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.
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References
Aakeröy CB (1997) Acta Crystallogr B 53:569
Braga D (2003) Chem Commun 22:2751
Walsh RDB, Bradner MW, Fleischman S, Morales LA, Moulton B, Rodriguez-Hornedo N, Zaworotko MJ (2003) Chem Commun 186
Wenger M, Bernstein J (2006) Angew Chem Int Ed 45:7966
Lehn J-M (2002) Science 295:2400
Desiraju GR (2002) Acc Chem Res 35:565
Crihfield A, Hartwell J, Phelps D, Walsh RB, Harris JL, Payne JF, Pennington WT, Hanks TW (2003) Cryst Growth Des 3:313
Britton D, Gleason WB (2002) Acta Crystallogr Sect E Struct Rep Online 58:o1375
Metrangolo P, Meyer F, Pilati T, Resnati G, Terraneo G (2007) Acta Crystallogr Sect E Struct Rep Online 63:o4243
Liantonio R, Metrangolo P, Pilati T, Resnati G (2002) Acta Crystallogr Sect E Struct Rep Online 58:o575
Walsh RB, Padgett CW, Metrangolo P, Resnati G, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:165
Cincic D, Friscic T, Jones W (2008) Chem Mater 20:6623
Metrangolo P, Pilati T, Resnati G, Stevenazzi A (2004) Chem Commun 1492
Cardillo P, Corradi E, Lunghi A, Meille SV, Messina MT, Metrangolo P, Resnati G (2000) Tetrahedron 56:5535
Syssa-Magale J-L, Boubekeur K, Schollhorn B (2005) J Mol Struct 737:103
Jay JI, Padgett CW, Walsh RDB, Hanks TW, Pennington WT (2001) Cryst Growth Des 1:501
Aakeröy CB, Wijethunga TK, Desper J (2014) CrystEngComm 16:28
Clark T, Hennemann M, Murray JS, Politzer P (2007) J Mol Model 13:291
Politzer P, Lane P, Concha MC, Ma Y, Murray JS (2007) J Mol Model 13:305
Göbell M, Tchitchanov BH, Murray JS, Politzer P, Klapötkel TM (2009) Nat Chem 1:229
Politzer P, Murray JS, Clark T (2010) Phys Chem Chem Phys 12:7748
Ji B, Wang W, Deng D, Zhang Y (2011) Cryst Growth Des 11:3622
Syssa-Magalé J, Boubekeur K, Palvadeau P, Meerschaut A, Schöllhorn B (2005) CrystEngComm 7:302
Syssa-Magalé J-L, Boubekeur K, Palvadeau P, Meerschaut A, Schöllhorn B (2004) J Mol Struct 691:79
Aakeröy CB, Chopade PD, Desper J (2011) Cryst Growth Des 11:5333
Khavasi HR, Tehrani AA (2013) CrystEngComm 15:5813
Bernstein J (2002) Polymorphism in molecular crystals, IUCr monographs on crystallography. Clarendon Press, Oxford
Metrangolo P, Resnati G, Pilati T, Biella S (2008) In: Metrangolo P, Resnati G (eds) Halogen bonding: fundamentals and applications. Springer, Berlin, p 105
De Santis A, Forni A, Liantonio R, Metrangolo P, Pilati T, Resnati G (2003) Chem Eur J 9:3974
Yamamoto HM, Kosaka Y, Maeda R, Yamaura J, Nakao A, Nakamura T, Kato R (2008) ACS Nano 2:143
Saccone M, Cavallo G, Metrangolo P, Pace A, Pibiri I, Pilati T, Resnati G, Terraneo G (2013) CrystEngComm 15:3102
Liu P, Ruan C, Li T, Ji B (2012) Acta Crystallogr Sect E Struct Rep Online 68(Pt 5):o1431
Cincic D, Friščić T, Jones W (2008) Chem Eur J 14:747
Cincic D, Friščić T, Jones W (2011) CrystEngComm 13:3224
Bertani R, Chaux F, Gleira M, Metrangolo P, Milani R, Pilati T, Resnati G, Sansotera M, Venzo A (2007) Inorg Chim Acta 360:1
Metrangolo P, Meyer F, Pilati T, Proserpio DM, Resnati G (2007) Chem Eur J 13:5765
Aakeröy CB, Rajbanshi A, Metrangolo P, Resnati G, Parisi MF, Desper J, Pilati T (2012) CrystEngComm 14:6366
Caronna T, Liantonio R, Logothetis TA, Metrangolo P, Pilati T, Resnati G (2004) J Am Chem Soc 126:4500
Metrangolo P, Meyer F, Pilati T, Proserpio DM, Resnati G (2008) Cryst Growth Des 8:654
Vartanian M, Lucassen ACB, Shimon LJW, van der Boom ME (2008) Cryst Growth Des 8:786
Baldrighi M, Metrangolo P, Meyer F, Pilati T, Proserpio D, Resnati G, Terraneo G (2010) J Fluorine Chem 131:1218
Marras G, Metrangolo P, Meyer F, Pilati T, Resnati G, Vij A (2006) New J Chem 30:1397
Scarso A, Shivanyuk A, Hayashida O, Rebek J Jr (2003) J Am Chem Soc 125:6239
Chen J, Rebek J Jr (2002) Org Lett 4:327
Aakeröy CB, Rajbanshi A, Desper J (2011) Chem Commun 47:11411
Focsaneanu K-S, Scaiano JC (2005) Photochem Photobiol Sci 4:817
Manandhar E, Broome JH, Myrick J, Lagrone W, Cragg PJ, Wallace KJ (2011) Chem Commun 47:8796
Zhang B, Sun J, Bi C, Yin G, Shi PY, Sheng L (2011) New J Chem 35:849
Xue L, Charles I, Arya DP (2002) Chem Commun 70
Okamoto A, Ochi Y, Saito I (2005) Chem Commun 1128
Nakamura M, Ohtoshi Y, Yamana K (2005) Chem Commun 5163
Østergaard M, Hrdlicka PJ (2011) Chem Soc Rev 40:5771
Figueira-Duarte TM, Mullen K (2011) Chem Rev 111:7260
Shen QJ, Wei HQ, Zou WS, Sun HL, Jin WJ (2012) CrystEngComm 14:1010
Jin H, Plonka AM, Parise JB, Goroff NS (2013) CrystEngComm 15:3106
Sharma Goel SK, Rezan SA, Misra VN, Tripathi KN (2003) J Mater Sci Lett 22:737
Chae SK, Park H, Yoon J, Lee CH, Ahn DJ, Kim JM (2007) Adv Mater 19:521
Ahn DJ, Kim JM (2008) Acc Chem Res 41:805
Goroff NS, Curtis SM, Webb JA, Fowler FW, Lauher JW (2005) Org Lett 7:1891
Clark SM, Friščić T, Jones W, Mandal A, Sun C, Parker JE (2011) Chem Commun 47:2526
Etter MC (1990) Acc Chem Res 23:120
Aakeröy CB, Epa KN, Forbes S, Desper J (2013) CrystEngComm 15:5946
Aakeröy CB, Epa KN, Forbes S, Schultheiss N, Desper J (2013) Chem A Eur J 19:14998
Aakeröy CB, Desper J, Smith MM (2007) Chem Commun 3936
Aakeröy CB, Baldrighi M, Desper J, Metrangolo P, Resnati G (2013) Chem A Eur J 19:16240
Aakeröy CB, Panikkattu S, Chopade PD (2013) J Desper CrystEngComm 15:3125
Messina MT, Metrangolo P, Panzeri W, Pilati T, Resnati G (2001) Tetrahedron 57:8543
Oh SY, Nickels CW, Garcia F, Jones W, Friščić T (2012) CrystEngComm 14:6110
Aakeröy CB, Chopade PD, Ganser C, Desper J (2011) Chem Commun 47:4688
Tothadi S, Desiraju GR (2013) Chem Commun 49:7791
Erdélyi M (2012) Chem Soc Rev 41:3547
Abraham MH (1993) Pure and Appl Chem 65:2503
Schneider H-J (2003) Method Prin Med Chem 19:21
Libri S, Jasim NA, Perutz RN, Brammer L (2008) J Am Chem Soc 130:7842
Metrangolo P, Panzeri W, Recupero F, Resnati G (2002) J Fluorine Chem 114:27
Cabot R, Hunter CA (2005) Chem Commun 2009
Laurence C, Queignec-Cabanetos M, Dziembowska T, Queignec R, Wojtkowiak BJ (1982) Chem Soc Perkin Trans 2 1605
Sarwar MG, Dragisic B, Salsberg LJ, Gouliaras C, Taylor MS (2010) J Am Chem Soc 132:1646
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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
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DOI: https://doi.org/10.1007/128_2014_567
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