Synthesis, Crystal Structure and Biological Activity of 1-Cyano-N-phenylcyclopropanecarboxamide

Abstract

A cyclopropane derivative, 1-cyano-N-phenylcyclopropanecarboxamide (C₁₁H₁₀N₂O) was synthesized and its structure was studied by X-ray diffraction, FTIR, ¹H NMR spectrum and MS. The crystals are monoclinic, space group Pbca with a = 10.0466(19), b = 9.6067(17), c = 20.790(3) Å, a = 90.00, b = 90.00, g = 90.00º, V = 2006.5(6)ų, Z = 8, F(000) = 784.00, D_c = 1.233 g/cm³, μ = 0.815 cm^-1, the final R = 0.0567 and wR = 0.1456. A total of 8716 reflections were collected, of which 1967 were independent (R_int = 0.045). Theoretical calculation of the title compound was carried out with B3LYP/6-31G (d.p.). The full geometry optimization was carried out using 6-31G(d.p.) basis set and the frontier orbital energy. The structure-activity relationship was also studied. The preliminary biological test showed that the synthesized compound is bioactive against the ketol-acid reductoisomerase of Escherichia coli.