Related Experiment Video
Updated: Jun 1, 2026
19:58
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
N'-(5-Bromo-2-methoxy-benzyl-idene)-2-methoxy-benzohydrazide
1Department of Chemistry, Chifeng University, Chifeng 024001, People's Republic of China.
Summary
This study details the crystal structure of a novel hydrazone compound, C(16)H(15)BrN(2)O(3). The molecule exhibits an E configuration and forms hydrogen-bonded chains in its solid state.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Hydrazone compounds are versatile organic molecules with diverse applications.
- Understanding the solid-state structure of organic compounds is crucial for predicting their properties and reactivity.
- The specific compound C(16)H(15)BrN(2)O(3) was synthesized and selected for structural analysis.
Purpose of the Study:
- To determine the precise three-dimensional molecular structure of the title hydrazone compound.
- To investigate the intermolecular interactions present in the crystal lattice.
- To elucidate the conformational preferences of the molecule in the solid state.
Main Methods:
- Single-crystal X-ray diffraction was employed to obtain detailed structural data.
- The crystal structure was solved and refined using standard crystallographic software.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
Main Results:
- The compound C(16)H(15)BrN(2)O(3) was confirmed to possess an E configuration around the C=N double bond.
- The molecule exhibits a twisted conformation, with a dihedral angle of 22.0(2)° between the two substituted benzene rings.
- Intermolecular N-H⋯O hydrogen bonds link the molecules into chains along the crystallographic c axis.
Conclusions:
- The crystal structure provides a definitive understanding of the molecular and supramolecular arrangement of this hydrazone.
- The observed conformation and hydrogen bonding pattern are key features influencing the compound's solid-state behavior.
- This structural data serves as a foundation for further studies on the chemical and physical properties of related hydrazone derivatives.
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.
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.
01:11Nucleophilic 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...
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
01:19Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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...