14933-78-9Relevant articles and documents
1H and 17O NMR study of H-bond dynamics in picolinic acid N-oxide solutions in acetonitrile-h3 and acetonitrile?d3: Novel aspects of old casus
Mar?alka, Arūnas,Dagys, Laurynas,Jakubkien?, Virginija,Tumkevi?ius, Sigitas,Balevicius, Vytautas
, p. 17 - 22 (2018)
Despite apparent similarity, two isotopomers of acetonitrile (ACN-h3 and ACN-d3) show unexpected differences in their structural and dynamic properties. These differences cannot be fully understood within the usual isotope effect and therefore called as unresolved casus. Sensing the solvent properties, the H-bond dynamics of picolinic acid N-oxide (PANO) in ACN was studied using 1H and 17O NMR. Several overlapping factors, like the presence of micro-traces of water, liquid-liquid equilibrium, effect of ionic ingredient, etc., which may cause the observed anomalies in the dependences of PANO chemical shift and signal width on temperature, were analyzed. The deuterium isotope effect on the phase separation in organic solute/water mixtures was deduced to be the crucial factor inducing those surprising differences between ACN-h3 and ACN-d3. Thus the casus could be resolved within the second-order phase transition model, in which the vibrational contributions to the intermolecular interaction energies would be properly taken into account.
APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS. PART 7. SYNTHESIS AND METALLATION OF 4-METHOXYPICOLIN- AND 2-METHOXYISONICOTIN-ANILIDES. A USEFUL METHOD FOR PREPARATION OF 2,3,4-TRISUBSTITUTED PYRIDINES
Epsztajn, Jan,Bieniek, Adam,Plotka, Mieczyslaw W.,Suwald, Krzysztof
, p. 7469 - 7476 (2007/10/02)
The synthesis and metallation of 4-methoxypicolin- and 2-methoxyisonicotin-anilides as a way of regiospecific transformation of picolinic and isonicotinic acids into 2,3,4-trisubstituted pyridines, is described.The resulted C-alkylated derivatives underwent smooth acid - catalysed conversion into the corresponding pyridones.