Related Experiment Video
Updated: Jun 1, 2026

07:06
Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
2-Hydr-oxy-N'-[(E)-(3-hydr-oxy-2-naphth-yl)methyl-ene]benzohydrazide
Summary
Hydrogen bonds dictate the molecular shape and crystal structure of a novel organic compound. Intermolecular bonds form chains, influencing the overall solid-state arrangement.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure
Background:
- Understanding intermolecular forces is crucial for predicting material properties.
- Hydrogen bonding plays a significant role in molecular conformation and crystal packing.
- The specific compound C(18)H(14)N(2)O(3) was investigated for its structural characteristics.
Purpose of the Study:
- To elucidate the molecular conformation of C(18)H(14)N(2)O(3) influenced by hydrogen bonding.
- To determine the crystal structure and intermolecular interactions.
- To analyze the role of hydrogen bonds in the solid-state arrangement.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond distances and angles to identify hydrogen bonding interactions.
- Dihedral angle measurements to quantify the molecular conformation.
Main Results:
- Intramolecular O-H⋯N and N-H⋯O hydrogen bonds were identified, influencing molecular conformation.
- The benzene and naphthalene planes exhibit a dihedral angle of 11.54(5)°.
- Intermolecular O-H⋯O hydrogen bonds link molecules into chains along the [01] direction.
Conclusions:
- Hydrogen bonding is a key factor governing the molecular conformation and crystal packing of C(18)H(14)N(2)O(3).
- The observed chain-like structure formed by intermolecular hydrogen bonds is a significant feature of the crystal lattice.
- This study provides insights into structure-property relationships driven by hydrogen bonding in organic crystals.
Related Concept Videos
Hydrolysis 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...
Diazonium 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.
Formation 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.
Nucleophilic 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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.

