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Nitrogen NMR study of some mesoionic oxadiazoles and thiadiazoles

✍ Scribed by Jarosław Jaźwiński; Olga Staszewska; Jerzy W Wiench; Lech Stefaniak; Shuki Araki; Graham A. Webb

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
120 KB
Volume
38
Category
Article
ISSN
0749-1581

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✦ Synopsis

N chemical shifts are reported for 10 mesoionic oxadiazoles and thiadiazoles. Some supporting 14 N and 13 C NMR data are also reported, together with some ab initio molecular orbital calculations and x-ray diffraction data. The relation between compound structure and 15 N chemical shifts is discussed. 14 N NMR measurements and ab initio molecular orbital calculations are employed to identify the charge distributions within the molecules studied. Some 1 J(C4,C5), 2 J( 15 N, 13 C) and 1 J( 15 N, 13 C) spin coupling data for mesoionic oxadiazoles, thiadiazoles and acetylosydnonimines are given. X-ray diffraction data for the picrate of acetylsydnonimine and a 3,1,2,-thiadiazole are reported. The bond lengths within the mesoionic backbone are intermediate between the values for single and double bonds, suggesting a conjugated bond system. The arrangement of the exocyclic group observed in the solid state for acetylosydnonimine corresponds to the arrangement predicted by solution NMR studies.

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