On the isomerism/tautomerism of hydrazones. Crystal structures, study in solution and theoretical calculations of new series of alpha-N-heterocyclic hydrazones
G. Giorgi et al., On the isomerism/tautomerism of hydrazones. Crystal structures, study in solution and theoretical calculations of new series of alpha-N-heterocyclic hydrazones, J CHEM S P2, (11), 2000, pp. 2259-2264
Citations number
28
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
The isomerism/tautomerism of new series of alpha -N-heterocyclic hydrazones
with chelating properties towards metal ions and potential biological acti
vity have been studied in the solid state by X-ray crystallography and in s
olution by nuclear magnetic resonance. Among possible syn-Z/anti-E isomers
and different tautomeric structures, the molecular structures of dimethylqu
inolylhydrazone 5 and its phthalazinyl analogue 6 have shown that both are
anti-E isomers. In 5 the mobile proton resides on the hydrazone nitrogen, b
ut in the phthalazine derivative 6 it is located on one endocyclic nitrogen
. The same isomeric structures are also confirmed in the solution by NMR ex
periments. While for 6 no other isomer is detected, the quinoline derivativ
es 1-5 show chemical equilibrium between the imino and amino tautomers in t
he solution, the latter being present in a very high amount (> 90%). The st
udy has also been extended to potential energy calculations of isolated mol
ecules and of molecules in the crystal lattice.