Atomic contributions to the optical rotation angle as a quantitative probe of molecular chirality

Science. 1998 Dec 18;282(5397):2247-50. doi: 10.1126/science.282.5397.2247.

Abstract

Chiral molecules are characterized by a specific rotation angle, the angle through which plane-polarized light is rotated on passing through an enantiomerically enriched solution. Recent developments in methodology allow computation of both the sign and the magnitude of these rotation angles. However, a general strategy for assigning the individual contributions that atoms and functional groups make to the optical rotation angle and, more generally, to the molecular chirality has remained elusive. Here, a method to determine the atomic contributions to the optical rotation angle is reported. This approach links chemical structure with optical rotation angle and provides a quantitative measure of molecular asymmetry propagation from a center, axis, or plane of chirality.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Ethylene Oxide / analogs & derivatives
  • Ethylene Oxide / chemistry*
  • Hexanes / chemistry*
  • Mathematics
  • Models, Chemical
  • Molecular Conformation
  • Molecular Structure
  • Optical Rotation*
  • Quantum Theory
  • Stereoisomerism*

Substances

  • 2-fluorohexane
  • Bridged Bicyclo Compounds, Heterocyclic
  • Hexanes
  • Ethylene Oxide