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Updated: Jun 3, 2026
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
Published on: November 15, 2017
Racemic (1,4-dioxan-2-yl)diphenylmethanol
Tomi Hsiao1, Robert M Buchanan, Mark S Mashuta
1Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
Summary
Benzophenone and dioxane react under microwave irradiation to form a racemic compound. This compound self-assembles into one-dimensional chains through robust hydrogen bonding interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Benzophenone and dioxane are common organic reagents.
- Microwave irradiation offers a rapid synthesis pathway.
- Understanding crystal packing and intermolecular forces is crucial in solid-state chemistry.
Purpose of the Study:
- To synthesize and characterize a novel compound from benzophenone and dioxane.
- To investigate the self-assembly behavior and crystal structure of the synthesized compound.
- To analyze the role of hydrogen bonding in the formation of one-dimensional chains.
Main Methods:
- Synthesis of the title compound (C17H18O3) using microwave irradiation.
- Crystallization of the compound as a racemic mixture.
- X-ray diffraction analysis to determine the crystal structure.
- Analysis of hydrogen bonding interactions (O-H···O distance and angle).
Main Results:
- Successful synthesis of the title compound, C17H18O3.
- The compound crystallizes as a racemic mixture.
- Formation of one-dimensional chains driven by strong O-H···O hydrogen bonds.
- Specific hydrogen bond parameters: distance of 1.99(3) Å and angle of 160(2)°.
Conclusions:
- Microwave irradiation is an effective method for synthesizing this benzophenone-dioxane derivative.
- The crystal structure reveals a propensity for self-assembly into linear chains.
- Strong hydrogen bonding plays a pivotal role in directing the supramolecular architecture.
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