Tautomerism of substituted salicylaldehyde and 2-diphenylphosphinebenzaldehyde 1′-phthalazinylhydrazones: X-ray crystallography and quantum chemical modeling
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- Levchenkov, S.I., Popov, L.D., Shcherbakov, I.N. et al. J Struct Chem (2013) 54: 952. doi:10.1134/S0022476613050168
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1′-Phthalazinylhydrazones of salicylaldehyde, its substituted derivatives, and 2-diphenylphosphine-benzaldehyde are synthesized and studied. A description is given of the structures salicylaldehyde 1′-phthalazinylhydrazone (1a) and 2-diphenylphosphinebenzaldehyde 1′-phthalazinylhydrazone (2), which exist in the crystal in the hydrazonophthalazone tautomeric form. Molecules of hydrazone 1a form in the crystal infinite stacks of hydrogen bonded dimers with intermolecular π-stacking interactions. A quantum chemical calculation is made of the geometry and total energy of the possible tautomers in vacuum and in aqueous and chloroform solutions. The hydrazonophthalazone tautomers are shown to be the most stable in all cases. The X-ray crystallography results are compared with the calculated data.