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Synthesis and structure of stable water-soluble phosphonium alkanoate zwitterions derived from 1,3,5-triaza-7-phosphaadamantane

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Abstract

1,3,5-triaza-7-phosphaadamantane (PTA) was shown to form phosphonium alkanoate zwitterions with unsaturated dicarboxylic acids in water in the absence of strong acids. Solid-state structures of the phosphonium salt (1) derived from maleic or fumaric acids and that of the zwitterionic product (2) of the reaction of PTA with citraconic and mesaconic acids were determined by single-crystal X-ray diffraction. DFT calculations gave insight into the mechanism of the reaction, including the relative reactivity of the four dicarboxylic acids, and revealed the reasons for the lack of phosphonium salt formation by PTA in strongly acidic aqueous solutions.

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Acknowledgments

This research was supported by the European Union and the State of Hungary, co-financed by the European Social Fund in the framework of TÁMOP-4.2.4.A/2-11/1-2012-0001 ‘National Excellence Program’ through a grant to A.U. Thanks are due to the Hungarian Research Fund (OTKA K101372) for financial support. The authors thank Dr. Gábor Papp for his help in the NMR measurements. The participation of Henrietta Molnár in the initial experiments is gratefully acknowledged. The research was supported by the EU and co-financed by the European Social Fund under the project ENVIKUT (TÁMOP-4.2.2.A-11/1/KONV-2012-0043).

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Authors and Affiliations

  1. MTA-DE Homogeneous Catalysis and Reaction Mechanisms Research Group, P.O.B. 7, Debrecen 10, 4010, Hungary

    Antal Udvardy, Mihály Purgel & Ferenc Joó

  2. Department of Physical Chemistry, University of Debrecen, P.O.B. 7, Debrecen 10, 4010, Hungary

    Antal Udvardy, Tímea Szarvas, Ferenc Joó & Ágnes Kathó

Authors
  1. Antal Udvardy
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  2. Mihály Purgel
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  3. Tímea Szarvas
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  4. Ferenc Joó
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  5. Ágnes Kathó
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Corresponding authors

Correspondence to Antal Udvardy or Ágnes Kathó.

Additional information

This paper is dedicated to Professor Magdolna Hargittai in recognition of her outstanding achievements in inorganic and structural chemistry.

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Udvardy, A., Purgel, M., Szarvas, T. et al. Synthesis and structure of stable water-soluble phosphonium alkanoate zwitterions derived from 1,3,5-triaza-7-phosphaadamantane. Struct Chem 26, 1323–1334 (2015). https://doi.org/10.1007/s11224-015-0618-4

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  • DOI: https://doi.org/10.1007/s11224-015-0618-4

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