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A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach

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Abstract

The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM]+, [BMIM]+ and [BM2IM]+) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation.

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References

  1. Bini R, Chiappe C, Llopsis Mestre V, Pomelli CS, Welton T (2008) Org Biomol Chem 6:2522. doi:10.1039/b802194e

    Article  CAS  Google Scholar 

  2. Tomasi J, Mennuci B, Cammi R (2005) Chem Rev 105:2999. doi:10.1021/cr9904009

    Article  CAS  Google Scholar 

  3. Wakai C, Oleinikova R, Ott M, Weingärtner H (2005) J Phys Chem B 109:17028. doi:10.1021/jp053946+

    Article  CAS  Google Scholar 

  4. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian, Inc., Wallingford, Gaussian 03, Revision C.02

  5. Bini R, Bortolini O, Chiappe C, Pieraccini D, Siciliano T (2007) J Phys Chem B 111:598. doi:10.1021/jp0663199

    Article  CAS  Google Scholar 

  6. Acevedo O, Jorgensen WL, Evanseck JD (2007) J Chem Theory Comput 3:132. doi:10.1021/ct6002753

    Article  CAS  Google Scholar 

  7. Sun H, Zhang D, Ma C, Liu C (2007) Int J Quantum Chem 107:1875. doi:10.1002/qua.21331

    Article  CAS  Google Scholar 

  8. Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F (2001) Theoretical Chemistry Institute, University of Wisconsin, Madison, NBO 5.0.

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Authors and Affiliations

  1. Dipartimento di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno Pisano 25, 56100, Pisa, Italy

    Riccardo Bini & Cinzia Chiappe

  2. Imperial College London, London, SW7 2AZ, UK

    Veronica L. Mestre & Thomas Welton

  3. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Risorgimento, 35, 56100, Pisa, Italy

    Christian S. Pomelli

Authors
  1. Riccardo Bini
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  2. Cinzia Chiappe
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  3. Veronica L. Mestre
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  4. Christian S. Pomelli
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  5. Thomas Welton
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Corresponding author

Correspondence to Christian S. Pomelli.

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Dedicated to the memory of Professor Oriano Salvetti and published as part of the Salvetti Memorial Issue.

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Bini, R., Chiappe, C., Mestre, V.L. et al. A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach. Theor Chem Acc 123, 347–352 (2009). https://doi.org/10.1007/s00214-009-0525-0

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  • DOI: https://doi.org/10.1007/s00214-009-0525-0

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