A DFT study on the mono lithium and sodium salts of N-(2-hydroxyphenyl)salicylaldimine

This computational organic chemistry study presents results based on density functional theory at the B3LYP/6-31G(d) and B3LYP/cc-PVTZ//B3LYP/6-31G(d) levels of theory. Other computational procedures (HF and MP2) are presented for model structures. Three main points were investigated: some of the electronic structure aspects, the relative stability of isomers, and aromaticity. The results suggest that the title salts are the first Schiff base systems in the literature to exist only in the N-H form, which is characterized as the zwitterion form. Also, the estimated delocalization of the π-electron density in the middle ring indicates that these compounds are the first examples of metalla-hetero[10]annulenes. Analysis of the electron density delocalization indicates that the title compounds are better conductors at the molecular level than the parent Schiff base, and therefore, can be considered as new building blocks for organic materials.