Synthesis, characterization, and Hirshfeld surface analysis of two Schiff bases: (E)-3-(((4-iodophenyl)imino)methyl)benzene-1,2-diol and (E)-3-(((3-bromo-4-methylphenyl)imino)methyl)-benzene-1,2-diol

ЖСХ, т.67, №4, 2026, 164073

Received: September, 7, 2025
Revised: January, 3, 2026
Accepted for publication: January, 5, 2026
DOI 10.26902/JSC_id164073
EDN: MXEDVD
Views: 116

¹ Department of Physics, Faculty of Sciences, Ondokuz Mayıs University, Atakum, Samsun, Turkey

² Department of Chemistry, Faculty of Sciences, Ondokuz Mayıs University, Atakum, Samsun, Turkey

³ Department of Fundamental Sciences, Faculty of Engineering and Natural Sciences, Samsun University, Samsun, Turkey

The title compounds, (E)-3-(((4-iodophenyl)imino)methyl)benzene-1,2-diol compound (1) and (E)-3-(((3-bromo-4-methylphenyl)imino)methyl)benzene-1,2-diol (2) are synthesized and comprehensively characterized through spectroscopic and crystallographic techniques, including single crystal X-ray diffraction, IR, UV-Vis, ¹H NMR, and ¹³C NMR analyses. Both compounds adopt an E configuration with respect to the C=N double bond and crystallize in the triclinic crystal system, space group P–1. Their crystal packings are primarily stabilized by O—H⋯O hydrogen bonds, complemented by C—H⋯π interactions, which extend the packing into a three-dimensional supramolecular framework. Hirshfeld surface analysis is employed to identify regions of potential hydrogen-bond formation and to quantify the relative contribution of different intermolecular contacts. The results reveal that C⋯H interactions dominate the surface contributions, underscoring their importance in the overall packing stability and molecular arrangement.

This is an excerpt of the article

SYNTHESIS, CHARACTERIZATION, AND HIRSHFELD SURFACE ANALYSIS OF TWO SCHIFF BASES: (E)-3-(((4-IODOPHENYL)IMINO)METHYL)BENZENE-1,2-DIOL AND (E)-3-(((3-BROMO-4-METHYLPHENYL)IMINO)METHYL)-BENZENE-1,2-DIOL.

Full text of the paper is published in Journal of Structural Chemistry.
DOI: 10.1134/S0022476626040116

Keywords: Schiff base, benzaldehyde, iodophenyl, bromine, crystal structure, Hirshfeld surface

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