Related Experiment Video
Updated: Jun 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
3-(2-Bromo-4,5-dimethoxy-phen-yl)propiononitrile.
This study reveals a novel intramolecular hydrogen bond in a C(11)H(12)BrNO(2) molecule, forming a five-membered ring. Intermolecular interactions further link these molecules in the crystal structure.
Area of Science:
- Crystallography
- Molecular Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular interactions is crucial for predicting material properties.
- Hydrogen bonds play a significant role in molecular assembly and conformation.
Purpose of the Study:
- To investigate the structural characteristics of the title compound, C(11)H(12)BrNO(2).
- To identify and analyze intramolecular and intermolecular hydrogen bonding interactions.
- To describe the conformational aspects of the molecule in the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and hydrogen bond geometries.
Main Results:
- A weak intramolecular C-H⋯Br hydrogen bond was identified, forming a five-membered ring with an envelope conformation.
- The hydrogen atom involved in the intramolecular bond is displaced by 0.486 Å from the ring plane.
- Intermolecular C-H⋯O hydrogen bonds were observed, mediating the linkage of molecules in the crystal structure.
Conclusions:
- The presence of both intramolecular and intermolecular hydrogen bonds influences the packing and conformation of the title compound.
- The study provides detailed structural insights into the hydrogen bonding network of C(11)H(12)BrNO(2).
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
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
Related Concept Videos
Radical Substitution: Allylic Bromination
Formation of Halohydrin from Alkenes
Structure and Nomenclature of Alcohols and Phenols
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Reactions at the Benzylic Position: Halogenation
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.