XLIV.—The relationship between the optical rotatory powers and the relative configurations of optically active compounds. The influence of certain inorganic haloids on the optical rotatory powers of α-hydroxy-acids, α-amino-acids, and their derivatives

George William Clough
1918 Journal of the Chemical Society Transactions  
THE discovery of the1 phenomenon known as the Walden inversion was made in connexion with transformations of certain derivatives of succinic acid, and it, therefore seemed possible that the change of configuration was due either t.o the presence of an atom of hydrogen attached t o the asymmetric carbon atom or to the fact that the optically active compounds in questior, were carboxylic acids. Although the configurative change may be due to one or both of these causes in certain cases, it has
more » ... n shown t h a t a Walden inversion can be effected in a compound containing a tertiary asymmetric carbon atom (McKenzie and Ctlough, T., 1910, 97, 1016), and also in compounds which do notl cont'ain a carboxyl * This specimen contained 5 per cent. of methyl d-lactate. Notwithstanding the fact that the influence of water on the rotatory power of methyl Z-lactate is opposite in sense t o t h a t of this solvent on the esters of d-malic acid or &tartaric acid, it is obvious that the changes of rotation caused by the inorganic haloids are the same in character for Z-lactic acid and methyl Z-lactate as
doi:10.1039/ct9181300526 fatcat:s4gigt2iyfc2dnkkrfvdr3zga4