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Topochemically controlled solid-state methyl rearrangement in thiocyanurates.

M Greenberg1, V Shteiman, M Kaftory

  • 1Department of Chemistry, Technion-Israel Institute of Technology, Haifa 32000, Israel.

Acta Crystallographica. Section B, Structural Science
|May 25, 2001
PubMed
Summary
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Polymorphic triazine thiones undergo solid-state methyl transfer reactions upon heating. These topochemically controlled rearrangements yield new triazine derivatives with significant enthalpy changes, driven by molecular energy differences.

Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Organic chemistry

Background:

  • 4,6-Dimethoxy-3-methyl-1,3,5-triazine-2(3H)-thione exhibits polymorphism, existing as needle and plate crystals.
  • Polymorph (9b) transforms into polymorph (9a) upon heating.
  • Triazine derivatives are known for diverse chemical reactivity.

Purpose of the Study:

  • To investigate the solid-state behavior of two triazine thione polymorphs.
  • To characterize the phase transitions and topochemical rearrangements.
  • To determine the driving forces behind the observed reactions.

Main Methods:

  • Single-crystal X-ray diffraction to determine crystal structures.
  • Differential scanning calorimetry (DSC) to study thermal transitions.

Related Experiment Videos

  • Ab initio energy calculations to assess reaction thermodynamics.

    • Main Results:

    • Needle crystals (9a) undergo O --> S methyl transfer at 378 K, yielding 1-methyl-4-methoxy-6-methylthio-1,3,5-triazine-2(1H)-one (75% yield).
    • Plate crystals (9b) undergo O --> S methyl transfer at 373 K, yielding 1-methyl-2,4-bismethylthio-1,3,5-triazine-6(1H)-one (quantitative yield).
    • Enthalpies of rearrangement were measured as -39.1 kJ/mol and -58.8 kJ/mol, respectively.

    Conclusions:

    • Solid-state methyl transfer reactions in triazine thiones are topochemically controlled.
    • Phase transitions and rearrangements are driven by differences in molecular energies.
    • Polymorphism significantly influences the solid-state reactivity of these compounds.