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Cycloaddition Reactions of Butadiene and 1,3‐Dipoles to Curved Arenes, Fullerenes, and Nanotubes: Theoretical Evaluation of the Role of Distortion Energies on Activation Barriers
Author(s) -
Osuna Sílvia,
Houk Kendall N.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901761
Subject(s) - cycloaddition , fullerene , oniom , azomethine ylide , computational chemistry , dipole , 1,3 dipolar cycloaddition , chemistry , density functional theory , nanotube , carbon nanotube , transition state , photochemistry , chemical physics , materials science , nanotechnology , organic chemistry , catalysis
Diels–Alder cycloadditions of butadiene and 1,3‐dipolar cycloadditions of azomethine ylide, fulminic acid, and the parent nitrone to polyacenes, fullerenes, and nanotubes have been investigated with density functional theory and ONIOM methods. Activation barriers obtained for cycloaddition reactions on planar and curved systems have been shown to be highly correlated to the energy needed to distort the reactants to the geometry of the transition state (TS).