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Updated: Jun 1, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-(m-Tolyl-imino-meth-yl)phenol
Alice Brink1, Andreas Roodt, Hendrik G Visser
1Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa.
Summary
This study reveals the non-planar structure of a C(14)H(13)NO compound, featuring a significant dihedral angle between its aromatic rings. Intramolecular hydrogen bonding leads to a stable phenol-imine tautomeric form.
Area of Science:
- Organic Chemistry
- Crystallography
Background:
- Understanding molecular geometry and bonding is crucial in organic chemistry.
- Tautomerism influences chemical properties and reactivity.
Purpose of the Study:
- To elucidate the three-dimensional structure of the title compound C(14)H(13)NO.
- To investigate the presence and implications of intramolecular hydrogen bonding.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of bond lengths, angles, and dihedral angles provided structural insights.
Main Results:
- The compound C(14)H(13)NO exhibits a non-planar conformation.
- A dihedral angle of 47.00(6)° was measured between the two aromatic ring planes.
- Intramolecular hydrogen bonding between the O-H group and the N atom was confirmed.
Conclusions:
- The observed hydrogen bonding stabilizes a phenol-imine tautomeric form.
- The non-planar structure and tautomerism are key features of this organic compound.
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