“Total Synthesis” Supramolecular Style: Design and Hydrogen-Bond-Directed Assembly of Ternary Supermolecules

Aakeröy, Christer B.; Beatty, Alicia M.; Helfrich, Brian A.

doi:10.1002/1521-3773(20010903)40:17<3240::aid-anie3240>3.0.co;2-x

Cited by 440 publications

(293 citation statements)

References 26 publications

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“…The patterns may be satisfactorily indexed on expanded versions of the known cell for BA:isoNCT. 22 There is a steady increase in the a-parameter with rising temperature Table S1. Partial Rietveld fits are given in Figure S5.…”

Section: Hot Stage Microscopymentioning

confidence: 99%

“…[12][13][14][15][16] Benzoic acid (BA) and isonicotinamide (isoNCT) have both been widely explored as co-formers for pharmaceutical co-crystal synthesis. [17][18][19][20][21] They are known to form both 1:1 (BA:isoNCT) 22 and 2:1 (BA 2 :isoNCT) 18 co-crystals. Possible synthetic routes to these include solution methods, 18,22 melt crystallisation, 21,23 template synthesis using BA crystals as a substrate, 21 and thermal inkjet printing.…”

Section: Introductionmentioning

confidence: 99%

“…[17][18][19][20][21] They are known to form both 1:1 (BA:isoNCT) 22 and 2:1 (BA 2 :isoNCT) 18 co-crystals. Possible synthetic routes to these include solution methods, 18,22 melt crystallisation, 21,23 template synthesis using BA crystals as a substrate, 21 and thermal inkjet printing. 17 The structures of both BA:isoNCT and BA 2 :isoNCT are given in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

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Thermal Behavior of Benzoic Acid/Isonicotinamide Binary Cocrystals

Buanz

Prior

Burley

et al. 2015

Crystal Growth & Design

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YesA comprehensive study of the thermal behavior of the 1:1 and 2:1 benzoic acid/isonicotinamide cocrystals is reported. The 1:1 material shows a simple unit cell expansion followed by melting upon heating. The 2:1 crystal exhibits more complex behavior. Its unit cell first expands upon heating, as a result of C–H···π interactions being lengthened. It then is converted into the 1:1 crystal, as demonstrated by significant changes in its X-ray diffraction pattern. The loss of 1 equiv of benzoic acid is confirmed by thermogravimetric analysis–mass spectrometry. Hot stage microscopy confirms that, as intuitively expected, the transformation begins at the crystal surface. The temperature at which conversion occurs is highly dependent on the sample mass and geometry, being reduced when the sample is under a gas flow or has a greater exposed surface area but increased when the heating rate is elevated

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Section: Hot Stage Microscopymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermal Behavior of Benzoic Acid/Isonicotinamide Binary Cocrystals

Buanz

Prior

Burley

et al. 2015

Crystal Growth & Design

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“…Since the odds are stacked firmly in favor of a homomeric product, how do we go about developing reliable and versatile synthetic methods for the directed assembly of co-crystals? This presentation will attempt to answer the question by outlining several modular hydrogen-bond driven strategies for the design and synthesis of binary and ternary supermolecules and co-crystals [1][2][3].…”

Section: Abstract: Hydrogen Bonds Co-crystals Molecular Recognitionmentioning

confidence: 99%

“…It is trivial with the existing search software [1] to find all CSD entries containing a particular solvent, say water, and a survey of the 50 most common solvents in the CSD has been published [2]. It might be interesting, however, to know if any of these solvates also exist in an unsolvated form; given a crystal structure of di-isopropylammonium chloride hydrate in the CSD, for example, one could wonder if a crystal structure of di-isopropylammonium chloride itself is present in the database.…”

mentioning

confidence: 99%

Searching the Cambridge Structural Database for solvatedvsunsolvated pairs

Streek¹,

Motherwell²

2006

Acta Cryst Sect A

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The more than 365,000 organic and organometallic small-molecule crystal structures in the Cambridge Structural Database (CSD) are a good source of data for understanding the crystal structures of solvates. It is trivial with the existing search software [1] to find all CSD entries containing a particular solvent, say water, and a survey of the 50 most common solvents in the CSD has been published [2]. It might be interesting, however, to know if any of these solvates also exist in an unsolvated form; given a crystal structure of di-isopropylammonium chloride hydrate in the CSD, for example, one could wonder if a crystal structure of di-isopropylammonium chloride itself is present in the database.A computer program was written that for a given solvent molecule finds all pairs of solvated versus unsolvated CSD entries; a list of solvate structures for which no unsolvated form exists in the CSD is also generated. These lists enable us to examine if properties such as the number of hydrogen-bond donors / acceptors or the molecular flexibility influence solvate formation. Results for hydrates will be presented.[1] Bruno, I.J.; Cole, J.C.; Edgington, P.R.; Kessler, M.; Macrae, C.F.;McCabe, P.; Pearson, J.; Taylor, R

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Polymorphic Crystal Forms and Cocrystals in Drug Delivery (Crystal Engineering)

Shan¹,

Zaworotko

2010

Burger's Medicinal Chemistry and Drug Discovery

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Active pharmaceutical ingredients, APIs, are most conveniently developed and delivered orally as solid dosage forms that contain a defined crystalline form of an API. This means that the pharmacokinetic profile of a dosage form is at the very least linked to the physicochemical properties of the crystal form that is selected for development. Furthermore, that crystal forms of new chemical entities are novel, lack obviousness, and have utility makes them patentable. Therefore, selection of a specific crystal form for a given API is a profoundly important step in drug development from clinical, legal, and regulatory perspectives. In this context, scientific developments that afford greater understanding of and diversity in the number of crystalline forms available for a given API, which have traditionally been limited to salts, polymorphs, and hydrates/solvates [(a) Byrn SR, Pfeiffer RR, Stowell JG. Solid State Chemistry of Drugs. 2nd ed. West Lafayette, IN: SSCI, Inc.; 1999. (b) Haleblian JK. J. Pharm. Sci. 1975;64:1269–1288.], are obviously of relevance to the pharmaceutical industry. The science of crystal engineering [(a) Etter MC. J Phys Chem 1991;95:4601–4610. (b) Zerkowski JA, MacDonald JC, Seto CT, Wierda DA, Whitesides GM. J Am Chem Soc 1994;116:2382–2391. (c) Pepinsky R. Phys Rev 1955;100:971. (d) Schmidt GMJ. Pure Appl Chem 1971;27:647–678. (e) Desiraju GR. Crystal Engineering: The Design of Organic Solids. Amsterdam: Elsevier; 1989. (f) Moulton B, Zaworotko MJ. Chem Rev 2001;101: 1629–1658. (g) Braga D. Chem Commun 2003;22:2751–2754. (h) Hosseini MW. Coord Chem Rev 2003;240:157–166. (i) Desiraju GR. Angew Chem Int Ed Engl 1995;34: 2311–2327.] focuses upon self‐assembly of existing molecules or ions and it has evolved in such a manner that a wide range of new crystal forms can be generated without the need to invoke covalent‐bond breakage or formation. This contribution will address the impact of crystal engineering upon our fundamental understanding of crystal form diversity and how physical properties of crystals can be customized via the emerging class of crystal forms that have been termed pharmaceutical cocrystals [(a) Almarsson Ö, Zaworotko MJ. Chem Commun 2004; 1889–1896. (b) Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. J Pharm Sci 2006;95:499–516. (c) Peterson ML, Hickey MB, Zaworotko MJ, Almarsson O. J Pharm Pharm Sci 2006;9:317–326. (d) Zaworotko M. Am Pharm Outsourc 2004;5: 16–23. (e) Shan N, Zaworotko MJ. Drug Discov Today 2008;13:440–446. (f) Blagden N, de Matas M, Gavan PT, Yoark P, Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates Adv Drug Del Rev 2007;59:617–630. (g) Nangia A. Cryst Growth Des 2008;8:1079–1081].

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“Total Synthesis” Supramolecular Style: Design and Hydrogen-Bond-Directed Assembly of Ternary Supermolecules

Cited by 440 publications

References 26 publications

Thermal Behavior of Benzoic Acid/Isonicotinamide Binary Cocrystals

Thermal Behavior of Benzoic Acid/Isonicotinamide Binary Cocrystals

Searching the Cambridge Structural Database for solvatedvsunsolvated pairs

Polymorphic Crystal Forms and Cocrystals in Drug Delivery (Crystal Engineering)

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