Electron and Proton Donating Ability of the Pyrrolyl and Diazolyl Derivatives of Cycloalkanones

To assess the donor-acceptor properties of the basic and acidic sites in pyrrolyl and diazolyl derivatives of cycloalkanones, the energies and the shapes of the frontier molecular orbitals of their tautomers and conformers were calculated and the maps of the charge density distribution were constructed. The competition of these sites in the formation of hydrogen and coordination bonds and the possibility of participation of the studied products as ligands in metal complexes were shown. Complexes of diazolyl derivatives with CuCl2 were obtained. The synthesis of 7-amino-2-(pyrrolidin-2-ylmethylene)indan-1-one was performed and its structure and propensity to UV-initiated E→Z isomerization were studied by NMR and IR spectroscopy.