Skip to main content

Halogen Bonding in Supramolecular Synthesis

  • Chapter
  • First Online:
Halogen Bonding I

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 358))

Abstract

Supramolecular synthesis is typically limited to one-pot reactions because of the reversibility of non-covalent bonds, and to overcome this restriction we need to be able to rank the relative structural importance of such interactions and build synthetic methods to utilize synthons which can operate side-by-side without interference. Halogen bonds have characteristics (strength and directionality) which potentially make them prime candidates as critical components of effective, transferable, and versatile supramolecular synthetic strategies. In this chapter, several halogen-bond driven crystal engineering strategies for the assembly of specific architectures in molecular solids are described in detail, and the utility of halogen bonds for the synthesis of co-crystals are addressed. Finally, the structural compatibility or competition between of halogen- and hydrogen bonds in the context of supramolecular synthesis are examined.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Aakeröy CB (1997) Acta Crystallogr B 53:569

    Article  Google Scholar 

  2. Braga D (2003) Chem Commun 22:2751

    Article  Google Scholar 

  3. Walsh RDB, Bradner MW, Fleischman S, Morales LA, Moulton B, Rodriguez-Hornedo N, Zaworotko MJ (2003) Chem Commun 186

    Google Scholar 

  4. Wenger M, Bernstein J (2006) Angew Chem Int Ed 45:7966

    Article  CAS  Google Scholar 

  5. Lehn J-M (2002) Science 295:2400

    Article  CAS  Google Scholar 

  6. Desiraju GR (2002) Acc Chem Res 35:565

    Article  CAS  Google Scholar 

  7. Crihfield A, Hartwell J, Phelps D, Walsh RB, Harris JL, Payne JF, Pennington WT, Hanks TW (2003) Cryst Growth Des 3:313

    Article  CAS  Google Scholar 

  8. Britton D, Gleason WB (2002) Acta Crystallogr Sect E Struct Rep Online 58:o1375

    Article  CAS  Google Scholar 

  9. Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G (2007) Acta Crystallogr Sect E Struct Rep Online 63:o4243

    Article  CAS  Google Scholar 

  10. Liantonio R, Metrangolo P, Pilati T, Resnati G (2002) Acta Crystallogr Sect E Struct Rep Online 58:o575

    Article  CAS  Google Scholar 

  11. Walsh RB, Padgett CW, Metrangolo P, Resnati G, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:165

    Article  CAS  Google Scholar 

  12. Cincic D, Friscic T, Jones W (2008) Chem Mater 20:6623

    Article  CAS  Google Scholar 

  13. Metrangolo P, Pilati T, Resnati G, Stevenazzi A (2004) Chem Commun 1492

    Google Scholar 

  14. Cardillo P, Corradi E, Lunghi A, Meille SV, Messina MT, Metrangolo P, Resnati G (2000) Tetrahedron 56:5535

    Article  CAS  Google Scholar 

  15. Syssa-Magale J-L, Boubekeur K, Schollhorn B (2005) J Mol Struct 737:103

    Article  CAS  Google Scholar 

  16. Jay JI, Padgett CW, Walsh RDB, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:501

    Article  CAS  Google Scholar 

  17. Aakeröy CB, Wijethunga TK, Desper J (2014) CrystEngComm 16:28

    Article  Google Scholar 

  18. Clark T, Hennemann M, Murray JS, Politzer P (2007) J Mol Model 13:291

    Article  CAS  Google Scholar 

  19. Politzer P, Lane P, Concha MC, Ma Y, Murray JS (2007) J Mol Model 13:305

    Article  CAS  Google Scholar 

  20. Göbell M, Tchitchanov BH, Murray JS, Politzer P, Klapötkel TM (2009) Nat Chem 1:229

    Article  Google Scholar 

  21. Politzer P, Murray JS, Clark T (2010) Phys Chem Chem Phys 12:7748

    Article  CAS  Google Scholar 

  22. Ji B, Wang W, Deng D, Zhang Y (2011) Cryst Growth Des 11:3622

    Article  CAS  Google Scholar 

  23. Syssa-Magalé J, Boubekeur K, Palvadeau P, Meerschaut A, Schöllhorn B (2005) CrystEngComm 7:302

    Article  Google Scholar 

  24. Syssa-Magalé J-L, Boubekeur K, Palvadeau P, Meerschaut A, Schöllhorn B (2004) J Mol Struct 691:79

    Article  Google Scholar 

  25. Aakeröy CB, Chopade PD, Desper J (2011) Cryst Growth Des 11:5333

    Article  Google Scholar 

  26. Khavasi HR, Tehrani AA (2013) CrystEngComm 15:5813

    Article  CAS  Google Scholar 

  27. Bernstein J (2002) Polymorphism in molecular crystals, IUCr monographs on crystallography. Clarendon Press, Oxford

    Google Scholar 

  28. Metrangolo P, Resnati G, Pilati T, Biella S (2008) In: Metrangolo P, Resnati G (eds) Halogen bonding: fundamentals and applications. Springer, Berlin, p 105

    Chapter  Google Scholar 

  29. De Santis A, Forni A, Liantonio R, Metrangolo P, Pilati T, Resnati G (2003) Chem Eur J 9:3974

    Article  Google Scholar 

  30. Yamamoto HM, Kosaka Y, Maeda R, Yamaura J, Nakao A, Nakamura T, Kato R (2008) ACS Nano 2:143

    Article  CAS  Google Scholar 

  31. Saccone M, Cavallo G, Metrangolo P, Pace A, Pibiri I, Pilati T, Resnati G, Terraneo G (2013) CrystEngComm 15:3102

    Article  CAS  Google Scholar 

  32. Liu P, Ruan C, Li T, Ji B (2012) Acta Crystallogr Sect E Struct Rep Online 68(Pt 5):o1431

    Article  CAS  Google Scholar 

  33. Cincic D, Friščić T, Jones W (2008) Chem Eur J 14:747

    Article  CAS  Google Scholar 

  34. Cincic D, Friščić T, Jones W (2011) CrystEngComm 13:3224

    Article  CAS  Google Scholar 

  35. Bertani R, Chaux F, Gleira M, Metrangolo P, Milani R, Pilati T, Resnati G, Sansotera M, Venzo A (2007) Inorg Chim Acta 360:1

    Article  Google Scholar 

  36. Metrangolo P, Meyer F, Pilati T, Proserpio DM, Resnati G (2007) Chem Eur J 13:5765

    Article  CAS  Google Scholar 

  37. Aakeröy CB, Rajbanshi A, Metrangolo P, Resnati G, Parisi MF, Desper J, Pilati T (2012) CrystEngComm 14:6366

    Article  Google Scholar 

  38. Caronna T, Liantonio R, Logothetis TA, Metrangolo P, Pilati T, Resnati G (2004) J Am Chem Soc 126:4500

    Article  CAS  Google Scholar 

  39. Metrangolo P, Meyer F, Pilati T, Proserpio DM, Resnati G (2008) Cryst Growth Des 8:654

    Article  CAS  Google Scholar 

  40. Vartanian M, Lucassen ACB, Shimon LJW, van der Boom ME (2008) Cryst Growth Des 8:786

    Article  CAS  Google Scholar 

  41. Baldrighi M, Metrangolo P, Meyer F, Pilati T, Proserpio D, Resnati G, Terraneo G (2010) J Fluorine Chem 131:1218

    Article  CAS  Google Scholar 

  42. Marras G, Metrangolo P, Meyer F, Pilati T, Resnati G, Vij A (2006) New J Chem 30:1397

    Article  CAS  Google Scholar 

  43. Scarso A, Shivanyuk A, Hayashida O, Rebek J Jr (2003) J Am Chem Soc 125:6239

    Article  CAS  Google Scholar 

  44. Chen J, Rebek J Jr (2002) Org Lett 4:327

    Article  CAS  Google Scholar 

  45. Aakeröy CB, Rajbanshi A, Desper J (2011) Chem Commun 47:11411

    Article  Google Scholar 

  46. Focsaneanu K-S, Scaiano JC (2005) Photochem Photobiol Sci 4:817

    Article  CAS  Google Scholar 

  47. Manandhar E, Broome JH, Myrick J, Lagrone W, Cragg PJ, Wallace KJ (2011) Chem Commun 47:8796

    Article  CAS  Google Scholar 

  48. Zhang B, Sun J, Bi C, Yin G, Shi PY, Sheng L (2011) New J Chem 35:849

    Article  CAS  Google Scholar 

  49. Xue L, Charles I, Arya DP (2002) Chem Commun 70

    Google Scholar 

  50. Okamoto A, Ochi Y, Saito I (2005) Chem Commun 1128

    Google Scholar 

  51. Nakamura M, Ohtoshi Y, Yamana K (2005) Chem Commun 5163

    Google Scholar 

  52. Østergaard M, Hrdlicka PJ (2011) Chem Soc Rev 40:5771

    Article  Google Scholar 

  53. Figueira-Duarte TM, Mullen K (2011) Chem Rev 111:7260

    Article  CAS  Google Scholar 

  54. Shen QJ, Wei HQ, Zou WS, Sun HL, Jin WJ (2012) CrystEngComm 14:1010

    Article  CAS  Google Scholar 

  55. Jin H, Plonka AM, Parise JB, Goroff NS (2013) CrystEngComm 15:3106

    Article  CAS  Google Scholar 

  56. Sharma Goel SK, Rezan SA, Misra VN, Tripathi KN (2003) J Mater Sci Lett 22:737

    Article  Google Scholar 

  57. Chae SK, Park H, Yoon J, Lee CH, Ahn DJ, Kim JM (2007) Adv Mater 19:521

    Article  CAS  Google Scholar 

  58. Ahn DJ, Kim JM (2008) Acc Chem Res 41:805

    Article  CAS  Google Scholar 

  59. Goroff NS, Curtis SM, Webb JA, Fowler FW, Lauher JW (2005) Org Lett 7:1891

    Article  CAS  Google Scholar 

  60. Clark SM, Friščić T, Jones W, Mandal A, Sun C, Parker JE (2011) Chem Commun 47:2526

    Article  Google Scholar 

  61. Etter MC (1990) Acc Chem Res 23:120

    Article  CAS  Google Scholar 

  62. Aakeröy CB, Epa KN, Forbes S, Desper J (2013) CrystEngComm 15:5946

    Article  Google Scholar 

  63. Aakeröy CB, Epa KN, Forbes S, Schultheiss N, Desper J (2013) Chem A Eur J 19:14998

    Article  Google Scholar 

  64. Aakeröy CB, Desper J, Smith MM (2007) Chem Commun 3936

    Google Scholar 

  65. Aakeröy CB, Baldrighi M, Desper J, Metrangolo P, Resnati G (2013) Chem A Eur J 19:16240

    Article  Google Scholar 

  66. Aakeröy CB, Panikkattu S, Chopade PD (2013) J Desper CrystEngComm 15:3125

    Article  Google Scholar 

  67. Messina MT, Metrangolo P, Panzeri W, Pilati T, Resnati G (2001) Tetrahedron 57:8543

    Article  CAS  Google Scholar 

  68. Oh SY, Nickels CW, Garcia F, Jones W, Friščić T (2012) CrystEngComm 14:6110

    Article  CAS  Google Scholar 

  69. Aakeröy CB, Chopade PD, Ganser C, Desper J (2011) Chem Commun 47:4688

    Article  Google Scholar 

  70. Tothadi S, Desiraju GR (2013) Chem Commun 49:7791

    Article  CAS  Google Scholar 

  71. Erdélyi M (2012) Chem Soc Rev 41:3547

    Article  Google Scholar 

  72. Abraham MH (1993) Pure and Appl Chem 65:2503

    Article  CAS  Google Scholar 

  73. Schneider H-J (2003) Method Prin Med Chem 19:21

    CAS  Google Scholar 

  74. Libri S, Jasim NA, Perutz RN, Brammer L (2008) J Am Chem Soc 130:7842

    Article  CAS  Google Scholar 

  75. Metrangolo P, Panzeri W, Recupero F, Resnati G (2002) J Fluorine Chem 114:27

    Article  CAS  Google Scholar 

  76. Cabot R, Hunter CA (2005) Chem Commun 2009

    Google Scholar 

  77. Laurence C, Queignec-Cabanetos M, Dziembowska T, Queignec R, Wojtkowiak BJ (1982) Chem Soc Perkin Trans 2 1605

    Google Scholar 

  78. Sarwar MG, Dragisic B, Salsberg LJ, Gouliaras C, Taylor MS (2010) J Am Chem Soc 132:1646

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Aakeröy, C.B., Spartz, C.L. (2014). Halogen Bonding in Supramolecular Synthesis. In: Metrangolo, P., Resnati, G. (eds) Halogen Bonding I. Topics in Current Chemistry, vol 358. Springer, Cham. https://doi.org/10.1007/128_2014_567

Download citation

Publish with us

Policies and ethics