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Even as recently as 1991 it was still believed that CH-O bonds would not have a major influence on molecular conformations: G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer Verlag, Berlin, 1991.
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For example, in the last years Kool et al. have shown that synthetic nonpolar nucleoside isosteres can replace normal DNA bases without affecting base pairing or replication properties: E. T. Kool, J. C. Morales, K. M. Guckian, Angew. Chem. Int. Ed. Engl. 2000, 39, 990-1009.
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note
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Crystallographic data (excluding structure factors) for the structure of 2·Cl have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-149249. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. [Fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk.]
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0031587446
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For a CH-O bond to a negatively charged carboxylate oxygen even a C⋯H distance of only 2.107 Å (corresponding to a C⋯O distance of 3.193 A with a bond angle of 176°) was reported: P. R. Mallison, K. Wozniak, G. T. Smith, K. L. McCormack, J. Am. Chem. Soc. 1997, 119, 11502-11509.
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0034640006
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Recently, Gokel and co-workers showed that within a series of lariat ethers even CH-O hydrogen bonds with bond lengths of >3.5 A are important structure determining interactions: E. S. Meadow, S. L. DeWall, L. J. Barbour, F. R. Fronczek, M.-S. Kim, G. W. Gokel, J. Am. Chem. Soc. 2000, 122, 3325-3335.
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0031882011
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4 due to other contributions such as preorganization or flexibility: F. H. Beijer, H. Kooijman, A. L. Spek, R. P. Sijbesma, E. W. Meijer, Angew. Chem. Int. Ed. Engl. 1998, 37, 75-78.
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A similar analysis was done recently to establish the relative contributions of π-π stacking and CH-O hydrogen bonds to the overall binding of bipyridinium guests by catenated hosts: K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1999, 121, 1479-1487.
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Williams, D.J.6
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