Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling
A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. H...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-03-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/22/3/485 |
| _version_ | 1818650056272642048 |
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| author | László Jicsinszky Marina Caporaso Emanuela Calcio Gaudino Cristina Giovannoli Giancarlo Cravotto |
| author_facet | László Jicsinszky Marina Caporaso Emanuela Calcio Gaudino Cristina Giovannoli Giancarlo Cravotto |
| author_sort | László Jicsinszky |
| collection | DOAJ |
| description | A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses. |
| first_indexed | 2024-12-17T01:44:09Z |
| format | Article |
| id | doaj.art-49c0bf97cdbc4a1cb09fb5ae24301b21 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T01:44:09Z |
| publishDate | 2017-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-49c0bf97cdbc4a1cb09fb5ae24301b212022-12-21T22:08:14ZengMDPI AGMolecules1420-30492017-03-0122348510.3390/molecules22030485molecules22030485Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball MillingLászló Jicsinszky0Marina Caporaso1Emanuela Calcio Gaudino2Cristina Giovannoli3Giancarlo Cravotto4Department of Drug Science and Technology, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDepartment of Drug Science and Technology, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDepartment of Drug Science and Technology, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDepartment of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyDepartment of Drug Science and Technology, University of Turin, Via P. Giuria 7, 10125 Turin, ItalyA number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses.http://www.mdpi.com/1420-3049/22/3/485high-energy ball millinganionic cyclodextrinsolvent-free reactionsrandom substitution |
| spellingShingle | László Jicsinszky Marina Caporaso Emanuela Calcio Gaudino Cristina Giovannoli Giancarlo Cravotto Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling Molecules high-energy ball milling anionic cyclodextrin solvent-free reactions random substitution |
| title | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
| title_full | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
| title_fullStr | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
| title_full_unstemmed | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
| title_short | Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling |
| title_sort | synthesis of randomly substituted anionic cyclodextrins in ball milling |
| topic | high-energy ball milling anionic cyclodextrin solvent-free reactions random substitution |
| url | http://www.mdpi.com/1420-3049/22/3/485 |
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