Chemical and Pharmaceutical Bulletin p. 768 - 773 (1994)
Update date:2022-08-11
Topics:
Kondo
Murase
Kuzuya
To provide the structural criteria for mechanically polymerizable vinyl monomers in metallic vessels, we carried out the MO calculations (AM1 method) of several acrylamide, acrylate and styrene derivatives as model compounds for such reactions. It was found that the nature of LUMO of vinyl monomers is closely related to the capability for initiation of mechanochemical polymerization. The following requisite concerning the nature of LUMO was shown to be a necessary condition for the activity of such reactions: Even if the LUMO energy is lower than 0.166 eV in the AM1 scheme, the LUMO coefficient must be highly localized in the vinyl group, when the monomer does not meet this criterion, the introduction of a saturated group such as an alkyl group to insulate electronically the π-electron system of vinyl group from the rest of the molecules will lead to the mechanically polymerizable monomers.
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