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Phenolic derivatives of aminopentadiynes

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  1. 1.

    Conditions were found for the synthesis of phenolic derivatives ofω-aminopentadiynes by the condensation of bromoaminopropynes with ethynylphenols.

  2. 2.

    An analysis of the IR spectra of the synthesizedω-aminopentadiynes disclosed that the butadiynyl group exhibits strong electron-acceptor properties, which causes a substantial strengthening of the intermolecular hydrogen bond of\(OH \ldots N\begin{array}{*{20}c} / \\ - \\ \backslash \\ \end{array} \) when compared with phenol and ethynylphenol.

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Literature cited

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    I. L. Kotlyarevskii and M. I. Bardamova, Izv. Akad. Nauk SSSR, Ser. Khim., 2073 (1964).

  2. 2.

    M. I. Bardamova, R. N. Myasnikova, and L. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 443 (1967).

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    L. R. Swett, W. B. Martin, J. D. Taylor, and G. M. Everett, Ann. New York Acad. Sci.,107, 891 (1963); I. P. Lapin, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva,9, 438 (1964); G. M. Everett, Nature, 177, 1238 (1956); G. M. Everett, L. E. Blockus, and I. M. Sheppered, Science,124, 79 (1956).

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    K. Nakanishi, Infrared Spectra and Structure of Organic Compounds [Russian Translation], IL (1965).

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    L. J. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL (1960), Chapter 6, p. 14.

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    E. K. Andrievskaya, I. L. Kotlyarevskii, and S. I. Dondo, Izv. Akad. Nauk SSSR, Ser. Khim., 1639 (1968).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 393–397, February, 1971.

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Myasnikova, R.N., Bardamova, M.I., Kotlyarevskii, I.L. et al. Phenolic derivatives of aminopentadiynes. Russ Chem Bull 20, 326–329 (1971). https://doi.org/10.1007/BF00869034

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  • Hydrogen
  • Phenol
  • Hydrogen Bond
  • Intermolecular Hydrogen Bond
  • Phenolic Derivative