120-79-6Relevant academic research and scientific papers
Theoretical, structural, vibrational, NMR, and thermal evidence of the inter- versus intramolecular hydrogen bonding in oxamides and thiooxamides
Desseyn,Perlepes,Clou,Blaton,Van Der Veken,Dommisse,Hansen
, p. 5175 - 5182 (2004)
This contribution describes the study of hydrogen bonding in secondary oxamides, monothiooxamides, and dithiooxamides by ab initio calculations, X-ray diffractions, NMR spectra, thermal analysis, and variable-temperature infrared and Raman spectroscopy. The results can all be interpreted as a function of the change in the strength and the nature of the hydrogen bonding by substituting oxygen for sulfur in the series CH3-HNCOCONHCH3, CH 3HNCSCONHCH3, CH3HNCSCSNHCH3 and by changing the steric influence of the alkyl group in a series of oxamides (RHNCOCNHR; R = CH3, C2H5, iC3H 7, tC49).
BIS(METHYLELEMENT)DITHIOOXAMID-DERIVATE VON Al, Ga, In, Si, Ge UND Sn; PLANARE METALLABICYCLEN UND VERDRILLTE STRUKTUREN
Halder, T.,Schwarz, W.,Weidlein, J.,Fischer, P.
, p. 29 - 48 (1983)
When trimethyl derivatives of aluminium, gallium and indium are reacted with dithiooxamides, (HNR-CS-)2 (R=H, Me, SiMe3), in a 1/2 molar ratio, 2 moles of methane are set free, and monomeric bis(dimethylmetal)dithiooxamides are formed.By 1H NMR, IR and Raman spectroscopy, two structural isomers have been established for these metalla complexes, both with a planar molecular back-bone of two fused five-membered rings, but different coordination of the two metal atoms (E- and Z-form); the centrosymmetric E-form has been characterized also by X-ray crystallography.Equivalent bis(trimethylelement)dithiooxamides of Si, Ge and Sn are obtained from the reaction of trimethylelement chlorides and N,N'-dimethyldithiooxamide.The stannyl derivative once again displays the planar bicyclic structural principle; for the silicium and germanium complexes, on the other hand, a non-chelate structure is established crystallographically where the two thiocarboxamide moieties are rotated by about 80o.In solution, the crystal modification isomerizes into an equilibrium mixture of three rotamers; their configuration is discussed in terms of 1H NMR spectral evidence (e.g. stepwise signal coalescence).
COMPLEXES OF GROUP IIb METALS WITH DITHIOOXAMIDES V - VIBRATIONAL SPECTRA AND THERMAL ANALYSIS OF THE CdLX2 COMPLEXES
Geboes, Peter,Plakatouras, John,Desseyn, Herman O.
, p. 821 - 832 (2007/10/02)
In acid media, CdX2 forms non-electrolyte CdLX2 (L=DTO, NN'DMDTO, TMDTO; X=Cl, Br, I) complexes with dithiooxamides.The ligands act as bidentates with S,S coordination.A thorough vibrational analysis (i.r. and Raman) has been performed for the Cd(H2NCSCSNH2)X2 (X=Cl, Br, I), the Cd(CH3NHCSCSNHCH3)X2 (X=Br, I) and the CdX2 (X=Cl, Br, I) complexes, by NH/ND and CH3/CD3 isotopic substitution.Stereochemistries varying from tetrahedral to octahedral structures are proposed based on spectroscopic evidence and the positions of the metal-ligand vibrations can be explained in terms of the HSAB principle.The thermal behaviour of the complexes has been studied, using isothermal as well as non-isothermal techniques.
STUDIES OF DIOXAMIDE AND DITHIO-OXAMIDE METAL COMPLEXES. PART 2. SYNTHESIS AND SPECTRAL CHARACTERISATION OF RNHC(S)C(S)NHR (R = ALKYL OR ARYL) COMPLEXES WITH SbX3 (X = Cl OR Br), BiCl3, SnX4 (X = Cl OR Br), AND TiCl4. CRYSTAL AND MOLECULAR STRUCTURES OF NN'-DI-ISOPROPYLDITHIO-OXAMIDE ...
Drew, Michael G. B.,Kisenyi, Jonathan M.,Willey, Gerald R.,Wandiga, Shem O.
, p. 1717 - 1722 (2007/10/02)
The synthesis and characterisation of a variety of SbX3L1.5 (X = Cl or Br), BiCl3L2, SnX4L (X = Cl or Br), and TiCl4L complexes i, Bun, cyclo-C6H11, or CH2Ph> is described.In all cases metal-sulphur bonds are formed following SS'-bidentate ligand attachment.The potential N-donor sites are not involved in co-ordination.The structural characterisation of the uncomplexed ligand PriNHC(S)C(S)NHPri (L3) and the antimony(III) complex SbCl3(L3)1.5 (1) are reported.Crystals of (1) are rhombohedral, space group with a = 11.80(1) Angstroem, α = 60.1(1) deg, and Z = 2. 1089 Unique data above background were collected and the structure refinded to R 0.068.Crystals of L3 are monoclinic, space group P21/c with a = 6.226(7), b = 8.067(11), c = 11.187(12) Angstroem, β = 91.0(1) deg, and Z = 2. 635 Data above background were measured and the structure refinded to R 0.077.The structure of (1) is a three-dimensional polymer.The octahedrally co-ordinated Sb atom lies on a three-fold axis and is strongly bound to three chlorine atoms and also weakly bound to three sulphur atoms from different ligands, which approach their positions trans to chlorine thus giving rise to an octahedral environment.There is no evidence for a stereochemically active lone pair associated with SbIII.In the structure of L3 the sulphur atoms are mutually trans and this orientation is retained on complexation.
Reactions of Cyanodithioformates with Primary Amines
Kibbel, H. U.,Kuecken, M.,Peters, E.,Weber, H.
, p. 41 - 48 (2007/10/02)
N-alkyldithiooxamides 3 and N,N-dialkyldithiooxamides 4 were synthesized in good yields by reaction of cyanodithioformates 1 with primary aliphatic amines.N-alkylcyanodithioformamides 2, intermediates in these reactions were obtained in very low yields only.The reaction of 1 and diaminoethane or 1,3-diaminopropane afforded imidazolidine-2-thione 5a respectively perhydropyrimidine-2-thione 5b.The reaction of 1 with 1-chloro-2-aminoethane did gave 2-thiocarbamoylthiazoline 7.
