Reactions of thioamides with metal carboxylates in organic media

Synthesis and crystal structures of bis(N-phenyl-3,5-dinitrothiobenzamidato)mercury(II) and bis(N-phenyl-4-nitrothiobenzamidato)mercury(II)

“…Hence, the two benzene rings are not exactly parallel and have slightly different distances to Hg (closest Hg Á Á Á C ¼ 2.979-3.319 Å and 3.008-3.279 Å ), and the S-Hg-S linkage is not strictly linear (174.37 ). By contrast, [Hg(thioacetanilide) 2 ] in the solid state is quite unsymmetrical, having a coordination interaction (also 3 ) for only one of the two ligands (shortest Hg Á Á Á C ¼ 2.963-3.275 Å ), while the other is oriented well away from mercury [15], and [HgL 2 ] in which L is a ligand with methoxy attached to the [13] finds about 20 examples of structures in which a mercury lies in an approximately perpendicular line above a benzene ring with at least one Hg Á Á Á C distance 5 3.1 Å (about 60 if the search is extended to 3.2 Å ), in many of which this arrangement is not imposed by intramolecular bonding constraints. In crystallographic studies, secondary interactions of mercury with aromatic rings have been investigated by NMR spectroscopy, magnetic measurements, and luminescence properties [17][18][19][20][21][22], and they appear to be weak but significant.…”

Catalytic Dehydrosulfurization of Thioamides to Nitriles by Gold Nanoparticles Supported on Carbon Nanotubes

“…Other routes leading to nitriles include the conversion of carboxylic acid, dehydration of amides or aldoximes, and oxidative coupling of alcohols to ammonia . Organic nitriles have also been prepared through dehydrosulfurization of thioamides but the latter transformation usually requires harsh conditions, strong oxidizing agents, toxic reagents or the use of stoichiometric noble metals …”

“…[7] Organic nitriles have also been prepared through dehydrosulfurization of thioamides but the latter transformation usually requires harsh conditions, [8] strong oxidizing agents, [9] toxic reagents [10] or the use of stoichiometric noble metals. [11] With these features in mind, we sought to develop a catalytic system based on the use of gold nanoparticles (AuNP) supported on carbon nanotubes (CNT). The emergence of nanostructured heterogeneous catalysts over the last two decades had profound impact on both practical and sustainable aspects of chemical processes.…”

Synthesis and Applications of Chalcogenoamide: Thio-, Seleno- and Telluroamides

“…Treatment of primary amides and thioamides with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) afforded nitriles in 65-87% yields [67]. Reactions of thioamides with metal carboxylates in organic solvents enable the selective preparation of nitriles, imides or amides depending on the substitution pattern of the starting materials [68]. Glycoamidines 49 are prepared by a mercury-promoted reaction of the corresponding thioamides with amines in 33-87% yields [69].…”