Computational prediction of salt and cocrystal structures - Does a proton position matter?

International Journal of Pharmaceutics

Volumn 418, Issue 2, 2011, Pages 187-198

  Mohamed, Sharmarke ^a   Tocher, Derek A ^a   Price, Sarah L ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Cocrystal; Crystal structure prediction; Crystallization; Proton transfer; Salt

Indexed keywords

4 CYANOPYRIDINE 4 FLUOROBENZOIC ACID; 4 CYANOPYRIDINIUM 4 FLUOROBENZOATE; 4 DIMETHYLAMINOPYRIDINIUM MALEIC ACID; CARBOXYLIC ACID; CARBOXYLIC ACID SALT; ISOPHTHALIC ACID; PROTON; PYRIDINE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENERGY; HYDROGEN BOND; PREDICTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

BENZOIC ACIDS; COMPUTER SIMULATION; CRYSTALLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; PROTONS; PYRIDINES; SALTS;

EID: 80052963861     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.03.063     Document Type: Article

References (56)

1. C.B. Aakeroy, M.E. Fasulo, and J. Desper Cocrystal or salt: does it really matter? Mol. Pharm. 4 2007 317 322 (Pubitemid 46983948)
2. A. Albert, and E.P. Serjeant The Determination of Ionization Constants: A Laboratory Manual 1984 Cambridge University Press
3. F.H. Allen The Cambridge Structural Database: a quarter of a million crystal structures and rising Acta Crystallogr. B 58 2002 380 388 (Pubitemid 135702674)
4. F.H. Allen, O. Kennard, and D.G. Watson Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds J. Chem. Soc. Perkin Trans. 2 1987 S1 S19
5. O. Almarsson, and M.J. Zaworotko Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem. Commun. 17 2004 1889 1896 (Pubitemid 39335992)
6. T. Beyer, and S.L. Price Dimer or catemer? Low-energy crystal packings for small carboxylic acids J. Phys. Chem. B 104 2000 2647 2655 (Pubitemid 33685483)
7. B.R. Bhogala, S. Basavoju, and A. Nangia Tape and layer structures in cocrystals of some di- and tricarboxylic acids with 4,4′-bipyridines and isonicotinamide. From binary to ternary cocrystals CrystEngComm 7 2005 551 562 (Pubitemid 41396850)
8. D.E. Braun, P.G. Karamertzanis, J.B. Arlin, A.J. Florence, V. Kahlenberg, D.A. Tocher, U.J. Griesser, and S.L. Price Solid-state forms of beta-resorcylic acid: how exhaustive should a polymorph screen be? Cryst. Growth Des. 11 2011 210 220
9. C.M. Breneman, and K.B. Wiberg Determining atom-centered monopoles from molecular electrostatic potentials - the need for high sampling density in formamide conformational-analysis J. Comput. Chem. 11 1990 361 373
10. H.C. Brown Determination of Organic Structures by Physical Methods 1955 Academic Press New York
11. Bruker AXS Inc.; 2003. SAINT+ Madison, Wisconsin, USA.
12. S.L. Childs, G.P. Stahly, and A. Park The salt-cocrystal continuum: the influence of crystal structure on ionization state Mol. Pharm. 4 2007 323 338 (Pubitemid 46983949)
13. J.A. Chisholm, and S. Motherwell COMPACK: a program for identifying crystal structure similarity using distances J. Appl. Crystallogr. 38 2005 228 231 (Pubitemid 40260770)
14. D.S. Coombes, S.L. Price, D.J. Willock, and M. Leslie Role of electrostatic interactions in determining the crystal structures of polar organic molecules. A distributed multipole study J. Phys. Chem. 100 1996 7352 7360 (Pubitemid 126789406)
15. S.R. Cox, L.Y. Hsu, and D.E. Williams Nonbonded potential function models for crystalline oxohydrocarbons Acta Crystallogr. A 37 1981 293 301
16. A.J. Cruz-Cabeza, G.M. Day, and W. Jones Towards prediction of stoichiometry in crystalline multicomponent complexes Chem. Eur. J. 14 2008 8830 8836
17. A.J. Cruz-Cabeza, G.M. Day, W.D.S. Motherwell, and W. Jones Prediction and observation of isostructurality induced by solvent incorporation in multicomponent crystals J. Am. Chem. Soc. 128 2006 14466 14467 (Pubitemid 44749839)
18. S.H. Dale, M.R.J. Elsegood, M. Hemmings, and A.L. Wilkinson The co-crystallisation of pyridine with benzenepolycarboxylic acids: the interplay of strong and weak hydrogen bonding motifs CrystEngComm 6 2004 207 214 (Pubitemid 40464487)
19. G.M. Day, T.G. Cooper, A.J. Cruz-Cabeza, K.E. Hejczyk, H.L. Ammon, S.X.M. Boerrigter, J. Tan, R.G. Della Valle, E. Venuti, J. Jose, S.R. Gadre, G.R. Desiraju, T.S. Thakur, B.P. van Eijck, J.C. Facelli, V.E. Bazterra, M.B. Ferraro, D.W.M. Hofmann, M. Neumann, F.J.J. Leusen, J. Kendrick, S.L. Price, A.J. Misquitta, P.G. Karamertzanis, G.W.A. Welch, H.A. Scheraga, Y.A. Arnautova, M.U. Schmidt, J. van de Streek, A. Wolf, and B. Schweizer Significant progress in predicting the crystal structures of small organic molecules - a report on the fourth blind test Acta Crystallogr. B 65 2009 107 125
20. G.R. Desiraju Crystal engineering: a brief overview J. Chem. Sci. 122 2010 667 675
21. M.C. Etter, J.C. MacDonald, and J. Bernstein Graph-set analysis of hydrogen-bond patterns in organic-crystals Acta Crystallogr. B 46 1990 256 262
22. A. Fischer, J. Vaughan, and W.J. Galloway Structure + reactivity in pyridine series. 1. Acid dissociation constants of pyridinium ions J. Chem. Soc. 1964 3591 3596
23. A.J. Florence, J. Bardin, B. Johnston, N. Shankland, T.A.N. Griffin, and K. Shankland Structure determination from powder data: Mogul and CASTEP Z. Kristallogr. 2009 215 220
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03 2003 Gaussian Inc Wallingford, CT
25. T. Friscic, and W. Jones Recent advances in understanding the mechanism of cocrystal formation via grinding Cryst. Growth Des. 9 2009 1621 1637
26. M. Habgood, M.A. Deij, J. Mazurek, S.L. Price, and J.H. ter Horst Carbamazepine co-crystallization with pyridine carboxamides: rationalization by complementary phase diagrams and crystal energy landscapes Cryst. Growth Des. 10 2010 903 912
27. M. Habgood, and S.L. Price Isomers, conformers, and cocrystal stoichiometry: insights from the crystal energy landscapes of caffeine with the hydroxybenzoic acids Cryst. Growth Des. 10 2010 3263 3272
28. N. Issa, P.G. Karamertzanis, G.W.A. Welch, and S.L. Price Can the formation of pharmaceutical cocrystals be computationally predicted? I. Comparison of lattice energies Cryst. Growth Des. 9 2009 442 453
29. S.L. Johnson, and K.A. Rumon Infrared spectra of solid 1:1 pyridine-benzoic acid complexes; the nature of the hydrogen bond as a function of the acid-base levels in the complex J. Phys. Chem. 69 2008 74 86
30. P.G. Karamertzanis, P.R. Anandamanoharan, P. Fernandes, P.W. Cains, M. Vickers, D.A. Tocher, A.J. Florence, and S.L. Price Toward the computational design of diastereomeric resolving agents: an experimental and computational study of 1-phenylethylammonium-2-phenylacetate derivatives J. Phys. Chem. B 111 2007 5326 5336 (Pubitemid 46854524)
31. P.G. Karamertzanis, A.V. Kazantsev, N. Issa, G.W.A. Welch, C.S. Adjiman, C.C. Pantelides, and S.L. Price Can the formation of pharmaceutical co-crystals be computationally predicted? II. Crystal structure prediction J. Chem. Theory Comput. 5 2009 1432 1448
32. P.G. Karamertzanis, and C.C. Pantelides Ab initio crystal structure prediction - I. Rigid molecules J. Comput. Chem. 26 2005 304 324 (Pubitemid 40206705)
33. S. Karki, T. Friscic, W. Jones, and W.D.S. Motherwell Screening for pharmaceutical cocrystal hydrates via neat and liquid-assisted grinding Mol. Pharm. 4 2007 347 354 (Pubitemid 46983951)
34. 15N NMR spectroscopy J. Am. Chem. Soc. 128 2006 8199 8210 (Pubitemid 43967764)
35. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P.A. Wood Mercury CSD 2.0 - new features for the visualization and investigation of crystal structures J. Appl. Crystallogr. 41 2008 466 470 (Pubitemid 351398224)
36. C.F. Macrae, P.R. Edgington, P. McCabe, E. Pidcock, G.P. Shields, R. Taylor, M. Towler, and J. De Streek Mercury: visualization and analysis of crystal structures J. Appl. Crystallogr. 39 2006 453 457 (Pubitemid 43806296)
37. S. Mohamed, D.A. Tocher, M. Vickers, P.G. Karamertzanis, and S.L. Price Salt or cocrystal? A new series of crystal structures formed from simple pyridines and carboxylic acids Cryst. Growth Des. 9 2009 2881 2889
38. D.D. Perrin Dissociation Constants of Organic Bases in Aqueous Solution 1965 Butteworths London
39. M. Polito, E. D'Oria, L. Maini, P.G. Karamertzanis, F. Grepioni, D. Braga, and S.L. Price The crystal structures of chloro and methyl ortho-benzoic acids and their co-crystal: rationalizing similarities and differences CrystEngComm 10 2008 1848 1854
40. S.L. Price The computational prediction of pharmaceutical crystal structures and polymorphism Adv. Drug Deliv. Rev. 56 2004 301 319 (Pubitemid 38201427)
41. S.L. Price Computed crystal energy landscapes for understanding and predicting organic crystal structures and polymorphism Acc. Chem. Res. 42 2009 117 126
42. S.L. Price, M. Leslie, G.W.A. Welch, M. Habgood, L.S. Price, P.G. Karamertzanis, and G.M. Day Modelling organic crystal structures using distributed multipole and polarizability-based model intermolecular potentials Phys. Chem. Chem. Phys. 12 2010 8478 8490
43. B. Sarma, N.K. Nath, B.R. Bhogala, and A. Nangia Synthon competition and cooperation in molecular salts of hydroxybenzoic acids and aminopyridines Cryst. Growth Des. 9 2009 1546 1557
44. T.R. Shattock, K.K. Arora, P. Vishweshwar, and M.J. Zaworotko Hierarchy of supramolecular synthons: persistent carboxylic acid⋯pyridine hydrogen bonds in cocrystals that also contain a hydroxyl moiety Cryst. Growth Des. 8 2008 4533 4545
45. G.M. Sheldrick SHELXL97 Göttingen 1997 University of Göttingen Germany
46. G.M. Sheldrick SHELXS97 Göttingen 1997 University of Göttingen Germany
47. G.M. Sheldrick SADABS (Version 2.03) Program for Bruker Area Detector Absorption Correction Gottingen 2001 University of Gottingen Germany
48. J.S. Stevens, S.J. Byard, and S.L.M. Schroeder Characterization of proton transfer in co-crystals by X-ray photoelectron spectroscopy (XPS) Cryst. Growth Des. 10 2010 1435 1442
49. J.S. Stevens, S.J. Byard, and S.L.M. Schroeder Salt or co-crystal? Determination of protonation state by X-ray photoelectron spectroscopy (XPS) J. Pharm. Sci. 99 2010 4453 4457
50. A.J. Stone Distributed multipole analysis: stability for large basis sets J. Chem. Theory Comput. 1 2005 1128 1132
51. J. van de Streek, and S. Motherwell Searching the Cambridge Structural Database for polymorphs Acta Crystallogr. B 61 2005 504 510 (Pubitemid 43923838)
52. J. van de Streek, M.A. Neumann, and M.A. Perrin Validation of dispersion-corrected density functional theory calculations for the crystal structure prediction of molecular salts: a crystal structure prediction study of pyridinium chloride CrystEngComm 12 2010 3827 3833
53. P. Verwer, and F.J.J. Leusen Computer simulation to predict possible polymorphs K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry vol. 12 1998 John Wiley and Sons Inc New York 327 365 (Pubitemid 128464098)
54. D.E. Williams, and S.R. Cox Nonbonded potentials for azahydrocarbons: the importance of the coulombic interaction Acta Crystallogr. B 40 1984 404 417
55. D.E. Williams, and D.J. Houpt Fluorine nonbonded potential parameters derived from crystalline perfluorocarbons Acta Crystallogr. B 42 1986 286 295
56. C.C. Wilson, X.L. Xu, A.J. Florence, and N. Shankland Temperature dependence of proton transfer in 4-chlorobenzoic acid New J. Chem. 30 2006 979 981 (Pubitemid 44000929)