Diethyl 2,2'-(ethane-1,2-diyldi-oxy)di-benzo-ate

Area of Science:

• Organic Chemistry
• Crystallography
• Molecular Structure

Background:

• Ethyl 2-hydroxy-benzoate is a common organic compound.
• 1,2-dichloro-ethane is a widely used industrial solvent and intermediate.
• Understanding molecular structure and conformation is crucial in organic synthesis and materials science.

Purpose of the Study:

• To synthesize and characterize the molecular structure of a novel compound formed from ethyl 2-hydroxy-benzoate and 1,2-dichloro-ethane.
• To investigate the conformational properties and crystal packing of the synthesized molecule.
• To elucidate the spatial arrangement of functional groups and aryl rings.

Main Methods:

• Chemical synthesis involving the reaction of ethyl 2-hydroxy-benzoate with 1,2-dichloro-ethane.
• Single-crystal X-ray diffraction for detailed molecular structure determination.
• Analysis of bond angles, torsion angles, and dihedral angles to describe molecular conformation.
• Examination of crystal packing forces.

Main Results:

• The title compound, C20H22O6, was successfully synthesized.
• The molecule exhibits a twofold rotation axis passing through the central ethylene bridge.
• A gauche conformation was observed for the ethylene bridge (O-C-C-O torsion angle: 73.2°).
• Planarity was noted for carboxyl, aryl, and O-CH2 groups (r.m.s. deviation: 0.01 Å).
• The two aryl rings are arranged at a dihedral angle of 67.94°.
• The ester ethyl group shows positional disorder (occupancy ratio 0.59:0.41).
• Crystal packing is primarily governed by van der Waals forces.

Conclusions:

• The study successfully characterized a new organic compound with a defined molecular structure.
• The observed conformation and crystal packing provide insights into intermolecular interactions.
• This research contributes to the understanding of structure-property relationships in organic molecules.