Conjugation‐Promoted Reaction of Open‐Cage Fullerene: A Density Functional Theory Study |
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Authors: | Dr Yong Guo Dr Jingjing Yan Prof Dr Niveen M Khashab |
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Institution: | Controlled Release and Delivery Lab (CRD), Center of Membrane Porous Materials, Chemical and Life Sciences and Engineering Division, King Abdullah University of Science and Technology (KAUST), Thuwal 23955‐6900 (Kingdom of Saudi Arabia) |
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Abstract: | Density functional theory calculations are performed to study the addition mechanism of e‐rich moieties such as triethyl phosphite to a carbonyl group on the rim of a fullerene orifice. Three possible reaction channels have been investigated. The obtained results show that the reaction of a carbonyl group on a fullerene orifice with triethyl phosphite most likely proceeds along the classical Abramov reaction; however, the classical product is not stable and is converted into the experimental product. An attack on a fullerene carbonyl carbon will trigger a rearrangement of the phosphate group to the carbonyl oxygen as the conversion transition state is stabilized by fullerene conjugation. This work provides a new insight on the reactivity of open‐cage fullerenes, which may prove helpful in designing new switchable fullerene systems. |
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Keywords: | computational chemistry Abramov reaction density functional theory fullerenes reaction mechanism |
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