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Publicly Available Published by De Gruyter April 28, 2013

Towards solvent-controlled reactivity in ionic liquids

  • Hon Man Yau , Sinead T. Keaveney , Bradley J. Butler , Eden E. L. Tanner , Max S. Guerry , Stephen R. D. George , Michelle H. Dunn , Anna K. Croft and Jason B. Harper

Ionic liquids are frequently touted as alternatives to traditional molecular solvents but are limited in their applicability as the outcome of reactions may be altered on moving from a molecular to an ionic solvent. This manuscript summarizes our progress towards a predictive framework through understanding how ionic solvents affect organic processes, with an emphasis on how these findings might be applied. Particularly, we will consider the importance of the mole fraction of the ionic liquid used, including some hitherto undisclosed results, as well as the importance of understanding the key interactions of the solvent with the components along the reaction coordinate.


Conference

, 2012-09-09 - 2012-09-13, International Conference on Physical Organic Chemistry (ICPOC-21), 21st, Durham, UK


J. P. Hallett, T. Welton. Chem. Soc. Rev.111, 3508 (2011).Search in Google Scholar

C. L. Hussey. Pure Appl. Chem.60, 1763 (1988). (http://dx.doi.org/10.1351/pac198860121763)Search in Google Scholar

R. H. Dubois, M. J. Zaworotko, P. S. White. Inorg. Chem.28, 2019 (1989). (http://dx.doi.org/10.1021/ic00310a001)Search in Google Scholar

J. S. Wilkes, M. J. Zaworotko. J. Chem. Soc., Chem. Commun.965 (1992). (http://dx.doi.org/10.1039/c39920000965)Search in Google Scholar

P. Bonhôte, A. Das, N. Papageorgiou, K. Kalanasundram, M. Grätzel. Inorg. Chem.35, 1168 (1996). (http://dx.doi.org/10.1021/ic951325x)Search in Google Scholar PubMed

J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser, R. D. Rogers. Chem. Commun.1765 (1998). (http://dx.doi.org/10.1039/a803999b)Search in Google Scholar

S. Z. El Abedin, F. Endres. Acc. Chem. Res.40, 1106 (2007). (http://dx.doi.org/10.1021/ar700049w)Search in Google Scholar PubMed

K. R. Seddon. Kinet. Catal. Engl. Transl.37, 693 (1996).10.1080/17508489609556283Search in Google Scholar

J. B. Harper, M. N. Kobrak. Mini Rev. Org. Chem.3, 253 (2006). (http://dx.doi.org/10.2174/157019306777935037)Search in Google Scholar

M. J. Earle, S. P. Katdare, K. R. Seddon. Org. Lett.6, 707 (2004). (http://dx.doi.org/10.1021/ol036310e)Search in Google Scholar PubMed

H. Zhang, F. Xu, X. Zhou, G. Zhang, C. Wang. Green Chem.9, 1208 (2007). (http://dx.doi.org/10.1039/b705480g)Search in Google Scholar

Garima , V. P. Srivastava, L. D. S. Yadav. Tetrahedron Lett.52, 4622 (2011). (http://dx.doi.org/10.1016/j.tetlet.2011.06.096)Search in Google Scholar

J.-M. Xu, Q. Wu, Q.-Y. Zhang, F. Zhang, X.-F. Lin. Eur. J. Org. Chem.1798 (2007). (http://dx.doi.org/10.1002/ejoc.200600999)Search in Google Scholar

B. C. Ranu, R. Jana, S. Sowmiah. J. Org. Chem.72, 3152 (2007). (http://dx.doi.org/10.1021/jo070015g)Search in Google Scholar PubMed

M. B. Smith, J. March. March’s Advanced Organic Chemistry, Wiley-Interscience, New York (2001).Search in Google Scholar

A. Aggarwal, N. L. Lancaster, A. R. Sethi, T. Welton. Green Chem.4, 517 (2002). (http://dx.doi.org/10.1039/b206472c)Search in Google Scholar

K. Crossey, C. Hardacre, M. E. Migaud, S. E. Norman. RSC Adv.2, 2988 (2012). (http://dx.doi.org/10.1039/c2ra20131c)Search in Google Scholar

J. D. Holbrey, K. R. Seddon. Clean Prod. Proc.1, 223 (1999).Search in Google Scholar

L. Cammarata, S. G. Kazarian, P. A. Salter, T. Welton. Phys. Chem. Chem. Phys.3, 5192 (2001). (http://dx.doi.org/10.1039/b106900d)Search in Google Scholar

K. R. Seddon, A. Stark, M. J. Torres. Pure Appl. Chem.72, 2275 (2000). (http://dx.doi.org/10.1351/pac200072122275)Search in Google Scholar

S. R. D. George, G. L. Edwards, J. B. Harper. Org. Biomol. Chem.8, 5354 (2010). (http://dx.doi.org/10.1039/c0ob00306a)Search in Google Scholar PubMed

Y. Pan, L. E. Boyd, J. F. Kruplak, W. E. Cleland, J. S. Wilkes, C. L. Hussey. J. Electrochem. Soc.158, F1 (2011). (http://dx.doi.org/10.1149/1.3505006)Search in Google Scholar

R. P. Swatloski, J. D. Holbrey, R. D. Rogers. Green Chem.5, 361 (2003). (http://dx.doi.org/10.1039/b304400a)Search in Google Scholar

C. E. Rosella, J. B. Harper. Tetrahedron Lett.50, 992 (2009). (http://dx.doi.org/10.1016/j.tetlet.2008.12.045)Search in Google Scholar

M. S. Guerry, S. R. D. George, M. H. Dunn, J. B. Harper. Unpublished results.Search in Google Scholar

S. T. Keaveney, J. B. Harper. Unpublished results.Search in Google Scholar

H. M. Yau, A. G. Howe, J. M. Hook, A. K. Croft, J. B. Harper. Org. Biomol. Chem.7, 3572 (2009). (http://dx.doi.org/10.1039/b909171h)Search in Google Scholar

B. J. Butler, J. B. Harper. Unpublished results.Search in Google Scholar

B. Y. W. Man, J. M. Hook, J. B. Harper. Tetrahedron Lett.46, 7641 (2005). (http://dx.doi.org/10.1016/j.tetlet.2005.08.064)Search in Google Scholar

P. Müller, J. C. Rossier. J. Chem. Soc., Perkin Trans. 22232 (2000). (http://dx.doi.org/10.1039/b004884o)Search in Google Scholar

H. M. Yau, S. A. Barnes, J. M. Hook, T. G. A. Youngs, A. K. Croft, J. B. Harper. Chem. Commun.3576 (2008). (http://dx.doi.org/10.1039/b805255g)Search in Google Scholar

S. G. Jones, H. M. Yau, E. Davies, J. M. Hook, T. G. A. Youngs, J. B. Harper, A. K. Croft. PhysChemChemPhys12, 1873 (2010).10.1039/B919831HSearch in Google Scholar

C. G. Hanke, A. Johansson, J. B. Harper, R. M. Lynden-Bell. Chem. Phys. Lett.374, 85 (2003). (http://dx.doi.org/10.1016/S0009-2614(03)00703-6)Search in Google Scholar

J. B. Harper, R. M. Lynden-Bell. Mol. Phys.102, 85 (2004). (http://dx.doi.org/10.1080/00268970410001668570)Search in Google Scholar

L. Crowhurst, N. L. Lancaster, J. M. P. Arlandis, T. Welton. J. Am. Chem. Soc.126, 11549 (2004). (http://dx.doi.org/10.1021/ja046757y)Search in Google Scholar PubMed

H. M. Yau, A. K. Croft, J. B. Harper. Faraday Disc.154, 365 (2012). (http://dx.doi.org/10.1039/c1fd00060h)Search in Google Scholar PubMed

D. T. Bowron, C. D’Agostino, L. F. Gladden, C. Hardacre, J. D. Holbrey, M. C. Lagunas, J. McGregor, M. D. Mantle, C. L. Mullan, T. G. A. Youngs. J. Phys. Chem. B114, 7760 (2010). (http://dx.doi.org/10.1021/jp102180q)Search in Google Scholar PubMed

A. Wulf, K. Fumino, R. Ludwig. Angew. Chem., Int. Ed.49, 449 (2010). (http://dx.doi.org/10.1002/anie.200905437)Search in Google Scholar PubMed

E. E. L. Tanner, H. M. Yau, A. K. Croft, J. B. Harper. Unpublished results.Search in Google Scholar

H. M. Yau, S. J. Chan, S. R. D. George, J. M. Hook, A. K. Croft, J. B. Harper. Molecules14, 2521 (2009). (http://dx.doi.org/10.3390/molecules14072521)Search in Google Scholar PubMed PubMed Central

A. Stoppa, J. Hunger, G. T. Hefter, R. Buchner. J. Chem. Phys. B116, 7509 (2012).10.1021/jp3020673Search in Google Scholar PubMed

Published Online: 2013-4-28
Published in Print: 2013-10-1

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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