Organic Letters
Letter
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similar interaction energies for the two types of surfaces. Thus,
the methyl ether oxygen appears to play a key role in modifying
the interaction energies with heterocyclic surfaces. The O-atom
does not appear to enhance the CH−π interaction directly.
Instead, the C−O dipole interacts with the heterocycle dipole,
which can strengthen or weaken the OCH3−aromatic
interaction. These stability trends may have some bearing on
many biologically important carbohydrate−aromatic interac-
tions. The attraction between C−O and heterocycle dipoles
explains the prevalence of carbohydrate−heteroarene interac-
tions. This dipole−dipole interaction could also be used to
optimize carbohydrate binding in synthetic and bioengineered
carbohydrate receptors. New molecular balances containing
other biologically relevant heterocyclic motifs, such as
tryptophane, pyrimidine, and purines, are currently being
developed in our laboratory to further investigate this
phenomenon.
ASSOCIATED CONTENT
■
S
* Supporting Information
Experimental details, characterization data for all newly reported
compounds, crystal data (cif) for 1′, 2′, and 6′, computational
details. This material is available free of charge via the Internet at
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AUTHOR INFORMATION
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Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the National Science Foundation
(NSF) grants CHE 1310139 and CHE 1300497.
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