Crystalline forms of selected agrochemical actives : design and synthesis of cocrystals
The research described in this disseration covers the crystal form screening of
two analogous agrochemical actives, thiophanate-methyl and thiophanate-ethyl,
as well as the discovery of seven 4-hydroxybenzoic acid cocrystals of selected
agrochemical actives. Polymorphs are crystal forms of a compound that have
the same composition, but a different arrangement of molecules. Cocrystals are
molecular crystals composed of two or more compounds, and refer mainly to
crystals which contain compounds that are solids at standard conditions.
Solvates are forms that have molecules of solvent in the crystal lattice and these
include hydrates, in which the solvent is water. The crystal forms of organic
compounds are investigated especially in the pharmaceutical and other
specialty chemical industries for better processing and activity of the
compounds as well as for intellectual property reasons.
Thiophanate-methyl was found to crystallize as two polymorphs and
fourteen solvates, while thiophanate-ethyl was found to crystallize as four
polymorphs and seven solvates. Identification of the forms was achieved
mostly with powder X-ray diffraction, but methods such as IR spectroscopy,
solid state NMR spectroscopy and thermogravimetric analysis were also used.
The crystal structures of most of the crystal forms were determined by single
crystal X-ray diffraction, allowing the inspection of intermolecular interactions
such as hydrogen bonding. Reliable hydrogen bonding motifs were identified
and used as supramolecular synthons in the design of new cocrystal forms.
Three cocrystals of thiophanate-methyl and eight cocrystals of thiophanateethyl
were found. The seven cocrystal forms of agrochemical actives with 4-
hydroxybenzoic acid show better properties in comparison to the pure forms,
and highlight the importance of cocrystallization in industrial applications.
The design and synthesis of cocrystals as well as the analysis of packing
and hydrogen bonding in crystal structures is reviewed in the literature part of
this thesis.
...
Publisher
University of JyväskyläISBN
978-951-39-4493-3ISSN Search the Publication Forum
0357-346XKeywords
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- Väitöskirjat [3586]
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