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1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions

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Anion Recognition in Supramolecular Chemistry

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 24))

Abstract

As the field of anion supramolecular chemistry continues to grow in its sophistication and understanding of the noncovalent interactions used to effectively bind anions, there exists new theoretical and experimental evidence for a necessary reexamination of the way in which the field views hydrogen bond donors. The heteroatom based hydrogen-bond donors (e.g., NH and OH) are well-known to provide strong stabilization to negatively charged species. However, new findings point to the untapped stabilization energy that lay dormant in extrinsically-activated CH hydrogen bonds. Computational studies showed that an activated aliphatic or aromatic CH can provide an amount of anion stabilization in the gas phase approaching that of conventional NH based donors. Discovery of the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition to provide 1,2,3-triazoles and the ability to readily “click” this functionality into anion receptors has allowed extensive experimental investigation of the ideas posed by these calculations. This chapter will focus on the evolution of the CH hydrogen bond from being viewed as a weak, secondary interaction to now being utilized as a powerful source of anion stabilization in macrocyclic and oligomeric receptors. In addition, the application of the anion binding power of the 1,2,3-triazole towards the preparation of mechanically interlocked structures will also be discussed.

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Abbreviations

CD:

Circular dichroism

DB24C8:

Dibenzo[24]crown-8

DIEA:

Diisopropylethylamine

DMF:

N, N-dimethylformamide

DMSO:

Dimethylsulfoxide

ESI-MS:

Electrospray ionization mass spectrometry

TBACl:

Tetrabutylammonium chloride

References

  1. Sato T, Konno H, Tanaka Y, Kataoka T, Nagai K, Wasserman HH, Ohkuma S (1998) J Biol Chem 273:21455

    Article  CAS  Google Scholar 

  2. Dutzler R, Campbell EB, Cadene M, Chait BT, MacKinnon R (2002) Nature 415:287

    Article  CAS  Google Scholar 

  3. Christianson DW, Lipscomb WN (1989) Acc Chem Res 22:62

    Article  CAS  Google Scholar 

  4. Kubik S, Reyhelter C, Stuwe S (2005) J Incl Phenom 52:137

    Article  CAS  Google Scholar 

  5. Moss B (1996) Chem Ind:407

    Google Scholar 

  6. Damian P, Pontius FW (1999) Environ Prot:24

    Google Scholar 

  7. Urbansky ET (1999) J Environ Manage 56:79

    Article  Google Scholar 

  8. Langard S, Norseth T (1979) Handbook on the toxicity of metals. Elsevier, New York

    Google Scholar 

  9. US EPA (2009) Interim Drinking Water Health Advisory for Perchlorate. US Environmental Protection Agency, Washington, DC. EPA 822-R-08-025

    Google Scholar 

  10. Bianchi A, Bowman-James K, Garcia-España E (1997) Supramolecular chemistry of anions. Wiley-VCH, New York

    Google Scholar 

  11. Sessler JL, Gale PA, Cho WS (2006) Anion receptor chemistry. RSC Cambridge, UK

    Google Scholar 

  12. Buhlmann P, Pretsch E, Bakker E (1998) Chem Rev 98:1593

    Article  Google Scholar 

  13. Oesch U, Amman D, Simon W (1986) Clin Chem 32:1448

    CAS  Google Scholar 

  14. Zahran E, Hua Y, Li Y, Flood AH, Bachas LG (2009) Anal Chem 82:368

    Article  Google Scholar 

  15. Wintergerst MP, Levitskaia TG, Moyer BA, Sessler JL, Delmau LH (2008) J Am Chem Soc 130:4129

    Article  CAS  Google Scholar 

  16. Fowler CJ, Haverlock TJ, Moyer BA, Shriver JA, Gross DE, Marquez M, Sessler JL, Hossain MA, Bowman-James K (2008) J Am Chem Soc 130:14386

    Article  CAS  Google Scholar 

  17. Nicolau KC, Sorensen EJ (1996) Classics in total synthesis. Wiley-VCH Weinheim, Germany

    Google Scholar 

  18. Sharpless KB, Finn MG, Kolb HC (2001) Angew Chem Int Ed 40:2004

    Article  Google Scholar 

  19. Schmidtchen FP (2006) Coord Chem Rev 250:2918

    Article  CAS  Google Scholar 

  20. Luecke H, Quiocho FA (1990) Nature 347:402

    Article  CAS  Google Scholar 

  21. Hofmeister F (1888) Arch Exp Pathol Pharmacol 24:247

    Article  Google Scholar 

  22. Taylor R, Kennard O (1982) J Am Chem Soc 104:5063

    Article  CAS  Google Scholar 

  23. Desiraju GR, Steiner T (1999) The weak hydrogen bond. Oxford University Press Inc, New York

    Google Scholar 

  24. Steiner T (1998) Acta Crystallogr B 54:456

    Article  Google Scholar 

  25. Farnham WB, Roe DC, Dixon DA, Calabrese JC, Harlow RL (1990) J Am Chem Soc 112:7007

    Article  Google Scholar 

  26. Davis AP, Gilmer JF, Perry JJ (1996) Angew Chem Int Ed Engl 35:1312

    Article  CAS  Google Scholar 

  27. Kwon JY, Jang YJ, Kim SK, Lee K-H, Kim JS, Yoon J (2004) J Org Chem 69:5155

    Article  CAS  Google Scholar 

  28. Ilioudis CA, Tocher DA, Steed JW (2004) J Am Chem Soc 126:12395

    Article  CAS  Google Scholar 

  29. Abouderbala LO, Belcher WJ, Boutelle MG, Cragg PJ, Dhaliwal J, Fabre M, Steed JW, Turner DR, Wallace KJ (2002) Chem Comm 4:358

    Article  Google Scholar 

  30. Wallace KJ, Belcher WJ, Turner DR, Syed KF, Steed JW (2003) J Am Chem Soc 125:9699

    Article  CAS  Google Scholar 

  31. Chmielewski MJ, Charon M, Jurczak J (2004) Org Lett 6:3501

    Article  CAS  Google Scholar 

  32. Bryantsev VS, Hay BP (2005) J Am Chem Soc 127:8282

    Article  CAS  Google Scholar 

  33. Bryantsev VS, Hay B (2005) Org Lett 7:5031

    Article  CAS  Google Scholar 

  34. Yoon D-W, Gross DE, Lynch VM, Sessler JL, Hay BP, Lee C-H (2008) Angew Chem Int Ed Engl 47:5038

    Google Scholar 

  35. Pedzisa L, Hay BP (2009) J Org Chem 74:2554

    Article  CAS  Google Scholar 

  36. Lee C-H, Na H-K, Yoon D-W, Won D-H, Cho W-S, Lynch VM, Shevchuk SV, Sessler JL (2003) J Am Chem Soc 125:7301

    Article  CAS  Google Scholar 

  37. Nishiyabu R, Palacios MA, Dehaen W, Anzenbacher P Jr (2006) J Am Chem Soc 128:11496

    Article  CAS  Google Scholar 

  38. Bruno G, Cafeo G, Kohnke FH, Nicolo F (2007) Tetrahedron 63:10003

    Article  CAS  Google Scholar 

  39. Ghosh S, Choudhury AR, Row Tayur NG, Maitra U (2005) Org Lett 7:1441

    Article  CAS  Google Scholar 

  40. Maeda H, Kusunose Y (2005) Chem Eur J 11:5661

    Article  CAS  Google Scholar 

  41. Fujimoto C, Kusunose Y, Maeda H (2006) J Org Chem 71:2389

    Article  CAS  Google Scholar 

  42. Maeda H (2007) Eur J Org Chem:5313

    Google Scholar 

  43. Zhu SS, Staats H, Brandhorst K, Grunenberg J, Gruppit F, Dalcanale E, Luetzen A, Rissanen K, Schalley CA (2008) Angew Chem Int Ed 47:788

    Article  CAS  Google Scholar 

  44. Berryman OB, Sather AC, Hay BP, Meisner JS, Johnson DW (2008) J Am Chem Soc 130:10895

    Article  CAS  Google Scholar 

  45. Huisgen R, Szeimies G, Mobius L (1967) Chem Ber 100:2484

    Article  Google Scholar 

  46. Huisgen R (1989) Pure Appl Chem 61:613

    Article  CAS  Google Scholar 

  47. Rostovstsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  Google Scholar 

  48. Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  Google Scholar 

  49. Scriven EFV, Turnbull K (1988) Chem Rev 88:297

    Article  CAS  Google Scholar 

  50. Meldal M, Tornøe CW (2008) Chem Rev 108:2952

    Article  CAS  Google Scholar 

  51. Rodionov VO, Fokin VV, Finn MG (2005) Angew Chem Int Ed 44:2210

    Article  CAS  Google Scholar 

  52. Rodionov VO, Presolski SI, Diaz DD, Fokin VV, Finn MG (2007) J Am Chem Soc 129:12705

    Article  CAS  Google Scholar 

  53. Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV (2008) J Am Chem Soc 130:8923

    Article  CAS  Google Scholar 

  54. Golas PL, Tsarevsky NV, Sumerlin BS, Matyajaszewski K (2006) Macromolecules 39:6451

    Article  CAS  Google Scholar 

  55. Baskin JM, Prescher JA, Laughlin ST, Agard NJ, Chang PV, Mille IA, Lo A, Codellia JA, Bertozzi CR (2007) Proc Nat Acad Sci USA 43:16793

    Article  Google Scholar 

  56. Becer CR, Hoogenboom R, Schuber US (2009) Angew Chem Int Ed 48:4900

    Article  CAS  Google Scholar 

  57. Oh K, Guan Z (2006) Chem Commun:3069

    Google Scholar 

  58. Patterson AW, Wood WJL, Hornsby M, Lesley S, Spraggon G, Elmman JA (2006) J Med Chem 49:6298

    Article  CAS  Google Scholar 

  59. Adam GC, Vanderwal CD, Sorensen EJ, Cravatt BF (2003) Angew Chem Int Ed 42:5480

    Article  CAS  Google Scholar 

  60. Li Y, Huffman JC, Flood AH (2007) Chem Commun:2692

    Google Scholar 

  61. Muedtner RM, Ostermeier M, Goddard R, Limberg C, Hecht S (2007) Chem Eur J 13:9834

    Article  Google Scholar 

  62. Aucagne V, Berná J, Crowley JD, Goldup SM, Hänni KD, Leigh DA, Lusby PJ, Ronaldson VE, Slawin AMZ, Viterisi A, Walker DB (2007) J Am Chem Soc 129:11950

    Article  CAS  Google Scholar 

  63. Goldup SM, Leigh DA, Long T, McGonigal PR, Symes MD, Wu J (2009) J Am Chem Soc 131:15924

    Article  CAS  Google Scholar 

  64. Palmer MH, Findlay RH, Gaskell AJ (1974) J Chem Soc Perkin Trans 2:420

    Google Scholar 

  65. Schuster O, Yang L, Raubenheimer HG, Albrecht M (2009) Chem Rev 109:3445

    Article  CAS  Google Scholar 

  66. Moore JS (1997) Acc Chem Res 30:402

    Article  CAS  Google Scholar 

  67. Li Y, Flood AH (2008) Angew Chem Int Ed 47:2649

    Article  CAS  Google Scholar 

  68. Li Y, Flood AH (2008) J Am Chem Soc 130:12111

    Article  CAS  Google Scholar 

  69. Nielsen KA, Cho WS, Lyskawa J, Levillain E, Lynch VM, Sessler JL, Jeppesen JO (2006) J Am Chem Soc 128:2444

    Article  CAS  Google Scholar 

  70. Chang KJ, Moon D, Lah MS, Jeong KS (2005) Angew Chem Int Ed 44:7926

    Article  CAS  Google Scholar 

  71. Bandyopadhyay I, Raghavachari K, Flood AH (2009) Chemphyschem 10:2535

    Article  CAS  Google Scholar 

  72. Boer FP, Neuman MA, Van Remootere FP, Steiner EC (1974) Inorg Chem 40:2936

    Google Scholar 

  73. Choi K, Hamilton AD (2001) J Am Chem Soc 123:2456

    Article  CAS  Google Scholar 

  74. Kubik S, Goddard R, Kirchner R, Nolting D, Seidel J (2001) Angew Chem Int Ed 40:2648

    Article  CAS  Google Scholar 

  75. Li Y, Pink M, Karty JA, Flood AH (2008) J Am Chem Soc 130:17293

    Article  CAS  Google Scholar 

  76. Juwarker H, Lenhardt JM, Pham DM, Craig SL (2008) Angew Chem Int Ed 47:3740

    Article  CAS  Google Scholar 

  77. Juwarker H, Lenhardt JM, Castillo JC, Zhao E, Krishnamurthy S, Jamiolkowski RM, Kim K-H, Craig SL (2009) J Org Chem 74:8924–8934

    Article  CAS  Google Scholar 

  78. Hecht S, Meudtner RM (2008) Angew Chem Int Ed 47:4926

    Article  Google Scholar 

  79. Fisher MG, Gale PA, Hiscock JR, Hursthouse MB, Light ME, Schmidtchen FP, Tong CC (2009) Chem Commun:3017

    Google Scholar 

  80. Romero T, Caballero A, Tarraga A, Molina P (2009) Org Lett 11:3466

    Article  CAS  Google Scholar 

  81. Schalley CA, Vögtle F, Dötz KH (2005) Templates in chemistry I. Springer, New York

    Google Scholar 

  82. Kumar A, Pandey PS (2008) Org Lett 10:165

    Article  CAS  Google Scholar 

  83. Coutrot F, Busseron E (2008) Chem Eur J 14:4784

    Article  CAS  Google Scholar 

  84. Braunschweig, AB, Ronconi CM, Han JY, Arico F, Cantrill SJ, Stoddart JF, Khan SI, White AJP, Williams DJ (2006) Eur J Org Chem:1857

    Google Scholar 

  85. Loeb SJ (2007) Chem Soc Rev 36:226

    Article  CAS  Google Scholar 

  86. Coutrot F, Romuald C, Busseron E (2008) Org Lett 10:3741

    Article  CAS  Google Scholar 

  87. Mullen KM, Mercurio J, Serpell CJ, Beer PD (2009) Angew Chem Int Ed 48:4781

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Indiana University, Bloomington, IN, 47405, USA

    Kevin P. McDonald, Yuran Hua & Amar H. Flood

Authors
  1. Kevin P. McDonald
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  2. Yuran Hua
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  3. Amar H. Flood
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Correspondence to Amar H. Flood .

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Editors and Affiliations

  1. School of Chemistry, University of Southampton, Southampton, SO17 1BJ, United Kingdom

    Philip A. Gale

  2. Dept. Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200 F, Leuven, 3001, Belgium

    Wim Dehaen

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McDonald, K.P., Hua, Y., Flood, A.H. (2010). 1,2,3-Triazoles and the Expanding Utility of Charge Neutral CH···Anion Interactions. In: Gale, P., Dehaen, W. (eds) Anion Recognition in Supramolecular Chemistry. Topics in Heterocyclic Chemistry, vol 24. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_38

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