Related Experiment Video
Updated: Jun 5, 2026
04:38
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
N'-(2-Bromo-benzyl-idene)-3,4,5-tri-methoxy-benzohydrazide methanol solvate
1School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
Researchers synthesized a novel compound using trimethoxy-benzohydrazide and bromo-benzaldehyde. Crystal structure analysis revealed near-planar aromatic rings and intermolecular hydrogen bonding forming molecular chains.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Benzohydrazide derivatives and benzaldehyde derivatives are important organic compounds.
- Hydrogen bonding plays a crucial role in the self-assembly of molecules.
Purpose of the Study:
- To synthesize a novel compound with potential applications in materials science.
- To elucidate the crystal structure and intermolecular interactions of the synthesized compound.
Main Methods:
- Condensation reaction between 3,4,5-trimethoxy-benzohydrazide and 2-bromo-benzaldehyde.
- Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
Main Results:
- The title compound, C(17)H(17)BrN(2)O(4)·CH(4)O, was successfully synthesized.
- The crystal structure revealed two approximately planar aromatic rings with a small dihedral angle (3.08°).
- Intermolecular N-H⋯O and O-H⋯O hydrogen bonds link the molecules into chains along the a axis.
Conclusions:
- The synthesis and structural characterization of the novel compound were achieved.
- The observed hydrogen bonding network dictates the supramolecular architecture in the solid state.
- This study provides insights into the structure-property relationships of related organic compounds.
More Related Videos
Related Concept Videos
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.
01:11Reactions 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.
03:08Hydroboration-Oxidation of Alkenes
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
02:46Halogenation of Alkenes
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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...
01:27Radical Substitution: Allylic Bromination
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...