Crystal to crystal transformation in the solid state

Kuroda, Reiko; Higashiguchi, Kenji; Hasebe, Sayoko; Imai, Yoshitane

doi:10.1039/b408971e

Cited by 67 publications

(67 citation statements)

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“…[153] Formation of charge transfer cocrystals can often be followed by eye due to the change in color. Kuroda et al [28,154] obtained three-component cocrystals based on racemic bis--naphthol, benzoquinone and anthracene. Importantly, the resulting cocrystal could not be obtained from solution and so required structure determination from X-ray powder diffraction (see Section 9).…”

Section: Charge Transfer Cocrystalsmentioning

confidence: 99%

“…On the other, this also derives from the fact that the reaction conditions studied are not always actually mechanochemical (and therefore they may not explicitly consider the formation of hot spots). Work from several groups has been summarized under three generic mechanisms, [21] specifically i. molecular transport across surfaces, [27] through the vapour phase, [27][28] or through the bulk of a crystal, [29] ii. formation of liquid eutectic intermediate phases,.…”

Section: Mechanistic Aspectsmentioning

confidence: 99%

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Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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Citation for published item:tmesD F vF nd edmsD gF tF nd folmD gF nd frgD hF nd gollierD F nd pri § s § i¡ D F nd qrepioniD pF nd rrrisD uF hF wF nd ryettD qF nd tonesD F nd uresD eF nd wkD tF nd winiD vF nd yrpenD eF qF nd rkinD sF F nd herouseD F gF nd teedD tF F nd ddellD hF gF @PHIPA 9wehnohemistry X opportunities for new nd lener synthesisF9D ghemil soiety reviewsFD RI @IAF ppF RIQERRUF Further information on publisher's website: Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details.

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Section: Charge Transfer Cocrystalsmentioning

confidence: 99%

Section: Mechanistic Aspectsmentioning

confidence: 99%

Mechanochemistry: opportunities for new and cleaner synthesis

et al. 2012

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“…The paste-like intermediate phase is expected in this case since the melting points of both reactants (40-42 °C for ovan and 103-107 °C for 4aa) are low enough for such behaviour and reaction pathway to take place. [7,[28][29][30][31][32][33] However the conversion to compound 1 was incomplete according to the PXRD data as can be seen in Figure 1 (left). For that reason, the reaction was repeated in a mortar by means of liquid-assisted grinding (LAGam) using 20 μL acetonitrile (MeCN) yielding in complete conversion of reactants into compound 1.…”

Section: Synthesis and Characterizationmentioning

confidence: 97%

“…Since the melting points of both reactants are well above 100 °C (104-108 °C for oOH and 133-136 °C for 2a4mp) the formation of a liquid or a paste was not expected. [7,[28][29][30][31][32][33] The reaction mixture starts to change its colour already after one minute of NGam of pOH and 3aa ( Figure S3a)). As expected from the values of the melting points of reactants (97-99 °C for pOH and 94-98 °C for 3aa) the route of conversion of reactants is via a paste-like intermediate phase.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…As expected from the values of the melting points of reactants (97-99 °C for pOH and 94-98 °C for 3aa) the route of conversion of reactants is via a paste-like intermediate phase. [7,[27][28][29][30][31][32] The paste forms slowly and starts to solidify after about 13 minutes of grinding. Finally, a red powder of compound 3 was obtained after 14 minutes of grinding and there were no traces of reactants in it, revealed by PXRD experiments (Figure 1 (right)).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

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Supramolecular Influence on Keto-Enol Tautomerism and Thermochromic Properties of o-Hydroxy Schiff Bases

Zbačnik¹,

Kaitner²

2016

Croat. Chem. Acta

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This work presents a study on thermo-optical properties of three Schiff bases (imines) in the solid state. The Schiff bases were obtained by means of mechanochemical synthesis using monosubstituted o-hydroxy aromatic aldehydes and monosubstituted aromatic amines. The keto-enol tautomerism and proton transfer via intramolecular O•••N hydrogen bond of the reported compounds was found to be influenced more by supramolecular interactions than by a temperature change. All products were characterised by powder X-ray diffraction (PXRD), FT-IR spectroscopy, thermogravimetric (TG) analysis and differential scanning calorimetry (DSC). Molecular and crystal structures of compounds 1, 2 and 3 were determined by single crystal X-ray diffraction (SCXRD). The molecules of 1 appear to be present as the enol-imine, the molecules of 2 as the keto-amine tautomer and the molecules of 3 exhibit keto-enol tautomeric equilibrium in the solid state. An analysis of Cambridge structural database (CSD) data on similar imines has been used for structural comparison.

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Mechanical Preparation of Crystalline Materials. An Oxymoron?

Braga

Dichiarante²,

Grepioni

et al. 2012

Supramolecular Chemistry

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The thesis developed in this chapter is that reactions taking place between molecular materials (intersolid) or within a molecular material (intrasolid) can be used to produce new crystalline materials in solvent‐free conditions and often with quantitative yields. The most common approach to intersolid and, to lesser extent, intrasolid processes is based on the mechanical cogrinding of the solid reactants, which implies comminution of the reactants. The implicit consequence of this is the lack of crystals of the product suitable for single‐crystal X‐ray diffraction. The mechanical process yields a polycrystalline or amorphous product, with structure and composition that often differ from that obtained from solution crystallization.

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Crystal to crystal transformation in the solid state

Cited by 67 publications

References 28 publications

Mechanochemistry: opportunities for new and cleaner synthesis

Mechanochemistry: opportunities for new and cleaner synthesis

Supramolecular Influence on Keto-Enol Tautomerism and Thermochromic Properties of o-Hydroxy Schiff Bases

Mechanical Preparation of Crystalline Materials. An Oxymoron?

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