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ASSOCIATED CONTENT
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S
* Supporting Information
Detailed experimental procedures; NMR, MS, IR, TGA, PXRD,
and reaction data; and crystallographic data (CIF). This material
4901.
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5-Dicarboxy-substituted arylureas (and related esters) are poor materials
for comparison since these esters prevent dimerization through steric
“shielding”. Modeling with the aryl rings aligned in-plane with the urea
carbonyl group clearly showed that the ester substituents of one urea
engender destablizing/unfavorable van der Waals interactions with a
second 3,5-dicarboxyurea ester before the carbonyl group of one molecule
is close enough to the NH groups of a second urea molecule for
intermolecular self-quenching.
AUTHOR INFORMATION
■
Corresponding Author
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
K.A.S. thanks Amgen for generous support and AFOSR for
initial support of this work. J.M.R. and B.M.F. thank the
Bordwell Chemistry Research Fund (NU) and a Northwestern
Summer URG program, respectively, for partial fellowship
support. O.K.F. and J.T.H. thank the AFOSR and DTRA
(Grant HDTRA1-09-1-0007) for financial support. The authors
acknowledge Chris Wilmer (NU) for assistance with modeling.
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