Related Experiment Video
Updated: Jun 2, 2026
06:54
Elucidating the Metabolism of 2,4-Dibromophenol in Plants
Published on: February 10, 2023
4,6-Dibromo-2,3-dimethyl-phenol
Acta Crystallographica. Section E, Structure Reports Online
|April 28, 2011
Summary
This study reveals the crystal structure of a novel organic compound, C(8)H(8)Br(2)O. The molecule exhibits near-planarity, with intermolecular hydrogen bonds forming chains and a notable short bromine-bromine interaction observed.
Area of Science:
- Crystallography
- Organic Chemistry
- Solid-State Chemistry
Background:
- Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties.
- Intermolecular interactions, such as hydrogen bonds and halogen bonds, significantly influence crystal packing and material characteristics.
Purpose of the Study:
- To determine and analyze the crystal structure of the title compound, C(8)H(8)Br(2)O.
- To investigate the molecular geometry, intermolecular interactions, and crystal packing of this novel compound.
Main Methods:
- Single-crystal X-ray diffraction was employed to collect diffraction data.
- The crystal structure was solved and refined using standard crystallographic software.
Main Results:
- The molecule C(8)H(8)Br(2)O was found to be approximately planar, with a maximum atomic deviation of 0.063 Å.
- Adjacent molecules are linked by intermolecular O-H⋯O hydrogen bonds, forming chains along the [010] direction.
- A short Br⋯Br interaction with a distance of 3.362 Å was observed between adjacent molecules.
Conclusions:
- The crystal structure of C(8)H(8)Br(2)O reveals a unique combination of hydrogen bonding and halogen interactions.
- The observed planarity and intermolecular interactions provide insights into the solid-state behavior and potential applications of this compound.
Related Concept Videos
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
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.
02:32Physical Properties of Alcohols and Phenols
Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
02:41Formation of Halohydrin from Alkenes
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
01:27Benzene to Phenol via Cumene: Hock Process
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...