Add time:07/31/2019         Source:sciencedirect.com

The hydroxamic acids R·CO·(NH·OH) have been investigated, in which R is H; CH3; CH2C1; CH3(CH2)10; CH3(CH2)14 and C6H5, respectively. Included in this work are some O- and N-derivatives of hydroxamic acids, and of methyl benzimidate. The spectra of the hydroxamic compounds are interpreted by analogy with the amide spectra, but with deuterated acids an important difference with respect to the amide spectra has been noted: a band in the region 1360–1430 cm−1 analogous to the amide III band, believed to be due mainly to the C-N stretching, does not move after deuteration. The hydrogen bonding of hydroxamic acids has been studied in the solid state and in solution, particularly with laurinohydroxamic acid. Monomeric molecules are intramolecularly bridged to 5-membered rings, which seem to be replaced by intermolecular bonds under conditions more favourable for association. The structure of hydroxamic acids and those derivatives which are capable of tautomeric changes is discussed.

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