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Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors

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2011
Authors
Veljković, Dušan
Janjić, Goran
Zarić, Snežana D.
Article (Published version)
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Abstract
The angular distribution of the C-H center dot center dot center dot O interactions of aromatic C-H donors was studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H center dot center dot center dot O interactions in the crystal structures from the CSD indicate that aromatic C-H donors do not show strong preference for linear contacts and that the preference depends on the type of the atom or group in the o-position to the interacting C-H group. Namely, the acceptor oxygen atom has possibility for simultaneous C-H center dot center dot center dot O interactions with the hydrogen atom in the o-position to the interacting C-H group. The C-H center dot center dot center dot O interactions of aromatic molecules with two hydrogen atoms in the o-positions do not show preference for linear contacts. Bifurcated interactions are observed in a substantial number of structures. Moreover, in the structures with a substituent in t...he o-position there is possibility for simultaneous interactions, depending on the nature of the substituent. The results of the ab initio calculations are in accord with the CSD data and show that the stabilization energy is larger for bifurcated than for linear interactions. The calculated energies at the MP2/cc-pVTZ level for linear C-H center dot center dot center dot O interactions of benzene with water, methanol, and acetone are 1.28, 1.47, 1.45 kcal mol(-1); while for bifurcated interactions are 1.38, 1.63, and 1.70 kcal mol(-1), respectively. Analysis of the data in the CSD and the ab initio calculations indicate that the vicinity of the other possible hydrogen donors in the aromatic molecules causes a small tendency for linear contact in the C-H center dot center dot center dot O interactions. The result that nonlinear interactions are not energetically disfavoured, because of the possibility for simultaneous interactions, can be very important for recognizing C-H center dot center dot center dot O interactions in biomolecules containing aromatic groups, like proteins.

Source:
Crystengcomm, 2011, 13, 15, 5005-5010
Publisher:
  • Royal Soc Chemistry, Cambridge
Funding / projects:
  • Noncovalent interactions of pi-systems and their role in molecular recognition (RS-172065)
  • Alexander von Humboldt Foundation (Germany)

DOI: 10.1039/c1ce05065f

ISSN: 1466-8033

WoS: 000292974000036

Scopus: 2-s2.0-82755167302
[ Google Scholar ]
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/793
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Veljković, Dušan
AU  - Janjić, Goran
AU  - Zarić, Snežana D.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/793
AB  - The angular distribution of the C-H center dot center dot center dot O interactions of aromatic C-H donors was studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H center dot center dot center dot O interactions in the crystal structures from the CSD indicate that aromatic C-H donors do not show strong preference for linear contacts and that the preference depends on the type of the atom or group in the o-position to the interacting C-H group. Namely, the acceptor oxygen atom has possibility for simultaneous C-H center dot center dot center dot O interactions with the hydrogen atom in the o-position to the interacting C-H group. The C-H center dot center dot center dot O interactions of aromatic molecules with two hydrogen atoms in the o-positions do not show preference for linear contacts. Bifurcated interactions are observed in a substantial number of structures. Moreover, in the structures with a substituent in the o-position there is possibility for simultaneous interactions, depending on the nature of the substituent. The results of the ab initio calculations are in accord with the CSD data and show that the stabilization energy is larger for bifurcated than for linear interactions. The calculated energies at the MP2/cc-pVTZ level for linear C-H center dot center dot center dot O interactions of benzene with water, methanol, and acetone are 1.28, 1.47, 1.45 kcal mol(-1); while for bifurcated interactions are 1.38, 1.63, and 1.70 kcal mol(-1), respectively. Analysis of the data in the CSD and the ab initio calculations indicate that the vicinity of the other possible hydrogen donors in the aromatic molecules causes a small tendency for linear contact in the C-H center dot center dot center dot O interactions. The result that nonlinear interactions are not energetically disfavoured, because of the possibility for simultaneous interactions, can be very important for recognizing C-H center dot center dot center dot O interactions in biomolecules containing aromatic groups, like proteins.
PB  - Royal Soc Chemistry, Cambridge
T2  - Crystengcomm
T1  - Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors
VL  - 13
IS  - 15
SP  - 5005
EP  - 5010
DO  - 10.1039/c1ce05065f
ER  - 
@article{
author = "Veljković, Dušan and Janjić, Goran and Zarić, Snežana D.",
year = "2011",
abstract = "The angular distribution of the C-H center dot center dot center dot O interactions of aromatic C-H donors was studied by analyzing data in the Cambridge Structural Database (CSD) and by ab initio calculations. The analysis of the C-H center dot center dot center dot O interactions in the crystal structures from the CSD indicate that aromatic C-H donors do not show strong preference for linear contacts and that the preference depends on the type of the atom or group in the o-position to the interacting C-H group. Namely, the acceptor oxygen atom has possibility for simultaneous C-H center dot center dot center dot O interactions with the hydrogen atom in the o-position to the interacting C-H group. The C-H center dot center dot center dot O interactions of aromatic molecules with two hydrogen atoms in the o-positions do not show preference for linear contacts. Bifurcated interactions are observed in a substantial number of structures. Moreover, in the structures with a substituent in the o-position there is possibility for simultaneous interactions, depending on the nature of the substituent. The results of the ab initio calculations are in accord with the CSD data and show that the stabilization energy is larger for bifurcated than for linear interactions. The calculated energies at the MP2/cc-pVTZ level for linear C-H center dot center dot center dot O interactions of benzene with water, methanol, and acetone are 1.28, 1.47, 1.45 kcal mol(-1); while for bifurcated interactions are 1.38, 1.63, and 1.70 kcal mol(-1), respectively. Analysis of the data in the CSD and the ab initio calculations indicate that the vicinity of the other possible hydrogen donors in the aromatic molecules causes a small tendency for linear contact in the C-H center dot center dot center dot O interactions. The result that nonlinear interactions are not energetically disfavoured, because of the possibility for simultaneous interactions, can be very important for recognizing C-H center dot center dot center dot O interactions in biomolecules containing aromatic groups, like proteins.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Crystengcomm",
title = "Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors",
volume = "13",
number = "15",
pages = "5005-5010",
doi = "10.1039/c1ce05065f"
}
Veljković, D., Janjić, G.,& Zarić, S. D.. (2011). Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors. in Crystengcomm
Royal Soc Chemistry, Cambridge., 13(15), 5005-5010.
https://doi.org/10.1039/c1ce05065f
Veljković D, Janjić G, Zarić SD. Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors. in Crystengcomm. 2011;13(15):5005-5010.
doi:10.1039/c1ce05065f .
Veljković, Dušan, Janjić, Goran, Zarić, Snežana D., "Are C-H center dot center dot center dot O interactions linear? The case of aromatic CH donors" in Crystengcomm, 13, no. 15 (2011):5005-5010,
https://doi.org/10.1039/c1ce05065f . .

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