X-ray, conformation and electronic structures of 1-nitropyrrolidine

The chemistry of pyrrolidine compounds has drawn much attention because of their biological activities. The crystal and molecular structure of 1-nitropyrrolidine (C4H8NNO2) at 150K, along with calculated structures (DFT and MP2), are reported herein. In the solid-state, the asymmetric part of the unit cell is composed of one quartermolecule at the position of two perpendicular mirror planes and the five membered ring is disordered over a mirror plane, revealing the twisted conformation. Both geometries suggest slight sp(3) hybridization of the amine nitrogen atom. The non-planar geometry suggests the lack of conjugation of the amine nitrogen lone pair with the nitro group, however the N-N bond distance indicates oppositely. (C) 2015 Elsevier B.V. All rights reserved.