Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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...

Criteria for Aromaticity and the Hückel 4n + 2 Rule

Criteria for Aromaticity and the Hückel 4n + 2 Rule

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 Hückel’s rule or the 4n + 2 rule.

Disubstituted Cyclohexanes: cis-trans Isomerism

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.

You might also read

Related Articles

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

Sort by

Same author

7-Ketocholesterol Links Sterol Homeostasis to Hedgehog Signaling and Stress-Survival Responses in MSCs from Patients with Acute Myeloid Leukemia.

International journal of molecular sciences·2026

Same author

7-Ketocholesterol Effects on Osteogenic Differentiation of Adipose Tissue-Derived Mesenchymal Stem Cells.

International journal of molecular sciences·2024

Same author

Structural and thermodynamic characterization of allosteric transitions in human serum albumin with metadynamics simulations.

Physical chemistry chemical physics : PCCP·2024

Same author

One-pot synthesis of γ-lactams from ketoaziridines.

Organic & biomolecular chemistry·2023

Same author

Copper-Mediated Intramolecular Interrupted CuAAC Selanylation.

The Journal of organic chemistry·2023

Same author

Resistance to a tyrosine kinase inhibitor mediated by changes to the conformation space of the kinase.

Physical chemistry chemical physics : PCCP·2023

Search research articles

Related Experiment Video

Updated: Jun 1, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

2-(4-Methoxy-phenyl-sulfin-yl)cyclo-hexan-1-one.

Julio Zukerman-Schpector, Elisângela Vinhato, Carlos R Cerqueira

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study reveals the distorted chair conformation of a cyclo-hexanone ring in a novel compound. Molecules form a 2D array through specific intermolecular interactions involving carbonyl and sulfinyl oxygen atoms.

More Related Videos

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Related Experiment Videos

Last Updated: Jun 1, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Area of Science:

Organic Chemistry
Crystallography
Supramolecular Chemistry

Background:

Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
Cyclo-hexanone derivatives are common motifs in organic synthesis and medicinal chemistry.

Purpose of the Study:

To elucidate the crystal structure and intermolecular interactions of a specific cyclo-hexanone compound.
To investigate the conformational preferences of the cyclo-hexanone ring and the role of sulfur and oxygen atoms in molecular assembly.

Main Methods:

Single-crystal X-ray diffraction analysis was performed to determine the three-dimensional structure.
Analysis of intermolecular contacts, including hydrogen bonds and van der Waals forces, was conducted.

Main Results:

The cyclo-hexanone ring adopts a distorted chair conformation.
An intramolecular S⋯O distance of 2.814(2) Å was observed.
Molecules self-assemble into a two-dimensional array mediated by C-H⋯O interactions.

Conclusions:

The specific conformation and intermolecular C-H⋯O contacts dictate the supramolecular architecture of the compound.
The findings provide insights into the crystal packing of cyclo-hexanone derivatives containing sulfinyl groups.