In this work, we study the difference in specific rotation of the stable conformers of two test chiral molecules: (S)-(+)-2-carene and (R)-3-methylcyclopentanone. We perform the analysis of the specific rotation in terms of rotational strength in configuration space, (S) over tildek, which provides information about the contribution of occupied-virtual molecular orbital pairs to this property. We show that, although a considerable number of excited configurations contribute to the total value of the specific rotation, only a limited number of configurations are necessary to explain the different sign and magnitude of the rotation between different conformers. The results in this work thus offer a promising picture for our ability to better understand and possibly predict the value of specific rotation of chiral molecules.