Proton Sandwiches: Nonclassical Carbocations with Tetracoordinate Protons

Exotic species: A number of unusual carbocations in which formally tetracoordinate protons are seemingly suspended between two CC bonds were studied computationally. An example, the “proton sandwich” derived from 1,5‐cyclooctadiene, is shown in the picture (C black, H white).

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-04, Vol.44 (18), p.2719-2723
Main Authors: Gutta, Pradeep, Tantillo, Dean J.
Format: Article
Language:English
Subjects:
alkenes
carbocations
Carbon - chemistry
Carbon - classification
Cations - chemistry
density functional calculations
Imaging, Three-Dimensional
Models, Molecular
Molecular Conformation
protonation
Protons
terpenoids
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Summary:Exotic species: A number of unusual carbocations in which formally tetracoordinate protons are seemingly suspended between two CC bonds were studied computationally. An example, the “proton sandwich” derived from 1,5‐cyclooctadiene, is shown in the picture (C black, H white).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461915