Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions
Само за регистроване кориснике
2012
Чланак у часопису (Објављена верзија)
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Приказ свих података о документуАпстракт
Stacking interactions between pyridine molecules and the influence of simultaneous hydrogen bonds were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The results show remarkably stronger stacking interactions of pyridines with hydrogen bonds, because of local parallel alignment interactions of OH bonds with the aromatic ring. Data in the crystal structures from the CSD and ab initio calculations show that normal distances (R) in stacking interactions of pyridines with simultaneous hydrogen bonds are shorter than those in stacking interactions without simultaneous hydrogen bonds. Furthermore, the calculated binding energies for stacking are substantially stronger when the pyridines have hydrogen bonds; the binding energy of the stacking interaction between pyridine water dimers is -6.86 kcal/mol, while that between pyridines is -4.08 kcal/mol. Surprisingly, in the minimum energy structure of the stacked pyridine water dimers, the cont...ribution of the local parallel-alignment interactions between water and the other pyridine (-2.98 kcal/mol) is slightly larger than the contribution of the stacking interaction between two pyridine molecules (-2.67 kcal/mol). The local influence of hydrogen bonds on stacking, via parallel alignment interactions, can be very important for all systems with heteroaromatic molecules and groups, especially DNA and RNA.
Извор:
Crystal Growth and Design, 2012, 12, 3, 1060-1063Издавач:
- Amer Chemical Soc, Washington
Финансирање / пројекти:
- Нековалентне интеракције pi-система и њихова улога у молекулском препознавању (RS-MESTD-Basic Research (BR or ON)-172065)
- Humboldt Foundation
DOI: 10.1021/cg201389y
ISSN: 1528-7483
WoS: 000301098700002
Scopus: 2-s2.0-84857961300
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ninković, Dragan AU - Janjić, Goran V. AU - Zarić, Snežana D. PY - 2012 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1256 AB - Stacking interactions between pyridine molecules and the influence of simultaneous hydrogen bonds were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The results show remarkably stronger stacking interactions of pyridines with hydrogen bonds, because of local parallel alignment interactions of OH bonds with the aromatic ring. Data in the crystal structures from the CSD and ab initio calculations show that normal distances (R) in stacking interactions of pyridines with simultaneous hydrogen bonds are shorter than those in stacking interactions without simultaneous hydrogen bonds. Furthermore, the calculated binding energies for stacking are substantially stronger when the pyridines have hydrogen bonds; the binding energy of the stacking interaction between pyridine water dimers is -6.86 kcal/mol, while that between pyridines is -4.08 kcal/mol. Surprisingly, in the minimum energy structure of the stacked pyridine water dimers, the contribution of the local parallel-alignment interactions between water and the other pyridine (-2.98 kcal/mol) is slightly larger than the contribution of the stacking interaction between two pyridine molecules (-2.67 kcal/mol). The local influence of hydrogen bonds on stacking, via parallel alignment interactions, can be very important for all systems with heteroaromatic molecules and groups, especially DNA and RNA. PB - Amer Chemical Soc, Washington T2 - Crystal Growth and Design T1 - Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions VL - 12 IS - 3 SP - 1060 EP - 1063 DO - 10.1021/cg201389y ER -
@article{ author = "Ninković, Dragan and Janjić, Goran V. and Zarić, Snežana D.", year = "2012", abstract = "Stacking interactions between pyridine molecules and the influence of simultaneous hydrogen bonds were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The results show remarkably stronger stacking interactions of pyridines with hydrogen bonds, because of local parallel alignment interactions of OH bonds with the aromatic ring. Data in the crystal structures from the CSD and ab initio calculations show that normal distances (R) in stacking interactions of pyridines with simultaneous hydrogen bonds are shorter than those in stacking interactions without simultaneous hydrogen bonds. Furthermore, the calculated binding energies for stacking are substantially stronger when the pyridines have hydrogen bonds; the binding energy of the stacking interaction between pyridine water dimers is -6.86 kcal/mol, while that between pyridines is -4.08 kcal/mol. Surprisingly, in the minimum energy structure of the stacked pyridine water dimers, the contribution of the local parallel-alignment interactions between water and the other pyridine (-2.98 kcal/mol) is slightly larger than the contribution of the stacking interaction between two pyridine molecules (-2.67 kcal/mol). The local influence of hydrogen bonds on stacking, via parallel alignment interactions, can be very important for all systems with heteroaromatic molecules and groups, especially DNA and RNA.", publisher = "Amer Chemical Soc, Washington", journal = "Crystal Growth and Design", title = "Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions", volume = "12", number = "3", pages = "1060-1063", doi = "10.1021/cg201389y" }
Ninković, D., Janjić, G. V.,& Zarić, S. D.. (2012). Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions. in Crystal Growth and Design Amer Chemical Soc, Washington., 12(3), 1060-1063. https://doi.org/10.1021/cg201389y
Ninković D, Janjić GV, Zarić SD. Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions. in Crystal Growth and Design. 2012;12(3):1060-1063. doi:10.1021/cg201389y .
Ninković, Dragan, Janjić, Goran V., Zarić, Snežana D., "Crystallographic and ab Initio Study of Pyridine Stacking Interactions. Local Nature of Hydrogen Bond Effect in Stacking Interactions" in Crystal Growth and Design, 12, no. 3 (2012):1060-1063, https://doi.org/10.1021/cg201389y . .