Related Experiment Video
Updated: May 27, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
3,8-Dimethyl-acenaphthyl-ene-1,2-dione
1School of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408100, Chongqing, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2011
Summary
The acenaphthene-quinone core in C(14)H(10)O(2) is planar. Molecules form columns in the crystal structure through pi-pi stacking interactions.
Area of Science:
- Crystallography
- Materials Science
Background:
- Acenaphthene-quinone derivatives are of interest in materials science.
- Understanding molecular packing is crucial for predicting material properties.
Purpose of the Study:
- To characterize the crystal structure of a specific acenaphthene-quinone compound.
- To investigate intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed.
- Analysis of molecular planarity and intermolecular interactions (pi-pi stacking) was performed.
Main Results:
- The acenaphthene-quinone core exhibits near-planarity (r.m.s. deviation of 0.0140 Å).
- Molecules engage in pi-pi stacking interactions with centroid-centroid distances of 3.766(3), 3.839(3), and 3.857(3) Å.
- These interactions lead to the formation of molecular columns parallel to the a axis.
Conclusions:
- The crystal structure reveals a planar acenaphthene-quinone core.
- Pi-pi stacking is a dominant intermolecular force, dictating the columnar arrangement of molecules.
- This structural information is vital for designing acenaphthene-quinone-based materials.
Related Concept Videos
01:29UV–Vis Spectroscopy: Woodward–Fieser Rules
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...
![[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12422.jpg&w=3840&q=75)
01:21[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
02:39Nomenclature of Alkynes
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
00:53Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
01:29Diels–Alder Reaction: Characteristics of Dienes
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...