What is it about?

Chiral model compounds were created from reacting potential protein-docking capable chiral 2-butanol with poisonous isothiocyanates to form thiocarbamates combining the properties of both and forcing the new compound to inherit the chirality of the alcohol. Specifically, left-handed (S)-butan-2-yl-N-(4-x-phenyl)thiocarbamates were synthesized, where x = NO2, OCH3, F, and Cl. The different substitutions on the 4-x location cause a variety of supramolecular differences which affect crystal packing, crystallographic axes lengths and crystal morphology, however in all studied cases the space group is P2(1), and two molecules combine to form hydrogen bonded dimers in form of S-C-N-H..S-C-N-H.. closed ring synthons.

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Why is it important?

Similar thiocarbamates have been investigated previously for their biological activities as potential drugs.


This research was part of an undergraduate study over several years, where the students were asked to explore ways to find new synthesis methods to create over two dozen new compounds of which a few are presented in this study. The co-author here was the final participant and helped to compile all necessary data by revisiting the synthesis steps and providing analytic characterizations.

Werner Kaminsky
University of Washington

Read the Original

This page is a summary of: Enantiopure (S)-butan-2-yl N-(4-x-phenyl)thiocarbamates, x = NO2, OCH3, F, and Cl, Acta Crystallographica Section E Crystallographic Communications, March 2023, International Union of Crystallography, DOI: 10.1107/s2056989023002591.
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