An unprecedented [5,6]-open adduct via a direct benzyne-C-60 cycloaddition
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- An unprecedented [5,6]-open adduct via a direct benzyne-C-60 cycloaddition
- Kim, Gyoungsik; Lee, Kyu Cheol; Kim, Jonggi; Lee, Jeong Chul; Lee, Sang Myeon; Lee, Jeong Chu; Seo, Jung Hwa; Choi, Won-Youl; Yang, Changduk
- [5,6]-Open adduct; [6,6]-Closed adduct; Benzyne; Buckminsterfullerene; Cycloaddition
- Issue Date
- PERGAMON-ELSEVIER SCIENCE LTD
- TETRAHEDRON, v.69, no.35, pp.7354 - 7359
- Cycloaddition is one of the best-studied types of reactions in the organic chemistry of fullerenes, engendering [6,6]-closed adducts in the vast majority of cases. Notwithstanding that a formation of open fulleroid structures is undoubtedly of theoretical interest, no one has demonstrated the conformation of [5,6]-open fulleroid via the direct cycloadditions. Here, we establish that cycloaddition between C60 and benzyne in situ generated from 2-amino-4,5-dibutoxybenzoic acid affords a new type of elusive [5,6]-open structure that is characterized on the basis of NMR, UV-vis spectroscopy, and cyclic voltammetry. Additionally, from density functional theory (DFT) calculations for possible [5,6]-open and [6,6]-closed adducts induced of benzyne-C60 reaction, as expected, features such as the charge distributions, binding characteristics, and frontier molecular orbital levels, are affected by the different binding modes in C60 cage.
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