Structure ofN S-butyl-N O-phenyl(thiooxamide)

Positional Isomerism and Steric Effects in the Self-Assemblies of Phenylene Bis-Monothiooxalamides

“…Regarding the supramolecular structure of the compounds herein reported, it is worth noting that compounds of the otriad form discrete dimers through motif VI; among them, The supramolecular structure of N-butyl-N′-phenyl-(thiooxalamide) (PhNHCOCSNHBu) has been reported. 9 This molecule is almost planar and self-assembles as dimers through N CS H•••O hydrogen bonding, motif II. Comparing with this molecule highlights that the second thiooxalyl arm in compounds 1−9 favors self-assembling by the increased number of hydrogen bonding donors and acceptors.…”

“…The supramolecular structure of N -butyl- N ′-phenyl­(thiooxalamide) (PhNHCO­CSNHBu) has been reported . This molecule is almost planar and self-assembles as dimers through N CS H···O hydrogen bonding, motif II .…”

“…Thiooxalamides, such as oxalamides, adopt the trans disposition between the amide proton and thiocarbonyl moieties which is stabilized by the formation of intramolecular NH•••SC hydrogen bonding interactions. 9 Differences between amides and thioamides have been attributed to the change from the electronegative oxygen atom to the larger, less electronegative sulfur atom. Thus, in the context of hydrogen bonding, the thiocarbonyl group is less polarized than the carbonyl since the electronegativities of C (2.55) and S (2.58) are almost equal.…”

“…Oxalamide derivatives are flat due to the formation of intramolecular hydrogen bonds between the acidic protons of amides and the carbonyl oxygen atoms of these fragments. − Thiooxalamides and oxalamides are isostructural analogues; they differ in size and polarity due to the exchange of oxygen by sulfur in one or both carbonyls. Thiooxalamides, such as oxalamides, adopt the trans disposition between the amide proton and thiocarbonyl moieties which is stabilized by the formation of intramolecular NH···SC hydrogen bonding interactions . Differences between amides and thioamides have been attributed to the change from the electronegative oxygen atom to the larger, less electronegative sulfur atom.…”