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Distonic Ions current article[edit]

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]

Article's current Bibliography[edit]

  1. Olah, George A. (2008). Superelectrophiles and their chemistry. Willey-Interscience. p. 287. ISBN 978-0-470-18511-7.
  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): 6235–6244. 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.

Additional Articles for Consideration[edit]

  1. Bjoernholm, Thomas, Steen Hammerum, and Dietmar Kuck. "Distonic ions as reacting species." Journal of the American Chemical Society 110.12 (1988): 3862-3869.
  2. Bouchoux, G. "Keto‐enol tautomers and distonic ions: The chemistry of [CnH2nO] radical cations. Part II." Mass Spectrometry Reviews 7.2 (1988): 203-255.
  3. Hammerum, Steen. "Distonic radical cations in gaseous and condensed phase." Mass Spectrometry Reviews 7.2 (1988): 123-202.
  4. Kenttämaa, Hilkka I. "Long‐lived distonic radical cations." Organic mass spectrometry 29.1 (1994): 1-10.
  5. Mourgues, Philippe, et al. "Bimolecular reactions of distonic ions: Proton transfer and hydrogen atom abstraction with˙ CH2OH2+." Organic mass spectrometry 28.10 (1993): 1098-1100.
  6. Postma, R., et al. "The [CH2= CHOH/H2O]+˙ system: A theoretical study of distonic ions, hydrogen‐bridged ions and ion–dipole complexes." Organic mass spectrometry 23.7 (1988): 503-510.
  7. Stirk, Krista M., et al. "The identification of distonic radical cations on the basis of a reaction with dimethyl disulfide." Journal of the American Chemical Society 114.22 (1992): 8604-8606.
  8. Stirk, Krista M., LK Marjatta Kiminkinen, and Hilkka I. Kenttamaa. "Ion-molecule reactions of distonic radical cations." Chemical reviews 92.7 (1992): 1649-1665.
  9. Xu, Young C., et al. "Organometallic Distonic Ions:+ FeC6H4. bul." Journal of the American Chemical Society 117.19 (1995): 5413-5414.
  10. Yates, Brian F., Willem J. Bouma, and Leo Radom. "Distonic radical cations: Guidelines for the assessment of their stability1." Tetrahedron 42.22 (1986): 6225-6234.

Plans for this article/ Outline[edit]

As you can see this article has little to nothing so I plan to expand greatly on this topic and add much more detail.

  • sections (adding sections is mandatory)

-brief general explanation
-table of contents
-history
-how it works
-any equations if necessary
-organize and add to bibliography

  • pictures


April 2019[edit]

Hello, I'm Flooded with them hundreds. I noticed that in this edit to Distonic ion, you removed content without adequately explaining why. In the future, it would be helpful to others if you described your changes to Wikipedia with an edit summary. If this was a mistake, don't worry, the removed content has been restored. If you think I made a mistake, or if you have any questions, you can leave me a message on my talk page. Thank you. -- Flooded w/them 100s 06:19, 21 April 2019 (UTC)[reply]