Conclusions
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1.
Nuclear magnetic resonance and infrared spectroscopies have been used to characterize the donor-acceptor complexes formed between vinyl aryl ethers and maleic anhydride; the values obtained for the equilibrium constant and the enthalpies and entropies of complexing suggest that there is a slight increase in the donor activity of the vinyl ether of phenol when a methyl group is introduced into its benzene ring.
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2.
Donor-acceptor interaction of the maleic anhydride with the vinyl aryl ethers leads to the formation ofπ complexes through weak charge transfer from the highest occupied orbital of the ether to the lowest vacant orbital of the anhydride. Quantum-chemical calculations and measurements of the chemical shifts on the13C and1H nuclei of the vinyl ethers under action from the MA indicate that the donor HOMO embraces the unshared electron pair of the oxygen and the π electrons of the double bond and the benzene ring.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 74–79, January, 1977.
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Smirnov, A.I., Deryabina, G.I., Ratovskii, G.V. et al. Donor-acceptor complexes of vinyl aryl ethers with maleic anhydride. Russ Chem Bull 26, 62–66 (1977). https://doi.org/10.1007/BF00921493
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DOI: https://doi.org/10.1007/BF00921493