Summary
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1.
The13C NMR spectra of a series of p-substituted aryl ethynyl ethers have been studied.
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2.
In the compounds studied, the degree of p− π conjugation of the triple bond with the ethereal oxygen is weakened because of competitive interaction of theπ-system of the benzene ring with the latter. The efficiency of the transfer of theπ-charge from oxygen to a triple bond is considerably higher than to a double bond.
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3.
An oxygen atom present between a benzene ring and a triple bond considerably weakens the influence of p-substituents on the triple bond, in contrast to the analogous influence on the double bond.
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4.
The introduction of one ortho substituent into the benzene ring has practically no effect on the intensity of p− π conjugation of the oxygen with the unsubstituted fragments.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, pp. 1301–1305, June, 1980.
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Proidakov, A.G., Kalabin, G.A., Lyashenko, G.S. et al. Study of conjugation effects by NMR spectroscopy. Russ Chem Bull 29, 921–924 (1980). https://doi.org/10.1007/BF00958808
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DOI: https://doi.org/10.1007/BF00958808