Structure of "Super Glue"

The piece of "super glue". The cyano and ester groups make this a highly polar polymer. Note that the polymerization creates a chiral center in each monomer unit. The anionic polymerization allows for the formation of either configuration and both are created in a random fashion. The model does reflect this. Now, the model of the piece of super glue shown is perhaps not all that realistic in some other aspects. Observe that the carboxyl groups in the model shown all are rather aligned. This can best be seen if you look at a "sticks" model. In reality, such an alignment does not occur because the rotations about the C-COOMe bonds are facile and the alignment shown is in fact electrostatically not good. Another aspect of this structure that is not realistic at all has to do with conformational properties about the alkane backbone. You can figure that out yourself. [Hint: There are many ways for the C-backbone to be all staggered!!] -- Finally, now take a look at the picture of "super glue" in the introduction to Chapter 26 for a realistic picture of "super glue".


Figure. A molecular model of the polymer of "super glue". Oligomerization started with hydroxide and ended with protonation.