Synthesis, conformational analysis, and molecular structure of 5-ethyl-5,6-dihydro-11H-dibenzo[b,e]azepine-6-thione

Abstract

5-Ethyl-5,6-dihydro-11H-dibenzo[b,e]azepine-6-thione has been synthesized and studied in the solid state and in solution by X-ray diffraction and 1H DNMR, respectively. The crystals are monoclinic, P21/n, a = 9.642(1), b = 13.757(2), c = 9.889((2) Å, β = 98.57(1)°, Z = 4. The structure has been solved by direct methods and refined to an R value of 0.040 for 1771 reflections with I > 2.5σ(I). The seven-membered ring has a slightly deformed boat conformation. The activation barrier associated with the inversion ring has been determined, being ΔG≠ = 21.6 kcal/mol.