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2542618131
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note
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Note that there are three distinct types of CH⋯O interactions discussed. In the adenine-uracil/thymine base-pair, the 1-1 dimer, and the intramolecularly hydrogen-bonded 2 the CH group is adjacent to two, one, and no nitrogen atoms, respectively. More flanking nitrogen atoms should make for a more acidic C - H group and a correspondingly stronger CH⋯O hydrogen bond.
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0001304039
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Söntjens, S. H. M.; Meijer, J. T.; Kooijman, H.; Spek, A. L.; van Genderen, M. H. P.; Sijbesma, R. P.; Meijer, E. W. Org. Lett. 2001, 3, 3887-3889.
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Sijbesma, R.P.6
Meijer, E.W.7
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2542621147
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note
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Other plausible explanations exist for the unusual stabilities reported herein. For example, differences in primary hydrogen bonding strengths, differences in the strength of the intramolecular hydrogen bond in 2 and 3, dipolar interactions, differential solvation, etc. may explain the results. These effects, although potentially quite important, are less readily discernible.
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