Thermal, Spectroscopic, and Crystallographic Analysis
of Mannose-Derived Linear Polyols
Version 2 2018-08-15, 21:13
Version 1 2018-04-16, 11:22
Posted on 2018-08-15 - 21:13
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.
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Mattsson, Ida; Lahtinen, Manu; Peuronen, Anssi; Sau, Abhijit; Gunell, Andreas; Saloranta-Simell, Tiina; et al. (2018). Thermal, Spectroscopic, and Crystallographic Analysis
of Mannose-Derived Linear Polyols. ACS Publications. Collection. https://doi.org/10.1021/acs.cgd.8b00263
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AUTHORS (7)
IM
Ida Mattsson
ML
Manu Lahtinen
AP
Anssi Peuronen
AS
Abhijit Sau
AG
Andreas Gunell
TS
Tiina Saloranta-Simell
RL
Reko Leino
KEYWORDS
Mannose-Derived Linear Polyolscompoundallylated d-mannosepowder X-ray diffractioncrystal X-ray diffractionBarbier-type metal-mediated allylationdisplay aggregation behaviorCP MAS 13 C NMR spectroscopyconformationpropargylatedsolutionracematerodlike mannose derivativesscanning calorimetry analysisallylated mannose forms