Journal of the American Chemical Society
COMMUNICATION
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(13) Estimated using FieldView 2.0.0, Cresset Biomolecular Dis-
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(15) Ab initio calculations on 2a indicate that energy minima with
short NH O=C distances are ∼16 kJ mol-1 above ground state. For
3 3 3
details see Supporting Information.
(16) Mascal, M. J. Chem. Soc., Perkin Trans. 2 1997, 1999.
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(18) For details, see Supporting Information.
(19) Jones, J. B.; Dodds, D. R. Can. J. Chem. 1987, 65, 2397.
(20) Diazides 5 (R = Me, Et) failed to explode on heating or impact.
Nonetheless, for preparative-scale work, they were handled exclusively
as e20% solutions in organic solvents.
(21) Timko, J. M.; Moore, S. S.; Walba, D. M.; Hiberty, P. C.; Cram,
D. J. J. Am. Chem. Soc. 1977, 99, 4207.
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(23) Octyl esters were used for optimal solubility in the organic
phase.
(24) Transport activity was also observed when receptors 2 were
added as solutions in methanol to preformed vesicles. However, rates
were often lower than observed for preincorporated 2, depending on the
choice of Ar and R and also on the exact method of addition. Details of
these experiments will be published separately.
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dx.doi.org/10.1021/ja1076102 |J. Am. Chem. Soc. 2011, 133, 1614–1617