X-ray crystallography, an essential tool for the determination of thermodynamic relationships between crystalline polymorphs
Tóm tắt
Từ khóa
Tài liệu tham khảo
Abbé Haüy, 1784
Klaproth, 1788, Phosphorsäure, ein Bestandteil des Apatits (digitally available from the Münchener Digitalisierungszentrum, http://www.mdz-nbn), Bergmännisches J, 1, 294
Stromeyer, 1814, De la différence chimique entre l’arragonite et le spath calcaire rhomboïdal, Ann Chim, 92, 254
Mitscherlich, 1823, Sur le rapport qui existe entre les proportions chimiques et la forme cristallin. IIIme mémoire : sur les corps qui affectent deux formes cristallines différentes, Ann Chim Phys, 24, 264
Bernstein, 1978, Conformational polymorphism – influence of crystal-structure on molecular-conformation, J Am Chem Soc, 100, 673, 10.1021/ja00471a001
Raiteri, 2005, Exploring polymorphism: the case of benzene, Angew Chem Int Ed, 44, 3769, 10.1002/anie.200462760
Gibbs, 1875, On the equilibrium of heterogeneous substances, first part, Trans Conn Acad, 3, 108
Gibbs, 1877, On the equilibrium of hetergeneous substances (concluded), Trans Conn Acad, 3, 343
Gibbs, 1928, 154
Gibbs, 1873, Graphical methods in the thermodynamics of fluids, Trans Conn Acad, 2, 309
Gibbs, 1873, A method of geometrical representation of the thermodynamic properties of substances by means of surfaces, Trans Conn Acad, 2, 382
Gibbs, 1906
La pharmacie à la recherche du polymorphe stable. L’usine nouvelle 2001;58–61.
Pertsin, 1987
Atahan-Evrenk, 2014, Prediction and calculation of crystal structures, methods and applications, 10.1007/978-3-319-05774-3
Neumann, 2008, A major advance in crystal structure prediction, Angew Chem Int Ed, 47, 2427, 10.1002/anie.200704247
Price, 2004, The computational prediction of pharmaceutical crystal structures and polymorphism, Adv Drug Deliver Rev, 56, 301, 10.1016/j.addr.2003.10.006
Gavezzotti, 2007, A solid state chemist's view of the crystal polymorphism of organic compounds, J Pharm Sci, 96, 2232, 10.1002/jps.20870
Dzyabchenko, 2008, From molecule to solid: prediction of organic crystal structures, Russian J Phys Chem, 82, 1663, 10.1134/S0036024408100075
Perrin, 2009, Crystal structure determination of the elusive paracetamol Form III, Chem Commun, 3181, 10.1039/b822882e
Clapeyron, 1834, Mémoire sur la puissance motrice de la chaleur, J Ecole Polytech, 18, 153
Bakhuis Roozeboom, 1901, 1
Le Chatelier, 1884, Sur un énoncé général des lois des équilibres chimiques, Comptes Rendus Acad Sci, 99, 786
Ostwald, 1897, Studien über die Bildung und Umwandlung fester Körper. 1. Abhandlung: Übersättigung und Überkaltung, Zeitschrift fuer Physikalische Chemie, 22, 289, 10.1515/zpch-1897-2233
Riecke, 1890, Spezielle Fälle von Gleichgewichterscheinungen eines aus mehreren Phasen zusammengesetzten Systemes, Z Phys Chem (Munich), 6, 411, 10.1515/zpch-1890-0135
Clausius, 1864
Clausius, 1868
Hatakeyama, 1999
Rollet, 1972
Höhne, 1996
Buerger, 1951, Crystallographic aspects of phase transformations, 183
Buerger, 1972, Phase transformations, Sov Phys Crystallogr, 16, 959
Verma, 1966
Burger, 1979, Polymorphism of pharmaceuticals and other molecular-crystals. 1. Theory of thermodynamic rules, Mikrochim Acta, 2, 259, 10.1007/BF01197379
Grunenberg, 1996, Theoretical derivation and practical application of energy temperature diagrams as an instrument in preformulation studies of polymorphic drug substances, Int J Pharm, 129, 147, 10.1016/0378-5173(95)04283-0
Caira, 1998, Crystalline polymorphism of organic compounds, Top Curr Chem, 198, 163, 10.1007/3-540-69178-2_5
Lehmann, 1888, 1
Bridgman, 1914, Change of phase under pressure I. The phase diagram of 11 substances with special reference to the melting curve, Phys Rev, 3, 126, 10.1103/PhysRev.3.126
Mallard, 1884, Sur la variation, avec la pression, de la température à laquelle se produit la transformation de l’iodure d’argent, Comptes Rendus Acad Sci, 99, 157
Kitaigorodsky, 1961
Anton-paar. http://www.anton-paar.com/fr-fr/produits/groupe/xrd/.
Oxcryo. http://www.oxcryo.com/coolers-for-diffraction/.
Jayaraman, 1983, Diamond anvil cell and high-pressure physical investigations, Rev Mod Phys, 55, 65, 10.1103/RevModPhys.55.65
Céolin, 1996, Phenomenology of polymorphism. 3. p T diagram and stability of piracetam polymorphs, J Solid State Chem, 122, 186, 10.1006/jssc.1996.0100
Gavezzotti, 2006, Molecular aggregation. Structure analysis and molecular simulation of crystals and liquids, 277
Goodman, 2004, A note on the relationship between organic solid density and liquid density at the triple point, J Chem Eng Data, 49, 1512, 10.1021/je034220e
Ceolin, 2015, The topological pressure-temperature phase diagram of ritonavir, an extraordinary case of crystalline dimorphism, Ann Pharm Fr, 73, 22, 10.1016/j.pharma.2014.09.003
Rietveld, 2015, Phenomenology of crystalline polymorphism: overal monotropic behavior of the cardiotonic agent FK664 forms A and B, J Therm Anal Calorim, 120, 1079, 10.1007/s10973-014-4366-2
Lide, 2003
Ledru, 2007, High pressure differential scanning Calorimetry investigations on the pressure dependence of the melting of paracetamol polymorphs I and II, J Pharm Sci, 96, 2784, 10.1002/jps.20903
Ceolin, 2008, Overall monotropic behavior of a metastable phase of biclotymol, 2,2′-methylenebis(4-chloro-3-methyl-isopropylphenol), inferred from experimental and topological construction of the related P-T state diagram, J Pharm Sci, 97, 3927, 10.1002/jps.21285
Barrio, 2009, Polymorphism of progesterone: relative stabilities of the orthorhombic phases I and II inferred from topological and experimental pressure-temperature phase diagrams, J Pharm Sci, 98, 1657, 10.1002/jps.21541
Rietveld, 2011, Dimorphism of the prodrug L-tyrosine ethyl ester: pressure-temperature state diagram and crystal structure of phase II, J Pharm Sci, 100, 4774, 10.1002/jps.22672
Rietveld, 2011, Enantiomer resolution by pressure increase: inferences from experimental and topological results for the binary enantiomer system (R)- and (S)-mandelic acid, J Phys Chem B, 115, 14698, 10.1021/jp209328d
Barrio, 2012, Pressure-temperature state diagram for the phase relationships between benfluorex hydrochloride forms I and II: a case of enantiotropic behavior, J Pharm Sci, 101, 1073, 10.1002/jps.22821
Rietveld, 2012, Overall stability for the ibuprofen racemate: experimental and topological results leading to the pressure-temperature phase relationships between its racemate and conglomerate, J Phys Chem B, 116, 5568, 10.1021/jp302508g
Perrin, 2013, Rimonabant dimorphism and its pressure-temperature phase diagram: a delicate case of overall monotropic behavior, J Pharm Sci, 102, 2311, 10.1002/jps.23612
Gana, 2013, Benzocaine polymorphism: pressure-temperature phase diagram involving forms II and III, Int J Pharm, 456, 480, 10.1016/j.ijpharm.2013.08.031
Bauer, 2001, Ritonavir: an extraordinary example of conformational polymorphism, Pharm Res, 18, 859, 10.1023/A:1011052932607
Rietveld, 2015, Rotigotine: unexpected polymorphism with predictable overall monotropic behavior, J Pharm Sci, 10.1002/jps.24626
Haüy, 1817, Comparaison des formes cristallines de la stontiane carbonatée avec celle de l’arragonite, Ann Chim Phys, 5, 439
Falini, 1996, Control of aragonite or calcite polymorphism by mollusk shell macromolecules, Science, 271, 67, 10.1126/science.271.5245.67
Neumann, 2015, Combined crystal structure prediction and high-pressure crystallization in rational pharmaceutical polymorph screening, Nat Commun, 6, 7793, 10.1038/ncomms8793