FEATURES OF ATOMIC INTERACTION IN THE MOLECULES OF FURAN, PYRROLE, AND THEIR 2-CHLORINE-SUBSTITUTED DERIVATIVES ACCORDING TO RESULTS OF <i>ab initio</i> CALCULATIONS

Abstract

The results of ab initio studies by the RHF/6-31G(d) method on the molecules of furan, pyrrole, and their 2-chlorine-substituted derivatives with full optimization of the geometry show that unshared electron pairs of their heteroatoms are not delocalized solely in the π-system of the heterocycle. The participation of these electron pairs in formation of bonding and other MOs does not make it possible to speak of substantial role for p,π -conjugation in the distribution of electron density in the molecules and its effect on the characteristics of the compounds. The results of the ab initio calculations were used to determine the 35Cl NQR parameters of the 2-chlorine-substituted molecules.

Authors: V. P. Feshin and E. V. Feshina.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (5), pp 543-548

http://link.springer.com/article/10.1007/BF02324636