Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

12.7K
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.
12.7K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.7K
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...
2.7K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

4.2K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
4.2K
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

11.7K
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...
11.7K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

13.2K
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).
13.2K
Directing and Steric Effects in Disubstituted Benzene Derivatives01:18

Directing and Steric Effects in Disubstituted Benzene Derivatives

4.2K
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...
4.2K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Light-Induced Conformational Switching of 2-Formyl Benzothiazole in Low Temperature Inert Gas Matrices.

Chemphyschem : a European journal of chemical physics and physical chemistry·2026
Same author

Band Dispersion and Site Preference in Ternary Transition Metal Silicides, Germanides, and Stannides RTX<sub>2</sub> (R = Rare Earth Metal or Ca, Sr, Ba, T = Transition Metal, X = Si, Ge, Sn).

Inorganic chemistry·2025
Same author

Pd(II)-Mediated Si-H Activation of <i>Ortho</i>-Silyl Arylphosphines: Complexes with Pd-Si Bonds and their Utility in Carbon-Carbon Coupling Reactions.

Inorganic chemistry·2025
Same author

Zn-Doped Cesium Bismuth Bromide Perovskites: Impact of Structural and Morphological Modifications on Linear and Non-Linear Optical Properties.

Small (Weinheim an der Bergstrasse, Germany)·2025
Same author

Probing the significance of phenylethyl ammonium doping in Cs<sub>3</sub>Bi<sub>2</sub>Br<sub>9</sub> halide perovskite nanosheets: a structural and optical perspective.

Dalton transactions (Cambridge, England : 2003)·2025
Same author

What Can Chemical Bonding Tell Us about Photoinduced Phase Transition Reactions in Inorganic Semiconductors? Insight from Bismuth-Antimony Selenide.

Inorganic chemistry·2024

Related Experiment Video

Updated: Mar 3, 2026

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.4K

An Iodabenzene Story.

Abdel Monem Rawashdeh1, Priyakumari Chakkingal Parambil2, Tao Zeng3

  • 1Department of Chemistry, Yarmouk University , Irbid 211-63, Jordan.

Journal of the American Chemical Society
|May 3, 2017
PubMed
Summary
This summary is machine-generated.

Researchers identified a novel "bird-like" iodabenzene molecule. Computational analysis suggests this unusual structure is stable enough for potential experimental detection and isolation.

More Related Videos

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

10.2K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.7K

Related Experiment Videos

Last Updated: Mar 3, 2026

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.4K
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

10.2K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.7K

Area of Science:

  • * Computational chemistry
  • * Organic chemistry
  • * Aromaticity studies

Background:

  • * Planar aromatic molecules with 8 π electrons are unstable.
  • * Meisenheimer complexes offer a precedent for stabilizing unusual electronic structures.
  • * Iodabenzene is a cyclic (CH)5I molecule with potential for unique electronic configurations.

Purpose of the Study:

  • * To investigate the electronic structure and stability of a non-planar iodabenzene isomer.
  • * To explore stabilization strategies for unusual π-electron systems.
  • * To assess the feasibility of synthesizing and detecting the proposed iodabenzene structure.

Main Methods:

  • * Density Functional Theory (DFT) calculations were employed.
  • * Electronic structure and charge distribution were analyzed.
  • * Reaction pathways and activation barriers were computed.

Main Results:

  • * A stable, non-planar
  • bird-like
  • iodabenzene isomer was computationally identified.
  • * This structure exhibits electronic properties analogous to Meisenheimer complexes.
  • * Substitution with π-acceptors can further stabilize the molecule.
  • * A significant energy barrier exists for conversion to a classical 5-iodocyclopentadiene structure.

Conclusions:

  • * The calculated stability and reaction barriers support the potential existence of the bird-like iodabenzene isomer.
  • * The findings suggest that experimental detection and isolation of this novel molecule may be achievable.
  • * This work expands the understanding of aromaticity and stabilization in organic molecules.