Optical rotation (OR) is the angle by which plane polarized light is rotated as it passes through an optically active medium. Two enantiomers will generate OR of same magnitude but opposite sign, so this property can be used to assign the absolute configuration of chiral molecules in a sample. Although the OR value can be determined experimentally, calculations are needed to match the OR sign to a specific enantiomer. Efforts have also been made to provide a more chemically intuitive picture of this structure-property relationship. Therefore, it is desirable to continue to pursue more accurate and efficient methods for performing OR simulations, and to better understand the limitations of practical approximate methods.