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Citation: LIANG Yun-Xiao, SHANG Zhen-Feng, XU Xiu-Fang, ZHAO Xue-Zhuang. Regioselectivity of 1,3-Butadiene Diels-Alder Cycloaddition to C₅₉XH(X=N, B)[J]. Acta Physico-Chimica Sinica, ;2008, 24(10): 1811-1816. doi: 10.1016/S1872-1508(08)60074-1 shu

Regioselectivity of 1,3-Butadiene Diels-Alder Cycloaddition to C₅₉XH(X=N, B)

1.
State Key Laboratory Base of Novel Functional Materials and Preparation Science, College of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, Zhejiang Province, P. R. China; Department of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received Date: 31 March 2008
Available Online: 8 September 2008

The regioselectivity of Diels-Alder cycloaddition of 1,3-butadiene to C59XH (X=N, B) has been studied theoretically by means of the semiempirical AM1 and DFT (B3LYP/6-31G*) methods. The mechanisms of the cycloaddition on some selected 6—6 bonds of C59XH (X=N, B) have been analyzed. For C59NH, the activation energies become lower with the addition site increasingly farther fromthe N atom; however, they are all higher than that of the reaction of 1,3-butadiene with C60. In contrast to C59NH, for the cycloaddition to C59BH, the activation energies corresponding to 2,12/r-and 2,12/f-transition states, in which the addition sites are the nearest ones to the B atom, are the lowest ones,and are lower than that of the reaction of 1,3-butadiene with C60 by over 18 kJ·mol-1, and the products corresponding to these two transition states are the most stable ones. The different electronic natures ofNandB atoms results in different effects on the Diels-Alder reactions of 1,3-butadiene with C59NH and C59BH; the former makes the reactivity of C59NH reduced and the latter makes the reactivity of C59BH enhanced, relative to that of C60.
- C59XH(X=N, B),
- Diels-Alder cycloaddition,
- Regioselectivity,
- AM1,
- DFT
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沈阳化工大学材料科学与工程学院沈阳 110142

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Regioselectivity of 1,3-Butadiene Diels-Alder Cycloaddition to C59XH(X=N, B)

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通讯作者: 陈斌, bchen63@163.com

Regioselectivity of 1,3-Butadiene Diels-Alder Cycloaddition to C₅₉XH(X=N, B)