Display options
Cite
Tomazela DM, Sabino AA, Sparrapan R, et al. Distonoid ions. J Am Soc Mass Spectrom. 2006;17(7):1014-1022doi: 10.1016/j.jasms.2006.03.008.
Tomazela, D. M., Sabino, A. A., Sparrapan, R., Gozzo, F. C., & Eberlin, M. N. (2006). Distonoid ions. Journal of the American Society for Mass Spectrometry, 17(7), 1014-1022. https://doi.org/10.1016/j.jasms.2006.03.008
Tomazela, Daniela Maria, et al. "Distonoid ions." Journal of the American Society for Mass Spectrometry vol. 17,7 (2006): 1014-1022. doi: https://doi.org/10.1016/j.jasms.2006.03.008
Tomazela DM, Sabino AA, Sparrapan R, Gozzo FC, Eberlin MN. Distonoid ions. J Am Soc Mass Spectrom. 2006 Jul;17(7):1014-1022. doi: 10.1016/j.jasms.2006.03.008. Epub 2006 May 19. PMID: 16713292.
Copy Download .nbib Format: NLM
Share it on

J Am Soc Mass Spectrom. 2006 Jul;17(7):1014-1022. doi: 10.1016/j.jasms.2006.03.008. Epub 2006 May 19.

Distonoid ions.

Journal of the American Society for Mass Spectrometry

Daniela Maria Tomazela, Adão A Sabino, Regina Sparrapan, Fabio C Gozzo, Marcos N Eberlin

Affiliations

  1. Thomson Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas-UNICAMP CP 6154, 13083-970, Campinas, SP, Brazil.
  2. Thomson Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas-UNICAMP CP 6154, 13083-970, Campinas, SP, Brazil. [email protected].

PMID: 16713292 DOI: 10.1016/j.jasms.2006.03.008

Abstract

By Yates, Bouma, and Radom's definition, distonic radical ions are those formally arising by ionization of diradicals or zwitterionic molecules (including ylides). These ions differ, therefore, from conventional radical ions by displaying the charge site and unpaired electron site (spin) localized mandatorily on separate atoms or group of atoms; that is, these sites are separated in all of their major resonance forms. Many conventional radical ions with a major resonance form in which charge and spin sites reside formally on the same atom or group of atoms display, however, high degree of discretionary (non-mandatory) charge-spin separation. By analogy with the metal/metalloid terminology, we propose that these distonic-like radical ions be classified as distonoid ions. Radical ions would, therefore, be divided into three sub-classes: conventional, distonic, and distonoid ions. B3LYP/6-311 + G(d,p) calculations for a proof-of-principle set of radical cations are used to demonstrate the existence of many types of distonoid ions with a high degree of discretionary charge-spin separation. Reliable calculations are indispensable for probing distonoid ions, since an ion that was expected to be distonoid (by the analysis of its resonance forms) is shown by the calculations to display a characteristic conventional-ion electronic distribution. Similarly to many distonic radical ions, and in sharp contrast to a conventional radical ion (ionized 1,4-dioxane), the gas-phase intrinsic bimolecular reactivity with selective neutrals of a representative distonoid ion, ionized 2-methylene 1,3-dioxolane, is found to include dual ion-radical type reactions.

References

  1. Chemistry. 2000 Jan;6(2):321-6 - PubMed
  2. J Org Chem. 1996 Dec 13;61(25):8726-8727 - PubMed
  3. J Am Soc Mass Spectrom. 1995 Jul;6(7):554-63 - PubMed
  4. J Am Soc Mass Spectrom. 1993 Feb;4(2):117-24 - PubMed
  5. J Am Soc Mass Spectrom. 1996 Dec;7(12):1245-50 - PubMed
  6. Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789 - PubMed
  7. J Am Soc Mass Spectrom. 2000 Aug;11(8):697-704 - PubMed
  8. J Am Soc Mass Spectrom. 2001 Feb;12(2):150-62 - PubMed
  9. Chem Commun (Camb). 2002 Jun 7;(11):1192-3 - PubMed
  10. J Am Soc Mass Spectrom. 2003 Mar;14(3):241-52 - PubMed
  11. Chemistry. 2000 Mar 3;6(5):897-905 - PubMed

Publication Types