ISSN:
0947-3440
Keywords:
Pyridinethione
;
Thiohydroxyamic acid ester
;
Pyridone
;
Alkoxyl radical precursor
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Although Barton's radical precursors, the O-acyl derivatives of 1-hydroxypyridine-2(1H)-thione 2, have been studied in detail for more than a decade, to date nothing has been reported on the solid state or the solution geometries of these molecules or the analogous oxo derivatives, the pyridones 7, 8. In view of this, selected O-alkyl and O-acyl derivatives of pyridinethiones and of 2-(1H)pyridones have been prepared and investigated by X-ray diffraction and NMR (COSY, NOE) experiments. The X-ray data indicate alternating bond lengths in the carbon framework of the heterocycles 2d, 3b, 7b, and 8 and long N—O bonds [1.394(4)-1.398(2) Å]. In all the compounds studied, the O-alkyl and the O-acyl groups are twisted out of the plane of the heterocycles, which is in accord with the VSEPR concept. Further, the thermal stabilities of thiohydroxamic acid derivatives 2, 3 and of substituted pyridones 7, 8 were studied by differential scanning calorimetry (DSC).
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961222
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