A H-1 AND C-13 NUCLEAR-MAGNETIC-RESONANCE AND X-RAY-DIFFRACTION STUDY OF THE TAUTOMERISM OF 2-HYDROXY AND 2,3-DIHYDROXY-PYRIDINE N-OXIDES - X-RAY MOLECULAR-STRUCTURE OF 2-HYDROXYPYRIDINE N-OXIDE

被引：18

作者：

BALLESTEROS, P

CLARAMUNT, RM

CANADA, T

FOCESFOCES, C

CANO, FH

ELGUERO, J

FRUCHIER, A

机构：

[1] CSIC, INST QUIM MED, E-28006 MADRID, SPAIN

[2] CSIC, INST QUIM FIS ROCASOLANO, UEI CRISTAL, E-28006 MADRID, SPAIN

[3] ECOLE NATL SUPER CHIM, CHIM ORGAN LAB, F-34075 MONTPELLIER, FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1990年 / 07期

关键词：

D O I：

10.1039/p29900001215

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

From a 1H and 13C NMR study, in dimethyl sulphoxide, of twelve 2-hydroxy-, 2,3-dihydroxy-pyridines, 2,3-dihydroxypyridine N-oxides, and their methoxy derivatives it is possible to conclude that both pyridin-2-ones and 1-hydroxypyridine-2-ones exist in solution as 2-oxo tautomers. The molecular structure of 2-hydroxypyridine N-oxide has been determined by X-ray diffraction methods; as in solution, this compound exists in the crystal state as the 1-hydroxypyridin-2-one tautomer.

引用

页码：1215 / 1219

页数：5

共 21 条

[1] SYSTEMATIC ANALYSIS OF STRUCTURAL DATA AS A RESEARCH TECHNIQUE IN ORGANIC-CHEMISTRY [J].

ALLEN, FH ;

KENNARD, O ;

TAYLOR, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (05) :146-153

[2] HYDROGEN BOND STUDIES .47. CRYSTAL STRUCTURE OF INTERMOLECULAR COMPLEX 2-PYRIDONE-6-CHLORO-2-HYDROXYPYRIDINE [J].

ALMLOF, J ;

KVICK, A ;

OLOVSSON, I .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1971, B 27 (JUN15) :1201-&

[3] STUDY OF THE CATALYTIC PROPERTIES OF TRIS (3,6-DIOXAHEPTYL) AMINE (TDA-1) IN HETEROAROMATIC NUCLEOPHILIC-SUBSTITUTION OF CHLOROPYRIDINES AND THEIR N-OXIDES [J].

BALLESTEROS, P ;

CLARAMUNT, RM ;

ELGUERO, J .

TETRAHEDRON, 1987, 43 (11) :2557-2564

[4]

CIGNITTI M, 1982, GAZZ CHIM ITAL, V112, P397

[5]

Elguero J, 1976, TAUTOMERISM HETEROCY

[6]

GARDNER JN, 1957, J CHEM SOC, P43075

[7]

JAFFE J, 1955, J AM CHEM SOC, V77, P4448

[8]

KATRITZKY AR, 1963, ADVANCES HETEROCYCLI, V1, P341

[9] HYDROGEN-BOND STUDIES .65. CRYSTAL-STRUCTURE OF 5-CHLORO-2-PYRIDONE, C5H4NOCL [J].

KVICK, A ;

BOOLES, SS .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1972, B 28 (NOV15) :3405-3409

[10]

LEZINA VP, 1974, B ACAD SCI USSR CH+, P99

← 1 2 3 →