Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis
Year
: 2016
Abstract: The mechanism (regioselectivity) of [3+2] cycloaddition reaction of indan-1-one enamines (1ad–1ce)
with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous onestep mechanism with a nonpolar character. Theoretical data
are in good agreement with the experimental results.
with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous onestep mechanism with a nonpolar character. Theoretical data
are in good agreement with the experimental results.
Keyword(s): Regioselectivity · [3+2] Cycloaddition · Aryl nitrile oxide · DFT reactivity indices
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Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis
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| contributor author | Amir Khojastehnezhad | en |
| contributor author | حسین عشقی | en |
| contributor author | Farid Moeinpour | en |
| contributor author | Arastou Raoufi | en |
| contributor author | Hossein Eshghi | fa |
| date accessioned | 2020-06-06T13:30:58Z | |
| date available | 2020-06-06T13:30:58Z | |
| date issued | 2016 | |
| identifier uri | http://libsearch.um.ac.ir:80/fum/handle/fum/3358103 | |
| description abstract | The mechanism (regioselectivity) of [3+2] cycloaddition reaction of indan-1-one enamines (1ad–1ce) with aryl nitrile oxide (2) has been investigated by density functional theory-based reactivity indices and activation energy calculations at B3LYP/6-31G(d) level of theory in the gas phase. Thermodynamic and kinetic parameters of the possible 3-regio/4-regio regioisomeric pathways have been determined. In all cases, the 3-regio pathways are more favorable compared to the 4-regio alternatives. Our results show that these cycloadditions follow an asynchronous onestep mechanism with a nonpolar character. Theoretical data are in good agreement with the experimental results. | en |
| language | English | |
| title | Mechanism of 1,3‑ dipolar cycloaddition reactions of indan‑ 1‑ one enamines with aryl nitrile oxide: a DFT analysis | en |
| type | Journal Paper | |
| contenttype | External Fulltext | |
| subject keywords | Regioselectivity · [3+2] Cycloaddition · Aryl nitrile oxide · DFT reactivity indices | en |
| journal title | Journal of the Iranian Chemical Society | fa |
| pages | 1629-1634 | |
| journal volume | 13 | |
| journal issue | 9 | |
| identifier link | https://profdoc.um.ac.ir/paper-abstract-1058139.html | |
| identifier articleid | 1058139 |