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In-Adamantane, a Small Inside-Out Molecule

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Karl K. Irikura*

Physical and Chemical Properties Division, National Institute of Standards and Technology, Gaithersburg, Maryland 20899-8380

J. Org. Chem., 2008, 73 (20), pp 7906–7908

DOI: 10.1021/jo801806w

Publication Date (Web): September 25, 2008

Section:

Physical Organic Chemistry

Abstract

The hydrocarbon in-adamantane (1), a high-energy adamantane isomer in which one methine hydrogen atom is inside the cage, is predicted by ab initio calculations to be isolable at dry ice temperature. It has 440 kJ/mol of hydrogenic strain but appears to be stable against dimerization, moisture, and air. The inverted CH bond is compressed, and the IR and NMR spectra are unusual. The symmetrical pentadecafluoro derivative (2) has an estimated half-life of 100 years at room temperature.

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In-Adamantane, a Small Inside-Out Molecule
Karl K. Irikura
The Journal of Organic Chemistry2008 73 (20), 7906-7908
- In-Adamantane, a Small Inside-Out Molecule
  Karl K. Irikura
  The Journal of Organic Chemistry2008 73 (20), 7906-7908
  The hydrocarbon in-adamantane (1), a high-energy adamantane isomer in which one methine hydrogen atom is inside the cage, is predicted by ab initio calculations to be isolable at dry ice temperature. It has 440 kJ/mol of hydrogenic strain but appears to ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links