Related Experiment Video
Updated: May 30, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
(E)-N'-[(2-Hydroxynaphthalen-1-yl)methylidene]nicotinohydrazide
This study details the molecular structure of C(17)H(13)N(3)O(2), revealing a near-planar conformation stabilized by intramolecular hydrogen bonding. Intermolecular hydrogen bonds further organize these molecules into crystal chains.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular conformation and intermolecular interactions is crucial in crystal engineering.
- Hydrogen bonding plays a significant role in dictating crystal packing and material properties.
Purpose of the Study:
- To elucidate the crystal structure and intermolecular interactions of the title compound, C(17)H(13)N(3)O(2).
- To analyze the conformational preferences and hydrogen bonding patterns within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
- Analysis of hydrogen bonding networks, including intramolecular and intermolecular interactions, was performed.
Main Results:
- The molecule exhibits a dihedral angle of 12.2° between the naphthyl and pyridine rings, indicating a near-planar conformation.
- An intramolecular O-H⋯N hydrogen bond forms a six-membered ring (S(6) motif), contributing to the molecule's planarity.
- Intermolecular N-H⋯N hydrogen bonds link molecules into chains along the crystallographic a axis.
Conclusions:
- The crystal structure of C(17)H(13)N(3)O(2) is characterized by significant planarity due to intramolecular hydrogen bonding.
- The observed intermolecular hydrogen bonding dictates the formation of one-dimensional chains in the solid state.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Related Concept Videos
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
2° Amines to N-Nitrosamines: Reaction with NaNO2
Nitrosation of Enols
Preparation of Nitriles
Role of Reduced Coenzymes NADH and FADH₂
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism