An augmented volume-based model of the glass transition temperature of 209 molecular liquids

Journal of Pharmaceutical Sciences

Volumn 102, Issue 6, 2013, Pages 1970-1980

  Preiss, Ulrich P ^a   Saleh, Muhammad I ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Computer aided drug design; Glass transition; Hierarchical cluster analysis; in silico modeling; Mathematical model; Multivariate analysis

Indexed keywords

AMORPHOUS STATE; ARTICLE; CLUSTER ANALYSIS; CRYSTAL; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; GLASS TRANSITION TEMPERATURE; LIQUID; MOLECULE;

EID: 84877899416     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23553     Document Type: Article

References (132)

1. Web of Knowledge, accessed June 27, 2012, at: http://www.isiknowledge.com.
2. Hancock BC, Zografi G. 1997. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci 86:1-12.
3. Craig DQ, Royall PG, Kett VL, Hopton, ML. 1999. The relevance of the amorphous state to pharmaceutical dosage forms: Glassy drugs and freeze dried systems. Int J Pharm 179:179-207.
4. Yu L. 2001. Amorphous pharmaceutical solids: Preparation, characterization and stabilization. Adv Drug Deliv Rev 48:27-42.
5. Langer M, Höltje M, Urbanetz NA, Brandt B, Höltje H-D, Lippold BC. 2003. Investigations on the predictability of the formation of glassy solid solutions of drugs in sugar alcohols. Int J Pharm 252:167-179.
6. Descamps M, Willart JF. 2007. Solid phase transformation in pharmaceuticals induced by mechanical processes. Acta Cryst A 63:s51-s52.
7. Noel TR, Ring SG, Whittam MA. 1990. Glass transitions in low-moisture foods. Trends Food Sci Technol 1:62-67.
8. Liu Y, Bhandari B, Zhou W. 2006. Glass transition and enthalpy relaxation of amorphous food saccharides: A review. J Agric Food Chem 54:5701-5717.
9. 2002. Amorphous food and pharmaceutical systems. In: Levine H, Ed. London, Cambridge: RSC Publishing, pp.
10. Fahy G, MacFarlane D, Angell CA, Meryman H. 1984. Vitrification as an approach to cryopreservation. Cryobiology 21:407-426.
11. Ishikawa W, Noguchi K, Kuwabaru Y, Shirota Y. 1993. Novel amorphous molecular materials: The starburst molecule 1, 3, 5-tris[N-(4-diphenyl-aminophenyl)phenylamino]benzene. Adv Mater 5:559-561.
12. Shirota Y. 2000. Organic materials for electronic and optoelectronic devices. J Mater Chem 10:1-25.
13. Yoshiiwa M, Kageyama H, Shirota Y, Wakaya F, Gamo K, Takai, M. 1996. Novel class of low molecular-weight organic resists for nanometer lithography. Appl Phys Lett 69:2605-2607.
14. Angell CA. 1967. Fundamental limitations on the low-temperature operation of electrolytic devices. J Electrochem Soc 114:1033-1035.
15. Hancock BC, Parks M. 2000. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res 17:397-404.
16. Bartenev GM. 1951. Variation of the vitrification temperature of silicate glasses with the velocity of cooling or heating. Dokl Akad Nauk SSSR 76:227-230.
17. Moynihan CT, Easteal AJ, Wilder J. 1974. Dependence of the glass transition temperature on heating and cooling rate. J Phys Chem 78:2673-2677.
18. Moynihan CT, Easteal AJ, DeBolt MA, Tucker J. 1976. Dependence of the fictive temperature of glass on cooling rate. J Am Ceram Soc 59:12-16.
19. Gutzow I, Ilieva D, Babalievski F, Yamakov V. 2000. Thermodynamics and kinetics of the glass transition: A generic geometric approach. J Chem Phys 112:10941-10948.
20. Cavagna A. 2009. Supercooled liquids for pedestrians. Phys Rep 476:51-124.
21. Clare BR, Bayley PM, Best AS, Forsyth M, MacFarlane DR. 2008. Purification or contamination? The effect of sorbents on ionic liquids. Chem Commun:2689-2691.
22. Eyring H. 1936. Viscosity, plasticity, and diffusion as examples of absolute reaction rates. J Chem Phys 4:283-291.
23. Cohen MH, Turnbull D. 1959. Molecular transport in liquids and glasses. J Chem Phys 31:1164-1169.
24. Ferry JD. 1980. Viscoelastic properties of polymers. New York: John Wiley and Sons.
25. Fox TG, Flory PJ. 1950. Second-order transition temperatures and related properties of polystyrene. I. Influence of molecular weight. J Appl Phys 21:581-591.
26. Wool RP. 2008. Twinkling fractal theory of the glass transition. J Polym Sci B 46:2765-2778.
27. Calleja FJB, Sanditov DS, Privalko VP. 2002. Review: The microhardness of non-crystalline materials. J Mater Sci 37:4507-4516.
28. Adam G, Gibbs JH. 1965. On the temperature dependence of cooperative relaxation properties in glass-forming liquids. J Chem Phys 43:139-146.
29. Debenedetti PG, Stillinger FH. 2001. Supercooled liquids and the glass transition. Nature 410:259-267.
30. Wang L-M, Angell CA, Richert R. 2006. Fragility and thermodynamics in nonpolymeric glass-forming liquids. J Chem Phys 125:074505.
31. Koop T, Bookhold J, Shiraiwa M, Pöschl U. 2011. Glass transition and phase state of organic compounds: Dependency on molecular properties and implications for secondary organic aerosols in the atmosphere. Phys Chem Chem Phys 13:19238-19255.
32. Turnbull D, Cohen M. 1958. Concerning reconstructive transformation and formation of glass. J Chem Phys 29:1049-1054.
33. Wales DJ. 2001. A microscopic basis for the global appearance of energy landscapes. Science 293:2067-2070.
34. Middleton TF, Wales DJ. 2001. Energy landscapes of some model glass formers. Phys Rev B 64:024205.
35. Katritzky AR, Rachwal P, Law KW, Karelson M, Lobanov VS. 1996. Prediction of polymer glass transition temperatures using a general quantitative structure-property relationship treatment. J Chem Inf Comput Sci 36:879-884.
36. Katritzky AR, Sild S, Lobanov VS. 1998. Quantitative structure-property relationship (QSPR) correlation of glass transition temperatures of high molecular weight polymers. J Chem Inf Comput Sci 38:300-304.
37. Mattioni BE, Jurs PC. 2002. Prediction of glass transition temperatures from monomer and repeat unit structure using computational neural networks. J Chem Inf Comput Sci 42:232-240.
38. Afantitis A, Melagraki G, Makridima K, Alexandridis A, Sarimveis H, Iglessi-Markopoulou O. 2005. Prediction of high weight polymers glass transition temperature using RBF neural networks. J Mol Struc THEOCHEM 716:193-198.
39. Cypcar CC, Camelio P, Lazzeri V, Mathias LJ, Waegell B. 1996. Prediction of the glass transition temperature of multicyclic and bulky substituted acrylate and methacrylate polymers using the energy, volume, mass (EVM) QSPR model. Macromolecules 29:8954-8959.
40. García-Domenech R, de Julián-Ortiz JV. 2002. Prediction of indices of refraction and glass transition temperatures of linear polymers by using graph theoretical indices. J Phys Chem B 106:1501-1507.
41. Yu X, Wang X, Li X, Gao J, Wang H. 2006. Prediction of glass transition temperatures for polystyrenes by a four-descriptors QSPR model. Macromol Theor Simul 15:94-99.
42. Yu X, Wang X, Wang H, Liu A, Zhang C. 2006. Prediction of the glass transition temperatures of styrenic copolymers using a QSPR based on the DFT method. J Mol Struc THEOCHEM 766:113-117.
43. Yu X, Yi B, Wang X, Xie Z. 2007. Correlation between the glass transition temperatures and multipole moments for polymers. Chem Phys 332:115-118.
44. Mattioni BE, Jurs PC. 2002. Prediction of glass transition temperatures from monomer and repeat unit structure using computational neural networks. J Chem Inf Comput Sci 42:75-81.
45. Yin S, Shuai Z, Wang Y. 2003. A quantitative structure-property relationship study of the glass transition temperature of OLED materials. J Chem Inf Comput Sci 43:970-977.
46. Xu J, Chen B. 2005. Prediction of glass transition temperatures of OLED materials using topological indices. J Mol Model 12:24-33.
47. Preiss UPRM, Slattery JM, Krossing I. 2009. In silico prediction of molecular volumes, heat capacities, and temperature-dependent densities of ionic liquids. Ind Eng Chem Res 48:2290-2296.
48. Preiss U, Jungnickel C, Thöming J, Krossing I, Luczak J, Diedenhofen M, Klamt A. 2009. Predicting the critical micelle concentrations of aqueous solutions of ionic liquids and other ionic surfactants. Chem Eur J 15:8880-8885.
49. Preiss U, Verevkin SP, Koslowski T, Krossing I. 2011. Going full circle: Phase-transition thermodynamics of ionic liquids. Chem Eur J 17:6508-6517.
50. Eiden P, Bulut S, Köchner T, Friedrich C, Schubert T, Krossing I. 2011. In silico predictions of the temperature-dependent viscosities and electrical conductivities of functionalized and nonfunctionalized ionic liquids. J Phys Chem B 115:300-309.
51. Preiss U, Emel'yanenko VN, Verevkin SP, Himmel D, Paulechka YU, Krossing I. 2010. Temperature-dependent prediction of the liquid entropy of ionic liquids. Chem Phys Chem 11:3425-3431.
52. - ionic liquids. Chem Phys Chem 12:2296-2310.
53. Preiss U. 2010. Quantum Chemical Studies of Weakly Coordinated Ionic Systems: Predictions of Chemical and Physical Properties. PhD. Thesis. Freiburg, Germany: Universität Freiburg.
54. Krossing I, Slattery JM. 2006. Semi-empirical methods to predict the physical properties of ionic liquids: An overview of recent developments. Z Phys Chem 220:1343-1359.
55. Krossing I, Slattery JM, Daguenet C, Dyson PJ, Oleinikova A, Weingärtner H. 2006. Why are ionic liquids liquid? A simple explanation based on lattice and solvation energies. J Am Chem Soc 128:13427-13434.
56. Slattery JM, Daguenet C, Dyson PJ, Schubert TJS, Krossing I. 2007. How to predict the physical properties of ionic liquids: A volume-based approach. Angew Chem Int Ed 46:5384-5388.
57. Ye C, Shreeve JM. 2007. Rapid and accurate estimation of densities of room-temperature ionic liquids and salts. J Phys Chem A 111:1456-1461.
58. Jenkins HDB, Roobottom HK, Passmore J, Glasser L. 1999. Relationships among ionic lattice energies, molecular (formula unit) volumes, and thermochemical radii. Inorg Chem 38:3609-3620.
59. 298, values from volume or density. 1. Inorganic materials. Inorg Chem 42:8702-8708.
60. Preiss U, Bulut S, Krossing I. 2010. In silico prediction of the melting points of ionic liquids from thermodynamic considerations: A case study on 67 salts with a melting point range of 337 degrees C. J Phys Chem B 114:11133-11140.
61. Preiss UP, Beichel W, Erle AMT, Paulechka YU, Krossing I. 2011. Is universal, simple melting point prediction possible? Chem Phys Chem 12:2959-2972.
62. Dannenfelser RM, Surendran N, Yalkowsky SH. 1993. Molecular symmetry and related properties. SAR QSAR Environ Res 1:273-292.
63. Dannenfelser R-M, Yalkowsky SH. 1996. Estimation of entropy of melting from molecular structure: A non-group contribution method. Ind Eng Chem Res 35:1483-1486.
64. Dannenfelser R-M, Yalkowsky SH. 1999. Predicting the total entropy of melting: Application to pharmaceuticals and environmentally relevant compounds. J Pharm Sci 88:722-724.
65. Jain A, Yang G, Yalkowsky SH. 2004. Estimation of total entropy of melting of organic compounds. Ind Eng Chem Res 43:4376-4379.
66. Krzyzaniak JF, Myrdal PB, Simamora P, Yalkowsky SH. 1995. Boiling point and melting point prediction for aliphatic, non-hydrogen-bonding compounds. Ind Eng Chem Res 34:2530-2535.
67. Zhao L, Yalkowsky SH. 1999. A combined group contribution and molecular geometry approach for predicting melting points of aliphatic compounds. Ind Eng Chem Res 38:3581-3584.
68. Jain A, Yalkowsky SH. 2004. Estimation of melting points of organic compounds. Ind Eng Chem Res 43:7618-7621.
69. Jain A, Yalkowsky SH. 2006. Estimation of melting points of organic compounds-II. J Pharm Sci 95:2562-2618.
70. Xu W, Cooper EI, Angell CA. 2003. Ionic liquids: Ion mobilities, glass temperatures, and fragilities. J Phys Chem B 107:6170-6178.
71. Xu W, Wang L-M, Nieman RA, Angell CA. 2003. Ionic liquids of chelated orthoborates as model ionic glassformers. J Phys Chem B 107:11749-11756.
72. Eckert F, Klamt A. 2002. Fast solvent screening via quantum chemistry: COSMO-RS approach. AlChE J 48:369-385.
73. Chandler D. 2005. Interfaces and the driving force of hydrophobic assembly. Nature 437:640-647.
74. Carpenter MR, Davies D, Matheson AJ. 1967. Measurement of the glass-transition temperature of simple liquids. J Chem Phys 46:2451-2454.
75. Johari GP, Goldstein M. 1971. Viscous liquids and the glass transition. III. Secondary relaxations in aliphatic alcohols and other nonrigid molecules. J Chem Phys 55:4245-4252.
76. Davies DB, Matheson AJ, Glover GM. 1973. Viscoelastic behaviour of some viscous liquids. Chem Soc Faraday Trans 2 69:305-314.
77. Fukuoka E, Makita M, Yamamura S. 1989. Glassy state of pharmaceuticals. III. Thermal properties and stability of glassy pharmaceuticals and their binary glass systems. Chem Pharm Bull 37:1047-1050.
78. Angell CA, Sare J, Sare E. 1978. Glass transition temperatures for simple molecular liquids and their binary solutions. J Phys Chem 82:2622-2629.
79. Rukiah M, Lefebvre J, Descamps M, Hemon S, Dzyabchenko A. 2004. Ab initio structure determination of m-toluidine by powder X-ray diffraction. J Appl Cryst 37:464-471.
80. Eibl S, Fitch A, Brunelli M, Evans AD, Pattison P, Plazanet M, Johnson MR, Alba-Simionesco C, Schober H. 2009. trans-Decahydronaphthalene (decalin) from powder diffraction data. Acta Crystallogr C 65:o278-o280.
81. van der Sluis P, Hezemans AMF, Kroon J. 1989. Crystallization of low-molecular-weight organic compounds for X-ray crystallography. J Appl Cryst 22:340-344.
82. Kim Y, Strauss HL, Snyder RG. 1989. Conformational disorder in crystalline n-alkanes prior to melting. J Phys Chem 93:7520-7526.
83. Muggli MW, Ward TC, Tchatchoua C, Ji Q, Mcgrath JE. 2003. End-group effect on physical aging and polymer properties for poly(ether sulfones). J Polymer Sci B 41:2850-2860.
84. Rane S, Gujrati PD. 2001. Importance of interactions for free-volume and end-group effects in polymers: An equilibrium lattice investigation. Phys Rev E 64:011801, and references therein.
85. Hancock BC, Zografi G. 1994. The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm Res 11:471-477.
86. Ding MS. 2003. Liquid phase boundaries, dielectric constant, and viscosity of PC-DEC and PC-EC binary carbonates. J Electrochem Soc 150:A455-A462.
87. 6 in propylene carbonate + diethyl carbonate. J Chem Eng Data 48:519-528.
88. 4 in propylene carbonate + diethyl carbonate. J Chem Eng Data 49:1102-1109.
89. Höhne GWH, Hemminger WF, Flammersheim H-J. 2003. Differential scanning calorimetry. 2nd ed. Berlin, Heidelberg, Germany: Springer.
90. Angell CA, Ngai KL, McKenna GB, McMillan PF, Martin SW. 2000. Relaxation in glassforming liquids and amorphous solids. J Appl Phys 88:3113-3157.
91. Wunderlich B. 1958. Theory of cold crystallization of high polymers. J Chem Phys 29:1395-1404.
92. Haida O, Suga H, Seki S. 1977. Calorimetric study of the glassy state XII. Plural glass-transition phenomena of ethanol. J Chem Thermodyn 9:1133-1148.
93. Greer A. 2000. Too hot to melt. Nature 404:134-135.
94. Schmelzer JWP, Müller R, Möller J, Gutzow IS. 2003. Theory of nucleation in viscoelastic media: Application to phase formation in glassforming melts. J Non-Cryst Solids 315:144-160.
95. Hatase M, Hanaya M, Oguni M. 2004. Studies of homogeneous-nucleation-based crystal growth: Significant role of phenyl ring in the structure formation. J Non-Cryst Solids 333:129-136, and references therein.
96. Graeser KA, Patterson JE, Zeitler JA, Gordon KC, Rades T. 2009. Correlating thermodynamic and kinetic parameters with amorphous stability. Eur J Pharm Sci 37:492-498.
97. Johari G, Goldstein M. 1971. Viscous liquids and the glass transition. III. Secondary relaxations in aliphatic alcohols and other nonrigid molecules. J Chem Phys 55:4245-4252.
98. Naito K, Miura P. 1993. Molecular design for nonpolymeric organic dye glasses with thermal stability: Relations between thermodynamic parameters and amorphous properties. J Phys Chem 97:6240-6248.
99. Erdmenger T, Vitz J, Wiesbrock F, Schubert US. 2008. Influence of different branched alkyl side chains on the properties of imidazolium-based ionic liquids. J Mater Chem 18:5267-5273.
100. Dudowicz J, Freed KF, Douglas JF. 2005. The glass transition temperature of polymer melts. J Phys Chem B 109:21285-21292.
101. Gibbs JW. 1878. On the equilibrium of heterogeneous substances: Abstract by the author. Am J Sci 16:441-458.
102. Steinbach I. 2009. Phase-field models in materials science. Model Simul Mater Sc 17:073001 and references therein.
103. Lu HM, Wen Z, Jiang Q. 2007. The solid-liquid interface energy of organic crystals. J Phys Org Chem 20:236-240.
104. Palmer RG. 1982. Broken ergodicity. Adv Phys 31:669-735.
105. Tanaka H. 1998. A simple physical model of liquid-glass transition: Intrinsic fluctuating interactions and random fields hidden in glass-forming liquids. J Phys Condens Matter 10:L207-L214.
106. Dasgupta C. 2005. Theoretical approaches to the glass transition in simple liquids. Pramana 64:679-694.
107. Etter MC. 1990. Encoding and decoding hydrogen-bond patterns of organic compounds. Acc Chem Res 23:120-126.
108. Chelli R, Procacci P, Cardini G, Della Valle RG, Califano S. 1999. Glycerol condensed phases Part I. A molecular dynamics study. Phys Chem Chem Phys 1:871-877.
109. Chelli R, Procacci P, Cardini G, Califano S. 1999. Glycerol condensed phases Part II. A molecular dynamics study of the conformational structure and hydrogen bonding. Phys Chem Chem Phys 1:879-885.
110. Blazhnov I, Magazù S, Maisano G, Malomuzh N, Migliardo F. 2006. Macro- and microdefinitions of fragility of hydrogen-bonded glass-forming liquids. Phys Rev E 73:031201.
111. Dahl T. 1994. The nature of stacking interactions between organic molecules elucidated by analysis of crystal structures. Acta Chem Scand 48:95-106.
112. Rapacioli M, Calvo F, Spiegelman F, Joblin C, Wales DJ. 2005. Stacked clusters of polycyclic aromatic hydrocarbon molecules. J Phys Chem A 109:2487-2497.
113. Rubeš M, Bludský O. 2008. Intermolecular π-π interactions in solids. Phys Chem Chem Phys 10:2611-2615.
114. Gafner G, Herbstein FH. 1960. The crystal and molecular structures of overcrowded halogenated compounds. I. Introductory survey. Acta Cryst 13:702-705.
115. g. J Phys Chem 86:3845-3852.
116. Jabrane S, Létoffé J, Claudy P. 1995. Vitrification and crystallization in the R(+)1, 2-propanediol- S(+)1, 2-propanediol system. Thermochim Acta 258:33-47.
117. Lipatov YS, Privalko VP. 1973. Dependence of the free volume fraction at the glass transition temperature on the molecular parameters of linear polymers. J Macromol Sci B 7:431-444.
118. Ertl P, Rohde B, Selzer P. 2000. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 43:3714-3717.
119. Johnson MA, Maggiora GM, Eds. 1990. Concepts and applications of molecular similarity. New York: Wiley.
120. Ward JH. 1963. Hierarchical grouping to optimize an objective function. J Am Statist Assoc 58:236-244.
121. Molecule File Converter, version 5.11.4, ChemAxon, 2012. Accessed February 13, 2013, at: http://www.chemaxon.com.
122. MOPAC2012, by Stewart JJP. Computational chemistry, Colorado Springs, Colorado. Accessed December 11, 2012, at: http://openmopac.net.
123. Stewart JJP. 2007. Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements. J Mol Modeling 13:1173-1213.
124. Korth M. 2010. Third-generation hydrogen-bonding corrections for semiempirical qm methods and force fields. J Chem Theory Comput 6:3808-3816.
125. Klamt A, Schüürmann G. 1993. COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans 2:799-805.
126. Dewar MJS, Ford GP. 1977. Ground states of molecules. 44. MINDO/3 calculations of absolute heat capacities and entropies of molecules without internal rotations. J Am Chem Soc 99:7822-7829.
127. Open Babel and Pybel, accessed April 12, 2013, at: http://openbabel.org/wiki/Main_Page.
128. Octave statistics package, accessed April 12, 2013, at: http://octave.sourceforge.net/statistics.
129. O'Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR. 2011. Open Babel: An open chemical toolbox. J Cheminf 3:33.
130. O'Boyle NM, Morley C, Hutchison GR. 2008. Pybel: A Python wrapper for the OpenBabel cheminformatics toolkit. Chem Cent J 2:5.
131. Eaton J W, Bateman D, Hauberg S. 2008. GNU Octave Manual Version 3. Network Theory Limited.
132. GNU Octave, accessed August 8, 2012, at: https://www.gnu.org/software/octave/.