Two‐dimensional vibrational potential energy surface for the ring bending and twisting of 1,3‐oxathiolane. Evidence for the anomeric effect resulting from –O–CH 2 –S– linkages Academic Article uri icon

abstract

  • The far-infrared spectra of 1,3-oxathiolane and its 2,2-d2isotopomer have been analyzed in terms of a two-dimensional vibrational potential energy surface expressed as a function of ring-bending and ring-twisting coordinates. The barrier to planarity was determined to be 2289 ±200 cm-1while the barrier to pseudorotation, representing the energy difference between the lowest energy twisted form and the highest energy bent form, was found to be 570±20 cm-l. The barrier to planarity is about 500 cm-1 higher than that of cyclopentane, and this is attributed to the anomeric effect resulting from the -O-CH2-S- linkage which tends to twist the molecule out of the planar configuration. © 1994 American Institute of Physics.

author list (cited authors)

  • Leibowitz, S., & Laane, J.

citation count

  • 8

publication date

  • August 1994