H-1, C-13 AND O-17 NMR-STUDY OF SUBSTITUTED NITROPYRIDINES

被引:25
作者
KOLEHMAINEN, E [1 ]
LAIHIA, K [1 ]
RASALA, D [1 ]
GAWINECKI, R [1 ]
机构
[1] PEDAGOG UNIV,INST CHEM,PL-25020 KIELCE,POLAND
关键词
H-1 NMR CHEMICAL SHIFTS AND COUPLING CONSTANTS; C-13; NMR; CHEMICAL SHIFTS AND COUPLING CONSTANTS; O-17 NMR CHEMICAL SHIFTS AND LINE WIDTHS; SUBSTITUTED 2-NITROPYRIDINES AND 3-NITROPYRIDINES; MOLECULAR MECHANICS;
D O I
10.1002/mrc.1260290904
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
H-1, C-13 and O-17 NMR spectra for 22 substituted nitropyridines were measured and their H-1 NMR spectra were analysed. The most significant variations in the NMR parameters are found for isomeric hydroxy derivatives, owing to the possibility of keto-enol tautomerism. The prevalence of the keto form is observed in 2- and 4-hydroxy derivatives, while the 3-hydroxy derivative exists in its enol form. Among the three nuclei studied, O-17 seems to be the best nucleus for probing the keto-enol tautomerism. No correlation is observed between the torsion angle of the nitro group and its O-17 NMR chemical shift. Molecular mechanics calculations were performed to clarify the torsional energetics of the nitro group and the preferences for keto-enol tautomerism.
引用
收藏
页码:878 / 884
页数:7
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