DOI: 10.1002/jps.20261. Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure‐temperature and temperature‐volume phase diagrams

Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure‐temperature and temperature‐volume phase diagrams

10.1002/jps.20261

Crossref journal-article

Elsevier BV

Journal of Pharmaceutical Sciences (78)

Bibliography

Espeau, P., CÃ©olin, R., Tamarit, J., Perrin, M., Gauchi, J., & Leveiller, F. (2005). Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressureâtemperature and temperatureâvolume phase diagrams. Journal of Pharmaceutical Sciences, 94(3), 524â539.

Authors 6

Philippe Espeau (first)
René Céolin (additional)
Josep‐Lluis Tamarit (additional)
Marc‐Antoine Perrin (additional)
Jean‐Pierre Gauchi (additional)
Franck Leveiller (additional)

References 73 Referenced 111

{'key': '10.1002/jps.20261_bb0010', 'series-title': 'Polymorphism in pharmaceutical solids', 'first-page': '35', 'article-title': 'Application of the phase rule to the characterization of polymorphic systems', 'author': 'Brittain', 'year': '1999'} / Polymorphism in pharmaceutical solids / Application of the phase rule to the characterization of polymorphic systems by Brittain (1999)
{'key': '10.1002/jps.20261_bb0015', 'series-title': 'Solid‐state chemistry of drugs', 'author': 'Byrn', 'year': '1982'} / Solid‐state chemistry of drugs by Byrn (1982)
10.1039/an9952002435 / Analyst / Analysis of organic polymorphs: A review by Threlfall (1995)
10.1023/A:1011052932607 / Pharm Res / Ritonavir: An extraordinary example of conformational polymorphism by Bauer (2001)
10.1023/A:1016241927429 / Pharm Res / Pharmaceutical solids: A strategic approach to regulatory considerations by Byrn (1995)
10.1016/S0022-4596(05)80247-6 / J Solid State Chem / Phenomenology of polymorphism. I. (p,T) representation of trimorphism. General Rules. Application to the case of 3,6‐dichloro‐2,5‐dihydroxyterephthalate by Céolin (1992)
10.1006/jssc.1993.1059 / J Solid State Chem / Phenomenology of polymorphism. II. Criteria for overall p,T monotropy, applications to monochloracetic acid and to hydrazine monohydrate by Céolin (1993)
10.1006/jssc.1996.0100 / J Solid State Chem / Phenomenology of polymorphism. III. p,T diagram and stability of Piracetam polymorphs by Céolin (1996)
10.1023/A:1016058123659 / Pharm Res / Polymorphism of sulfanilamide: (II) Stability hierarchy of α‐, β‐ and γ‐forms from energy calculations by the atom–atom potential method and from the construction of the p, T phase diagram by Toscani (1996)
10.1006/jssc.2001.9456 / J Solid State Chem / Phenomenology of polymorphism. IV. The trimorphism of ferrocene and the overall metastability of its triclinic phase by Toscani (2002)
10.1016/S0040-6031(98)00442-0 / Thermochim Acta / An up‐to‐date approach to drug polymorphism by Toscani (1998)
10.1016/0040-6031(92)85019-R / Thermochim Acta / A new insight into phase separation in the As‐Te glasses from the (p,T) diagram of As2Te3 by Toscani (1992)
10.1016/S0040-6031(01)00561-5 / Thermochim Acta / Differential scanning calorimetry studies on substances with non‐negligible vapour pressure: T‐v and P‐T diagrams of adamantane by Espeau (2001)
10.1021/cm0112237 / Chem Mater / Polymorphism of 2‐methyl‐2‐chloropropane and 2,2‐dimethyl propane (neopentane): Thermodynamic evidence for a high‐pressure orientationally disordered rhombohedral phase through topological p, T diagrams by Barrio (2002)
{'key': '10.1002/jps.20261_bb0080', 'first-page': '123', 'article-title': 'Tetramorphism of fananserine: p,T diagram and stability hierarchy from crystal structure determinations and thermodynamic studies', 'volume': '11', 'author': 'Giovannini', 'year': '2001', 'journal-title': 'J Phys IV'} / J Phys IV / Tetramorphism of fananserine: p,T diagram and stability hierarchy from crystal structure determinations and thermodynamic studies by Giovannini (2001)
10.1515/zpch-1890-0635 / Z Phys Chem / Spezielle Fälle von Gleichgewichtserscheinungen eines aus mehreren Phase zusammengesetzten Systemes by Riecke (1890)
{'key': '10.1002/jps.20261_bb0090', 'series-title': 'Phase theory: The thermodynamics of heterogeneous equilibria', 'author': 'Oonk', 'year': '1981'} / Phase theory: The thermodynamics of heterogeneous equilibria by Oonk (1981)
10.1016/0927-796X(95)00188-3 / Mat Sci Eng R / Topology of P‐T‐X phase diagrams of binary systems. Polymorphism, metastable states and high‐pressure equilibria by Greenberg (1996)
10.1107/S0567740876012223 / Acta Crystallogr B / The monoclinic form of p‐hydroxyacetanilide by Haisa (1976)
10.1107/S0567740874007473 / Acta Crystallogr B / The orthorhombic form of p‐hydroxyacetanilide by Haisa (1974)
10.1016/0378-5173(95)04127-3 / Int J Pharm / A new pure paracetamol for direct compression: The orthorhombic form by Di Martino (1996)
10.1016/S0378-5173(99)00157-X / Int J Pharm / Formation and compression characteristics of prismatic polyhedral and thin plate‐like crystals of paracetamol by Garekani (1999)
10.1016/S0378-5173(00)00550-0 / Int J Pharm / Highly compressible paracetamol. I. Crystallization and characterization by Garekani (2000)
10.1021/js970483d / J Pharm Sci / Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution by Nichols (1998)
10.1107/S0108270197018386 / Acta Crystallogr C / The monoclinic form of acetaminophen at 150 K by Naumov (1998)
10.1016/S0009-2614(97)01180-9 / Chem Phys Lett / Zero point motion of the librating methyl group in p‐hydroxyacetanilide by Wilson (1997)
10.1016/S0921-4526(96)00889-7 / Physica B / Single‐crystal neutron diffraction of bio‐active small molecules by Wilson (1997)
10.1016/S0022-2860(96)09593-2 / J Mol Struct / Neutron diffraction of p‐hydroxyacetanilide (paracetamol): Libration or disorder of the methyl group at 100 K by Wilson (1997)
10.1016/S0301-0104(99)00138-X / Chem Phys / Methyl group dynamics in paracetamol and acetanilide: Probing the static properties of intermolecular hydrogen bonds formed by peptide groups by Johnson (1999)
10.1524/zkri.2000.215.11.693 / Z Kristallogr / Variable temperature study of the crystal structure of paracetamol (p‐hydroxyacetanilide), by single crystal neutron diffraction by Wilson (2000)
10.1007/BF02700697 / J Struct Chem / Anisotropy of crystal structure distortion in organic molecular crystals of drugs induced by hydrostatic compression by Shakhtshneider (1999)
10.1107/S0108768199013634 / Acta Crystallogr B / Anisotropy of crystal structure distortion of the monoclinic polymorph of acetaminophen at high hydrostatic pressures by Boldyreva (2000)
10.1007/BF01979491 / J Therm Anal / Preparation and physical characterization of forms II and III of paracetamol by Di Martino (1997)
10.1023/A:1016004206043 / J Therm Anal Calorim / Thermal behavior of paracetamol‐polymeric excipients mixtures by Giordano (2002)
10.1021/ja0102787 / J Am Chem Soc / The prediction, morphology, and mechanical properties of the polymorphs of paracetamol by Beyer (2001)
10.1016/0378-5173(86)90149-3 / Int J Pharm / True density and thermal expansion of pharmaceutical solids: Comparison of methods and assessment of crystallinity by Duncan‐Hewitt (1986)
{'key': '10.1002/jps.20261_bb0190', 'series-title': 'Thermomicroscopy in the analysis of pharmaceuticals', 'first-page': '183', 'author': 'Kühnert‐Brandstätter', 'year': '1971'} / Thermomicroscopy in the analysis of pharmaceuticals by Kühnert‐Brandstätter (1971)
10.1016/S0040-6031(99)00342-1 / Thermochim Acta / Thermal characterization of some new xanthine derivatives by Dănilă (2000)
10.1016/S0022-3697(00)00062-7 / J Phys Chem Solids / Thermally induced structural changes of acetaminophen in phase transition between the solid and liquid states monitored by combination analysis of FT‐IR/DSC microscopic system by Lin (2000)
10.1016/S0099-5428(08)60064-7 / Analytical profiles of drug substances / Acetaminophen by Fairbrother (1974)
10.1016/0378-5173(84)90104-2 / Int J Pharm / Non‐linear van't Hoff solubility‐temperature plots and their pharmaceutical interpretation by Grant (1984)
10.1002/jps.2600791214 / J Pharm Sci / Effects of solvent medium on solubility. V. Enthalpic and entropic contributions to the free energy changes of di‐substituted benzene derivatives in ethanol:water and ethanol:cyclohexane mixtures by Manzo (1990)
10.1016/0378-5173(92)90161-T / Int J Pharm / Solid‐state properties of drugs. I. Estimation of heat capacities for fusion and thermodynamic functions for solutions from aqueous solubility‐temperature dependence measurements by Prankerd (1992)
10.1007/BF02546623 / J Therm Anal / A DSC compositional analysis of some binary organic mixtures of pharmaceutical significance by Becket (1993)
{'key': '10.1002/jps.20261_bb0230', 'first-page': '421', 'article-title': 'Interaction between acetaminophen and β‐cyclodextrin by powder compaction', 'volume': '4', 'author': 'Gazzaniga', 'year': '1994', 'journal-title': 'STP Pharma Sci'} / STP Pharma Sci / Interaction between acetaminophen and β‐cyclodextrin by powder compaction by Gazzaniga (1994)
10.1248/cpb.44.1061 / Chem Pharm Bull / The behavior of paracetamol in mixtures of amphiprotic‐aprotic solvents. Relationship of solubility curves to specific and nonspecific interactions by Romero (1996)
10.1023/A:1012148910975 / Pharm Res / Differential molar heat capacities to test ideal solubility estimations by Neau (1997)
10.1021/js970137w / J Pharm Sci / An investigation into the melting behavior of binary mixes and solid dispersions of paracetamol and PEG4000 by Lloyd (1997)
10.1021/je990124v / J Chem Eng Data / Solubility of paracetamol in pure solvents by Granberg (1999)
10.1248/cpb.47.302 / Chem Pharm Bull / Paracetamol‐propyphenazone interaction and formulation difficulties associated with eutectic formation in combination solid dosage forms by Z̆alac (1999)
10.1007/BF01197380 / Mikrochim Acta (Wien) / On the polymorphism of pharmaceuticals and other molecular crystals. II. Applicability of thermodynamic rules by Buerger (1979)
10.1002/jps.2600840812 / J Pharm Sci / Inferring thermodynamic stability relationship of polymorphs from melting data by Yu (1995)
{'key': '10.1002/jps.20261_bb0270', 'first-page': '1', 'article-title': 'Zur Interpretation von Polymorphie‐Untersuchungen', 'volume': '28', 'author': 'Buerger', 'year': '1982', 'journal-title': 'Acta Pharm Technol'} / Acta Pharm Technol / Zur Interpretation von Polymorphie‐Untersuchungen by Buerger (1982)
10.1023/A:1010184805966 / J Therm Anal Calorim / In situ characterization of polymorphic forms. The potential of Raman techniques by Szelagiewicz (1999)
10.1023/A:1010180123331 / J Therm Anal Calorim / Thermodynamic analysis of DSC data for acetaminophen polymorphs by Sacchetti (2001)
{'key': '10.1002/jps.20261_bb0285', 'first-page': '1903', 'article-title': 'Conditions of preparation and crystallization of amorphous paracetamol', 'volume': '75', 'author': 'Politov', 'year': '2001', 'journal-title': 'Russ J Phys Chem'} / Russ J Phys Chem / Conditions of preparation and crystallization of amorphous paracetamol by Politov (2001)
10.1002/jps.10169 / J Pharm Sci / Physical stability of amorphous pharmaceuticals: Importance of configurational thermodynamic quantities and molecular mobility by Zhou (2002)
10.1016/0040-6031(94)01949-H / Thermochim Acta / Thermal analysis of glassy pharmaceuticals by Kerc̆ (1995)
10.1248/cpb.48.1105 / Chem Pharm Bull / Molecular mobility of the paracetamol amorphous form by Di Martino (2000)
10.1107/S0021889891006441 / J Appl Cryst / Indexing of powder diffraction patterns for low‐symmetry lattices by the successive dichotomy method by Boultif (1991)
10.1107/S0021889881009618 / J Appl Cryst / Unit‐cell refinement from powder diffraction scans by Pawley (1981)
10.1107/S0021889899009930 / J Appl Cryst / PowderSolve: A complete diffraction package for crystal structure solution from powder diffraction patterns by Engel (1999)
{'key': '10.1002/jps.20261_bb0320', 'series-title': "Introduction à l'étude de la métallurgie", 'first-page': '392', 'author': 'Le Châtelier', 'year': '1912'} / Introduction à l'étude de la métallurgie by Le Châtelier (1912)
10.1007/BF01375110 / Z Phys / Die thermische Ausdehnung von Quarzglas im Temperaturbereich von 0 bis 1060°C by Otto (1963)
{'key': '10.1002/jps.20261_bb0330', 'series-title': 'Statistics for experimenters', 'first-page': '116', 'author': 'Box', 'year': '1978'} / Statistics for experimenters by Box (1978)
{'key': '10.1002/jps.20261_bb0335', 'series-title': 'Applied regression analysis', 'first-page': '28', 'author': 'Draper', 'year': '1981'} / Applied regression analysis by Draper (1981)
10.1007/BF01908495 / J Therm Anal / Etude, par ATD, du diagramme d'état de l'arsenic et mesure de son enthalpie de fusion aux conditions du point triple by Rouland (1982)
{'key': '10.1002/jps.20261_bb0345', 'series-title': 'Phase equilibria, phase diagrams and phase transformations: Their thermodynamic basis', 'author': 'Hillert', 'year': '1998'} / Phase equilibria, phase diagrams and phase transformations: Their thermodynamic basis by Hillert (1998)
Gibbs JW.1873.Graphical methods in the thermodynamics of fluids. Trans Conn AcadII:309–342.A method of geometrical representation of thermodynamic properties of substances by means of surfaces. Trans Conn AcadII:382–404.
{'key': '10.1002/jps.20261_rf0350', 'first-page': '1', 'article-title': 'The scientific papers of J. Willard Gibbs. Vol. 1. Thermodynamics', 'year': '1906'} / The scientific papers of J. Willard Gibbs. Vol. 1. Thermodynamics (1906)
10.1023/A:1016079400592 / J Therm Anal Calorim / Effect of high pressure on the polymorphs of paracetamol by Boldyreva (2002)
{'key': '10.1002/jps.20261_bb0360', 'first-page': '1333', 'article-title': 'The role of hydrogen bonds in the pressure‐induced structural distortion of 4‐hydroxyacetanilide crystals', 'volume': '76', 'author': 'Boldyreva', 'year': '2002', 'journal-title': 'Pol J Chem'} / Pol J Chem / The role of hydrogen bonds in the pressure‐induced structural distortion of 4‐hydroxyacetanilide crystals by Boldyreva (2002)
{'key': '10.1002/jps.20261_bb0365', 'first-page': '1', 'article-title': 'The errors in lattice energy minimisation studies: Sensitivity to experimental variations in the molecular structure of paracetamol', 'volume': '34', 'author': 'Beyer', 'year': '2000', 'journal-title': 'Cryst Eng Comm'} / Cryst Eng Comm / The errors in lattice energy minimisation studies: Sensitivity to experimental variations in the molecular structure of paracetamol by Beyer (2000)

Dates

Type	When
Created	20 years, 8 months ago (Dec. 30, 2004, 7:49 p.m.)
Deposited	4 years, 2 months ago (July 3, 2021, 12:28 a.m.)
Indexed	3 days, 3 hours ago (Sept. 4, 2025, 9:15 a.m.)
Issued	20 years, 6 months ago (March 1, 2005)
Published	20 years, 6 months ago (March 1, 2005)
Published Print	20 years, 6 months ago (March 1, 2005)

Funders 0

None

BibTeX

@article{Espeau_2005, title={Polymorphism of paracetamol: Relative stabilities of the monoclinic and orthorhombic phases inferred from topological pressure‐temperature and temperature‐volume phase diagrams}, volume={94}, ISSN={0022-3549}, url={http://dx.doi.org/10.1002/jps.20261}, DOI={10.1002/jps.20261}, number={3}, journal={Journal of Pharmaceutical Sciences}, publisher={Elsevier BV}, author={Espeau, Philippe and Céolin, René and Tamarit, Josep‐Lluis and Perrin, Marc‐Antoine and Gauchi, Jean‐Pierre and Leveiller, Franck}, year={2005}, month=mar, pages={524–539} }

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    {
      "key": "10.1002/jps.20261_bb0090",
      "series-title": "Phase theory: The thermodynamics of heterogeneous equilibria",
      "author": "Oonk",
      "year": "1981"
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      "DOI": "10.1016/0927-796X(95)00188-3",
      "article-title": "Topology of P\u2010T\u2010X phase diagrams of binary systems. Polymorphism, metastable states and high\u2010pressure equilibria",
      "volume": "16",
      "author": "Greenberg",
      "year": "1996",
      "journal-title": "Mat Sci Eng R"
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      "first-page": "1283",
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      "article-title": "The monoclinic form of p\u2010hydroxyacetanilide",
      "volume": "32",
      "author": "Haisa",
      "year": "1976",
      "journal-title": "Acta Crystallogr B"
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      "first-page": "2510",
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      "article-title": "The orthorhombic form of p\u2010hydroxyacetanilide",
      "volume": "30",
      "author": "Haisa",
      "year": "1974",
      "journal-title": "Acta Crystallogr B"
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      "first-page": "1",
      "DOI": "10.1016/0378-5173(95)04127-3",
      "article-title": "A new pure paracetamol for direct compression: The orthorhombic form",
      "volume": "128",
      "author": "Di Martino",
      "year": "1996",
      "journal-title": "Int J Pharm"
    },
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      "key": "10.1002/jps.20261_bb0115",
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      "first-page": "77",
      "DOI": "10.1016/S0378-5173(99)00157-X",
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      "volume": "187",
      "author": "Garekani",
      "year": "1999",
      "journal-title": "Int J Pharm"
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      "first-page": "87",
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      "article-title": "Highly compressible paracetamol. I. Crystallization and characterization",
      "volume": "208",
      "author": "Garekani",
      "year": "2000",
      "journal-title": "Int J Pharm"
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    {
      "key": "10.1002/jps.20261_bb0125",
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      "first-page": "684",
      "DOI": "10.1021/js970483d",
      "article-title": "Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution",
      "volume": "87",
      "author": "Nichols",
      "year": "1998",
      "journal-title": "J Pharm Sci"
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    {
      "key": "10.1002/jps.20261_bb0130",
      "doi-asserted-by": "crossref",
      "first-page": "653",
      "DOI": "10.1107/S0108270197018386",
      "article-title": "The monoclinic form of acetaminophen at 150 K",
      "volume": "54",
      "author": "Naumov",
      "year": "1998",
      "journal-title": "Acta Crystallogr C"
    },
    {
      "key": "10.1002/jps.20261_bb0135",
      "doi-asserted-by": "crossref",
      "first-page": "531",
      "DOI": "10.1016/S0009-2614(97)01180-9",
      "article-title": "Zero point motion of the librating methyl group in p\u2010hydroxyacetanilide",
      "volume": "280",
      "author": "Wilson",
      "year": "1997",
      "journal-title": "Chem Phys Lett"
    },
    {
      "key": "10.1002/jps.20261_bb0140",
      "doi-asserted-by": "crossref",
      "first-page": "84",
      "DOI": "10.1016/S0921-4526(96)00889-7",
      "article-title": "Single\u2010crystal neutron diffraction of bio\u2010active small molecules",
      "volume": "234\u2013236",
      "author": "Wilson",
      "year": "1997",
      "journal-title": "Physica B"
    },
    {
      "key": "10.1002/jps.20261_bb0145",
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      "first-page": "207",
      "DOI": "10.1016/S0022-2860(96)09593-2",
      "article-title": "Neutron diffraction of p\u2010hydroxyacetanilide (paracetamol): Libration or disorder of the methyl group at 100 K",
      "volume": "405",
      "author": "Wilson",
      "year": "1997",
      "journal-title": "J Mol Struct"
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      "key": "10.1002/jps.20261_bb0150",
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      "first-page": "49",
      "DOI": "10.1016/S0301-0104(99)00138-X",
      "article-title": "Methyl group dynamics in paracetamol and acetanilide: Probing the static properties of intermolecular hydrogen bonds formed by peptide groups",
      "volume": "244",
      "author": "Johnson",
      "year": "1999",
      "journal-title": "Chem Phys"
    },
    {
      "key": "10.1002/jps.20261_bb0155",
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      "first-page": "693",
      "DOI": "10.1524/zkri.2000.215.11.693",
      "article-title": "Variable temperature study of the crystal structure of paracetamol (p\u2010hydroxyacetanilide), by single crystal neutron diffraction",
      "volume": "215",
      "author": "Wilson",
      "year": "2000",
      "journal-title": "Z Kristallogr"
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    {
      "key": "10.1002/jps.20261_bb0160",
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      "first-page": "892",
      "DOI": "10.1007/BF02700697",
      "article-title": "Anisotropy of crystal structure distortion in organic molecular crystals of drugs induced by hydrostatic compression",
      "volume": "40",
      "author": "Shakhtshneider",
      "year": "1999",
      "journal-title": "J Struct Chem"
    },
    {
      "key": "10.1002/jps.20261_bb0165",
      "doi-asserted-by": "crossref",
      "first-page": "299",
      "DOI": "10.1107/S0108768199013634",
      "article-title": "Anisotropy of crystal structure distortion of the monoclinic polymorph of acetaminophen at high hydrostatic pressures",
      "volume": "56",
      "author": "Boldyreva",
      "year": "2000",
      "journal-title": "Acta Crystallogr B"
    },
    {
      "key": "10.1002/jps.20261_bb0170",
      "doi-asserted-by": "crossref",
      "first-page": "447",
      "DOI": "10.1007/BF01979491",
      "article-title": "Preparation and physical characterization of forms II and III of paracetamol",
      "volume": "48",
      "author": "Di Martino",
      "year": "1997",
      "journal-title": "J Therm Anal"
    },
    {
      "key": "10.1002/jps.20261_bb0175",
      "doi-asserted-by": "crossref",
      "first-page": "575",
      "DOI": "10.1023/A:1016004206043",
      "article-title": "Thermal behavior of paracetamol\u2010polymeric excipients mixtures",
      "volume": "68",
      "author": "Giordano",
      "year": "2002",
      "journal-title": "J Therm Anal Calorim"
    },
    {
      "key": "10.1002/jps.20261_bb0180",
      "doi-asserted-by": "crossref",
      "first-page": "5086",
      "DOI": "10.1021/ja0102787",
      "article-title": "The prediction, morphology, and mechanical properties of the polymorphs of paracetamol",
      "volume": "123",
      "author": "Beyer",
      "year": "2001",
      "journal-title": "J Am Chem Soc"
    },
    {
      "key": "10.1002/jps.20261_bb0185",
      "doi-asserted-by": "crossref",
      "first-page": "75",
      "DOI": "10.1016/0378-5173(86)90149-3",
      "article-title": "True density and thermal expansion of pharmaceutical solids: Comparison of methods and assessment of crystallinity",
      "volume": "28",
      "author": "Duncan\u2010Hewitt",
      "year": "1986",
      "journal-title": "Int J Pharm"
    },
    {
      "key": "10.1002/jps.20261_bb0190",
      "series-title": "Thermomicroscopy in the analysis of pharmaceuticals",
      "first-page": "183",
      "author": "K\u00fchnert\u2010Brandst\u00e4tter",
      "year": "1971"
    },
    {
      "key": "10.1002/jps.20261_bb0195",
      "doi-asserted-by": "crossref",
      "first-page": "69",
      "DOI": "10.1016/S0040-6031(99)00342-1",
      "article-title": "Thermal characterization of some new xanthine derivatives",
      "volume": "343",
      "author": "D\u0103nil\u0103",
      "year": "2000",
      "journal-title": "Thermochim Acta"
    },
    {
      "key": "10.1002/jps.20261_bb0200",
      "doi-asserted-by": "crossref",
      "first-page": "1889",
      "DOI": "10.1016/S0022-3697(00)00062-7",
      "article-title": "Thermally induced structural changes of acetaminophen in phase transition between the solid and liquid states monitored by combination analysis of FT\u2010IR/DSC microscopic system",
      "volume": "61",
      "author": "Lin",
      "year": "2000",
      "journal-title": "J Phys Chem Solids"
    },
    {
      "key": "10.1002/jps.20261_bb0205",
      "series-title": "Analytical profiles of drug substances",
      "doi-asserted-by": "crossref",
      "first-page": "5",
      "DOI": "10.1016/S0099-5428(08)60064-7",
      "article-title": "Acetaminophen",
      "author": "Fairbrother",
      "year": "1974"
    },
    {
      "key": "10.1002/jps.20261_bb0210",
      "doi-asserted-by": "crossref",
      "first-page": "25",
      "DOI": "10.1016/0378-5173(84)90104-2",
      "article-title": "Non\u2010linear van't Hoff solubility\u2010temperature plots and their pharmaceutical interpretation",
      "volume": "18",
      "author": "Grant",
      "year": "1984",
      "journal-title": "Int J Pharm"
    },
    {
      "key": "10.1002/jps.20261_bb0215",
      "doi-asserted-by": "crossref",
      "first-page": "1109",
      "DOI": "10.1002/jps.2600791214",
      "article-title": "Effects of solvent medium on solubility. V. Enthalpic and entropic contributions to the free energy changes of di\u2010substituted benzene derivatives in ethanol:water and ethanol:cyclohexane mixtures",
      "volume": "79",
      "author": "Manzo",
      "year": "1990",
      "journal-title": "J Pharm Sci"
    },
    {
      "key": "10.1002/jps.20261_bb0220",
      "doi-asserted-by": "crossref",
      "first-page": "233",
      "DOI": "10.1016/0378-5173(92)90161-T",
      "article-title": "Solid\u2010state properties of drugs. I. Estimation of heat capacities for fusion and thermodynamic functions for solutions from aqueous solubility\u2010temperature dependence measurements",
      "volume": "84",
      "author": "Prankerd",
      "year": "1992",
      "journal-title": "Int J Pharm"
    },
    {
      "key": "10.1002/jps.20261_bb0225",
      "doi-asserted-by": "crossref",
      "first-page": "537",
      "DOI": "10.1007/BF02546623",
      "article-title": "A DSC compositional analysis of some binary organic mixtures of pharmaceutical significance",
      "volume": "40",
      "author": "Becket",
      "year": "1993",
      "journal-title": "J Therm Anal"
    },
    {
      "key": "10.1002/jps.20261_bb0230",
      "first-page": "421",
      "article-title": "Interaction between acetaminophen and \u03b2\u2010cyclodextrin by powder compaction",
      "volume": "4",
      "author": "Gazzaniga",
      "year": "1994",
      "journal-title": "STP Pharma Sci"
    },
    {
      "key": "10.1002/jps.20261_bb0235",
      "doi-asserted-by": "crossref",
      "first-page": "1061",
      "DOI": "10.1248/cpb.44.1061",
      "article-title": "The behavior of paracetamol in mixtures of amphiprotic\u2010aprotic solvents. Relationship of solubility curves to specific and nonspecific interactions",
      "volume": "44",
      "author": "Romero",
      "year": "1996",
      "journal-title": "Chem Pharm Bull"
    },
    {
      "key": "10.1002/jps.20261_bb0240",
      "doi-asserted-by": "crossref",
      "first-page": "601",
      "DOI": "10.1023/A:1012148910975",
      "article-title": "Differential molar heat capacities to test ideal solubility estimations",
      "volume": "14",
      "author": "Neau",
      "year": "1997",
      "journal-title": "Pharm Res"
    },
    {
      "key": "10.1002/jps.20261_bb0245",
      "doi-asserted-by": "crossref",
      "first-page": "991",
      "DOI": "10.1021/js970137w",
      "article-title": "An investigation into the melting behavior of binary mixes and solid dispersions of paracetamol and PEG4000",
      "volume": "86",
      "author": "Lloyd",
      "year": "1997",
      "journal-title": "J Pharm Sci"
    },
    {
      "key": "10.1002/jps.20261_bb0250",
      "doi-asserted-by": "crossref",
      "first-page": "1391",
      "DOI": "10.1021/je990124v",
      "article-title": "Solubility of paracetamol in pure solvents",
      "volume": "44",
      "author": "Granberg",
      "year": "1999",
      "journal-title": "J Chem Eng Data"
    },
    {
      "key": "10.1002/jps.20261_bb0255",
      "doi-asserted-by": "crossref",
      "first-page": "302",
      "DOI": "10.1248/cpb.47.302",
      "article-title": "Paracetamol\u2010propyphenazone interaction and formulation difficulties associated with eutectic formation in combination solid dosage forms",
      "volume": "47",
      "author": "Z\u0306alac",
      "year": "1999",
      "journal-title": "Chem Pharm Bull"
    },
    {
      "key": "10.1002/jps.20261_bb0260",
      "doi-asserted-by": "crossref",
      "first-page": "273",
      "DOI": "10.1007/BF01197380",
      "article-title": "On the polymorphism of pharmaceuticals and other molecular crystals. II. Applicability of thermodynamic rules",
      "volume": "II",
      "author": "Buerger",
      "year": "1979",
      "journal-title": "Mikrochim Acta (Wien)"
    },
    {
      "key": "10.1002/jps.20261_bb0265",
      "doi-asserted-by": "crossref",
      "first-page": "966",
      "DOI": "10.1002/jps.2600840812",
      "article-title": "Inferring thermodynamic stability relationship of polymorphs from melting data",
      "volume": "84",
      "author": "Yu",
      "year": "1995",
      "journal-title": "J Pharm Sci"
    },
    {
      "key": "10.1002/jps.20261_bb0270",
      "first-page": "1",
      "article-title": "Zur Interpretation von Polymorphie\u2010Untersuchungen",
      "volume": "28",
      "author": "Buerger",
      "year": "1982",
      "journal-title": "Acta Pharm Technol"
    },
    {
      "key": "10.1002/jps.20261_bb0275",
      "doi-asserted-by": "crossref",
      "first-page": "23",
      "DOI": "10.1023/A:1010184805966",
      "article-title": "In situ characterization of polymorphic forms. The potential of Raman techniques",
      "volume": "57",
      "author": "Szelagiewicz",
      "year": "1999",
      "journal-title": "J Therm Anal Calorim"
    },
    {
      "key": "10.1002/jps.20261_bb0280",
      "doi-asserted-by": "crossref",
      "first-page": "345",
      "DOI": "10.1023/A:1010180123331",
      "article-title": "Thermodynamic analysis of DSC data for acetaminophen polymorphs",
      "volume": "63",
      "author": "Sacchetti",
      "year": "2001",
      "journal-title": "J Therm Anal Calorim"
    },
    {
      "key": "10.1002/jps.20261_bb0285",
      "first-page": "1903",
      "article-title": "Conditions of preparation and crystallization of amorphous paracetamol",
      "volume": "75",
      "author": "Politov",
      "year": "2001",
      "journal-title": "Russ J Phys Chem"
    },
    {
      "key": "10.1002/jps.20261_bb0290",
      "doi-asserted-by": "crossref",
      "first-page": "1863",
      "DOI": "10.1002/jps.10169",
      "article-title": "Physical stability of amorphous pharmaceuticals: Importance of configurational thermodynamic quantities and molecular mobility",
      "volume": "91",
      "author": "Zhou",
      "year": "2002",
      "journal-title": "J Pharm Sci"
    },
    {
      "key": "10.1002/jps.20261_bb0295",
      "doi-asserted-by": "crossref",
      "first-page": "81",
      "DOI": "10.1016/0040-6031(94)01949-H",
      "article-title": "Thermal analysis of glassy pharmaceuticals",
      "volume": "248",
      "author": "Kerc\u0306",
      "year": "1995",
      "journal-title": "Thermochim Acta"
    },
    {
      "key": "10.1002/jps.20261_bb0300",
      "doi-asserted-by": "crossref",
      "first-page": "1105",
      "DOI": "10.1248/cpb.48.1105",
      "article-title": "Molecular mobility of the paracetamol amorphous form",
      "volume": "48",
      "author": "Di Martino",
      "year": "2000",
      "journal-title": "Chem Pharm Bull"
    },
    {
      "key": "10.1002/jps.20261_bb0305",
      "doi-asserted-by": "crossref",
      "first-page": "987",
      "DOI": "10.1107/S0021889891006441",
      "article-title": "Indexing of powder diffraction patterns for low\u2010symmetry lattices by the successive dichotomy method",
      "volume": "24",
      "author": "Boultif",
      "year": "1991",
      "journal-title": "J Appl Cryst"
    },
    {
      "key": "10.1002/jps.20261_bb0310",
      "doi-asserted-by": "crossref",
      "first-page": "357",
      "DOI": "10.1107/S0021889881009618",
      "article-title": "Unit\u2010cell refinement from powder diffraction scans",
      "volume": "14",
      "author": "Pawley",
      "year": "1981",
      "journal-title": "J Appl Cryst"
    },
    {
      "key": "10.1002/jps.20261_bb0315",
      "doi-asserted-by": "crossref",
      "first-page": "1169",
      "DOI": "10.1107/S0021889899009930",
      "article-title": "PowderSolve: A complete diffraction package for crystal structure solution from powder diffraction patterns",
      "volume": "32",
      "author": "Engel",
      "year": "1999",
      "journal-title": "J Appl Cryst"
    },
    {
      "key": "10.1002/jps.20261_bb0320",
      "series-title": "Introduction \u00e0 l'\u00e9tude de la m\u00e9tallurgie",
      "first-page": "392",
      "author": "Le Ch\u00e2telier",
      "year": "1912"
    },
    {
      "key": "10.1002/jps.20261_bb0325",
      "doi-asserted-by": "crossref",
      "first-page": "337",
      "DOI": "10.1007/BF01375110",
      "article-title": "Die thermische Ausdehnung von Quarzglas im Temperaturbereich von 0 bis 1060\u00b0C",
      "volume": "175",
      "author": "Otto",
      "year": "1963",
      "journal-title": "Z Phys"
    },
    {
      "key": "10.1002/jps.20261_bb0330",
      "series-title": "Statistics for experimenters",
      "first-page": "116",
      "author": "Box",
      "year": "1978"
    },
    {
      "key": "10.1002/jps.20261_bb0335",
      "series-title": "Applied regression analysis",
      "first-page": "28",
      "author": "Draper",
      "year": "1981"
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    {
      "key": "10.1002/jps.20261_bb0340",
      "doi-asserted-by": "crossref",
      "first-page": "143",
      "DOI": "10.1007/BF01908495",
      "article-title": "Etude, par ATD, du diagramme d'\u00e9tat de l'arsenic et mesure de son enthalpie de fusion aux conditions du point triple",
      "volume": "23",
      "author": "Rouland",
      "year": "1982",
      "journal-title": "J Therm Anal"
    },
    {
      "key": "10.1002/jps.20261_bb0345",
      "series-title": "Phase equilibria, phase diagrams and phase transformations: Their thermodynamic basis",
      "author": "Hillert",
      "year": "1998"
    },
    {
      "key": "10.1002/jps.20261_or0010",
      "unstructured": "Gibbs JW.1873.Graphical methods in the thermodynamics of fluids. Trans Conn AcadII:309\u2013342.A method of geometrical representation of thermodynamic properties of substances by means of surfaces. Trans Conn AcadII:382\u2013404."
    },
    {
      "key": "10.1002/jps.20261_rf0350",
      "first-page": "1",
      "article-title": "The scientific papers of J. Willard Gibbs. Vol. 1. Thermodynamics",
      "year": "1906"
    },
    {
      "key": "10.1002/jps.20261_bb0355",
      "doi-asserted-by": "crossref",
      "first-page": "437",
      "DOI": "10.1023/A:1016079400592",
      "article-title": "Effect of high pressure on the polymorphs of paracetamol",
      "volume": "68",
      "author": "Boldyreva",
      "year": "2002",
      "journal-title": "J Therm Anal Calorim"
    },
    {
      "key": "10.1002/jps.20261_bb0360",
      "first-page": "1333",
      "article-title": "The role of hydrogen bonds in the pressure\u2010induced structural distortion of 4\u2010hydroxyacetanilide crystals",
      "volume": "76",
      "author": "Boldyreva",
      "year": "2002",
      "journal-title": "Pol J Chem"
    },
    {
      "key": "10.1002/jps.20261_bb0365",
      "first-page": "1",
      "article-title": "The errors in lattice energy minimisation studies: Sensitivity to experimental variations in the molecular structure of paracetamol",
      "volume": "34",
      "author": "Beyer",
      "year": "2000",
      "journal-title": "Cryst Eng Comm"
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  "alternative-id": [
    "S0022354916317233"
  ],
  "URL": "http://dx.doi.org/10.1002/jps.20261",
  "relation": {},
  "ISSN": [
    "0022-3549"
  ],
  "subject": [],
  "container-title-short": "Journal of Pharmaceutical Sciences",
  "published": {
    "date-parts": [
      [
        2005,
        3
      ]
    ]
  }
}