Conclusions
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1.
In molecules of amides of trimethylsilylpropiolic acid the relative basicity of the O atom is significantly increased in comparison with trimethylsilylethynylcarbonyl compounds due to π-conjugation of the carbonyl group with the nitrogen lone electron pair. The Me3SiCsC group donates electrons to the amide fragment.
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2.
For amides of trimethylsilylpropiolic acid and trimethylsilylethynylcarbonyl compounds a correlation exists between the C=O group vibrational frequencies and the relative alkalinity of the carbonyl O atom (ΔvOH).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1101–1104, May, 1986.
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Chipanina, N.N., Shergina, N.I., Khlopenko, N.A. et al. Spectroscopic investigation of trimethylsilylpropiolic acid amides. Russ Chem Bull 35, 998–1000 (1986). https://doi.org/10.1007/BF00955366
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DOI: https://doi.org/10.1007/BF00955366