15309-72-5

Upstream product

• 15309-69-0 N-(4-pyridyl)-p-toluenesulfonamide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 127-65-1 chloroamine-T 
• 98-59-9 p-toluenesulfonyl chloride 
• 126957-71-9 S-(1-Methyl-4-pyridinio)-N,N'-bis(p-tolylsulfonyl)sulfodiimidat 

Relevant academic research and scientific papers

Pyridoneimines and pyridonemethides: Substituent- and solvent-tunable intramolecular charge transfer and geometric isomerism

We have prepared and fully characterized by means of multinuclear NMR and UV-vis spectroscopy a series of pyridoneimines and pyridonemethides in order to show how it is possible to finely tune φ-electron structure properties by properly exploiting substituent and solvent effects. Substituents with different electron-withdrawing capacities were introduced in pyridoneimines 2-4, pyridonemethides 5 and 6, and pyridine sulfonamido derivatives 7-9. The anisochrony of the carbon position of the azinium ring (geometric isomerism) and the exploitation of previously reported 13C and 15N shift/φ-electron density relationships allowed the investigation of the extent of intramolecular charge transfer from the donor group to the acceptor pyridinium moiety. By combining different substitutions with the polarity of the surrounding media, we were able to access a whole range of push-pull electron structures in solution, from fully aromatic-zwitterionic to quinoidneutral, through many possible intermediate situations along the path. Due to the strict correlation between the φ-electron structure of push-pull derivatives and many photonic properties such as nonlinear optical activity, we believe that the achieved results should be valuable for the development of new efficient, tailor-made, heteroaromatic systems with optimized features as advanced organic materials.

REAKTIONEN VON THIOXOHETEROCYCLEN MIT N-CHLORAMIDEN II. N-SUBSTITUIERTE 2- ODER 4-THIOPYRIDONE UND NATRIUM-N-CHLORBENZOLSULFONAMIDE

N-Substituted 2- and 4-pyridinethiones A react with sodium-N-chlorobenzenesulfonamides 1 to N-phenylsulfonyl-S-pyridylidenesulfimides B, N,N'-bis(phenylsulfonyl)-S-pyridiniosulfodiimidates C and N-pyridylidenebenzenesulfonamides D.The constitution of the new pyridiniosulfodiimidates C is proved by X-ray crystal structure of one compound C and by 1H-NMR spectra of all 1-methylpyridinio-compounds C, which have a downfield shift for the N-methyl-δ-values.Formation, stabilities, IR-, 1H-NMR-spectra and bond systems of A-D are discussed.Key words: Pyridinethiones; sodium N-chlorobenzenesulfonamides; N-phenylsulfonyl-S-pyridylidenesulfimides; N,N'-bis(phenylsulfonyl)-S-pyridiniosulfodiimidates; N-pyridylidenebenzenesulfonamides; polarity of sulfur bonds.