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Structure of silylated benzohydroxamic acids

✍ Scribed by Jan Schraml; Magdalena Kvíčalová; Ludmila Soukupová; Vratislav Blechta

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
48 KB
Volume
37
Category
Article
ISSN
0749-1581

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✦ Synopsis

NMR spectra ( 13 C, 15 N and 29 Si) of the products of trimethylsilylation and tert-butyldimethylsilylation of benzohydroxamic acid and model derivatives of benzohydroximic acid were studied in solutions. The products are shown to have the structure of (Z)(syn)-O,O 0 -bis(trimethylsilyl) and -O,O 0 -di(tert-butyldimethylsilyl) derivatives of benzohydroximic acid [i.e. (Z)-trimethylsilyl ester of N-(trimethylsiloxy)benzoimidic acid and (Z)-tertbutyldimethylsilyl ester of N-(tert-butyldimethylsilyl)benzoimidic acid, respectively]. Whereas 15 N NMR chemical shifts are the most useful NMR parameter for differentiation between derivatives of hydroxamic and hydroximic tautomers, differentiation between Z and E stereoisomers of hydroximic acid derivatives is more reliable on the basis of 1 J 13 C, 13 C coupling within the C-C N moiety.

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