Subscribe to RSS
DOI: 10.1055/s-0035-1562622
N-Heterocyclic Carbenes, Ionic Liquids, and Reactive Small Molecules: A Conversation between a Student and His Professor
Publication History
Received: 26 July 2016
Accepted after revision: 27 July 2016
Publication Date:
14 September 2016 (online)
Abstract
Over the last ten years, Professor Jason Clyburne’s research has explored many different topics, but all are linked by the themes of unusual chemistry and interesting material properties. His lab is situated at Saint Mary’s University in Halifax, Nova Scotia, and he is the chair of Environmental Science with a cross-appointment in chemistry. Students often drop by to chat, and this review is an example of the type of discussion that occurs when he is trying to recruit them into his group. It is written in the form of a discussion between myself, a B.Sc. student, and Professor Clyburne, and it focuses on his interests in synthetic main group and materials chemistry. The general discussion includes asides and references to other work, to provide context.
1 Introduction
2 N-Heterocyclic Carbenes
3 Ionic Liquids
4 Reactions in Ionic Liquids
5 CO2 Capture with Ionic Liquids
6 Halide and Pseudo-Halide Adducts of CO2
7 Chemical Capture of CO2
8 Conclusion and Closing Remarks
-
References
- 1a Schwab P, France MB, Ziller JW, Grubbs RH. Angew. Chem., Int. Ed. Engl. 1995; 34: 2039
- 1b Schwab P, Grubbs RH, Ziller JW. J. Am. Chem. Soc. 1996; 118: 100
- 1c Scholl M, Trnka TM, Morgan JP, Grubbs RH. Tetrahedron Lett. 1999; 40: 2247
- 2 Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
- 3 Arduengo AJ. III. Harlow R. L., Kline M. 1991; 113: 361
- 4 Canal JP, Ramnial T, Dickie DA, Clyburne JA. C. Chem. Commun. 2006; 1809
- 5 Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
- 6a Kim Y.-J, Streitwieser A. J. Am. Chem. Soc. 2002; 124: 5757
- 6b Alder RW, Allen PR, Williams SJ. J. Chem. Soc., Chem. Commun. 1995; 1267
- 7a Herrmann WA, Elison M, Fischer J, Köcher C, Artus GR. J. Chem. Eur. J. 1996; 2, 772
- 7b Herrmann WA, Köcher C, Gooben LJ, Artus GR. J. Chem. Eur. J. 1996; 2: 1627
- 8a Nguyen T, Sutton AD, Brynda M, Fettinger JC, Long GJ, Power PP. Science 2005; 310: 844
- 8b Power PP. Chem. Rev. 1999; 99: 3463
- 9a Clyburne JA. C, McMullen N. Coord. Chem. Rev. 2000; 210: 73
- 9b McCollum BM, Bodovitch J.-C, Clyburne JA. C, Mitra A, Percival PW, Tomasik A, West R. Chem. Eur. J. 2009; 15: 8409
- 9c Ramnial T, McKenzie I, Gorodetsky B, Tsang EM. W, Clyburne JA. C. Chem. Commun. 2004; 1054
- 9d Twamley B, Haubrich ST, Power PP. Adv. Organomet. Chem. 1999; 44: 1
- 10a Murphy LJ, Robertson KN, Masuda JD, Clyburne JA. C. NHC Complexes of Main Group Elements: Novel Structures Reactivity and Catalytic Behaviour. In N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis. Nolan SP. Wiley-VCH; Weinheim: 2014
- 10b Abeysekera D, Robertson KN, Cameron TS, Clyburne JA. C. Organometallics 2001; 20: 5532
- 10c Jenkins HA, Abeysekera D, Dickie DA, Clyburne JA. C. J. Chem. Soc., Dalton Trans. 2002; 3919
- 10d Dickie DA, Choytun DD, Jennings MC, Clyburne JA. C. J. Organomet. Chem. 2004; 689: 2186
- 10e Dickie DA, Jalali H, Samant RG, Jennings MC, Clyburne JA. C. Can. J. Chem. 2004; 82: 1346
- 11 Tolman CA. Chem. Rev. 1997; 77: 313
- 12 Huang J, Schanz H.-J, Stevens ED, Nolan SP. Organometallics 1999; 18: 2370
- 13a Arduengo AJ. III. Acc. Chem. Res. 1999; 32: 913
- 13b Cowley AH. J. Organomet. Chem. 2001; 617: 105
- 14a Herrmann WA, Köcher C. Angew. Chem., Int. Ed. Engl. 1997; 36: 2162
- 14b Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1290
- 14c Gallivan JP, Jordan JP, Grubbs RH. Tetrahedron Lett. 2005; 46: 2577
- 15a Herrmann WA, Öfele K, Elison M, Kühn FE, Roesky PW. J. Organomet. Chem. 1994; 480: C7
- 15b Abernethy CD, Codd GM, Spicer MD, Taylor MK. J. Am. Chem. Soc. 2003; 125: 1128
- 16 Bertrand G. Carbene Chemistry . Marcel Dekker Inc; New York: 2002
- 17 IUPAC; Compendium of Chemical Terminology; http://goldbook.iupac.org/L03511 (accessed June 2016).
- 18 IUPAC; Compendium of Chemical Terminology; http://goldbook.iupac.org/B00745 (accessed June 2016).
- 19 Cowan JA, Clyburne JA. C, Davidson MG, Harris RL. W, Howard JA. K, Küpper P, Leech MA, Richards SP. Angew. Chem. Int. Ed. 2002; 41: 1432
- 20 Giffin NA, Makramalla M, Hendsbee AD, Robertson KN, Sherren C, Pye CC, Masuda JD, Clyburne JA. C. Org. Biomol. Chem. 2011; 9: 3672
- 21a Elaiwi A, Hitchcock PB, Seddon KR, Srinivasan N, Tan YM, Welton T, Zora JA. J. Chem. Soc., Dalton Trans. 1995; 3467
- 21b Avent AG, Chanloner PA, Day MP, Seddon KR, Welton T. J. Chem. Soc., Dalton Trans. 1994; 3405
- 22 Walden P. Bull. Acad. Imper. Sci. (St. Petersburg) 1914; 1800
- 23 Welton T. Chem. Rev. 1999; 99: 2071
- 24 Wilkes JS. Green Chem. 2002; 4: 73
- 25 Atwood JL, Atwood JD. Inorganic Compounds with Unusual Properties . In Advances in Chemistry, Series No. 150 . American Chemical Society; Washington DC: 1976: 112
- 26 Wilkes JS, Zaworokto MJ. J. Chem. Soc., Chem. Commun. 1992; 965
- 27 Krossing I, Raabe I. Angew. Chem. Int. Ed. 2004; 43: 2066
- 28 Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
- 29 Knochel P, Jones P In Organozinc Reagents . Oxford University Press; New York: 1999. Chap 1
- 30a Koszinowski K, Böhrer P. Organometallics 2009; 28: 100
- 30b Koszinowski K, Böhrer P. Organometallics 2009; 28: 771
- 31 MacIntosh IS, Sherren CN, Robertson KN, Masuda JD, Pye CC, Clyburne JA. C. Organometallics 2010; 29: 2063
- 32a Clegg W, Conway B, Hevia E, McCall MD, Russo L, Mulvey RE. J. Am. Chem. Soc. 2009; 131: 2375
- 32b Krasovskiy A, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333
- 32c Mosrin M, Monzon G, Bresser T, Knochel P. Chem. Commun. 2009; 5615
- 32d Metzger A, Piller FM, Knochel P. Chem. Commun. 2008; 5824
- 32e Mosrin M, Knochel P. Org. Lett. 2009; 11: 1837
- 33 McCann LC, Hunter HN, Clyburne JA. C, Organ MG. Angew. Chem. Int. Ed. 2012; 51: 7024
- 34 Ramnial T, Taylor SA, Bender ML, Gorodetsky B, Lee PT. K, Dickie DA, McCollum BM, Pye CC, Walsby CJ, Clyburne JA. C. J. Org. Chem. 2008; 73: 801
- 35 Dupont J, Spencer J. Angew. Chem. Int. Ed. 2004; 43: 5296
- 36 Nair V, Bindu S, Sreekumar V. Angew. Chem. Int. Ed. 2004; 43 5130
- 37 Islam MM, Imase T, Okajima T, Takahashi M, Niikura Y, Kawashima N, Nakamura Y, Ohsaka T. J. Phys. Chem. A 2009; 113: 912
- 38 Murphy LJ, Robertson KN, Kemp RA, Tuononen HM, Clyburne JA. C. Chem. Commun. 2015; 51: 3942
- 39 Tobiesen FA, Svendsen HF, Mejdell T. Ind. Eng. Chem. Res. 2007; 46: 7811
- 40 Harper ND, Nizio KD, Hendsbee AD, Masuda JD, Robertson KN, Murphy LJ, Johnson MB, Pye CC, Clyburne JA. C. Ind. Eng. Chem. Res. 2011; 50: 2822
- 41 Doyle KA, Murphy LJ, Paula ZA, Land MA, Robertson KN, Clyburne JA. C. Ind. Eng. Chem. Res. 2015; 54: 8829
- 42 Illioudis CA, Georganopoulou DG, Steed JW. J. Mater. Chem. 2002; 4: 26
- 43a Strazisar BR, Anderson RR, White CM. Energy Fuels 2003; 17: 1034
- 43b Freguia S, Rochelle GT. AIChE J. 2003; 49: 1676
- 44 Burdon J, Lallu N, Billing D, Burmeister D, Yearsley C, Wang M, Gunson A, Young H. Postharvest Biol. Technol. 2005; 65: 133
- 45 Burg SP, Burg EA. Science 1965; 148: 1190
- 46 Qiao H, Shen Z, Huang SS, Schmitz RJ, Urich MA, Briggs SP, Ecker JR. Science 2012; 338: 390
- 47a Adams DO, Yang SF. Trends Biochem. Sci. 1981; 6: 161
- 47b Peiser GD, Wang T.-T, Hoffman NE, Yang SF, Liu H.-W, Walsh CT. Proc. Natl. Acad. Sci. U.S.A. 1984; 81: 3059
- 48 Charng Y.-Y, Chou S.-J, Jiaang W.-T, Chen S.-T, Yang SF. Arch. Biochem. Biophys. 2001; 385: 179
- 49 Murphy LJ, Robertson KN, Harroun SG, Brosseau CL, Werner-Zwanziger U, Moilanen J, Tuononen HM, Clyburne JA. C. Science 2014; 344: 75
- 50 Alabugin I, Mohamed RK. Science 2014; 344: 45
- 51 Wöhler F, Liebig J. Ann. Pharm. 1832; 3: 249
- 53 Ugai T, Tanaka R, Dokawa T. J. Pharm. Soc. Jpn. 1943; 63: 296
- 54 Biju AT, Kuhl N, Glorius F. Acc. Chem. Res. 2011; 44: 1182
- 55 Berkessel A, Elfert S, Yatham VR, Neudörfl J.-M, Schlörer NE, Teles JH. Angew. Chem. Int. Ed. 2012; 51: 12370
- 56 Zhang X, Gross U, Seppelt K. Angew. Chem, Int. Ed. Engl. 1995; 34: 1858
- 57 Parkin G. Chem. Rev. 2004; 104: 699
- 58a Savile CK, Lalonde JJ. Curr. Opin. Biotechnol. 2011; 22: 818
- 58b Vinoba M, Bhagiyalakshmi M, Grace AN, Kim DH, Yoon Y, Nam SC, Baek IH, Jeong SK. J. Phys. Chem. B 2013; 117: 5683
- 59a Ackermann SL, Wolstenholme DJ, Frazee C, Deslongchamps G, Riley SH. M, Decken A, McGrady GS. Angew. Chem. Int. Ed. 2015; 54: 164
- 59b Ackermann SL, Wolstenholme DJ, Frazee C, Deslongchamps G, Riley SH. M, Decken A, McGrady GS. Angew. Chem. Int. Ed. 2015; 54: 7470
- 60 Hurmalainen J, Land MA, Robertson KN, Roberts CJ, Morgan IS, Tuononen HM, Clyburne JA. C. Angew. Chem. Int. Ed. 2015; 54: 7484
- 61 Oelkers EH, Gislason S, Matter J. Elements 2008; 4: 333
- 62 Matter JM, Stute M, Snæbjörnsdottir SÓ, Oelkers EH, Gislason SR, Aradottir ES, Sigfusson B, Gunnarsson I, Sigurdardottir H, Gunnlaugsson E, Axelsson G, Alfredsson HA, Wolff-Boenisch D, Mesfin K, Taya DF, Hall J, Dideriksen K, Broecker WS. Science 2016; 352: 1312
- 63 Sita LR, Babcock JR, Xi R. J. Am. Chem. Soc. 1996; 118: 10912
- 64a Dickie DA, Coker EN, Kemp RA. Inorg. Chem. 2011; 50: 11288
- 64b Dickie DA, Kemp RA. Organometallics 2014; 33: 6511
- 65 Dickie DA, Barker MT, Land MA, Hughes KE, Clyburne JA. C, Kemp RA. Inorg. Chem. 2015; 54: 11121
- 66 Barry BM, Dickie DA, Murphy LJ, Clyburne JA. C, Kemp RA. Inorg. Chem. 2013; 52: 8312
- 67 Felix AM, Boro BJ, Dickie DA, Tang Y, Saria JA, Moasser B, Stewart CA, Frost BJ, Kemp RA. Main Group Chem. 2012; 11: 13