期刊
TETRAHEDRON
卷 69, 期 35, 页码 7354-7359出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.06.073
关键词
Buckminsterfullerene; Benzyne; [5,6]-Open adduct; [6,6]-Closed adduct; Cycloaddition
资金
- Basic Science Research Program through the National Research Foundation of Korea (NRF)
- Ministry of Science, ICT and Future Planning [2013R1A1A1A05004475, 2010-0019408, 2010-0026916]
- New & Renewable Energy of the Korea Institute of Energy Technology Evaluation and Planning (KETEP) grant
- Korea government Ministry of Knowledge Economy [20123010010140]
- framework of Research and Development Program of the Korea Institute of Energy Research (KIER) [B3-2415]
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 C-60 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-C-60 reaction, as expected, features such as the charge distributions, binding characteristics, and frontier molecular orbital levels, are affected by the different binding modes in C-60 cage. (C) 2013 Published by Elsevier Ltd.
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