Quantum chemical study in exploring the role of donor→acceptor interactions in 1,3-bis carbene-stabilized guanidinium cations

Guanidinium species are highly basic and hence mostly exist in cationic state. Because these cations carry electron-deficient centers, they can be stabilized with the help of electron-donating ligands like N -heterocyclic carbenes. A few novel guanidinium cationic species stabilized by electron-donating ligands were designed and quantum chemically evaluated. It was shown that strong hydrogen bonds and tautomerism are the important characteristics of these species. Further, the possibility of donor→acceptor coordination interactions in these species have been explored between the electron-donating carbenes and the central guanidinium unit. The results suggest that the title compounds can be considered as ligand-stabilized guanidinium cations similar to the ligand-stabilized N + and N 3 + centers. Graphical abstract