Related Experiment Video
Updated: May 31, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
(1E,4E)-1,5-Bis(2,6-difluoro-phen-yl)penta-1,4-dien-3-one
Summary
This study details the crystal structure of a fluorinated organic compound, C(17)H(10)F(4)O. The molecule exhibits a nearly planar conformation and forms intermolecular connections via hydrogen bonds and pi-pi stacking in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Materials Science
Background:
- Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
- Fluorinated organic compounds often display unique electronic and structural characteristics.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(17)H(10)F(4)O.
- To analyze the molecular conformation and packing in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond distances, angles, and non-covalent interactions was performed.
Main Results:
- The molecule is nearly planar with a dihedral angle of 5.59° between phenyl rings.
- An E conformation was observed around the olefinic bonds.
- Intermolecular C-H⋯O hydrogen bonds and slipped π-π stacking were identified as key crystal packing forces.
Conclusions:
- The crystal structure of C(17)H(10)F(4)O reveals a near-planar geometry and specific intermolecular interactions.
- These findings contribute to the understanding of structure-property relationships in fluorinated organic materials.
Related Concept Videos
01:14Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
02:43E1 Reaction: Stereochemistry and Regiochemistry
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. In the example discussed, the presence of water as a weak base favors elimination over substitution to generate two alkenes. Given that alkenes’ stability increases with the number of alkyl groups across the double bond, typically, E1 reactions lead to the Zaitsev product, for this is more substituted and stable than the Hofmann product.
![[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.
01:18Benzene 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...
01:16Structure of Conjugated Dienes
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
01:29Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.