Thermal, spectroscopic and crystallographic analysis of mannose-derived linear polyols
Mattsson, I., Lahtinen, M., Peuronen, A., Sau, A., Gunell, A., Saloranta-Simell, T., & Leino, R. (2018). Thermal, spectroscopic and crystallographic analysis of mannose-derived linear polyols. Crystal Growth and Design, 18(5), 3151-3160. https://doi.org/10.1021/acs.cgd.8b00263
Published inCrystal Growth and Design
© 2018 American Chemical Society
The major diastereomer formed in the Barbier-type metal-mediated allylation of D-mannose has previously been shown to adopt a perfectly linear conformation, both in solid state and in solution, resulting in the formation of hydrogen-bonded networks and subsequent aggregation from aqueous solution upon stirring. Here, a comprehensive study of the solid state structure of both the allylated D-mannose and its racemic form has been conducted. The binary melting point diagram of the system was determined by differential scanning calorimetry analysis, and the obtained results, along with structure determination by single crystal X-ray diffraction, confirmed that allylated mannose forms a true racemate. Further examination by powder X-ray diffraction and CP MAS 13C NMR spectroscopy revealed polymorphism both in the pure enantiomer and in the racemate. In addition, the propargylated and hydrogenated analogues of allylated D-mannose were prepared and subjected to thermal and spectroscopic analyses. The crystal structure of the propargylated compound was successfully determined, showing a linear molecular conformation similar to that found for allylated D-mannose. Both new compounds likewise display aggregation behavior in water, further verifying that the low-energy linear conformation plays a significant role in this unusual behavior of these rodlike mannose derivatives. ...
PublisherAmerican Chemical Society
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Academy Project, AoF
Additional information about fundingAuthor IM received funding from the doctoral network Graduate School in Chemical Engineering and the Parliament Office Commission of the Åland Parliament. Authors ML and AP received funding from the Academy of Finland, project no 277250. Notes The authors declare no competing financial interest.
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