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Updated: Jun 23, 2026
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
4-Chloro-1-naphthol.
Ewa Rozycka-Sokolowska1, Bernard Marciniak
1Institute of Chemistry and Environmental Protection, Jan Dlugosz University, al. Armii Krajowej 13/15, 42-200 Czestochowa, Poland.
Summary
This study reveals how molecules of C(10)H(7)ClO pack together using hydrogen bonds and pi-pi stacking. Similar packing arrangements were observed in related compounds, highlighting substituent effects on molecular overlap.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Organic Chemistry
Background:
- Understanding molecular packing is crucial for predicting material properties.
- Hydrogen bonding and pi-pi stacking are key non-covalent interactions influencing crystal structures.
- Previous studies have explored similar chlorinated organic compounds.
Purpose of the Study:
- To elucidate the crystal structure of C(10)H(7)ClO.
- To investigate the role of hydrogen bonding and pi-pi stacking in molecular assembly.
- To compare the packing of C(10)H(7)ClO with its analogues.
Main Methods:
- Single-crystal X-ray diffraction was used to determine the crystal structure.
- Analysis of intermolecular interactions, including hydrogen bonds and pi-pi stacking.
- Comparative structural analysis of the title compound and its analogues.
Main Results:
- Molecules of C(10)H(7)ClO form C(2) chains via O-H...O hydrogen bonds parallel to the c axis.
- Intermolecular pi-pi stacking interactions stabilize the crystal structure.
- A close similarity in molecular packing and pi-stacking was observed among analogues.
- The degree of spatial overlap in pi-stacks is influenced by substituents.
Conclusions:
- The crystal structure of C(10)H(7)ClO is characterized by hydrogen-bonded chains and pi-stacking.
- Structural similarities exist between C(10)H(7)ClO and its analogues.
- Substituent effects play a significant role in modulating pi-stacking interactions and molecular overlap.
