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• W2050833307 abstract "Studies on modified DNA oligomers and polymerase reactions have previously demonstrated that canonical nucleobases can exhibit stable and even selective pairing with shape-complementary fluorobenzene nucleotides. Because of the fluorination of the pairing edges, hydrogen bonds are believed to be absent, and the local DNA stability has been attributed to π-stacking and shape complementarity. Using two-color resonant two-photon ionization and fluorescence emission spectroscopies, we show here that supersonically cooled complexes of the nucleobase analogue 2-pyridone with seven substituted fluorobenzenes (1-fluorobenzene, 1,2- and 1,4-difluorobenzene, 1,3,5- and 1,2,3-trifluorobenzene, 1,2,4,5- and 1,2,3,4-tetrafluorobenzene) are hydrogen-bonded and not π-stacked. The S1 ↔ S0 vibronic spectra show intermolecular vibrational frequencies that are characteristic for doubly hydrogen bonded complexes. The bands shift to the blue with increasing hydrogen-bond strength; the measured spectral blue shifts δν are in excellent agreement with the ab initio calculated shifts. The spectral shifts are also linearly correlated with the calculated hydrogen-bond dissociation energies D0, published in a companion paper (Frey, J. A.; Leist, R.; Leutwyler, S. J. Phys. Chem. A 2006, 110, 4188). This correlation allows us to reliably estimate the ground-state dissociation energies as D0 ≈ 6 kcal/mol of the 2-pyridone·fluorobenzene complexes from the observed spectral shifts." @default.
• W2050833307 created "2016-06-24" @default.
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• W2050833307 date "2006-03-01" @default.
• W2050833307 modified "2023-10-03" @default.
• W2050833307 title "Fluorobenzene−Nucleobase Interactions: Hydrogen Bonding or π-Stacking?" @default.
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• W2050833307 doi "https://doi.org/10.1021/jp057100h" @default.
• W2050833307 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/16553368" @default.
• W2050833307 hasPublicationYear "2006" @default.
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