Why are alkane eliminations from ionized alkanes so abundant?
Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Traeger, John C. [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1998 |
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| Schlagwörter: |
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| Anmerkung: |
© American Society for Mass Spectrometry 1998 |
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| Übergeordnetes Werk: |
Enthalten in: Journal of the American Society for Mass Spectrometry - Springer-Verlag, 1990, 9(1998), 1 vom: Jan., Seite 21-28 |
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| Übergeordnetes Werk: |
volume:9 ; year:1998 ; number:1 ; month:01 ; pages:21-28 |
| Links: |
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| DOI / URN: |
10.1016/S1044-0305(97)00225-0 |
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OLC2078703346 |
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| 520 | |a Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. | ||
| 650 | 4 | |a Wide Energy Range | |
| 650 | 4 | |a Appearance Energy | |
| 650 | 4 | |a Broad Energy Range | |
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| 650 | 4 | |a Alkane Elimination | |
| 700 | 1 | |a McAdoo, David J. |4 aut | |
| 700 | 1 | |a Hudson, Charles E. |4 aut | |
| 700 | 1 | |a Giam, C. S. |4 aut | |
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10.1016/S1044-0305(97)00225-0 doi (DE-627)OLC2078703346 (DE-He213)S1044-0305(97)00225-0-p DE-627 ger DE-627 rakwb eng 530 VZ 11 ssgn Traeger, John C. verfasserin aut Why are alkane eliminations from ionized alkanes so abundant? 1998 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © American Society for Mass Spectrometry 1998 Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. Wide Energy Range Appearance Energy Broad Energy Range Narrow Energy Range Alkane Elimination McAdoo, David J. aut Hudson, Charles E. aut Giam, C. S. aut Enthalten in Journal of the American Society for Mass Spectrometry Springer-Verlag, 1990 9(1998), 1 vom: Jan., Seite 21-28 (DE-627)130977357 (DE-600)1073671-2 (DE-576)277732093 1044-0305 nnns volume:9 year:1998 number:1 month:01 pages:21-28 https://doi.org/10.1016/S1044-0305(97)00225-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_40 GBV_ILN_70 GBV_ILN_168 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4313 AR 9 1998 1 01 21-28 |
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10.1016/S1044-0305(97)00225-0 doi (DE-627)OLC2078703346 (DE-He213)S1044-0305(97)00225-0-p DE-627 ger DE-627 rakwb eng 530 VZ 11 ssgn Traeger, John C. verfasserin aut Why are alkane eliminations from ionized alkanes so abundant? 1998 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © American Society for Mass Spectrometry 1998 Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. Wide Energy Range Appearance Energy Broad Energy Range Narrow Energy Range Alkane Elimination McAdoo, David J. aut Hudson, Charles E. aut Giam, C. S. aut Enthalten in Journal of the American Society for Mass Spectrometry Springer-Verlag, 1990 9(1998), 1 vom: Jan., Seite 21-28 (DE-627)130977357 (DE-600)1073671-2 (DE-576)277732093 1044-0305 nnns volume:9 year:1998 number:1 month:01 pages:21-28 https://doi.org/10.1016/S1044-0305(97)00225-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_40 GBV_ILN_70 GBV_ILN_168 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4313 AR 9 1998 1 01 21-28 |
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10.1016/S1044-0305(97)00225-0 doi (DE-627)OLC2078703346 (DE-He213)S1044-0305(97)00225-0-p DE-627 ger DE-627 rakwb eng 530 VZ 11 ssgn Traeger, John C. verfasserin aut Why are alkane eliminations from ionized alkanes so abundant? 1998 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © American Society for Mass Spectrometry 1998 Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. Wide Energy Range Appearance Energy Broad Energy Range Narrow Energy Range Alkane Elimination McAdoo, David J. aut Hudson, Charles E. aut Giam, C. S. aut Enthalten in Journal of the American Society for Mass Spectrometry Springer-Verlag, 1990 9(1998), 1 vom: Jan., Seite 21-28 (DE-627)130977357 (DE-600)1073671-2 (DE-576)277732093 1044-0305 nnns volume:9 year:1998 number:1 month:01 pages:21-28 https://doi.org/10.1016/S1044-0305(97)00225-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_40 GBV_ILN_70 GBV_ILN_168 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4313 AR 9 1998 1 01 21-28 |
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10.1016/S1044-0305(97)00225-0 doi (DE-627)OLC2078703346 (DE-He213)S1044-0305(97)00225-0-p DE-627 ger DE-627 rakwb eng 530 VZ 11 ssgn Traeger, John C. verfasserin aut Why are alkane eliminations from ionized alkanes so abundant? 1998 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © American Society for Mass Spectrometry 1998 Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. Wide Energy Range Appearance Energy Broad Energy Range Narrow Energy Range Alkane Elimination McAdoo, David J. aut Hudson, Charles E. aut Giam, C. S. aut Enthalten in Journal of the American Society for Mass Spectrometry Springer-Verlag, 1990 9(1998), 1 vom: Jan., Seite 21-28 (DE-627)130977357 (DE-600)1073671-2 (DE-576)277732093 1044-0305 nnns volume:9 year:1998 number:1 month:01 pages:21-28 https://doi.org/10.1016/S1044-0305(97)00225-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_40 GBV_ILN_70 GBV_ILN_168 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4313 AR 9 1998 1 01 21-28 |
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10.1016/S1044-0305(97)00225-0 doi (DE-627)OLC2078703346 (DE-He213)S1044-0305(97)00225-0-p DE-627 ger DE-627 rakwb eng 530 VZ 11 ssgn Traeger, John C. verfasserin aut Why are alkane eliminations from ionized alkanes so abundant? 1998 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier © American Society for Mass Spectrometry 1998 Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. Wide Energy Range Appearance Energy Broad Energy Range Narrow Energy Range Alkane Elimination McAdoo, David J. aut Hudson, Charles E. aut Giam, C. S. aut Enthalten in Journal of the American Society for Mass Spectrometry Springer-Verlag, 1990 9(1998), 1 vom: Jan., Seite 21-28 (DE-627)130977357 (DE-600)1073671-2 (DE-576)277732093 1044-0305 nnns volume:9 year:1998 number:1 month:01 pages:21-28 https://doi.org/10.1016/S1044-0305(97)00225-0 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-PHY SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_40 GBV_ILN_70 GBV_ILN_168 GBV_ILN_4012 GBV_ILN_4219 GBV_ILN_4313 AR 9 1998 1 01 21-28 |
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For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. 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Traeger, John C. ddc 530 ssgn 11 misc Wide Energy Range misc Appearance Energy misc Broad Energy Range misc Narrow Energy Range misc Alkane Elimination Why are alkane eliminations from ionized alkanes so abundant? |
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why are alkane eliminations from ionized alkanes so abundant? |
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Why are alkane eliminations from ionized alkanes so abundant? |
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Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. © American Society for Mass Spectrometry 1998 |
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Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. © American Society for Mass Spectrometry 1998 |
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Abstract Eliminations of alkanes consisting of the side chain plus a hydrogen from ionized alkylcycloalkanes are unusually abundant among such processes. For example, ethane is eliminated from ionized ethylcyclopentane more than 10 times more often than it is from its acyclic isomers. To explore why, we characterized the eliminations of ethane from ionized ethylcyclopentane and of butane, 2-methylpropane, and cyclohexane from isomeric butylcyclohexane ions. We hypothesized that one reason these alkane eliminations are particularly favored is that the partners in the complex do not readily escape from reactive configurations. Supporting this, hydrogens are transferred to butyl partners from around cyclohexyl rings, demonstrating that the partners in cycloalkyl-containing complexes do react with each other through several configurations. A very prominent cyclohexane elimination from ionized tert-butylcyclohexane demonstrates that alkane elimination is abundant no matter which partner in the intermediate ion-neutral complex bears the charge. $ C_{4} $$ H_{8} $+ is the dominant dissociation product of ionized tert-butylcyclohexane, even though the formation of the cyclohexene ion plus 2-methylpro-pane is thermochemically favored, a highly unusual ordering among mass spectral fragmentations. This is attributed to H-atom transfer from a tret-butyl ion to a cyclohexyl radical being preferred over transfer of hydride in the opposite direction. The effect of energy on the magnitude of alkane eliminations and the associated simple dissociations was elucidated utilizing photoionization mass spectrometry. Appearance energies show that forces of attraction between the partners are less than 30 kJ $ mol^{−1} $, no stronger than when both partners are acyclic. However, the shapes of photoionization efficiency curves demonstrate that these alkane eliminations are significant over a wide energy range, in contrast to most other alkane eliminations. Thus, ionized cycloalkanes generate unusually stable ion-neutral complexes; this is probably the reason alkane eliminations through them are so abundant. Alkane eliminations from acyclic alkane ions are also very abundant, suggesting that ion-neutral complexes formed from alkylcycloalkane and alkane ions have a common feature which makes energy relatively ineffective in driving the partners apart. © American Society for Mass Spectrometry 1998 |
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