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Updated: Jun 1, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
(+)-(S,S)-1,3-Bis[(tetra-hydro-furan-2-yl)-meth-yl]thio-urea
Abstract:
The title compound, C(11)H(20)N(2)O(2)S, is an enanti-omerically pure heterocycle-substituted thio-urea synthesized under solvent-free conditions. The thio-urea unit adopts a ZZ conformation, with the HN-(C=S)-NH core almost planar and the tetra-hydro-furfuryl groups placed below and above this plane. The whole mol-ecule thus approximates to noncrystallographic C(2) symmetry. Unexpectedly, the C=S group is not involved in inter-molecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, mol-ecules form a one-dimensional network based on weak N-H⋯O(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 2(1) screw axis along [100].
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