Collect. Czech. Chem. Commun.
1986, 51, 249-263
https://doi.org/10.1135/cccc19860249
Structure and ring inversion of 2-pyrrolidone. Semiempirical quantum chemical study and analysis of X-ray data
Györgi Bánhegyia, János Ángyánb and Márton Kajtárc
a Research Institute for Plastics Industry, H-1950, Budapest, Hungary
b CHINOIN Research Center, H-1325, Budapest, Hungary
c Institute of Organic Chemistry, Eotvos University, H-1445, Budapest, Hungary
Abstract
The equilibrium structure and the ring inversion potential of the 2-pyrrolidone molecule has been studied by the semiempirical CNDO/2 and INDO methods. The calculated geometrical parameters are compared with experimental X-ray data with earlier Consistent Force Field (CFF) results. The ring inversion is analyzed in terms of two types of puckering coordinates. The CNDO/2 method was found to yield a strongly nonplanar 2-pyrrolidone ring due to the overestimation of the amide pyramidality while INDO calculations led to a slightly nonplanar ring with an extremely low barrier of inversion.
