Related Experiment Videos
11-Methyl-2,3-benzodipyrrin-1-one.
Raymond Bonnett1, Majid Motevalli, Fiona J Swanson
1Department of Chemistry, Queen Mary, University of London, Mile End Road, London E1 4NS, England. r.bonnett@qmul.ac.uk
Acta Crystallographica. Section C, Crystal Structure Communications
|December 8, 2004
Summary
This study synthesized a novel benzopyrromethenone compound. The fused benzo ring minimally impacts the dipyrrin-1-one skeleton's molecular dimensions.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Pyrromethenone derivatives are important in various chemical applications.
- Understanding the structural impact of fused rings is crucial for designing new molecules.
Purpose of the Study:
- To synthesize and characterize a novel benzopyrromethenone derivative.
- To investigate the structural and electronic effects of a fused benzo ring on the dipyrrin-1-one skeleton.
Main Methods:
- Base-catalyzed condensation reaction between phthalimidine and 2-formyl-1-methylpyrrole.
- Single crystal X-ray diffraction analysis to determine molecular and crystal structure.
- Comparison of structural data with related polyalkyldipyrrin-1-one compounds.
Main Results:
- Successful synthesis of the title compound, C(14)H(12)N(2)O, with alternative names 11-methyl-2,3-benzopyrromethenone and 3-[(1-methylpyrrol-2-yl)methylidene]-2,3-dihydro-1H-isoindol-1-one.
- Obtained yellow orthorhombic crystals (space group Pbca) from ethanol.
- The molecule exhibits near planarity with Z(-)antiperiplanar geometry and forms intermolecular hydrogen bonds between lactam functions in pairs.
Conclusions:
- The fused benzo ring has a negligible effect on the overall molecular dimensions of the dipyrrin-1-one core.
- The study provides valuable structural insights into benzopyrromethenone derivatives, relevant for further synthetic modifications and applications.