Abstract
This chapter discusses the phenomenon of polymorphism in organic and organometallic compounds. Polymorphism is first introduced and then, to give the work some context, background information is given concerning properties and techniques for characterizing the solid phases. In particular, desolvation and interconverstion are examined, and the gas–solid reactions are presented as a successful route to obtaining new crystalline phases. Co-crystal definition is then described and the problem in distinguishing co-crystals and salts is evaluated.
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References
Bernstein J (2002) Polymorphism in molecular crystals. Oxford University Press, Oxford, p 352
Dunitz JD, Bernstein J (1995) Acc Chem Res 28:193–200
Klaproth MH (1798) Bergmannische J I:294–299
Mitscherlich E (1823) Abhl Akad Berlin 43
McCrone WC (1965) In: Fox D, Labes MM, Weissemberg A (eds) Polymorphism in physics and chemistry of the organic solid state, vol 2. Interscience, New York, p 726
Findlay AF (1951) The phase rule and its applications, 9th edn. Dover, New York, pp 7–16
Buerger MJ, Bloom MC (1937) Z Kristallogr 96:182–200
Sirota NN (1982) Cryst Res Technol 17:661–691
Kuhnert-Brandstatter M (1965) Pure Appl Chem 10:133–144
Kuhnert-Brandstatter M (1971) Thermomicroscopy in the analysis of pharmaceuticals. International series of monographs in analytical chemistry, vol 45. Pergamon, Oxford
Sarma JARP, Desiraju GR (1999) In: Seddon KR, Zaworotko M (eds) Crystal engineering: the design and application of functional solids. Kluwer, Dorderecht, pp 325–356
Griesser UJ (2002) Acta Crystallogr A 58(suppl):c241
Gorbitz CH, Hersleth HP (2000) Acta Crystallogr B 56:526–534
Griesser UJ, Burger A (1999) Acta Crystallogr A 55(suppl):400
Desiraju GR (1989) Crystal engineering: the design of organic solids. Elsevier, Amsterdam
Braga D, Grepioni F, Orpen AG (eds) (1999) Crystal engineering: from molecules and crystals to materials. In: Proceedings of the NATO Advanced Study Institute. 12–23 May 1999, Erice, Italy, p 500
Braga D, Grepioni F, Desiraju GR (1998) Chem Rev 98:1375–1405
Blake AJ, Champness NR, Hubberstey P, Li W-S, Withersby MA, Schroder M (1999) Coord Chem Rev 183:117–138
Moulton B, Zaworotko MJ (2001) Chem Rev 101:1629–1658
Griesser UJ (2006) In: Hilfiker R (ed) The importance of solvates. Wiley, Weinheim, pp 211–233
Braga D, Maini L, de Sanctis G, Rubini K, Grepioni F, Chierotti MR, Gobetto R (2003) Chem Eur J 9:5538–5548
Vishweshwar P, McMahon JA, Peterson ML, Hickey MB, Shattock TR, Zaworotko MJ (2005) Chem Commun, pp 4601–4603
Seddon KR (2004) Cryst Growth Des 4:1087–1087
Bernstein J (2005) Chem Commun, pp 5007–5012
Nangia A (2006) Cryst Grow Des 6:2
Burger A (1983) Topics in pharmaceutical sciences. Elsevier, Amsterdam, p 347
Cabri W, Ghetti P, Pozzi G, Alpegiani M (2007) Org Process Res Dev 11:64–72
Lara-Ochoa F, Espinosa-Perez G (2007) Cryst Growth Des 7:1213– 1215
Raw AS, Yu LX (2004) Adv Drug Delivery Rev 56:235–236
Yu L, Stephenson GA, Mitchell CA, Bunnell CA, Snorek SV, Bowyer JJ, Borchardt TB, Stowell JG, Byrn SR (2000) J Am Chem Soc 122:585
Chen S, Xi H, Yu L (2005) J Am Chem Soc 127:17439–17444
Braga D, Bernstein J (2007) In: Dario B, Grepioni F (eds) Crystal polymorphism: challenges at crossroads of science and technology. Wiley, Weinheim, pp 293–314
Gobetto R (2007) In: Braga D, Grepioni F (eds) Solid state NMR. Wiley, Weinheim, pp 266–292
Grunenberg A, Henck JO, Siesler HW (1996) Int J Pharm 129:147–158
Henck J-O, Kuhnert-Brandstatter M (1999) J Pharm Sci 88:103–108
Almarsson O, Zaworotko MJ (2004) Chem Commun, p 1889
Aakeröy CB, Beatty AM, Helfrich BA (2001) Angew Chem Int Ed 40:3240–3242
Price CP, Grzesiak AL, Matzger AJ (2005) J Am Chem Soc 127:5512–5517
Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR (2004) Adv Drug Delivery Rev 56:275–300
Braga D, Grepioni F (2005) Chem Commun, pp 3635–3645
Trask AV, Shan N, Motherwell WDS, Jones W, Feng S, Tan RBH, Carpenter KJ (2005) Chem Commun, pp 880–882
Braga D, Grepioni F (2004) Angew Chem Int Ed 43:4002–4011
Griesser UJ, Burger A (1991) Eur J Pharm Biopharm 37:118
York P (2005) Chem World 2:50
Shekunov YB, York P (2001) J Cryst Growth 211:122
Desiraju GR (2003) Crystal design: structure and function. Wiley, Chichester, p 420
Bauer J, Spanton S, Henry R, Quick J, Dziki W, Porter W, Morris J (2001) Pharm Res 18:859
Kirpal A (1907) Monatsh Chem 28:439–445
Tong ML, Wang J, Hu S (2005) J Solid State Chem 178:1518–1525
Tong ML, Wang J, Hu S, Batten SR (2005) Inorg Chem Commun 8:48–51
Senevirathna MKI, Pitigala P, Perera VPS, Tennakone K (2005) Langmuir 21:2997–3001
International Centre for Diffraction Data (2005) Powder diffraction file PDF-2. ICDD, Newton Square, PA
Takusagawa F, Hirotsu K, Shimada A (1973) Bull Chem Soc Jpn 46:2669–2675
Braga D, Maini L, Fagnano C, Taddei P, Chierotti MR, Gobetto R (2007) Chem Eur J 13:1222–1230
Braga D, Maini L (2004) Chem Commun, pp 976–977
Braga D, Rubini K, Maini L (2004) Cryst Eng Commun 6:236–238
Braga D, Cojazzi G, Abati A, Maini L, Polito M, Scaccianoce L, Grepioni F (2000) J Chem Soc Dalton Trans, pp 3969–3975
Caira MR (1998) Top Curr Chem 198:163–208
Caira MR, Nassimbeni LR, Timme M (1995) J Pharm Sci 84:884–888
De Villiers MM, Van der Watt JG, Lotter AP (1991) Drug Dev Ind Pharm 17:1295–1303
Braga D, Maini L, Grepioni F (1999) Chem Commun, pp 937–938
Chen X, Morris KR, Griesser UJ, Byrn SR, Stowell JG (2002) J Am Chem Soc 124:15012–15019
Braga D, Cadoni M, Grepioni F, Maini L, Rubini K (2006) Cryst Eng Commun 8:756–763
Braga D, Grepioni F, Polito M, Chierotti MR, Ellena S, Gobetto R (2006) Organometallics 25:4627–4633
Lewis TC, Tocher DA, Price SL (2004) Cryst Grow Des 4:979–987
Bolton W (1963) Acta Cryst 16:166–173
Jeffrey GA, Ghose S, Warwicker JO (1961) Acta Cryst 14:881–887
Al-Karaghouli AR, Abdul-Wahab B, Ajaj E, Al-Asaff S (1977) Acta Crystallogr Sect B Struct Sci B33:1655–1660
Braga D, Cadoni M, Grepioni F, Maini L, Streek JVD (2007) New J Chem 11:1935–1940 doi: 10.1039/b704772j
Etter MC, Reutzel SM, Choo CG (1993) J Am Chem Soc 115:4411–4412
Zaworotko MJ (2007) Cryst Grow Des 7:4–9
Hickey MB, Peterson ML, Scoppettuolo LA, Morrisette SL, Vetter A, Guzman H, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson O (2007) Eur J Pharm Biopharm 67:112–119
Trask AV (2007) Mol Pharm 4:301–309
Desiraju GR (2003) Cryst Eng Commun 5:466–467
Dunitz JD (2003) Cryst Eng Commun 5:506
Aakeroy CB, Salmon DJ (2005) Cryst Eng Commun 7:439
Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ (2006) J Pharm Sci 95:499–516
Stahly GP (2007) Cryst Growth Des 7:1007–1026
Bernstein J (2005) Cryst Growth Des 5:1661–1662
Nangia A (2006) Cryst Growth Des 6:2–4
Bond AD (2007) Cryst Eng Commun 9:833–834
Bock H, Holl S (2001) Z Naturforsch B 56:111
Hassel OJH (1954) Acta Chem Scand 8:873
Hassel O, Stromme KO (1959) Acta Chem Scand 13:1775
Bond AD (2003) Chem Commun, pp 250–251
Bond AD (2006) Cryst Eng Commun 8:333–337
Takayanagi H, Toubai Y, Goto M, Yamaguchi S, Ogura H (1991) Chem Pharm Bull 39:2491
Banerjee A, Brown CJ (1985) Acta Crystallogr Sect C Cryst Struct Commun 41:82
Herbstein FH, Kaftory M (1976) Acta Crystallogr Sect B Struct Sci 32:387
Childs SL, Stahly GP, Park A (2007) Mol Pharm 4:323–338
Wilson CC (2001) Acta Crystallogr Sect B Struct Sci B57:435–439
Steiner T, Majerz I, Wilson CC (2001) Angew Chem Int Ed 40: 2651–2654
Wiechert D, Mootz D (1999) Angew Chem Int Ed 38:1974–1976
Braga D, Maini L, Polito M, Grepioni F (2004) Struct Bond 111:1– 32
Gobetto R, Nervi C, Valfre E, Chierotti MR, Braga D, Maini L, Grepioni F, Harris RK, Ghi PY (2005) Chem Mater 17:1457– 1466
Gobetto R, Nervi C, Chierotti MR, Braga D, Maini L, Grepioni F, Harris RK, Hodgkinson P (2005) Chem Eur J 11:7461–7471
Sreekanth BR, Vishweshwar P, Vyas K (2007) Chem Commun, pp 2375–2377
Bucar D-K, Henry RF, Lou X, Borchardt TB, Zhang GGZ (2007) Chem Commun, pp 525–527
Zhang GGZ, Henry RF, Borchardt TB, Lou X (2007) J Pharm Sci 96:990–995
Childs SL, Hardcastle KI (2007) Cryst Eng Commun 9:364–367
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Braga, D., Grepioni, F., Maini, L., Polito, M. (2009). Crystal Polymorphism and Multiple Crystal Forms. In: Hosseini, M. (eds) Molecular Networks. Structure and Bonding, vol 132. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-01367-6_7
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DOI: https://doi.org/10.1007/978-3-642-01367-6_7
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