Related Experiment Video
Updated: Jun 5, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
1-(2',4'-Difluoro-biphenyl-4-yl)ethanone.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the crystal structure of C(14)H(10)F(2)O, revealing specific molecular arrangements. Key findings include intermolecular interactions like C-H⋯F and π-π stacking that influence crystal packing.
Area of Science:
- Crystallography
- Solid-state chemistry
- Molecular structure analysis
Background:
- Understanding the three-dimensional arrangement of atoms and molecules in crystalline solids is fundamental to materials science.
- Intermolecular forces play a crucial role in determining the macroscopic properties of crystalline compounds.
- Detailed structural analysis provides insights into chemical bonding and potential applications.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(14)H(10)F(2)O.
- To identify and quantify the intermolecular interactions governing the crystal packing.
- To provide a detailed description of the molecular conformation and arrangement in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the crystal structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided conformational information.
- Intermolecular interactions, including hydrogen bonds and π-π stacking, were identified and characterized.
Main Results:
- The crystal structure contains two crystallographically independent molecules with significant dihedral angles between benzene rings (46.9(2)° and 47.6(2)°).
- Molecules form dimers through C-H⋯F interactions, which are further organized into columns along the b axis via π-π interactions (centroid-centroid distance = 3.8221 Å).
- C-F⋯π interactions (C⋯centroid distance = 3.5919 Å) were also observed, contributing to the overall crystal packing.
Conclusions:
- The crystal packing of C(14)H(10)F(2)O is dictated by a combination of C-H⋯F, π-π stacking, and C-F⋯π interactions.
- The identified intermolecular interactions provide a basis for understanding the compound's solid-state properties.
- This structural data serves as a foundation for further investigations into related fluorinated organic compounds.
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...
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
02:36Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
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...
![[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.