Regioselectivity of the Pauson-Khand Reaction in Single-Walled Carbon Nanotubes
Chemical functionalization of nanotubes, in which their properties can be combined with those of other classes of materials, is fundamental to improve the physicochemical properties of nanotubes for potential technological applications. In this work, we theoretically and experimentally examine the P...
| Autores: | , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:10256/15927 |
| Acceso en línea: | http://hdl.handle.net/10256/15927 |
| Access Level: | acceso abierto |
| Palabra clave: | Reaccions d'addició Addition reactions Pauson-Khand, Reacció de Pauson-Khand reaction Nanotubs Nanotubes |
| Sumario: | Chemical functionalization of nanotubes, in which their properties can be combined with those of other classes of materials, is fundamental to improve the physicochemical properties of nanotubes for potential technological applications. In this work, we theoretically and experimentally examine the Pauson-Khand reaction (PKR) on zig-zag, armchair, and chiral single-walled carbon nanotubes (SWCNTs). Our benchmarked density functional theory (DFT) calculations show that an alternative pathway to the widely accepted Magnus reaction pathway has significantly lower energy barriers, thus suggesting the use of this alternative pathway to predict whether a PKR on SWCNTs is favored or hampered. Accessible energy barriers of up to 16 kcal/mol are estimated and our results suggest that semiconducting SWCNTs react faster than metallic ones, although both types can be functionalized. Guided by our theoretical predictions, cyclopentenones are successfully attached to SWCNTs by heating and are, subsequently, characterized in the laboratory |
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