Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution
Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring,...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Pichierri, Fabio [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2023 |
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| Schlagwörter: |
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| Anmerkung: |
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
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| Übergeordnetes Werk: |
Enthalten in: Structural chemistry - Dordrecht : Springer Science Business Media B.V., 1990, 34(2023), 6 vom: 07. Okt., Seite 2237-2247 |
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| Übergeordnetes Werk: |
volume:34 ; year:2023 ; number:6 ; day:07 ; month:10 ; pages:2237-2247 |
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| DOI / URN: |
10.1007/s11224-023-02235-8 |
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| Katalog-ID: |
SPR053986148 |
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| 520 | |a Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. | ||
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10.1007/s11224-023-02235-8 doi (DE-627)SPR053986148 (SPR)s11224-023-02235-8-e DE-627 ger DE-627 rakwb eng Pichierri, Fabio verfasserin aut Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2023), 6 vom: 07. Okt., Seite 2237-2247 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2023 number:6 day:07 month:10 pages:2237-2247 https://dx.doi.org/10.1007/s11224-023-02235-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2023 6 07 10 2237-2247 |
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10.1007/s11224-023-02235-8 doi (DE-627)SPR053986148 (SPR)s11224-023-02235-8-e DE-627 ger DE-627 rakwb eng Pichierri, Fabio verfasserin aut Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2023), 6 vom: 07. Okt., Seite 2237-2247 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2023 number:6 day:07 month:10 pages:2237-2247 https://dx.doi.org/10.1007/s11224-023-02235-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2023 6 07 10 2237-2247 |
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10.1007/s11224-023-02235-8 doi (DE-627)SPR053986148 (SPR)s11224-023-02235-8-e DE-627 ger DE-627 rakwb eng Pichierri, Fabio verfasserin aut Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2023), 6 vom: 07. Okt., Seite 2237-2247 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2023 number:6 day:07 month:10 pages:2237-2247 https://dx.doi.org/10.1007/s11224-023-02235-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2023 6 07 10 2237-2247 |
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10.1007/s11224-023-02235-8 doi (DE-627)SPR053986148 (SPR)s11224-023-02235-8-e DE-627 ger DE-627 rakwb eng Pichierri, Fabio verfasserin aut Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2023), 6 vom: 07. Okt., Seite 2237-2247 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2023 number:6 day:07 month:10 pages:2237-2247 https://dx.doi.org/10.1007/s11224-023-02235-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2023 6 07 10 2237-2247 |
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10.1007/s11224-023-02235-8 doi (DE-627)SPR053986148 (SPR)s11224-023-02235-8-e DE-627 ger DE-627 rakwb eng Pichierri, Fabio verfasserin aut Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 Enthalten in Structural chemistry Dordrecht : Springer Science Business Media B.V., 1990 34(2023), 6 vom: 07. Okt., Seite 2237-2247 (DE-627)31886276X (DE-600)2018832-8 1572-9001 nnns volume:34 year:2023 number:6 day:07 month:10 pages:2237-2247 https://dx.doi.org/10.1007/s11224-023-02235-8 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 34 2023 6 07 10 2237-2247 |
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Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. 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Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution Molecular structure (dpeaa)DE-He213 Carbocation (dpeaa)DE-He213 Quantum Chemistry (dpeaa)DE-He213 DFT (dpeaa)DE-He213 QTAIM (dpeaa)DE-He213 |
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isomers and neutral precursors of the cyclopentenium ion, cyclo-$ c_{5} %$ h_{7} $+: structural diversity, vibrational spectra, and charge distribution |
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Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution |
| abstract |
Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
| abstractGer |
Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
| abstract_unstemmed |
Abstract The cyclopentenium carbocation, cyclo-$ C_{5} %$ H_{7} $+ or $ CP^{+} $, and eight cyclic isomers were computationally investigated with quantum chemistry methods. These nine isomers display a significant structural diversity: three have a five-membered ring, four have a four-membered ring, and other two have a three-membered ring. The most stable isomer after $ CP^{+} $ is the dimethyl-cyclopropenium cation which is a %$2\pi%$ aromatic molecule. The vibrational spectra of the nine cyclic isomers were simulated and the normal modes associated to the most intense peaks were identified. The charge distribution in the cyclic carbocations was explored with the quantum theory of atoms in molecules (QTAIM). It appears that the less stable isomers have in their rings either one carbon atom with a large negative charge or two/three linked carbon atoms with a small negative charge. Neutral derivatives of type CP-R (R = H, F, Cl, Br, I, and OH) were also investigated since they represent potential precursors in the large-scale generation of $ CP^{+} $. Among them, 3-iodo-cyclopentene is the precursor with the lowest bond dissociation enthalpy for the heterolytic rupture of the C–R bond. © The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law. |
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6 |
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Isomers and neutral precursors of the cyclopentenium ion, cyclo-$ C_{5} %$ H_{7} $+: structural diversity, vibrational spectra, and charge distribution |
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https://dx.doi.org/10.1007/s11224-023-02235-8 |
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10.1007/s11224-023-02235-8 |
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2024-07-03T23:17:30.742Z |
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| score |
7.4001417 |