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( E )-4-{[(4-Methoxynaphthalen-1-yl)methylidene]amino}phenol

In plain language

A specific Schiff base compound, with the chemical formula C18H15NO2, was synthesised through the condensation reaction of 4-hydroxy aniline and 4-methoxy-1-naphthaldehyde dissolved in ethanol. Examination of the molecular geometry shows that the dihedral angle between the phenol ring and the mean plane of the naphthalene ring system is 75.81 (6) degrees. In the solid crystal form, the individual molecules are connected via O—H...N and C—H...O hydrogen bonds. These bonds enclose distinct R 3 3 (18) ring motifs, producing continuous zigzag chains extending along the c-axis. Additionally, the resulting chains are linked to one another by C—H...pi interactions, which assemble into extended molecular slabs running parallel to the ac crystallographic plane.

Key takeaways

  • The Schiff base compound C18H15NO2 was synthesised via condensation of 4-hydroxy aniline and 4-methoxy-1-naphthaldehyde in ethanol.
  • The dihedral angle between the phenol ring and the naphthalene ring system mean plane is 75.81 (6) degrees.
  • Molecules in the crystal form zigzag chains along the c-axis connected by O—H...N and C—H...O hydrogen bonds enclosing R 3 3 (18) ring motifs.
  • C—H...pi interactions link the zigzag chains into slabs lying parallel to the ac plane.

Why it matters

Determining the precise three-dimensional structure and packing behaviour of newly synthesised chemical compounds is fundamental to basic chemistry. Documenting the specific hydrogen-bonding networks, dihedral angles, and intermolecular interactions provides foundational knowledge regarding how organic molecules assemble in the solid state, contributing to the broader reference library of molecular crystallography.

Commercialisation angle

The abstract does not indicate an application pathway.

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Abstract

The title Schiff base compound, C 18 H 15 NO 2 , was synthesized via the condensation reaction of 4-hydroxy aniline and 4-methoxy-1-naphthaldehyde in ethanol. The dihedral angle between the phenol ring and the mean plane of the naphthalene ring system is 75.81 (6)°. In the crystal, the molecules are linked by O—H...N and C—H...O hydrogen bonds, enclosing R 3 3 (18) ring motifs and forming zigzag chains propagating along the c -axis direction. The chains are linked via C—H...π interactions forming slabs lying parallel to the ac plane.

Research topics

  • Crystal structures of chemical compounds
  • Synthesis of Organic Compounds
  • Axial and Atropisomeric Chirality Synthesis

Read the original research

This page summarises published work. The authoritative version sits with the publisher.

DOI: 10.1107/s2414314626008552

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