24197-72-6Relevant academic research and scientific papers
Conformational preferences in 2-nitrophenylthiolates: Interplay between intra-and intermolecular forces; structures of (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, s-(2-nitrophenyl)-benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione
Low, John N.,Storey, Emily J.,McCarron, Mary,Wardell, James L.,Ferguson, George,Glidewell, Christopher
, p. 58 - 67 (2000)
In (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, C15H13NO2S (1) (orthorhombic Pbca), the nitro group is almost coplanar with the adjacent aryl ring, but the dihedral angles between the nitro-aryl and styryl fragments is ～121°. The molecules are linked by paired C-H...O hydrogen bonds in a chain of rings. In S-(2-nitrophenyl)benzenecarbothiolate, C13H9NO3S (2) (monoclinic P21/a), the nitro group is rotated by 33.0 (2)° out of the plane of the adjacent aryl ring and the thiobenzoate group is strongly twisted away from the plane of the disubstituted aryl ring. The molecules of (2) are linked into chains by C-H...O hydrogen bonds, and each chain is linked to two neighbouring chains by means of aromatic π...π stacking interactions. In 1-(2-nitrophenylthio)-2,5-pyrrolidinedione, C10H8N2O4S (3) (monoclinic P21/a), the nitro group is again almost coplanar with the adjacent aryl ring, but the pyrrolidinedione unit is almost orthogonal to the O2NC6H4SN plane. There are three types of C-H...O hydrogen bond in the structure, and these link the molecules into a two-dimensional net. The conformations of these molecules have been investigated by SCF calculations and two energy minima have been identified for each: the molecules of (1) and (3) adopt conformations in their crystals which are close to those at the overall energy minima calculated for isolated molecules, while molecules of (2) adopt a conformation in the crystal close to that calculated for the local energy minimum. Comparisons are made with the structures of some related compounds and it is concluded that, while the nature of the two conformational minima is determined by intramolecular forces, the choice between them is determined primarily by intermolecular forces.
An improved, general procedure to S-aryl thiol esters: A new synthetic application of dry arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Degani, Iacopo,Dughera, Stefano,Fochi, Rita
, p. 1225 - 1230 (2007/10/03)
The reaction between dry arenediazonium o-benzenedisulfonimides (1) and sodium thioacetate or thiobenzoate in anhydrous acetonitrile at room temperature is an efficient and safe procedure, of general validity, for the preparation of S-aryl thiol esters. The products can be easily purified and the yields are always very high. Of the 28 considered examples, the average yield of the S-aryl thioacetates (7) was 86% and that of the S-aryl thiobenzoates (8) 88%. It was possible to recover, in good amount and from all the reactions, o-benzenedisulfonimide (9), reusable for the preparation of salts 1.
Spectroelectrochemical study of the nucleophilic substitution of diacyl disulfides by 2-nitrophenyl thiolate ions in N,N-dimethylacetamide
Ahrika,Anouti,Robert,Paris
, p. 1867 - 1874 (2007/10/03)
S-Aryl thiol esters RC(O)SAr and ArS2- ions are the end products resulting from the reactions between bis(2-nitrophenyl) disulfide Ar2S2 and thiocarboxylate ions RC(O)S- (R = Me, Ph) at 20°C. The apparent SNAr process in fact occurs in two steps as shown by UV-vis absorption spectrophotometry coupled with voltammetry: (i) formation of diacyl disulfides [RC(O)]2S2 and ArS- ions by redox exchange; (ii) subsequent nucleophilic substitution of 2-nitrophenyl thiolate ions at the carbonyl carbon of diacyl disulfides.
