6,6′-Dimethyl-1,1′,5,5′-tetraaza-6,6′-bi(bicyclo[3.1.0]hexane): synthesis and investigation of molecular structure by quantum-chemical calculations, NMR spectroscopy and X-ray diffraction analysis

A new diaziridine derivative with two bicyclic diaziridine-containing moieties in one molecule, 6,6′-dimethyl-1,1′,5,5′-tetraaza-6,6′-bi(bicyclo[3.1.0]hexane) (BiDiMDAH), has been synthesized for the first time. Its molecular structure investigated gas phase by means of quantum-chemical (QC) calculations, CDCl3 solution 1D and 2D NMR spectroscopy solid state X-ray diffraction (XRD) technique. It was found QC calculations that BiDiMDAH molecule a free presents single conformer C2 symmetry trans orientation methyl groups about carbons connecting cycles. The 5-memebered rings to be essentially planar. In order explain conformational preferences BiDiMDAH, natural bond orbitals (NBO) atoms molecules (AIM) analyses have performed. According XRD data, crystallizes space group P21/c resembling obtained lowest energy form. However, relative arrangement is similar transition states. data revealed only present agreement studies. gaseous standard enthalpy formation estimated 106.1±1.2 kcal/mol G4 theory.