New hydrogen-bond-aided supramolecular synthon: a case study of 2,4,6-trinitroaniline

摘要: We have demonstrated that 2-nitroanilines and similar nitro compounds having a six-membered ring closed by an intramolecular H-bond tend to form centrosymmetric dimers in the crystalline phase. The probability of dimer formation is estimated be 15% according database search Cambridge Structural Database. Bonding interactions are found two ON⋯H–N hydrogen bonds O⋯O interaction, with total energy adding up ca. 6 kcal mol−1. bonding nature was proven means topological analysis experimental charge density obtained from high-resolution single crystal X-ray diffraction experiment as well theoretical results DFT MP2 calculations.