Applequist, Jon; Rivers, Prince; Applequist, Douglas E. published the article 《Theoretical and experimental studies of optically active bridgehead-substituted adamantanes and related compounds》. Keywords: bromopropionitriles optical activity; adamantanes optical activity; optical activity adamantanes.They researched the compound: 2-Bromopropanenitrile( cas:19481-82-4 ).Reference of 2-Bromopropanenitrile. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:19481-82-4) here.
An exptl. and theoretical study of the optical activity of α-bromopropionitrile (I) and an analogous bridgehead-substituted adamantane derivative, 3-methyl-5-bromo-1-cyanoadamantane (II), was carried out. The synthesis and resolution of II via the corresponding carboxylic acid and amide are described. Specific rotations of <1° are found for each, confirming expectations of a large reduction in rotation when mol. asymmetry is due to substituents at the adamantane bridgeheads. A theoretical interest in I and II exists because the symmetry of the substituents is such that first-order (pairwise) contributions to the rotation are expected to vanish. An atom polarizability model, treated earlier by Boys, is considered as a basis for calculating higher order contributions in these mols. The basic assumption is that the atoms are isotropically polarizable point particles located at their nuclei. A simple generalization of polarizability theory is presented, in which perturbation contributions of any order may be easily calculated The calculations are carried out for the third-and fourth-order contributions to rotation in I and II for the atom polarizability model, noting that the first and second orders vanish. The main conclusions are: (i) the calculated and observed rotatory dispersion constants are roughly comparable in magnitude, suggesting that the assumed mechanism of optical activity is significant; (ii) the fourth-order contributions are larger than those of third order, implying that a number of still higher terms are also important, and raising serious doubts about the usefulness of the perturbation expansion; (iii) it is not possible to correlate sign of rotation with absolute configuration on the basis of the third-and fourth-order calculations There are many compounds similar to this compound(19481-82-4)Reference of 2-Bromopropanenitrile. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.
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