JOURNAL ARTICLE

Synthesis, Isolation, and Addition Patterns of Trifluoromethylated <i>D</i><sub>5<i>h</i></sub> and <i>I</i><sub><i>h</i></sub> Isomers of Sc<sub>3</sub>N@C<sub>80</sub>: Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>18</sub> andSc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>14</sub>

Abstract

Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub> and Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub> were trifluoromethylated with CF<sub>3</sub>I at 400 °C, affording mixtures of CF<sub>3</sub> derivatives. After separation with HPLC, the first multi-CF<sub>3</sub> derivative of Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub>, Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>18</sub>, and three new isomers of Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>14</sub> were investigated by X-ray crystallography. The Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>18</sub> molecule is characterized by a large number of double C−C bonds and benzenoid rings within the <i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub> cage and a fully different position of the Sc<sub>3</sub>N unit compared to that in the pristine Sc<sub>3</sub>N@<i>D</i><sub>5<i>h</i></sub>-C<sub>80</sub>. A detailed comparison of five Sc<sub>3</sub>N@<i>I</i><sub><i>h</i></sub>-C<sub>80</sub>(CF<sub>3</sub>)<sub>14</sub> isomers reveals a strong influence of the exohedral additions on the behavior of the Sc<sub>3</sub>N cluster inside the <i>I</i><sub><i>h</i></sub>-C<sub>80</sub> cage.

Keywords:
Molecule Derivative (finance) Structural isomer Cluster (spacecraft) Double bond Cis–trans isomerism

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Topics

Fluorine in Organic Chemistry
Life Sciences →  Pharmacology, Toxicology and Pharmaceutics →  Pharmaceutical Science
Synthesis and characterization of novel inorganic/organometallic compounds
Physical Sciences →  Chemistry →  Inorganic Chemistry
Inorganic Fluorides and Related Compounds
Physical Sciences →  Chemistry →  Inorganic Chemistry

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