Theoretical characterization of electronic structures and properties of C-F···H-C pseudohydrogen bonds
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The weak intermolecular interactions between 2-F-tetrahydrofuran and imidazole, pyrimidine, adenine, and guanine were studied theoretically using density functional B3LYP/6-311++G** and HF/6-311++G** methods. The results showed that both conventional N...H hydrogen bond and C-F...H-C pseudohydrogen bond (PHB) structures coexist in the four complexes. The weak intermolecular interaction energies indicate that the relative stabilities of the four complexes are in the order guanine...F > imidazole ...F > adenine...F > pyrimidine...F. The characteristics of the four PHBs were determined using geometry optimizations, stretching vibrational frequencies, and natural bond orbital and electron density topological properties calculations. The most important result is that the F group of 2-F-tetrahydrofuran can activate the C-H to accept electrons from another molecule, and C-F...H-C PHB formation is relatively favorable.
Keywordsweak interaction pseudohydrogen bond electronic structure electron density topological property
- 9.Lv F Z, Peng Z H, Zhang L L, et al. A new type of hydrogen-bonded LBL photoalignment film for liquid crystal (in Chinese). Acta Phy-Chim Sin, 2009, 25: 273–277Google Scholar
- 13.Bats J W, Parsch J, Engels J W. 1-deoxy-1-(4-fluorophenyl)-beta-D-ribofuranose, its hemihydrate, and 1-deoxy-1-(2,4-difluorophenyl)-beta-D-ribofuranose: Structural evidence for intermolecular C-H...F-C interactions. Acta Crystallogr Sect C-Cryst Struct Commun, 2000, 56: 201–205CrossRefGoogle Scholar
- 18.Bergstrom D E, Swartling D J, Wisor A, et al. Evaluation of thymidine, dideoxythymidine and fluorine substituted deoxyribonucleoside geometry by the Mindo/3 technique: The effect of fluorine substitution on nucleoside geometry and biological activity. Nucleosides Nucleotides, 1991, 10: 693–697CrossRefGoogle Scholar
- 24.Bader R F W. Atoms in Molecules: A Quantum Theory. New York: Clarendon Press, 1990Google Scholar
- 25.Glendening E D, Badenhoop J K, Reed A E, et al. Natural bond orbital program. Version 5.0. Madison, WI: Theoretical Chemistry Institute, University of Wisconsin, 2001Google Scholar
- 26.Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 03 E. 01. Pittsburgh PA: Gaussian Inc, 2004Google Scholar
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