Synthesis and Molecular Structures of 1-Carboxyl-4-Amino-2-Aza-3-Oxo-[2.2.2] Bicyclooctane

Abstract

The novel bicycloamino acid, 1−carboxyl−4−amino−2−aza−3−oxo−[2.2.2] bicyclooctane was synthesized and its physical characteristics have been compared to those predicted using quantum chemical calculations. The crystal structure of novel compound was determined by X-ray diffraction measurements at room temperature. Unit cell is monoclinic, with space group P 21/n (14) and a = 5.8587(6) Ǻ, b = 11.2454(16) Ǻ, c = 13.9723(16) Ǻ, β=97.840(6)°, Z = 2. Refinement was performed using all 1598 reflections with R = 0.4085 and wR = 0.6024. Theoretical calculation of full optimization and atomic net charge, and frontier orbital energies of the title compound was carried out at the B3LYP/6−31G(d,p) level. The NMR chemical shielding tensors and vibrational frequencies were calculated with B3LYP/6-311+G(2d, p)− level in which were close values and similar spectrum structures with experimental results and used to interpret the experimental measurements.