined the crystal structure of a compound at 120 K, revealing intricate π-π stacking and hydrogen bonding interactions between four independent molecules in the asymmetric unit.

Keywords:
benzene-1,2,4,5-tetrolcovalent organic frameworkcrystal structurehydrogen bondshydrox­yl

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Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Molecular interactions

Background:

  • Understanding molecular arrangement is crucial for predicting material properties.
  • Crystal structure determination provides fundamental insights into intermolecular forces.

Purpose of the Study:

  • To elucidate the crystal structure of the title compound.
  • To analyze the nature of π-π stacking and hydrogen bonding in the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction at 120 K.
  • Analysis of crystallographic data to identify molecular symmetry and packing.

Main Results:

  • The compound crystallizes in the triclinic space group P.
  • Four independent molecules were observed in the asymmetric unit.
  • Distinct π-π stacking interactions and inter-molecular hydrogen bonds involving hydroxy groups were identified.

Conclusions:

  • The crystal structure reveals a complex network of intermolecular interactions.
  • The observed π-π stacking and hydrogen bonding dictate the compound's solid-state architecture.
  • This structural information is vital for further studies on the compound's physical and chemical properties.