T. Yamane, Yoshiaki Ito, T. Ashida
Mar 1, 1992
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Journal
Bulletin of the Chemical Society of Japan
Abstract
The crystal structures of N-benzoyl-8-oxa-6-azabicyclo[3.2.1]octan-7-one (Bz-BOL), N-benzoyl-e-caprolactam (Bz-CLA), and N-benzoyl-2-pyrrolidone (Bz-PYR) have been determined in order to clarify the relation between their structures and reactivities by N-benzoyl substitution. Bz-BOL belongs to monoclinic, P21/n, a = 10.372(1), b = 23.155(5), c = 9.737(4) A, β = 100.92(2)°, Z = 8. Bz-CLA is monoclinic, P21/c, a = 9.234(2), b = 8.532(3), c = 15.097(3) A, β = 92.42(2)°, Z = 4. Bz-PYR is monoclinic, P21/n, a = 10.801(3), b = 6.020(1), c = 15.082(3) A, β = 97.95(2)°, Z = 4. The final R-values are 0.049 for 2867 reflections of Bz-BOL, 0.069 for 1634 reflections of Bz-CLA, and 0.053 for 1175 reflections of Bz-PYR. In these compounds the orientaion of the benzoyl moiety against the lactam moiety is essentially the same, and the phenyl group is nearly perpendicular to the lactam-amide plane. The C–N bond distance of the lactam moieties in benzoyl derivatives is significantly prolonged, as compared with that in the...