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Volumn 6, Issue 10, 2004, Pages 1649-1652

With regard to the hydrogen bonding in complexes of pyridylureas, less is more. A role for shape complementarity and CH⋯O interactions?

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE; HYDROGEN; PYRIDYLUREA DERIVATIVE; TETRAAZAANTHRACENEDIONE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

EID: 2542511756     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495016     Document Type: Article
Times cited : (40)

References (31)
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    • See the Supporting Information
    • See the Supporting Information.
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    • Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. Eur. J. 1999, 5, 3581-3594. Hobza, P.; Sponer, J.; Cubero, E.; Orozco, M.; Luque, F. J. J. Phys. Chem. B 2000, 104, 6286-6292. Asensio, A.; Kobko, N.; Dannenberg, J. J. J. Phys. Chem. A 2003, 107, 6441-6443.
    • (1999) Chem. Eur. J. , vol.5 , pp. 3581-3594
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    • Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. Eur. J. 1999, 5, 3581-3594. Hobza, P.; Sponer, J.; Cubero, E.; Orozco, M.; Luque, F. J. J. Phys. Chem. B 2000, 104, 6286-6292. Asensio, A.; Kobko, N.; Dannenberg, J. J. J. Phys. Chem. A 2003, 107, 6441-6443.
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    • Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. Eur. J. 1999, 5, 3581-3594. Hobza, P.; Sponer, J.; Cubero, E.; Orozco, M.; Luque, F. J. J. Phys. Chem. B 2000, 104, 6286-6292. Asensio, A.; Kobko, N.; Dannenberg, J. J. J. Phys. Chem. A 2003, 107, 6441-6443.
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    • note
    • 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.
  • 31
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    • note
    • 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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