Wikipedia

C–H···O interaction: Difference between revisions

Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
Citation bot (talk | contribs)
Bots
5,184,895 edits
Add: s2cid. | Use this bot. Report bugs. | Suggested by AManWithNoPlan | #UCB_CommandLine
 
(48 intermediate revisions by 24 users not shown)
Line 1:
sinceIn [[chemistry]], a '''C–H···O interaction''' is occasionally described as a special type of weak [[hydrogen bond]]. These interactions frequently they occur in the structures of important [[biomolecule]]s like [[amino acid]]s, [[protein]]s, [[sugar]]ssugars, DNA and RNA.<ref>G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, 1999, OxfordUniversity Press, Oxford (1999).</ref> C–H...O interactions represent 20-25% of all hydrogen bonds in proteins.<ref>M. S. Weiss, Trends Biochem. Sci., 2001, 26, 521.</ref>▼
{{Orphan|date=July 2014}}
 
 
In [[chemistry]], a '''C–H···O interaction''' represents a special type of weak [[hydrogen bond]]. Although weak, these hydrogen bonds are very important in nature,
▲since they occur in the structures of important [[biomolecule]]s like [[amino acid]]s, [[protein]]s, [[sugar]]s, DNA and RNA.<ref>G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, 1999, OxfordUniversity Press, Oxford (1999).</ref> C–H...O interactions represent 20-25% of all hydrogen bonds in proteins.<ref>M. S. Weiss, Trends Biochem. Sci., 2001, 26, 521.</ref>
== History ==
 
The C–H···O interaction was discovered in 1937 by [[Samuel Glasstone]]. Glasstone studied properties of mixtures of [[acetone]] with different [[Halogenation|halogenated derivative]]s of [[hydrocarbon]]s and realized that [[Molecular dipole moment|dipole moment]]s of these mixtures differ from dipole moments of pure substances. He explained this by establishing the concept of C–H···O interactions. The first crystallographic analysis of C-H ⋯O [[Hydrogen bond|hydrogen bonds]] were published by [[June Sutor]] in 1962.<ref>{{Cite journal|last=Schwalbe|first=Carl H.|date=2012|title=June Sutor and the C–H ··· O hydrogen bonding controversy|journal=Crystallography Reviews|volume=18|issue=3|pages=191–206|doi=10.1080/0889311x.2012.674945|s2cid=96289568 |issn=0889-311X}}</ref>
 
== Properties ==
Similar to [[hydrogen bonds]], a C–H···O interaction involves [[Non-covalent interactions#Dipole-induced dipole|interactions of dipoles]] and therefore has [[Directionality (molecular biology)|directionality]].<ref>T. Steiner, G. R. Desiraju, Chem. Commun., 1998, 891.</ref> The directionality of a C–H···O interaction is usually defined by the angle ''α'' between the С, Н and О atoms (angle ''α''), and the distance ''d'' between the O and HC atoms (distance ''d''). In a С–Н···О interaction, the angle ''α'' is in the range between 90 toand 180º°, and the distance ''d'' is usually smaller than 3.2 &nbsp;[[ArmstrongAngstrom|Å]].<ref>T. Steiner, CrystRev, 2003, 9, 2-3, 177.</ref> Bond strength is less than 1&nbsp;kcal/mol. In the case of [[aromatic]] C–H donors, C–H···O interactions are not linear due to influence of [[aromatic ring]] substituents near the interacting C-H group. <ref>D. Ž.Veljković, G. V. Janjić, S. D. Zarić, "Are C–H···O interactions linear? Case of aromatic CH donors.", CrystEngComm, 2011, 13, 5005. DOI:{{doi| 10.1039/C1CE05065F }}</ref> <ref> J. Lj. Dragelj, G. V. Janjić, D. Ž. Veljković and S. D. Zarić, "Crystallographic and ab initio Study of Pyridine CH/O Interactions. Linearity of the interactions and influence of pyridine classical hydrogen bonds", CrystEngComm, (2013), vol. 15, 10481. DOI: 10.1039/C3CE40759D</ref> If aromatic molecules involved in С–Н···О interaction belong to the group of [[Polycyclic aromatic hydrocarbon|polycyclic aromatic hydrocarbons]], the strength of C–H···O interactions increases with the number of aromatic rings.<ref>{{Cite journal|date=2018-03-01|title=Strong CH/O interactions between polycyclic aromatic hydrocarbons and water: Influence of aromatic system size|journal=Journal of Molecular Graphics and Modelling|language=en|volume=80|pages=121–125|doi=10.1016/j.jmgm.2017.12.014|pmid=29331729|issn=1093-3263|last1=Veljković|first1=Dušan Ž.|url=http://cherry.chem.bg.ac.rs/handle/123456789/2815}}</ref>▼
 
C–H···O interactions can be important in [[drug design]]., Thesebeing interactionspresent influence thein structurestructures of therapeutic proteins,<ref>K. Ramanathan, V. Shanthi, R. Sethumadhavan, Int J Pharm Pharm Sci, 2011, 3, 3, 324.</ref> and [[aromatic amino acid]]s from therapeutic proteins often donate hydrogen atoms and form C–H···O interactions. C–H···O interactions can also strenghten some other type of [[noncovalent interaction]]s, like O-H...π interactions.<ref>D. P. Malenov, G. V. Janjić, D. Ž. Veljković, S. D. Zarić, "Mutual influence of parallel, CH/O, OH/π and lone pair/π interactions in water/benzene/water system", Computational and Theoretical Chemistry, (2013), vol. 1018, 59 - 65. DOI: 10.1016/j.comptc.2013.05.030</ref> and [[nucleic acid]]s.<ref>D. Ž Veljković, V. B Medakovic, J. M. Andric and S. D. Zaric, "C–H/O interactions of nucleic bases with water molecule. Crystallographic and quantum chemical study.", CrystEngComm, 2014., DOI: 10.1039/C4CE00595C</ref> ▼
 
O-H···C and N-H···C type interactions could also play a significant role and were first analyzed in 1993.<ref> M.A. Viswamitra, R. Radhakrishnan, J. Bandekar, G. R. Desiraju, "Evidence for O-H···C and N-H···C hydrogen bonding in crystalline alkynes, alkenes, and aromatics", J. Am. Chem. Soc. 1993, 115, 4868-4869.DOI:10.1021/ja00064a055 </ref>
Two main characteristics of a C–H···O interaction are [[directionality]] and [[interaction energy]]. Based on directionality it was shown that C–H···O interactions are hydrogen bonds, and not [[van der Waals]] interactions.<ref>T. Steiner, G. R. Desiraju, Chem. Commun., 1998, 891.</ref>
▲The directionality of a C–H···O interaction is usually defined by the angle between С, Н and О atoms (angle ''α''), and the distance between the O and H atoms (distance ''d''). In a С–Н···О interaction, the angle ''α'' is in the range between 90 to 180º, and the distance ''d'' is usually smaller than 3.2 [[Armstrong|Å]].<ref>T. Steiner, CrystRev, 2003, 9, 2-3, 177.</ref> In the case of [[aromatic]] C–H donors, C–H···O interactions are not linear due to influence of [[aromatic ring]] substituents near the interacting C-H group. <ref>D. Ž.Veljković, G. V. Janjić, S. D. Zarić, "Are C–H···O interactions linear? Case of aromatic CH donors.", CrystEngComm, 2011, 13, 5005. DOI: 10.1039/C1CE05065F </ref> <ref> J. Lj. Dragelj, G. V. Janjić, D. Ž. Veljković and S. D. Zarić, "Crystallographic and ab initio Study of Pyridine CH/O Interactions. Linearity of the interactions and influence of pyridine classical hydrogen bonds", CrystEngComm, (2013), vol. 15, 10481. DOI: 10.1039/C3CE40759D </ref>
The interaction energy of a C–H···O interaction is in the range of 1.0 - 2.0 kcal/mol. However, in the case of very [[acid]]ic hydrogen atoms, this value could be much higher.
 
▲C–H···O interactions can be important in [[drug design]]. These interactions influence the structure of therapeutic proteins,<ref>K. Ramanathan, V. Shanthi, R. Sethumadhavan, Int J Pharm Pharm Sci, 2011, 3, 3, 324.</ref> and [[aromatic amino acid]]s from therapeutic proteins often donate hydrogen atoms and form C–H···O interactions. C–H···O interactions can also strenghten some other type of [[noncovalent interaction]]s, like O-H...π interactions.<ref>D. P. Malenov, G. V. Janjić, D. Ž. Veljković, S. D. Zarić, "Mutual influence of parallel, CH/O, OH/π and lone pair/π interactions in water/benzene/water system", Computational and Theoretical Chemistry, (2013), vol. 1018, 59 - 65. DOI: 10.1016/j.comptc.2013.05.030</ref>
== References ==
 
{{reflist}}
 
{{Chemical bonds}}
 
{{DEFAULTSORT:C-H O interaction}}
[[Category:Organic chemistry]]
Retrieved from "https://en.wikipedia.org/wiki/C–H···O_interaction"