Distonic ions are chemical species that contain two ionic charges on the same molecule, separated by two or more carbon or heteroatoms.[1] A feature of distonic radical ions is that their charges and radical sites are in different locations (on separate atoms), unlike regular radicals where the formal charge and unpaired electron are in the same location. These molecular species are created by ionization of either zwitterions or diradicals; ultimately, a neutral molecule loses an electron.[2] Through experimental research distonic radicals have been found to be extremely stable gas phase ions[3] and can be separated into different classes depending on the inherent features of the charged portion of the ion.[4]
A distonic ion, showing that the molecule's radical site and charge are in different locations.
In 1984 scientists Bouma, Radom and Yates originated the term through extensive experimental research but they were not the first to deal with distonic ions. Experiments date back to the 1970s with Gross and McLafferty who were the first to propose the idea of such a species.[5]
Several efficient techniques are available to detect the presence of distonic ions; the most appropriate method will depend on the ion's internal energy and lifespan.[3] Collisions between ions and uncharged molecules allow one to detect the location of the radical and charge site in order to confirm that the ion is not just a regular radical ion.[7] When a molecule is ionized and can structurally be classified as a distonic ion, the molecule's kinetics and thermodynamic properties have been greatly altered. However, additional chemical properties are based on the reactions of the central excited ions. Mass spectrometry techniques are used to study their chemistry.[8]
Experimental dataedit
Distonic ions have been extensively examined due to their unique behavior and how commonly they can occur.[2] It has been shown that in most cases distonic ions have a bonding arrangement corresponding to that of the original molecule before ionization occurred; but that distonic ions are less stable than before ionization occurred; even so, distonic ions are considered stable ions and have caught many scientists' attention because they possess more stability than its traditional isomer.[clarification needed][3] It may be difficult to decipher the functions[clarification needed] of the charge and radical site because distonic ions are limited to elementary reactions such as unimolecular reactions involving highly excited and short-lived species.[9]
Referencesedit
^Muller, P. (1994). "Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)". Pure and Applied Chemistry. 66 (5): 1077–1184. doi:10.1351/pac199466051077. ISSN 1365-3075. S2CID 195819485.
^ abTomazela, Daniela Maria; Sabino, Adão A.; Sparrapan, Regina; Gozzo, Fabio C.; Eberlin, Marcos N. (July 2006). "Distonoid ions". Journal of the American Society for Mass Spectrometry. 17 (7): 1014–1022. doi:10.1016/j.jasms.2006.03.008. PMID 16713292.
^ abcStirk, Krista M.; Kiminkinen, L. K. Marjatta; Kenttamaa, Hilkka I. (November 1992). "Ion-molecule reactions of distonic radical cations". Chemical Reviews. 92 (7): 1649–1665. doi:10.1021/cr00015a008.
^Hill, Brian T.; Poutsma, John C.; Chyall, Leonard J.; Hu, Jun; Squires, Robert R. (September 1999). "Distonic ions of the 'ate' class". Journal of the American Society for Mass Spectrometry. 10 (9): 896–906. doi:10.1016/S1044-0305(99)00053-7. S2CID 97267758.
^Williams, Peggy E.; Jankiewicz, Bartlomiej J.; Yang, Linan; Kenttamaa, Hilkka I. (12 November 2013). "ChemInform Abstract: Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites". ChemInform. 44 (46): no. doi:10.1002/chin.201346233.
^Hill, Brian T.; Poutsma, John C.; Chyall, Leonard J.; Hu, Jun; Squires, Robert R. (September 1999). "Distonic ions of the "Ate" class". Journal of the American Society for Mass Spectrometry. 10 (9): 896–906. doi:10.1016/S1044-0305(99)00053-7. S2CID 97267758.
^Yu, Sophia J.; Holliman, Christopher L.; Rempel, Don L.; Gross, Michael L. (1993-10-01). "The .beta.-distonic ion from the reaction of pyridine radical cation and ethene: a demonstration of high-pressure trapping in Fourier transform mass spectrometry". Journal of the American Chemical Society. 115 (21): 9676–9682. doi:10.1021/ja00074a037. ISSN 0002-7863.
^Stirk, Krista G.; Kenttamaa, Hilkka I. (1991-07-01). "Radical type reactivity in a .gamma.-distonic radical cation: a gas-phase experimental study". Journal of the American Chemical Society. 113 (15): 5880–5881. doi:10.1021/ja00015a062. ISSN 0002-7863.
"Distonic radical cations : Guidelines for the assessment of their stability". Tetrahedron. 42 (22): 6225–6234. January 1986. doi:10.1016/S0040-4020(01)88084-4.
Stirk, Krista M.; Orlowski, Joseph C.; Leeck, Diane T.; Kenttamaa, H. I. (October 1992). "The identification of distonic radical cations on the basis of a reaction with dimethyl disulfide". Journal of the American Chemical Society. 114 (22): 8604–8606. doi:10.1021/ja00048a038. ISSN 0002-7863.
Hammerum, Steen (1988). "Distonic radical cations in gaseous and condensed phase". Mass Spectrometry Reviews. 7 (2): 123–202. Bibcode:1988MSRv....7..123H. doi:10.1002/mas.1280070202. ISSN 1098-2787.
Bjoernholm, Thomas.; Hammerum, Steen.; Kuck, Dietmar. (1988-06-01). "Distonic ions as reacting species". Journal of the American Chemical Society. 110 (12): 3862–3869. doi:10.1021/ja00220a023. ISSN 0002-7863.
February 26, 2024
distonic, chemical, species, that, contain, ionic, charges, same, molecule, separated, more, carbon, heteroatoms, feature, distonic, radical, ions, that, their, charges, radical, sites, different, locations, separate, atoms, unlike, regular, radicals, where, f. Distonic ions are chemical species that contain two ionic charges on the same molecule separated by two or more carbon or heteroatoms 1 A feature of distonic radical ions is that their charges and radical sites are in different locations on separate atoms unlike regular radicals where the formal charge and unpaired electron are in the same location These molecular species are created by ionization of either zwitterions or diradicals ultimately a neutral molecule loses an electron 2 Through experimental research distonic radicals have been found to be extremely stable gas phase ions 3 and can be separated into different classes depending on the inherent features of the charged portion of the ion 4 A distonic ion showing that the molecule s radical site and charge are in different locations Contents 1 History 2 Ion structure 3 Experimental data 4 ReferencesHistory editIn 1984 scientists Bouma Radom and Yates originated the term through extensive experimental research but they were not the first to deal with distonic ions Experiments date back to the 1970s with Gross and McLafferty who were the first to propose the idea of such a species 5 nbsp 6 Example of distonic ion in the class ateIon structure editSeveral efficient techniques are available to detect the presence of distonic ions the most appropriate method will depend on the ion s internal energy and lifespan 3 Collisions between ions and uncharged molecules allow one to detect the location of the radical and charge site in order to confirm that the ion is not just a regular radical ion 7 When a molecule is ionized and can structurally be classified as a distonic ion the molecule s kinetics and thermodynamic properties have been greatly altered However additional chemical properties are based on the reactions of the central excited ions Mass spectrometry techniques are used to study their chemistry 8 Experimental data editDistonic ions have been extensively examined due to their unique behavior and how commonly they can occur 2 It has been shown that in most cases distonic ions have a bonding arrangement corresponding to that of the original molecule before ionization occurred but that distonic ions are less stable than before ionization occurred even so distonic ions are considered stable ions and have caught many scientists attention because they possess more stability than its traditional isomer clarification needed 3 It may be difficult to decipher the functions clarification needed of the charge and radical site because distonic ions are limited to elementary reactions such as unimolecular reactions involving highly excited and short lived species 9 References edit Muller P 1994 Glossary of terms used in physical organic chemistry IUPAC Recommendations 1994 Pure and Applied Chemistry 66 5 1077 1184 doi 10 1351 pac199466051077 ISSN 1365 3075 S2CID 195819485 a b Tomazela Daniela Maria Sabino Adao A Sparrapan Regina Gozzo Fabio C Eberlin Marcos N July 2006 Distonoid ions Journal of the American Society for Mass Spectrometry 17 7 1014 1022 doi 10 1016 j jasms 2006 03 008 PMID 16713292 a b c Stirk Krista M Kiminkinen L K Marjatta Kenttamaa Hilkka I November 1992 Ion molecule reactions of distonic radical cations Chemical Reviews 92 7 1649 1665 doi 10 1021 cr00015a008 Hill Brian T Poutsma John C Chyall Leonard J Hu Jun Squires Robert R September 1999 Distonic ions of the ate class Journal of the American Society for Mass Spectrometry 10 9 896 906 doi 10 1016 S1044 0305 99 00053 7 S2CID 97267758 Williams Peggy E Jankiewicz Bartlomiej J Yang Linan Kenttamaa Hilkka I 12 November 2013 ChemInform Abstract Properties and Reactivity of Gaseous Distonic Radical Ions with Aryl Radical Sites ChemInform 44 46 no doi 10 1002 chin 201346233 Hill Brian T Poutsma John C Chyall Leonard J Hu Jun Squires Robert R September 1999 Distonic ions of the Ate class Journal of the American Society for Mass Spectrometry 10 9 896 906 doi 10 1016 S1044 0305 99 00053 7 S2CID 97267758 Yu Sophia J Holliman Christopher L Rempel Don L Gross Michael L 1993 10 01 The beta distonic ion from the reaction of pyridine radical cation and ethene a demonstration of high pressure trapping in Fourier transform mass spectrometry Journal of the American Chemical Society 115 21 9676 9682 doi 10 1021 ja00074a037 ISSN 0002 7863 Holman R W Rozeboom M D Gross M L Warner C D January 1986 Mass spectrometry for investigations of gas phase radical cation chemistry Tetrahedron 42 22 6235 6244 doi 10 1016 S0040 4020 01 88085 6 Stirk Krista G Kenttamaa Hilkka I 1991 07 01 Radical type reactivity in a gamma distonic radical cation a gas phase experimental study Journal of the American Chemical Society 113 15 5880 5881 doi 10 1021 ja00015a062 ISSN 0002 7863 Distonic radical cations Guidelines for the assessment of their stability Tetrahedron 42 22 6225 6234 January 1986 doi 10 1016 S0040 4020 01 88084 4 Stirk Krista M Orlowski Joseph C Leeck Diane T Kenttamaa H I October 1992 The identification of distonic radical cations on the basis of a reaction with dimethyl disulfide Journal of the American Chemical Society 114 22 8604 8606 doi 10 1021 ja00048a038 ISSN 0002 7863 Hammerum Steen 1988 Distonic radical cations in gaseous and condensed phase Mass Spectrometry Reviews 7 2 123 202 Bibcode 1988MSRv 7 123H doi 10 1002 mas 1280070202 ISSN 1098 2787 Bjoernholm Thomas Hammerum Steen Kuck Dietmar 1988 06 01 Distonic ions as reacting species Journal of the American Chemical Society 110 12 3862 3869 doi 10 1021 ja00220a023 ISSN 0002 7863 Retrieved from https en wikipedia org w index php title Distonic ion amp oldid 1188108211, wikipedia, wiki, book, books, library,
