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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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References

  1. Byrne PA, Gilheany D (2013) Chem Soc Rev 42:6670–6696

    Article  CAS  Google Scholar 

  2. Kolodiazhnyi OI (1999) Phosphorus ylides. Chemistry and applications in organic synthesis. Wiley, Weinheim

    Book  Google Scholar 

  3. Shi M, Xu B (2002) J Org Chem 67:294–297

    Article  CAS  Google Scholar 

  4. Wu J, Zhang D, Wei S (2005) Synth Commun 35:1213–1222

    Article  CAS  Google Scholar 

  5. El-Batta A, Jiang C, Zhao W, Anness R, Cooksy AL, Bergdahl M (2007) J Org Chem 72:5244–5259

    Article  CAS  Google Scholar 

  6. Islami MR, Yavari I, Tikdan AM, Ebrahimi L, Razee S, Bijanzadeh HR (2002) Russ Chem Bull 51:2244–2247

    Article  CAS  Google Scholar 

  7. Li CJ, Chan TH (2007) Comprehensive organic reactions in aqueous media, 2nd edn. Wiley, Hoboken

    Book  Google Scholar 

  8. Kim JN, Lee KA, Kim HS, Im YJ (2001) Bull Korean Chem Soc 22:351–352

    CAS  Google Scholar 

  9. Balema VP, Wiench JW, Pruski M, Pecharsky VK (2002) Chem Commun 2002:724–725

    Article  Google Scholar 

  10. Joó F (2001) Aqueous organometallic catalysis. Kluwer, Dordrecht

    Book  Google Scholar 

  11. Larpent C, Patin H (1988) Tetrahedron 44:6107–6118

    Article  CAS  Google Scholar 

  12. Darensbourg DJ, Joó F, Kathó Á, Stafford JNW, Bényei A (1994) Inorg Chem 33:175–177

    Article  CAS  Google Scholar 

  13. Moiseev DV, James BR, Hu TQ (2007) Inorg Chem 46:4704–4712

    Article  CAS  Google Scholar 

  14. Moiseev DV, James BR, Gushchin AV (2014) Eur J Inorg Chem 2014:6275–6280

    Article  CAS  Google Scholar 

  15. Moiseev DV, James BR, Gushchin AV (2013) Phosphorous Sulfur Silicon 188:678–690

    Article  CAS  Google Scholar 

  16. Bényei A, Stafford JNW, Kathó Á, Darensbourg DJ, Joó F (1993) J Mol Catal 84:157–163

    Article  Google Scholar 

  17. Phillips DA, Gonsalvi L, Romerosa A, Vizza F, Peruzzini M (2004) Coord Chem Rev 248:955–993

    Article  CAS  Google Scholar 

  18. Bravo J, Bolano S, Gonsalvi L, Peruzzini M (2010) Coord Chem Rev 254:555–607

    Article  CAS  Google Scholar 

  19. Scolaro C, Bergamo A, Brescacin L, Delfino R, Cocchietto M, Laurenczy G, Geldbach TJ, Sava G, Dyson PJ (2005) J Med Chem 48:4161–4171

    Article  CAS  Google Scholar 

  20. Darensbourg MY, Daigle DJ (1975) Inorg Chem 14:1217–1218

    Article  CAS  Google Scholar 

  21. Daigle DJ, Pepperman AB, Vail SL (1974) J Heterocycl Chem 11:407–408

    Article  CAS  Google Scholar 

  22. Daigle DJ (1998) Inorg Synth 32:40–41

    Article  CAS  Google Scholar 

  23. Fisher KJ, Alyea EC, Shahnazarian N (1990) Phosphorous Sulfur Silicon 48:37–40

    Article  CAS  Google Scholar 

  24. Joó F, Nádasdi L, Bényei A, Csiba P, Kathó Á (1995) Aqueous organometallic chemistry and catalysis. In: Horváth IT, Joó F (eds) NATO ASI series, 3. High technology, vol 5. Kluwer, Dordrecht, pp 23–32

    Google Scholar 

  25. Joó F, Nádasdi L, Bényei A, Darensbourg DJ (1996) J Organomet Chem 512:45–50

    Article  Google Scholar 

  26. Assmann B, Angermaier K, Paul M, Riede J, Schmidbaur H (1995) Chem Ber 128:891–900

    Article  CAS  Google Scholar 

  27. He Z, Tang X, Chen Y, He Z (2006) Adv Synth Catal 348:413–417

    Article  CAS  Google Scholar 

  28. Tang X, Zhang B, He Z, Gao R, He Z (2007) Adv Synth Catal 349:2007–2017

    Article  CAS  Google Scholar 

  29. Romerosa A, Campos-Malpartida T, Lidrissi C, Saoud M, Serrano-Ruiz M, Peruzzini M, Garrido-Cárdenas JA, García-Maroto F (2006) Inorg Chem 45:1289–1298

    Article  CAS  Google Scholar 

  30. Altomare A, Cascarano G, Giacovazzo C, Guagliardi A (1993) J Appl Crystallogr 26:343–350

    Article  Google Scholar 

  31. Sheldrick GM (2008) Acta Cryst. A64:112–122

    Article  Google Scholar 

  32. Farrugia LJ (1999) J Appl Cryst 32:837–838

    Article  CAS  Google Scholar 

  33. Zhao Y, Truhlar D (2008) Theor Chem Acc 120:215–241

    Article  CAS  Google Scholar 

  34. McLean AD, Chandler GS (1980) J Chem Phys 72:5639–5648

    Article  CAS  Google Scholar 

  35. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi S, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski WG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Rev. A.1, Gaussian, Inc., Wallingford, CT

  36. Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999–3093

    Article  CAS  Google Scholar 

  37. Scalmani G, Frisch GJ (2010) J Chem Phys 132:114110–114115

    Article  Google Scholar 

  38. Peng C, Schlegel HB (1994) Isr J Chem 33:449–454

    Article  Google Scholar 

  39. Peng C, Ayala PY, Schlegel HB, Frisch MJ (1996) J Comput Chem 17:49–56

    Article  CAS  Google Scholar 

  40. Fluck E, Forster J-E, Weidlein J, Hadicke E (1977) Z Naturforsch B Chem Sci 32:499–501

    Google Scholar 

  41. Shahat M (1952) Acta Cryst 5:763–768

    Article  CAS  Google Scholar 

Download references

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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