Strong overcrowding in dimethyl 2-(dimethylamino)terephthalate

Area of Science:

• Organic Chemistry
• Crystallography
• Computational Chemistry

Background:

• Steric hindrance significantly influences molecular geometry and reactivity.
• Ortho-substitution patterns in aromatic compounds can lead to unique structural deviations.

Purpose of the Study:

• To elucidate the molecular structure of C(12)H(15)NO(4).
• To investigate the effects of steric hindrance from adjacent ester and dimethylamine groups.

Main Methods:

• X-ray crystallography was employed to determine the solid-state molecular structure.
• Ab initio quantum mechanical calculations were used to confirm observed structural deformations.

Main Results:

• The ester carbonyl group is non-coplanar with the aromatic ring.
• The amine nitrogen atom exhibits a pyramidal arrangement.
• An adjacent ester group's carbon atom deviates from the aromatic ring's plane.

Conclusions:

• Steric interactions between ortho ester and dimethylamine groups cause significant molecular distortions.
• Computational methods validate the experimentally observed structural anomalies.