4-Meth-oxy-2-{(E)-[(thio-phen-2-yl)methyl-imino]-meth-yl}phenol

Area of Science:

• Organic Chemistry
• Crystallography
• Supramolecular Chemistry

Background:

• Schiff bases are versatile organic compounds with diverse applications.
• Understanding the tautomeric forms and hydrogen bonding is crucial for predicting molecular behavior.
• Intra-molecular interactions significantly influence molecular conformation and properties.

Purpose of the Study:

• To elucidate the tautomeric form and intra-molecular hydrogen bonding of a specific Schiff base.
• To analyze the molecular conformation, including dihedral angles between aromatic rings.
• To investigate the crystal packing forces, such as C-H···O and C-H···π interactions.

Main Methods:

• Single-crystal X-ray diffraction analysis to determine the three-dimensional molecular structure.
• Analysis of hydrogen bonding networks and ring formation (e.g., S(6) ring).
• Calculation and interpretation of dihedral angles to quantify molecular twisting.

Main Results:

• The Schiff base exists in the phenol-imine tautomeric form.
• An intra-molecular O-H⋯N hydrogen bond forms a stable S(6) ring.
• A significant dihedral angle of 67.83° between the thienyl and phenol rings indicates a highly twisted molecular structure.
• Crystal packing is stabilized by weak C-H⋯O and C-H⋯π interactions.

Conclusions:

• The studied Schiff base exhibits specific tautomerism and intra-molecular hydrogen bonding, dictating its conformation.
• The observed molecular twist is a key structural feature influencing its properties.
• Weak intermolecular forces play a role in the overall crystal lattice.