C–H···O interaction

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In chemistry, a C–H···O interaction is occasionally described as a special type of weak hydrogen bond. These interactions frequently occur in the structures of important biomolecules like amino acids, proteins, sugars, DNA and RNA.[1][2]

History

The C–H···O interaction was discovered in 1937 by

dipole moments 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 bonds were published by June Sutor in 1962.[3]

Properties

Similar to

aromatic ring substituents near the interacting C-H group.[6][7] If aromatic molecules involved in С–Н···О interaction belong to the group of polycyclic aromatic hydrocarbons, the strength of C–H···O interactions increases with the number of aromatic rings.[8]

C–H···O interactions can be important in drug design, being present in structures of therapeutic proteins,[9][10] and nucleic acids.[11]

O-H···C and N-H···C type interactions could also play a significant role and were first analyzed in 1993.[12]

References

  1. ^ G. R. Desiraju, T. Steiner, The Weak Hydrogen Bond in Structural Chemistry and Biology, 1999, OxfordUniversity Press, Oxford (1999).
  2. ^ M. S. Weiss, Trends Biochem. Sci., 2001, 26, 521.
  3. S2CID 96289568
    .
  4. ^ T. Steiner, G. R. Desiraju, Chem. Commun., 1998, 891.
  5. ^ T. Steiner, CrystRev, 2003, 9, 2-3, 177.
  6. doi:10.1039/C1CE05065F
  7. ^ 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
  8. PMID 29331729
    .
  9. ^ K. Ramanathan, V. Shanthi, R. Sethumadhavan, Int J Pharm Pharm Sci, 2011, 3, 3, 324.
  10. ^ 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
  11. ^ 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
  12. ^ 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
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