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3-(1-Chlorovinyl)-2,4,6-trimethoxybenzaldehyde
A K Panda1, M R Parthasarathy, W Errington
1Department of Chemistry, University of Delhi, Delhi 110 007, India.
Acta Crystallographica. Section C, Crystal Structure Communications
|February 15, 2001
Summary
Researchers synthesized a novel compound using the Vilsmeier-Haack reaction. Structural analysis revealed unique substituent twists and one-dimensional chains formed by intermolecular hydrogen bonding.
Area of Science:
- Organic Chemistry
- Crystallography
Background:
- Phloroacetophenone is a key starting material in organic synthesis.
- The Vilsmeier-Haack reaction is a versatile method for formylation and chlorination.
Purpose of the Study:
- To synthesize and characterize a novel compound derived from phloroacetophenone.
- To investigate the structural and conformational properties of the synthesized molecule.
Main Methods:
- Synthesis via the Vilsmeier-Haack reaction.
- X-ray crystallography for structural determination.
- Analysis of intermolecular interactions.
Main Results:
- Successful synthesis of the title compound (C12H13ClO4).
- Observed significant twisting (approx. 75 degrees) of chlorovinyl and methoxy groups relative to the aromatic plane.
- Identified one-dimensional chains formed by C-H...O intermolecular hydrogen bonding along the a-axis.
Conclusions:
- The Vilsmeier-Haack reaction provides an effective route to this novel substituted compound.
- The molecule exhibits distinct conformational features with specific substituent orientations.
- Intermolecular hydrogen bonding plays a crucial role in the solid-state structure, leading to chain formation.