Abstract
The structures of 1,2,3-indantrionemonooxime have been investigated in gas, solution and solid states using a combination of quantum-chemical calculations, NMR spectroscopy and X-ray crystallography and has been shown to exist exclusively as the oxime tautomer. Two basic rotameric forms are proposed, the ‘closed’ form which shows intramolecular hydrogen bonding between the oxime group and one of the carbonyl oxygens and the ‘open’ form which shows no intramolecular interaction. Quantum-chemical calculations indicate that the ‘closed’ form is favoured in the gas phase and in non-polar solvents, while in polar solvents the ‘open’ form is stabilised through intermolecular interactions. These results are confirmed by 13C solution state NMR spectroscopy. In the solid state only the ‘open’ rotamer is observed with the crystal structure stabilised by intermolecular hydrogen bonding. Two crystallographically non-equivalent forms of this rotamer are observed in the crystal structure and also confirmed in the 13C solid state NMR spectrum.
Published Version
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