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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
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Radicals: Electronic Structure and Geometry01:07

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Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
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Crystal structure of 4-bromo-cinnamic anhydride.

Yuliana Ramos Cotrina1, Jhesua Valencia1, Ronan Le Lagadec2

  • 1Laboratorio de Química Inorgánica y Catálisis Programa de Química Universidad del Quindío, Carrera 15 Calle 12 Norte Armenia 630004 Colombia.

Acta Crystallographica. Section E, Crystallographic Communications
|October 8, 2025
PubMed
Summary

This study characterizes the crystal structure of a novel p-halogenated cinnamic anhydride, revealing insights into molecular interactions and potential applications in crystal design.

Keywords:
O⋯π contactscinnamic anhydridecrystal structuresupra­molecular inter­actions

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Area of Science:

  • Crystallography
  • Materials Science
  • Organic Chemistry

Background:

  • Cinnamic acid derivatives are versatile organic compounds with diverse applications.
  • Understanding the solid-state structure of halogenated cinnamic anhydrides is crucial for predicting their properties and designing new materials.
  • Previous structural characterization of p-halogenated cinnamic anhydrides was limited.

Purpose of the Study:

  • To determine the crystal structure of (E)-3-(4-bromo-phenyl)prop-2-enoyl (E)-3-(4-bromo-phenyl)prop-2-enoate.
  • To analyze the intermolecular interactions governing the crystal packing.
  • To investigate the potential of these compounds in crystal engineering.

Main Methods:

  • Single-crystal X-ray diffraction was employed to elucidate the molecular and crystal structure.
  • Hirshfeld surface analysis and fingerprint plots were used to quantify intermolecular interactions.
  • Computational methods were utilized to calculate interaction energies.

Main Results:

  • The crystal structure reveals molecules adopting an E configuration and a gauche conformation across the anhydride bridge.
  • Intermolecular interactions include C-H⋯O hydrogen bonds and slipped π-π stacking interactions.
  • Hirshfeld analysis highlights significant contributions from Br⋯H/H⋯Br and O⋯H/H⋯O contacts.
  • Stacking interactions provide the dominant stabilization (up to -48.9 kJ/mol), followed by hydrogen bonding (-37.9 kJ/mol).

Conclusions:

  • This work presents the first structural characterization of a p-halogenated cinnamic anhydride.
  • The findings provide a fundamental understanding of the crystal packing and intermolecular forces in this class of compounds.
  • The study suggests potential applications in crystal design using cinnamic derivatives.