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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

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.
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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...
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation01:14

Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.

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Related Experiment Video

Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

(E)-N'-[(2-Hydroxy-1-naphthyl)methyl-ene]benzohydrazide monohydrate.

Yan Qiao1, Xiuping Ju, Zhiqing Gao

  • 1Dongchang College, Liaocheng University, Liaocheng, 250059, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online
|May 18, 2011
PubMed
Summary

This study details the crystal structure of a novel organic compound, C(18)H(14)N(2)O(2)·H(2)O. Molecular conformation is influenced by intramolecular hydrogen bonds and observed intermolecular interactions, including pi-pi stacking.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Understanding molecular interactions is crucial in crystal engineering.
  • The specific compound C(18)H(14)N(2)O(2)·H(2)O presents an interesting case for structural analysis.
  • Hydrogen bonding and pi-pi interactions are key non-covalent forces dictating crystal packing.

Purpose of the Study:

  • To elucidate the crystal structure of C(18)H(14)N(2)O(2)·H(2)O.
  • To investigate the role of intramolecular and intermolecular interactions in the compound's conformation and packing.
  • To characterize the nature and extent of hydrogen bonding and pi-pi interactions within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided conformational insights.
  • Intermolecular and intramolecular interactions, including hydrogen bonds and pi-pi stacking, were identified and quantified.

Main Results:

  • The crystal structure of C(18)H(14)N(2)O(2)·H(2)O was successfully determined.
  • A small dihedral angle (5.18°) between the benzene and naphthalene systems indicates near-planarity.
  • Intramolecular N-H⋯O hydrogen bonds influence conformation, while intermolecular N-H⋯O, O-H⋯O hydrogen bonds and pi-pi interactions (centroid-centroid distance 3.676 Å) govern crystal packing.

Conclusions:

  • The crystal structure reveals a specific arrangement dictated by a combination of hydrogen bonding and pi-pi interactions.
  • The findings contribute to the understanding of structure-property relationships in organic crystalline materials.
  • This detailed structural analysis provides a foundation for further studies on related compounds and their applications.