Tautomerism is an important concept in organic chemistry and a key element in many applications. This motivated us in this study to investigate the electronic structure of the conjugated NCCCN skeleton by studying the properties of malonaldimine as the simplest form. The analysis confirms that the it-system allows efficient electron density flow (delocalization). On the other hand, this skeleton features a valuable energy barrier for the hydrogen-bridge form. These two characteristics are corner stones for designing unsymmetrically functionalized skeletons for molecular switching and signaling.