Distonic ion

Distonic ions are chemical species that contain 2 ionic charges on the same molecule. The charges must be separated by two or more carbon or hetero atoms to count as distonic (distant). Otherwise it is a gitonic (close) ion. For example, the acid-catalyzed Grewe-cyclization is a well-known reaction based on formation of a distonic ion, initiating the ring closing step as a superelectrophile.[1] Distonic radical ions were first discovered in the gas phase by Michael L. Gross.[2] In recent years there has been a tremendous effort to identify new distonic species, characterize their reactivity, and measure their stability.[3][4][5]

See also

References

  1. ↑ Olah, George A. (2008). "Superelectrophiles and their chemistry". Willey-Interscience: 287.
  2. ↑ Holman, R. (1986). "Mass spectrometry for investigations of gas-phase radical cation chemistry the two step cycloaddition of the benzene radical cation and 1,3-butadiene". Tetrahedron. 42 (22): 6235. doi:10.1016/S0040-4020(01)88085-6.
  3. ↑ Tomazela DM, Sabino AA, Sparrapan R, Gozzo FC, Eberlin MN (July 2006). "Distonoid ions". J. Am. Soc. Mass Spectrom. 17 (7): 1014–22. doi:10.1016/j.jasms.2006.03.008. PMID 16713292.
  4. ↑ Ibrahim Y, Mabrouki R, Meot-Ner M, El-Shall MS (February 2007). "Hydrogen bonding interactions of pyridine*+ with water: stepwise solvation of distonic cations". J Phys Chem A. 111 (6): 1006–14. Bibcode:2007JPCA..111.1006I. doi:10.1021/jp067390h. PMID 17286357.
  5. ↑ Bouchoux G, Berruyer F, Hiberty PC, Wu W (2007). "Classical and distonic radical cations: a valence bond approach". Chemistry. 13 (10): 2912–9. doi:10.1002/chem.200600985. PMID 17200931.


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