Exoconformers ofN-(pyridin-2-yl)- andN-(pyridin-3-yl)norbornene-5,6-dicarboximide crystals

Abstract

Two isomeric pyridine-substituted norbornenedicarboximide derivatives, namely N-(pyridin-2-yl)-exo-norbornene-5,6-dicarboximide, (I), and N-(pyridin-3-yl)-exo-norbornene-5,6-dicarboximide, (II), both C(14)H(12)N(2)O(4), have been crystallized and their structures unequivocally determined by single-crystal X-ray diffraction. The molecules consist of norbornene moieties fused to a dicarboximide ring substituted at the N atom by either pyridin-2-yl or pyridin-3-yl in an anti configuration with respect to the double bond, thus affording exo isomers. In both compounds, the asymmetric unit consists of two independent molecules (Z' = 2). In compound (I), the pyridine rings of the two independent molecules adopt different conformations, i.e. syn and anti, with respect to the methylene bridge. The intermolecular contacts of (I) are dominated by C-H...O interactions. In contrast, in compound (II), the pyridine rings of both molecules have an anti conformation and the two independent molecules are linked by carbonyl-carbonyl interactions, as well as by C-H...O and C-H...N contacts.

Structural, Spectroscopic (FT-IR, Raman and NMR), Non-linear Optical (NLO), HOMO-LUMO and Theoretical (DFT/CAM-B3LYP) Analyses of N-Benzyloxycarbonyloxy-5-Norbornene-2,3-Dicarboximide Molecule

“…Therefore, norbornenes are very attractive momomers for macromolecular design of poymers with desired properties [7]. Besides, some norbornene-dicarboximides show binding affinity and selectivity towards serotonin receptors [8,9]. The synthesis and some chemical properties of Nb e n z y l o x y c a r b o n y l o x y -5 -n o r b o r n e n e -2,3dicarboximide can be found in literature [10].…”