Polymer Bulletin, Vol.34, No.5-6, 685-690, 1995
A Comparison of the Pvcilo Calculated Stabilization Energies of the da Complexes of N-Phenylmaleimide and 4-Phenyl-L,2,4-Triazoline-3,5-Dione with Methyl Vinyl Ether
A PVCILO method has been used to compare the stabilization energies of the electron donor electron acceptor complexes between methyl vinyl ether as donor and the enophiles, 4-phenyl 1-1,2,4-triazoline-3,5-dione (1) and N-phenylmaleimide (2), respectively, as acceptor. A stabilization energry difference in favor of the more reactive 1 was obtained, which is being interpreted as an explanation for the enhanced rate of reaction of 1 vs 2, often by factors >10(4).
Keywords:ELECTROPHILIC AROMATIC-SUBSTITUTION;DONOR-ACCEPTOR COMPLEX;ENE REACTION;STEREOCHEMICAL EVIDENCE;DIELS-ALDER;4-SUBSTITUTED 1;2;4-TRIAZOLINE-3;5-DIONES;ALTERNATING COPOLYMERIZATION;BIS-TRIAZOLINEDIONES;PARTICIPATION;POLYMERS