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E-grāmata: Polymorphism in Molecular Crystals

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(Professor Chemistry, Emeritus, Ben-Gurion University of the Negev)
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Polymorphism in Molecular CrystalsPalielināt
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Most people are familiar with the fact that diamond and graphite are both composed only of carbon; yet they have very different properties which result from the very different structures of the two solids - they are polymorphs of carbon. Understanding the relationship between the structures and the properties of materials is of fundamental importance in developing and producing new materials with improved or new properties. The existence of polymorphic systems allows the direct study of the connection between structures and properties. This book provides grounding on the fundamental structural and energetic basis for polymorphism, the preparation and characterization of polymorphic substances and its importance in the specific areas of pharmaceuticals, pigments and high energy (explosive) materials. The closing chapter describes the intellectual property implications and some of the precedent patent litigations in which polymorphism has played a central role. The book contains over 2500 references to provide a ready entry into the relevant literature.

Recenzijas

excellent and very informative. . . Many well selected examples are discussed which guide a new researcher into the field. It is also a fantastic source of historical, fundamental and up to date papers and reviews (110 pages of references). This book then can be read by a beginner in the field but also by an active researcher in polymorphism, crystal engineering or crystal chemistry. * Claude Lecomte, Universite de Lorraine, Acta Crystallographica * Review from previous edition Joel Bernstein's book represents the single most important source for the development of critical understanding of polymorphism and its commercial and industrial importance and might well play a decisive role in categorizing and reorganizing problems and endeavours on polymorphism-related research. * Current Engineering Practice * ... clear, vigorous, well-written and very readable ... There seems to be nothing relevant that Bernstein has not included; his scholarship and command and study of the vast literature are remarkable ... an excellent work. * Current Engineering Practice * ... an excellent resource book and a very good read ... can be recommended strongly both for content and interest. * Crystallographic Newsletter * ... a delight to review this eagerly awaited tome ... In the end, the proof of the pudding is in the eating, and in my opinion, Bernstein has served us a nutritional feast here. Enjoy! * Cryst. Growth Des. * It will be the book, for a long time to come, to which students and researchers will turn with confidence, as well as pleasure, in all questions of polymorphism in molecular crystals. * Structural Chemistry *

Abbreviations xxv
1 Introduction And Historical Background
1(40)
1.1 Introduction
1(2)
1.2 Definitions and nomenclature
3(12)
1.2.1 Polymorphism
3(2)
1.2.2 Some additional adjectival polymorphisms: pros and cons
5(2)
1.2.3 Pseudopolymorphism, solvates, and hydrates
7(4)
1.2.4 Conventions for naming polymorphs
11(4)
1.3 Is this material polymorphic?
15(15)
1.3.1 Occurrence of polymorphism
15(5)
1.3.2 Literature sources of polymorphic compounds
20(6)
1.3.3 Polymorphic compounds in the Cambridge Structural Database
26(2)
1.3.4 Powder Diffraction File
28(1)
1.3.5 Patent literature
28(1)
1.3.6 Polymorphism of elements and inorganic compounds
29(1)
1.3.7 Polymorphism in macromolecular crystals
29(1)
1.4 Historical perspective
30(9)
1.5 Commercial/industrial importance of polymorphism---some additional comments
39(2)
2 Fundamentals
41(37)
2.1 Introduction
41(1)
2.2 The thermodynamics of molecular crystals
41(14)
2.2.1 The phase rule
42(1)
2.2.2 Thermodynamic relations in polymorphs
43(2)
2.2.3 Energy versus temperature diagrams---the Gibbs free energy
45(2)
2.2.4 Enantiotropism and monotropism
47(1)
2.2.5 Phase diagrams in terms of pressure and temperature
47(5)
2.2.6 Heat-of-transition rule
52(1)
2.2.7 Heat-of-fusion rule
52(1)
2.2.8 Entropy-of-fusion rule
53(1)
2.2.9 Heat-capacity rule
53(1)
2.2.10 Density rule
53(1)
2.2.11 Infrared rule
54(1)
2.3 Kinetic factors determining the formation of polymorphic modifications
55(3)
2.4 Structural fundamentals
58(18)
2.4.1 Form versus habit
59(4)
2.4.2 Structural characterization and comparison of polymorphic systems
63(13)
2.5 Thermodynamics and kinetics of crystallization---signs of a changing paradigm
76(2)
3 Exploring The Crystal Form Landscape
78(58)
3.1 General considerations
79(1)
3.2 Aggregation and nucleation
79(8)
3.3 Thermodynamic versus kinetic crystallization conditions
87(2)
3.4 Monotropism, enantiotropism, and crystallization strategy
89(1)
3.5 The polymorph (solid form) screen
90(24)
3.5.1 General comments
90(3)
3.5.2 When to carry out a solid form screen?
93(1)
3.5.3 What comprises a solid form screen?
94(8)
3.5.4 What is the time frame for a solid form screen?
102(3)
3.5.5 What are the variables in a crystallization?
105(1)
3.5.6 High throughput (HT) screening for solid forms
105(4)
3.5.7 A specific example of a solid form screen---axitinib
109(5)
3.6 Concomitant polymorphs
114(17)
3.6.1 Concomitant polymorphs---crystallization methods and conditions
115(5)
3.6.2 Concomitant polymorphs---examples of different classes of compounds
120(8)
3.6.3 Concomitant polymorphs---the structural approach
128(3)
3.7 Disappearing polymorphs
131(4)
3.8 A final note
135(1)
4 Analytical Techniques For Studying And Characterizing Polymorphs And Polymorphic Transitions
136(79)
4.1 Introduction
136(1)
4.2 Optical/hot stage microscopy
137(9)
4.3 Thermal methods
146(9)
4.4 X-ray crystallography
155(14)
4.5 Infrared spectroscopy
169(7)
4.6 Raman spectroscopy
176(5)
4.7 Solid-state nuclear magnetic resonance (SSNMR) spectroscopy
181(13)
4.8 Electron microscopy
194(13)
4.9 Atomic force microscopy (AFM) and scanning tunneling microscopy (STM)
207(1)
4.10 Density measurements
207(1)
4.11 New technologies and "hyphenated techniques"
208(1)
4.12 Are two samples polymorphs of the same compound?
209(2)
4.13 Concluding remarks
211(4)
5 Computational Aspects Of Polymorphism
215(58)
5.1 Introduction
215(1)
5.2 Molecular shape and energetics
216(1)
5.3 Intermolecular interactions and energetics
217(3)
5.4 Presenting and comparing polymorphs
220(1)
5.5 Some early examples of conformational polymorphism
221(5)
5.6 What are conformational polymorphs good for?
226(1)
5.7 Computational studies of the energetics of polymorphic systems
226(3)
5.8 Some exemplary studies of conformational polymorphism
229(8)
5.9 The computational prediction of polymorphs
237(10)
5.9.1 Early developments
237(3)
5.9.2 Subsequent activity
240(7)
5.10 The computational comparison of polymorphs
247(26)
5.10.1 Introduction
247(1)
5.10.2 Comparison based on geometry criteria
247(1)
5.10.3 Comparison of crystal structures using Hirshfeld surfaces
248(9)
5.10.4 Conformational polymorphs
257(10)
5.10.5 Comparison of energetic environment
267(1)
5.10.6 Partitioning of lattice energy
268(2)
5.10.7 Comparison of X-ray powder diffraction patterns
270(3)
6 Polymorphism And Structure---Property Relations
273(69)
6.1 Introduction
273(1)
6.2 Bulk properties
274(47)
6.2.1 Electrical conductivity
274(11)
6.2.2 Organic magnetic materials
285(8)
6.2.3 Photovoltaicity and photoconductivity
293(3)
6.2.4 Nonlinear optical activity and second harmonic generation
296(7)
6.2.5 Chromoisomerism, photochromism, thermochromism, mechanochromism, etc.
303(16)
6.2.6 The thermo-photo-mechanosalient effect---"hopping" or "jumping" crystals
319(1)
6.2.7 Other physical properties
320(1)
6.3 Molecular properties
321(11)
6.3.1 Infrared and Raman spectroscopy
321(2)
6.3.2 UV/vis absorption spectroscopy
323(7)
6.3.3 Excimer emission
330(1)
6.3.4 Excited state diffraction studies
331(1)
6.4 Photochemical reactions
332(3)
6.5 Thermal reactions and gas--solid reactions
335(1)
6.6 Pressure studies
336(1)
6.7 A variety of emission phenomena
337(4)
6.8 Concluding remarks
341(1)
7 Polymorphism Of Pharmaceuticals
342(34)
7.1 Introduction
342(2)
7.2 Occurrence of polymorphism in pharmaceuticals
344(1)
7.3 Importance of polymorphism in pharmaceuticals
345(8)
7.3.1 Dissolution rate and solubility
346(1)
7.3.2 Bioavailability
346(5)
7.3.3 Following phase changes and mixtures of forms
351(2)
7.4 Screening for crystal forms
353(6)
7.4.1 Solvent selection
354(1)
7.4.2 Screening specifically for hydrates and solvates
355(1)
7.4.3 Use of gels
356(1)
7.4.4 Use of ionic liquids
356(1)
7.4.5 Obtaining a difficult stable or unstable new form
357(1)
7.4.6 New techniques and conditions
358(1)
7.5 Polymorphism in pharmaceutical co-crystals
359(1)
7.6 Chemical similarity is not a predictor of similar polymorphic behavior
360(3)
7.7 Excipients
363(1)
7.8 Microscopy and thermomicroscopy of pharmaceuticals
364(1)
7.9 Thermal analysis of pharmaceuticals
365(2)
7.10 The importance of metastable forms
367(3)
7.11 The importance of amorphous forms
370(2)
7.12 Obtaining a difficult stable or unstable new form
372(2)
7.13 Concluding remarks
374(2)
8 Polymorphism Of Pigments And Dyes
376(22)
8.1 Introduction
376(2)
8.2 Occurrence of polymorphism among pigments
378(6)
8.3 Polymorphism in some specific groups of pigments
384(11)
8.3.1 Quinacridones
384(2)
8.3.2 Perylenes
386(2)
8.3.3 Phthalocyanines
388(5)
8.3.4 Some other pigments---old and new
393(2)
8.4 Isomorphism of pigments
395(3)
9 Polymorphism Of High Energy Materials
398(31)
9.1 Introduction
398(2)
9.2 The "alphabet" of high energy molecular materials
400(2)
9.3 Individual systems
402(27)
9.3.1 Aliphatic materials
403(13)
9.3.2 Aromatic materials
416(13)
10 Polymorphism And Patents
429(28)
10.1 Introduction
429(2)
10.2 Novelty and obviousness in crystal form patents
431(1)
10.3 The scientific perspective
432(2)
10.3.1 Novelty from a scientific perspective
432(1)
10.3.2 Obviousness from a scientific perspective
432(2)
10.4 Some representative crystal form patent litigations
434(22)
10.4.1 Cefadroxil
434(3)
10.4.2 Terazosin hydrochloride
437(1)
10.4.3 Ranitidine hydrochloride
438(3)
10.4.4 Paroxetine hydrochloride
441(2)
10.4.5 Armodafinil
443(4)
10.4.6 Tapentadol hydrochloride
447(6)
10.4.7 Habit, not form: aspartame
453(3)
10.5 Concluding remarks
456(1)
References 457(110)
Index 567
Joel Bernstein earned his Ph.D. in physical chemistry at Yale University for research on solid-state spectroscopy of organic compounds. Following postdoctoral stints at UCLA and the Weizmann Institute of Science, he joined the faculty of the newly established Ben-Gurion University of the Negev, where until 2010 he was the Carol and Barry Kaye Professor of Applied Science in the Chemistry Department. From 2010-2016, he was Global Distinguished Professor of Chemistry at New York University, both in Abu Dhabi and Shanghai. His research interests center on the organic solid state, with emphasis on understanding and utilizing polymorphism, structure-property relationships, hydrogen-bonding patterns and graph sets and organic conducting materials. He has published nearly 200 research and review articles and chapters on these subjects. He has served as a consultant to many multinational pharmaceutical companies and as a testifying witness in patent litigations on the solid-state chemistry of drugs.
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