Thermal, Spectroscopic, and Crystallographic Analysis of Mannose-Derived Linear Polyols

Ida Mattsson, Manu Lahtinen, Anssi Peuronen, Abhijit Sau, Andreas Gunell, Tiina Saloranta-Simell, Reko Leino*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3151-3160
Number of pages10
JournalCrystal Growth and Design
Volume18
Issue number5
DOIs
Publication statusPublished - 2 May 2018

Fingerprint Dive into the research topics of 'Thermal, Spectroscopic, and Crystallographic Analysis of Mannose-Derived Linear Polyols'. Together they form a unique fingerprint.

Cite this