Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone
Abstract The mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron de...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Abdullah, Harun [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2022 |
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| Schlagwörter: |
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| Anmerkung: |
© The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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: Theoretical chemistry accounts - Berlin : Springer, 1962, 141(2022), 10 vom: 17. Sept. |
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| Übergeordnetes Werk: |
volume:141 ; year:2022 ; number:10 ; day:17 ; month:09 |
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| DOI / URN: |
10.1007/s00214-022-02915-4 |
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| Katalog-ID: |
SPR048134228 |
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| 520 | |a Abstract The mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. | ||
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10.1007/s00214-022-02915-4 doi (DE-627)SPR048134228 (SPR)s00214-022-02915-4-e DE-627 ger DE-627 rakwb eng Abdullah, Harun verfasserin aut Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 Opoku, Ernest (orcid)0000-0002-4271-6838 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 141(2022), 10 vom: 17. Sept. (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:141 year:2022 number:10 day:17 month:09 https://dx.doi.org/10.1007/s00214-022-02915-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA 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_65 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_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 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 141 2022 10 17 09 |
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10.1007/s00214-022-02915-4 doi (DE-627)SPR048134228 (SPR)s00214-022-02915-4-e DE-627 ger DE-627 rakwb eng Abdullah, Harun verfasserin aut Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 Opoku, Ernest (orcid)0000-0002-4271-6838 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 141(2022), 10 vom: 17. Sept. (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:141 year:2022 number:10 day:17 month:09 https://dx.doi.org/10.1007/s00214-022-02915-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA 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_65 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_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 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 141 2022 10 17 09 |
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10.1007/s00214-022-02915-4 doi (DE-627)SPR048134228 (SPR)s00214-022-02915-4-e DE-627 ger DE-627 rakwb eng Abdullah, Harun verfasserin aut Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 Opoku, Ernest (orcid)0000-0002-4271-6838 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 141(2022), 10 vom: 17. Sept. (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:141 year:2022 number:10 day:17 month:09 https://dx.doi.org/10.1007/s00214-022-02915-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA 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_65 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_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 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 141 2022 10 17 09 |
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10.1007/s00214-022-02915-4 doi (DE-627)SPR048134228 (SPR)s00214-022-02915-4-e DE-627 ger DE-627 rakwb eng Abdullah, Harun verfasserin aut Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 Opoku, Ernest (orcid)0000-0002-4271-6838 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 141(2022), 10 vom: 17. Sept. (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:141 year:2022 number:10 day:17 month:09 https://dx.doi.org/10.1007/s00214-022-02915-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA 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_65 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_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 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 141 2022 10 17 09 |
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10.1007/s00214-022-02915-4 doi (DE-627)SPR048134228 (SPR)s00214-022-02915-4-e DE-627 ger DE-627 rakwb eng Abdullah, Harun verfasserin aut Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 Opoku, Ernest (orcid)0000-0002-4271-6838 aut Enthalten in Theoretical chemistry accounts Berlin : Springer, 1962 141(2022), 10 vom: 17. Sept. (DE-627)25490971X (DE-600)1463180-5 1432-2234 nnns volume:141 year:2022 number:10 day:17 month:09 https://dx.doi.org/10.1007/s00214-022-02915-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA 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_65 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_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 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 141 2022 10 17 09 |
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Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. 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Abdullah, Harun |
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Abdullah, Harun misc DFT calculations misc [3 + 2] cycloadditions misc GEDT misc Chemoselectivity misc Nitrile oxide Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
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Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone DFT calculations (dpeaa)DE-He213 [3 + 2] cycloadditions (dpeaa)DE-He213 GEDT (dpeaa)DE-He213 Chemoselectivity (dpeaa)DE-He213 Nitrile oxide (dpeaa)DE-He213 |
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misc DFT calculations misc [3 + 2] cycloadditions misc GEDT misc Chemoselectivity misc Nitrile oxide |
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misc DFT calculations misc [3 + 2] cycloadditions misc GEDT misc Chemoselectivity misc Nitrile oxide |
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Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
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Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
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quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
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Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
| abstract |
Abstract The mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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 mechanism, regio-, chemo-, diastereo-, stereo- and enantio-selectivity of the [3 + 2] cycloaddition reaction of aryl nitrile oxides with 5-acetoxy-2(5H)-furanone has been performed by means of several computational approaches, namely, activation and reaction energies, global electron density transfer (GEDT), DFT reactivity indices and rate constants. The titled reaction leads to formation of 2-isoxalines which are important intermediates for the construction of many synthetically important cycloadducts. The calculations were performed using hybrid density functionals M06-2X, B3LYP and MPWB1K together with split valence triple zeta basis set 6-311++ G(d,p). Chemo- and regio-selectivity is not affected by the nature of substituent on the aryl nitrile oxides. IRC calculations and activation energies show that this reaction follows an asynchronous concerted mechanism. Analysis of the electrophilic $ P_{A} $+ and nucleophilic $ P_{A} $− Parr functions at the different reaction sites in the 5-acetoxy-2(5H)-furanone indicates that the aryl nitrile oxides add across the atomic centers with the highest Mulliken atomic spin densities. The results reported herein are in good agreement with previous experimental works. The GEDT calculations unravel the low polar character of the [3 + 2] cycloaddition reactions. Overall, the viability of these [3 + 2] cycloaddition reactions depends on the low polar character, which also depends on the electrophilic and nucleophilic character of the reacting 5-acetoxy-2(5H)-furanone and aryl nitrile oxides, respectively. © The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2022. Springer Nature or its licensor 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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| container_issue |
10 |
| title_short |
Quantum chemical study on the mechanism and selectivity of [3 + 2] cycloaddition reactions of aryl nitrile oxides with furanone |
| url |
https://dx.doi.org/10.1007/s00214-022-02915-4 |
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Opoku, Ernest |
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10.1007/s00214-022-02915-4 |
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2024-07-03T17:13:30.171Z |
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| score |
7.400387 |