rac‐3‐Benzoyl‐2‐methylpropionic acid and its organic salts: possibilities of Yang photocyclization in crystals |
| |
Authors: | Julia Bą kowicz,Ilona Turowska‐Tyrk |
| |
Abstract: | The analysis of the crystal structures of rac‐3‐benzoyl‐2‐methylpropionic acid, C11H12O3, (I), morpholinium rac‐3‐benzoyl‐2‐methylpropionate monohydrate, C4H10NO+·C11H11O3−·H2O, (II), pyridinium [hydrogen bis(rac‐3‐benzoyl‐2‐methylpropionate)], C5H6N+·(H+·2C11H11O3−), (III), and pyrrolidinium rac‐3‐benzoyl‐2‐methylpropionate rac‐3‐benzoyl‐2‐methylpropionic acid, C4H10N+·C11H11O3−·C11H12O3, (IV), has enabled us to predict and understand the behaviour of these compounds in Yang photocyclization. Molecules containing the Ar—CO—C—C—CH fragment can undergo Yang photocyclization in solvents but they can be photoinert in the crystalline state. In the case of the compounds studied here, the long distances between the O atom of the carbonyl group and the γ‐H atom, and between the C atom of the carbonyl group and the γ‐C atom preclude Yang photocyclization in the crystals. Molecules of (I) are deprotonated in a different manner depending on the kind of organic base used. In the crystal structure of (III), strong centrosymmetric O...H...O hydrogen bonds are observed. |
| |
Keywords: | |
|
|