Theoretical investigation of an energetic fullerene derivative

A self‐consistent estimation method for the thermochemical properties of N ‐methyl‐3‐(2′,4′,6′‐trinitrobenzene)‐fulleropyrrolidine (MTNBFP) is presented. This method is based on enthalpy of formation (Δ f H   m ⊖ ) and enthalpy of combustion obtained from BLYP/DNP calculations of the total energies and frequencies for MTNBFP. The enthalpy of formation was calculated by an optimized set of isodesmic reactions given the available experimental Δ f H   m ⊖of relative compounds. MTNBFP has a high enthalpy of formation, 2782.2 kJ/mol. Detonation velocity and detonation pressure were also presented in terms of Kamlet and Jacobs equations. Drop hammer impact sensitivity tests and blasting point per 5 s tests indicate MTNBFP may be a potential candidate primary explosive. To understand the test results well, we proposed a series of chemical reaction mechanisms and interpreted the relationship between impact sensitivity and electronic structures from the viewpoint of nitro group charge, electrostatic potential, and vibrational modes. © 2010 Wiley Periodicals, Inc. J Comput Chem, 2010