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

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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.
Removing one hydrogen from the intervening CH2 group...
2.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.8K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
2.8K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.1K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
1.9K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.9K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as...
10.9K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.4K

You might also read

Related Articles

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

Sort by
Same author

Dual MXene/COF separator with ion-sieving channels and electrocatalytic surfaces for high-performance and durable Li-S batteries.

Nanoscale·2026
Same author

Performance of wrist-worn home sleep apnea testing (watch-PAT) among individuals with chronic insomnia: a comparative study with polysomnography.

Frontiers in neurology·2026
Same author

Tailoring the Cu Local Microenvironment to Create Formate Conversion-Desorption Equilibrium for Industrial Level Formaldehyde Electrooxidation.

Angewandte Chemie (International ed. in English)·2026
Same author

Speech as a biomarker for supported diagnosis of major depressive disorder using self-supervised representations.

Nature communications·2026
Same author

Navigating a fragmented lifeworld: a phenomenological study of schizophrenia among China's Z Generation.

BMC psychiatry·2026
Same author

Case Report: Pulmonary alveolar proteinosis and fibrosis associated with indium-tin-oxide exposure.

Frontiers in medicine·2026

Related Experiment Video

Updated: Aug 2, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

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

Published on: March 20, 2017

10.5K

Aromatic chloroosmacyclopentatrienes.

Zhenwei Chu1, Guomei He1, Chuan Shi2

  • 1Department of Materials Science and Engineering, College of Materials, Xiamen University, Xiamen 361005, China.

National Science Review
|April 17, 2023
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel aromatic chloroosmacyclopentatrienes, the first metallaaromatics featuring a chlorine atom. X-ray diffraction revealed a short Os-ClC bond, indicating potential M=ClC bonding in these unique organometallic compounds.

Keywords:
chlorometallacyclopentatrienehalocarbon complexmetallacycleso-ethynylphenyl alkynesosmium

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K

Related Experiment Videos

Last Updated: Aug 2, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
09:45

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

Published on: March 20, 2017

10.5K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.1K

Area of Science:

  • Organometallic Chemistry
  • Aromaticity Studies
  • Materials Science

Background:

  • Aromatic metallacycles are of significant research interest.
  • Existing aromatic metallacycles primarily incorporate carbon, nitrogen, oxygen, or sulfur atoms.

Purpose of the Study:

  • To synthesize and characterize novel aromatic chloroosmacyclopentatrienes.
  • To investigate the structural and bonding properties of metallacycles containing a chlorine atom.

Main Methods:

  • Synthesis of chloroosmacyclopentatrienes.
  • Single-crystal X-ray diffraction analysis.
  • Spectroscopic characterization.

Main Results:

  • Successful synthesis and structural confirmation of aromatic chloroosmacyclopentatrienes.
  • Demonstration of the first structurally verified metallaaromatic framework containing a chlorine atom.
  • X-ray diffraction revealed a very short Os-ClC bond distance.

Conclusions:

  • Aromatic chloroosmacyclopentatrienes represent a new class of metallaaromatic compounds.
  • The short Os-ClC distance suggests significant M=ClC bond character.
  • These findings expand the scope of known aromatic metallacycles.