Sulfur hydrogen bonding and internal dynamics in the monohydrates of thenyl mercaptan and thenyl alcohol

Abstract

Water forms weak H-bonds with thenyl compounds, simultaneously retaining internal mobility in the dimer.

C–H⋯S hydrogen bonding interactions

“…Studies of S-based HB acceptors generally focus on N-H, O-H, and other more traditional HB donors, with little investigation of C-HÁ Á ÁS HBs. [26][27][28][29] We find this omission surprising, as both work from our labs and others has shown that C-H HB donors exhibit a specific preference for sulfur-based HB acceptors. [30][31][32][33] For example, in our work in supramolecular anion recognition, we were inspired to investigate C-H HB donors for binding hydrosulfide (HS À ) after successful use of these receptors for Cl À binding.…”

Setting up the HyDRA blind challenge for the microhydration of organic molecules

“…In contrast to the THF situation, the monohydrate of THT has been structurally characterised in much detail 70 , also with respect to the water orientation relative to the ring. We are not aware of a complementary vibrational gas phase study and thus consider this to be a valuable diversification of the test set, also in preparation for more challenging thio compounds 83 . In TFE, as in many fluorinated alcohols 72 , the first solvating water acts primarily as a hydrogen bond acceptor, but the symmetric stretching mode is only subtly shifted from the water monomer value by this interaction and by an additional donor contact to the CF 3 group.…”

t BuOLi-promoted terminal alkyne functionalizations by aliphatic thiols and alcohols

“…9 Especially, non-covalent interactions like S–H⋯S, S–H⋯O, O–H⋯S, N–H⋯S etc . relating to the sulfur centers are still under consideration from both experimental 10 and theoretical 11 viewpoints because carbon–sulfur (C–S) bonds are universally found in non-natural and natural products. 12 Interestingly, controlling the stability of radicals is one of the important tasks to afford any selectivity in a chemical reaction.…”