Related Experiment Video
Updated: May 22, 2026
08:43
Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Methyl 5-bromo-2-hy-droxy-benzoate
Summary
This study details the crystal structure of a bromine-containing organic compound. Molecules form chains via hydrogen bonds and exhibit weak pi-pi interactions in the solid state.
Area of Science:
- Crystallography
- Organic Chemistry
- Solid-State Chemistry
Background:
- Understanding molecular interactions in the solid state is crucial for materials science.
- Crystal structure analysis reveals intermolecular forces that dictate bulk properties.
- The title compound, C(8)H(7)BrO(3), was investigated for its structural characteristics.
Purpose of the Study:
- To determine the precise three-dimensional arrangement of atoms in the title compound.
- To identify and characterize the intermolecular interactions present in the crystal lattice.
- To elucidate the packing motifs and hydrogen bonding networks.
Main Methods:
- Single-crystal X-ray diffraction was employed to collect diffraction data.
- The crystal structure was solved and refined using standard crystallographic software.
- Analysis of bond lengths, bond angles, and intermolecular distances was performed.
Main Results:
- The title compound, C(8)H(7)BrO(3), exhibits a nearly planar molecular geometry.
- Molecules are linked into C(6) chains through intermolecular O-H⋯O hydrogen bonds along the [010] direction.
- Weak aromatic π-π interactions were observed with centroid-centroid distances of approximately 3.98 Å.
Conclusions:
- The crystal structure is dominated by a hydrogen-bonding network, forming 1D chains.
- The observed planarity and π-π interactions contribute to the overall crystal packing.
- This structural information provides a foundation for understanding the compound's physical and chemical properties.
More Related Videos
Related Concept Videos
01:11Reactions at the Benzylic Position: Halogenation
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
01:37NMR Spectroscopy of Benzene Derivatives
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling constants depend...
01:28Multiple Halogenation of Methyl Ketones: Haloform Reaction
A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic acyl substitution.
01:11Nucleophilic Aromatic Substitution: Elimination–Addition
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
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.
01:10Hydrolysis 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...