Abstract
The aims of crystal engineering are the understanding of intermolecular interactions and their application in the design of crystal structures with specific architectures and properties. In general, all types of crystal structures may be considered but this article is limited to organic molecular solids. Because of the molecular basis of organic chemistry, the obvious question arises as to whether there are simple connections between the structures of molecules and the crystals that they form. Answers to such questions may be found through a better and more comprehensive understanding of the interactions that control crystal packing. These interactions include strong and weak hydrogen bonds. Patterns of interactions, such as would be useful in a predictive sense, can be obtained by manual inspection or more rigorously with the use of crystallographic databases. Such patterns are termed supramolecular synthons and they depict the various ways in which complementary portions of molecules approach one another. The identification of synthons is then a key step in the design and analysis of crystal structures. Such ideas are also important in the understanding of phenomena such as biological recognition and drug-enzyme binding. Pattern identification also leads to the possibility of comparison of crystal structures. The use of the supramolecular synthon concept facilitates such efforts and in this regard it may be mentioned that synthons combine topological characteristics with chemical information, thereby offering a simplification that is optimal to drawing such comparisons.
Keywords
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Lehn J-M (1994) Perspectives in supramolecular chemistry: from the lock-and-key image to the information paradigm. In: Behr JP (ed) Perspectives in supramolecular chemistry, vol 1. The lock-and-key principle. The state of the art-100 years on. Wiley, Chichester, p307
Desiraju GR, Sharma CVK (1995) Crystal engineering and molecular recognition. Twin facets of supramolecular chemistry. In: Desiraju GR (ed) Perspectives in supramolecular chemistry, vol 2. The crystal as a supramolecular entity. Wiley, Chichester, p 31
Dunitz JD (1995) Thoughts on crystals as supermolecules. In: Desiraju GR (ed) Perspectives in supramolecular chemistry, vol 2. The crystal as a supramolecular entity. Wiley, Chichester, p 1
Kitaigorodskii AI (1973) Molecular crystals and molecules. Academic Press, New York
Desiraju GR (1989) Crystal engineering. The design of organic solids. Elsevier, Amsterdam
Desiraju GR (1996) Review of general principles. In: MacNicol DD, Toda F, Bishop R (eds) Comprehensive supramolecular chemistry, vol 6. Solid-state supramolecular chemistry: crystal engineering. Pergamon, Oxford, p 1
Corey EJ (1967) Pure Appl Chem 14:19
Corey EJ (1988) Chem Soc Rev 17: 111
Desiraju GR (1995) Angew Chem Int Ed Engl 34:2311
Corey EJ, Cheng X-M (1989) The logic of chemical synthesis. Wiley, New York
Desiraju GR (1998) Connections between molecular and supramolecular structure. Implications for self-assembly. In: Wuest JD (ed) Self-assembly in synthetic chemistry. NATO ARW Series, in press
Desiraju GR (1997) Chem Comm 1475
Reddy DS, Craig DC, Desiraju GR (1996) J Am Chem Soc 118:4090
Thaimattam R, Reddy DS, Xue F, Mak TCW, Nangia A, Desiraju GR (1998) New J Chem 143
Seebach D (1990) Angew Chem Int Ed Engl 29:1320
Fuhrhop J, Penzlin G (1994) Organic synthesis. Concepts, methods, starting materials, 2nd edn. VCH, Weinheim
Hanessian S, Franco J, Larouche B (1990) Pure Appl Chem 62:1887
Ho T-L (1988) Carbocycle construction in terpene synthesis. VCH, Weinheim
Nicolaou KC, Sorensen EJ (1995) Classics in total synthesis. VCH, Weinheim
Prinzbach H, Weber K (1994) Angew Chem Int Ed Engl 33:2239
Osawa E, Yonemitsu O (ed) (1992) Carbocyclic cage compounds. Chemistry and applications. VCH, New York
Woodward RB (1973) Pure Appl Chem 33:145
Eschenmoser A, Winter CE (1977) Science 196:1410
Armstrong RW, Beau J-M, Cheon SH, Christ WJ, Fujioka H, Ham W-H, Hawkins LD, Jin H, Kang SH, Kishi Y, Martinelli MJ, McWhorter WW, Mizuno M, Nakata M, Stutz AE, Talamas FX, Taniguchi M, Tino JA, Ueda K, Uenishi J, White JB, Yonaga M (1989) J Am Chem Soc 111:7530
Trost BM (1991) Science 254:1471
Holton RA, Somoza C, Kim H-B, Liang F, Biediger RJ, Boatman PD, Shindo M, Smith CC, Kim S, Nadizadeh H, Suzuki Y, Tao C, Vu P, Tang S, Zhang P, Murthi KK, Gentile LN, Liu JH (1994) J Am Chem Soc 116:1597
Nicolaou KC, Yang Z, Liu JJ, Ueno H, Natermet PG, Guy RK, Claiborne CF, Renaud J, Couladouros EA, Paulvannan K, Sorensen EJ (1994) Nature 367:630
Philp D, Stoddart JF (1996) Angew Chem Int Ed Engl 35:1154
Gavezzotti A, Filippini G (1994) J Phy Chem 98:4831
Gavezzotti A (1994) Acc Chem Res 27:309
Robertson JM (1951) Proc Roy Soc London Ser A 207:101
Desiraju GR, Gavezzotti A (1989) Acta Crystallogr B45:473
Ermer O, Eling A (1994) J Chem Soc Perkin Trans 2 925
Hanessian S, Simard M, Roelens S (1995) J Am Chem Soc 117:7630
Allen FA, Hoy VJ, Howard JAK, Thalladi VR, Desiraju GR, Wilson CC, McIntyre GJ (1997) JAm Chem Soc 119:3477
Allen FH, Davies JE, Galloy, JJ, Johnson O, Kennard O, Macrae CF, Mitchell EM, Mitchell GF, Smith JM, Watson DG (1991) J Chem Inf Comput Sci 31:187
Katz AK, Glusker JP, Nangia A, Desiraju GR (1997) unpublished results
Desiraju GR (1989) J Chem Soc Chem Commun 179
Zimmerman SC, Murray TJ (1993) Phil Trans R Soc Lond A 345:49
Burrows AD, Chan C-W, Chowdhry MM, McGrady JE, Mingos DMP (1995) Chem Soc Rev 329
Pranata J, Wierschke SG, Jorgensen WL (1991) JAm Chem Soc 113:2810
Jeffrey GA, Saenger W (1991) Hydrogen bonding in biological systems. Springer, Berlin Heidelberg NewYork
Lehn J-M (1990) Angew Chem Int Ed Engl 29:1304
Bryce MR (ed) (1997) J Mater Chem 7:1069 (Special issue on molecular assemblies and nanochemistry)
Lehn J-M, Mascal M, DeCian A, Fischer J (1990) J Chem Soc Chem Commun 479
Steiner T ( 1996) Cryst Rev 6:1
Desiraju GR (1996) Acc Chem Res 29:441
Steiner T (1997) Chem Commun 727
Biradha K, Nangia A, Desiraju GR, Carrell CJ, Carrell HL (1997) J Mater Chem 1111
MacGillivray LR, Atwood JL (1997) Chem Commun 477
Ashton PR, Collins AN, Fyfe MCT, Menzer S, Stoddart JF, Williams DJ (1997) Angew Chem Int Ed Engl 36:735
Sutor DJ (1962) Nature 195:68
Rubin J, Brennan T, Sundaralingam M (1972) Biochemistry 11:3112
Derewenda ZS, Lee L, Derewenda U (1995) J Mol Biol 252:248
Steiner T, Saenger W (1992) J Am Chem Soc 114:10,146
Wahl MC, Sundaralingam M (1997) Trends Biochem Sci 22:97
Leonard GA, McAuley-Hecht K, Brown T, Hunter WN (1995) Acta Crystallogr D51:136
Zhurkin VB, Raghunathan G, Ulyanov NB, Camerini-Otero RD, Jernigan RL (1994) J Mol Biol 239:181
Starikov EB, Steiner T (1997) Acta Crystallogr D53:345
Auffinger P, Louise-May S, Westhof E (1996) Faraday Discuss 103:151
Behr J-P (ed) (1994) Perspectives in supramolecular chemistry, vol 1. The lock-and-key principle. The state of the art 100 years on. Wiley, Chichester
Jorgensen WL (1991) Science 254:954
Boyd DB (1995) Computer-aided molecular design. In: Kent A, Williams JG (eds) Encyclopedia of computer science and technology, vol 33. Marcel Dekker, New York, p 41
Böhm H-J, Klebe G (1996) Angew Chem Int Ed Engl 35:2588
Klebe G (1994) J Mol Biol 237:212
Hahn M (1995) J Med Chem 38:2080
Nangia A, Biradha K, Desiraju GR (1996) J Chem Soc Perkin Trans 2 943
Threlfall TL (1995) Analyst 120:2435
Sarma JARP, Desiraju GR (1998) Polymorphism and pseudopolymorphism in organic crystals. A Cambridge Structural Database study. In: Seddon KR, Zaworotko MJ (eds), Crystal engineering. The design and applications of functional solids. NATO ASI Series, in press
McCrone WC (1965) Polymorphism. In: Fox D, Labes MM, Weissberger A (eds) Physics and chemistry of the organic solid state, vol 2. Interscience, New York, p 725
Buerger MJ, Bloom MC (1937) ZKristallogr A96:182
Davey RJ, Blagden N, Potts GD, Docherty R (1997) J Am Chem Soc 119:1767
Byrn SR (1982) Solid-state chemistry of drugs. Academic Press, New York, p 79
DeCamp WH (1996) Regulatory considerations in crystallisation processes for bulk pharmaceutical industry. A reviewer’s perspective. In: Myerson AS, Green DA, Meenan P (eds), Proceedings of 3rd International Workshop on Crystal Growth of Organic Materials. ACS Series, Washington DC, p 66
Dunitz JD, Bernstein J (1995) Acc Chem Res 28:193
Etter MC (1990) Acc Chem Res 23:120
Etter MC, MacDonald JC, Bernstein J (1990) Acta Crystallogr B46:256
Bernstein J, Davis RE, Shimoni L, Chang N-L (1995) Angew Chem Int Ed Engl 34:1555
Coupar PI, Ferguson G, Glidewell C (1996) Acta Crystallogr C52:2524
Kubicki M, Kindopp TW, Capparelli MV, Codding PW (1996) Acta Crystallogr B52:487
Subramanian K, Lakshmi S, Rajagopalan K, Koellner G, Steiner T (1996) J Mol Struct 384:121
Gavezzotti A (1996) Curr Opin Solid State Mater Sci 1:501
Hulliger J, Rogin P, Quintel A, Rechsteiner P, König O, Wübbenhorst M (1997) Adv Mater 9:662
Corey EJ, Barnes-Seeman D, Lee TW (1997) Tetrahedron Lett 38:1699
Pan F, Wong MS, Gramlich V, Brosshard Günter P (1996) Chem Comm 1557
Hoss R, König O, Kramer-Hoss V, Berger U, Rogin P, Hulliger J (1996) Angew Chem Int Ed Engl 35:2204
Navon O, Bernstein J, Khodorkovsky V (1997) Angew Chem Int Ed Engl 36:601
Carlucci L, Ciani G, Gudenberg DWv, Proserpio DM, Sironi A (1997) Chem Commun 631
Michaelides A, Skoulika S, Kiritsis V, Raptopoulou C, Terzis A (1997) J Chem Res (S) 204
Kräutler B, Müller T, Maynollo J, Gruber K, Kratky C, Ochsenbein P, Schwarzenbach D, Bürgi H-B (1996) Angew Chem Int Ed Engl 35:1204
Rowland RS (1995) Am Cryst Assoc Abstr 23:63
Thalladi VR, Nangia A, Desiraju GR (1997) unpublished results
Steiner T, Starikov EB, Amado AM, Teixeira-Dias JJC (1995) J Chem Soc Perkin Trans 2 1321
Madhavi NNL, Nangia A, Desiraju GR (1997) unpublished results
Brock CP, Duncan LL (1994) Chem Mater 6:1307
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Nangia, A., Desiraju, G.R. (1998). Supramolecular Synthons and Pattern Recognition. In: Weber, E., et al. Design of Organic Solids. Topics in Current Chemistry, vol 198. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-69178-2_2
Download citation
DOI: https://doi.org/10.1007/3-540-69178-2_2
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-64645-7
Online ISBN: 978-3-540-69178-5
eBook Packages: Springer Book Archive