C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study
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2014
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The C-H/O interactions of nucleic bases with a water molecule were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H/O interactions in the crystal structures from the CSD indicates that nucleic base-water C-H/O interactions do not show preference for linear contacts. The results of the ab initio calculations are in accord with the CSD data and show that the bifurcated C-H/N-H interactions are stronger than linear interactions for all nucleic bases. The bifurcated C-H/N-H interactions are also stronger than the bifurcated C-H/C-H interactions. The strongest interaction is the bifurcated C6-H/N1-H interaction of uracil with an energy of -5.46 kcal mol(-1) calculated at the MP2/cc-pVTZ level. All linear C-H/O interactions, except one with adenine, are stronger than -2.0 kcal mol(-1). The strongest linear interaction is with uracil, -3.59 kcal mol(-1). The calculated electrostatic potential maps for nucleic base mole...cules can explain the results we obtained for interaction energies. The results show that C-H/O interactions of nucleic bases with a water molecule are substantially stronger than C-H/O interactions of benzene (-1.28 kcal mol(-1)) and pyridine (-1.97 kcal mol(-1)). The investigation of C-H/O interactions of nucleic bases with water could shed light on the intermolecular interactions of DNA or RNA bases with other molecules.
Izvor:
CrystEngComm, 2014, 16, 43, 10089-10096Izdavač:
- Royal Soc Chemistry, Cambridge
Finansiranje / projekti:
- Nekovalentne interakcije pi-sistema i njihova uloga u molekulskom prepoznavanju (RS-MESTD-Basic Research (BR or ON)-172065)
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3684
DOI: 10.1039/c4ce00595c
ISSN: 1466-8033
WoS: 000343861900017
Scopus: 2-s2.0-84907919360
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Veljković, Dušan Ž. AU - Medaković, Vesna AU - Andrić, Jelena M. AU - Zarić, Snežana D. PY - 2014 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1868 AB - The C-H/O interactions of nucleic bases with a water molecule were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H/O interactions in the crystal structures from the CSD indicates that nucleic base-water C-H/O interactions do not show preference for linear contacts. The results of the ab initio calculations are in accord with the CSD data and show that the bifurcated C-H/N-H interactions are stronger than linear interactions for all nucleic bases. The bifurcated C-H/N-H interactions are also stronger than the bifurcated C-H/C-H interactions. The strongest interaction is the bifurcated C6-H/N1-H interaction of uracil with an energy of -5.46 kcal mol(-1) calculated at the MP2/cc-pVTZ level. All linear C-H/O interactions, except one with adenine, are stronger than -2.0 kcal mol(-1). The strongest linear interaction is with uracil, -3.59 kcal mol(-1). The calculated electrostatic potential maps for nucleic base molecules can explain the results we obtained for interaction energies. The results show that C-H/O interactions of nucleic bases with a water molecule are substantially stronger than C-H/O interactions of benzene (-1.28 kcal mol(-1)) and pyridine (-1.97 kcal mol(-1)). The investigation of C-H/O interactions of nucleic bases with water could shed light on the intermolecular interactions of DNA or RNA bases with other molecules. PB - Royal Soc Chemistry, Cambridge T2 - CrystEngComm T1 - C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study VL - 16 IS - 43 SP - 10089 EP - 10096 DO - 10.1039/c4ce00595c ER -
@article{ author = "Veljković, Dušan Ž. and Medaković, Vesna and Andrić, Jelena M. and Zarić, Snežana D.", year = "2014", abstract = "The C-H/O interactions of nucleic bases with a water molecule were studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H/O interactions in the crystal structures from the CSD indicates that nucleic base-water C-H/O interactions do not show preference for linear contacts. The results of the ab initio calculations are in accord with the CSD data and show that the bifurcated C-H/N-H interactions are stronger than linear interactions for all nucleic bases. The bifurcated C-H/N-H interactions are also stronger than the bifurcated C-H/C-H interactions. The strongest interaction is the bifurcated C6-H/N1-H interaction of uracil with an energy of -5.46 kcal mol(-1) calculated at the MP2/cc-pVTZ level. All linear C-H/O interactions, except one with adenine, are stronger than -2.0 kcal mol(-1). The strongest linear interaction is with uracil, -3.59 kcal mol(-1). The calculated electrostatic potential maps for nucleic base molecules can explain the results we obtained for interaction energies. The results show that C-H/O interactions of nucleic bases with a water molecule are substantially stronger than C-H/O interactions of benzene (-1.28 kcal mol(-1)) and pyridine (-1.97 kcal mol(-1)). The investigation of C-H/O interactions of nucleic bases with water could shed light on the intermolecular interactions of DNA or RNA bases with other molecules.", publisher = "Royal Soc Chemistry, Cambridge", journal = "CrystEngComm", title = "C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study", volume = "16", number = "43", pages = "10089-10096", doi = "10.1039/c4ce00595c" }
Veljković, D. Ž., Medaković, V., Andrić, J. M.,& Zarić, S. D.. (2014). C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study. in CrystEngComm Royal Soc Chemistry, Cambridge., 16(43), 10089-10096. https://doi.org/10.1039/c4ce00595c
Veljković DŽ, Medaković V, Andrić JM, Zarić SD. C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study. in CrystEngComm. 2014;16(43):10089-10096. doi:10.1039/c4ce00595c .
Veljković, Dušan Ž., Medaković, Vesna, Andrić, Jelena M., Zarić, Snežana D., "C-H/O interactions of nucleic bases with a water molecule: a crystallographic and quantum chemical study" in CrystEngComm, 16, no. 43 (2014):10089-10096, https://doi.org/10.1039/c4ce00595c . .