Theoretical Study on the Reactivity and Regioselectivity of the Diels-Alder Reaction of Fullerene: Effects of Charges and Encapsulated Lanthanum on the Bis-Functionalization of C70.

Title Theoretical Study on the Reactivity and Regioselectivity of the Diels-Alder Reaction of Fullerene: Effects of Charges and Encapsulated Lanthanum on the Bis-Functionalization of C70.
Authors C.X. Cui; Y.J. Liu; Y.P. Zhang; L.B. Qu; Z.P. Zhang
Journal J Phys Chem A
DOI 10.1021/acs.jpca.6b10231
Abstract

Bis-adducts of fullerenes are important for both material and biological science. The first added substituent greatly impacts the reactivity and regioselectivity of fullerene. What determines the bond reactivity and how to control the regioselectivity are two crucial questions in synthesizing bis-adduct of C70. Recently, an unexpected 12 o'clock isomer of anthracene bis-adduct of C70 was prepared with high yield by the Diels-Alder (DA) reaction although three possible isomers (12, 2, and 5 o'clock isomers) may be formed. In the current study, the beneath mechanism is systematically investigated by density functional theory methods. Moreover, effects of charges and encapsulated lanthanum atom on the regioselectivity are reported. The computational results successfully rationalize experimental observations by Venkata et al. A possible way to change the regioselectivity of DA reaction is put forward. The kinetical promotion effect of an encapsulated La atom on the 12 o'clock reaction is elucidated.

Citation C.X. Cui; Y.J. Liu; Y.P. Zhang; L.B. Qu; Z.P. Zhang.Theoretical Study on the Reactivity and Regioselectivity of the Diels-Alder Reaction of Fullerene: Effects of Charges and Encapsulated Lanthanum on the Bis-Functionalization of C70.. J Phys Chem A. 2017;121(2):523531. doi:10.1021/acs.jpca.6b10231

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Lanthanum

See more Lanthanum products. Lanthanum (atomic symbol: La, atomic number: 57) is a Block F, Group 3, Period 6 element with an atomic weight of 138.90547. Lanthanum Bohr ModelThe number of electrons in each of lanthanum's shells is [2, 8, 18, 18, 9, 2] and its electron configuration is [Xe] 5d1 6s2. The lanthanum atom has a radius of 187 pm and a Van der Waals radius of 240 pm. Lanthanum was first discovered by Carl Mosander in 1838. In its elemental form, lanthanum has a silvery white appearance.Elemental Lanthanum It is a soft, malleable, and ductile metal that oxidizes easily in air. Lanthanum is the first element in the rare earth or lanthanide series. It is the model for all the other trivalent rare earths and it is the second most abundant of the rare earths after cerium. Lanthanum is found in minerals such as monazite and bastnasite. The name lanthanum originates from the Greek word Lanthaneia, which means 'to lie hidden'.

Carbon

See more Carbon products. Carbon (atomic symbol: C, atomic number: 6) is a Block P, Group 14, Period 2 element. Carbon Bohr ModelThe number of electrons in each of Carbon's shells is 2, 4 and its electron configuration is [He]2s2 2p2. In its elemental form, carbon can take various physical forms (known as allotropes) based on the type of bonds between carbon atoms; the most well known allotropes are diamond, graphite, amorphous carbon, glassy carbon, and nanostructured forms such as carbon nanotubes, fullerenes, and nanofibers . Carbon is at the same time one of the softest (as graphite) and hardest (as diamond) materials found in nature. It is the 15th most abundant element in the Earth's crust, and the fourth most abundant element (by mass) in the universe after hydrogen, helium, and oxygen. Carbon was discovered by the Egyptians and Sumerians circa 3750 BC. It was first recognized as an element by Antoine Lavoisier in 1789.

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