Mono- and multiply-functionalized fullerene derivatives through 1,3-dipolar cycloadditions: A DFT study

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• 作者：Maryam Anafcheh ; Reza Ghafouri
• 关键词：1 ; 3-Dipolar cycloaddition ; Multiply-functionalized fullerene ; Electrophilicity ; DFT
• 刊名：Physica E
• 出版年：February, 2014
• 年：2014
• 卷：56
• 期：Complete
• 页码：351-356
• 全文大小：740 K

文摘

We have performed a computational study to investigate the electronic and chemical properties of mono- and multiply-functionalized fullerene derivatives through the [2+3] cycloaddition reactions of 1,3 dipoles such as nitriloxide (HC氓N⁺-O^{鈭?/sup>), azide (N氓N+-NH鈭?/sup>) and azomethine ylides () with C₆₀ fullerene. The 1,3-dipolar cycloadditions (1,3 DCs) of one to six dipoles with a C₆₀ molecule are theoretically investigated in terms of geometry, energies, electronic structures, stability and the electrophilicity index. Negative values of reaction energies E_r are obtained, which indicate the exothermic character of the adsorption process. Generally, absolute values of E_r for the C₆₀/()_n compounds are always larger than those of their corresponding compounds C₆₀/(HC氓N+-O鈭?/sup>)_n and C₆₀/(N氓N+-NH鈭?/sup>)_n. The results indicate that the successive 1,3-DC reactions of nitriloxides (HC氓N+-O鈭?/sup>) and azides (N氓N+-NH鈭?/sup>), n=1,2, 4 and 6 on the exterior surface of fullerene increases the electrophilicity while the reverse trend is observed for C₆₀/()_n. Furthermore, electrophilicity values for the C₆₀/(HC氓N+-O鈭?/sup>)_n and C₆₀/(N氓N+-NH鈭?/sup>)_n compounds are always greater than those of C₆₀.}