Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 604-608 |
| Seitenumfang | 5 |
| Fachzeitschrift | Journal of Physical Chemistry Letters |
| Jahrgang | 14 |
| Ausgabenummer | 2 |
| Frühes Online-Datum | 12 Jan. 2023 |
| Publikationsstatus | Veröffentlicht - 19 Jan. 2023 |
Abstract
The prereactive intermediate in the furan-maleic anhydride cycloaddition, a classical Diels-Alder reaction, has been captured and characterized in pulsed jets by Fourier transform microwave spectroscopy for the first time. The observed species is stabilized by the π-π* interaction between the two moieties, which connects to the endo channel of the cycloaddition. The secondary interactions between the C=C and C=O in the observed isomer are accountable for its lower energy with respect to the one with the exo channel. The present study tries to fill the significant void of the experimental information on prereactive intermediates as the first stage of Diels-Alder cycloadditions, by outlining the stability of the prereactive intermediate and its accurate molecular structure and by emphasizing the role of the π-π* interaction in governing the stereochemical outcome of the reaction.
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in: Journal of Physical Chemistry Letters, Jahrgang 14, Nr. 2, 19.01.2023, S. 604-608.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Insights into the Diels-Alder Reaction of Furan with Maleic Anhydride from Its Prereactive Intermediate
AU - Zhang, Xinyue
AU - Tian, Xiao
AU - Li, Jiayi
AU - Li, Meng
AU - Gao, Tianyue
AU - Zou, Siyu
AU - Chen, Junhua
AU - Xu, Xuefang
AU - Gou, Qian
AU - Grabow, Jens Uwe
N1 - Funding Information: We are grateful for the financial support from the National Natural Science Foundation of China (Grant No. 22073013), Chongqing Talents: Exceptional Young Talents Project (Grant No. cstc2021ycjh-bgzxm0027), and Fundamental Research Funds for the Central Universities (Grant Nos. 2020CDJXZ002 and 2022CDJXY-003). J.-U.G acknowledges support from the Deutsche Forschungsgemeinschaft (DFG).
PY - 2023/1/19
Y1 - 2023/1/19
N2 - The prereactive intermediate in the furan-maleic anhydride cycloaddition, a classical Diels-Alder reaction, has been captured and characterized in pulsed jets by Fourier transform microwave spectroscopy for the first time. The observed species is stabilized by the π-π* interaction between the two moieties, which connects to the endo channel of the cycloaddition. The secondary interactions between the C=C and C=O in the observed isomer are accountable for its lower energy with respect to the one with the exo channel. The present study tries to fill the significant void of the experimental information on prereactive intermediates as the first stage of Diels-Alder cycloadditions, by outlining the stability of the prereactive intermediate and its accurate molecular structure and by emphasizing the role of the π-π* interaction in governing the stereochemical outcome of the reaction.
AB - The prereactive intermediate in the furan-maleic anhydride cycloaddition, a classical Diels-Alder reaction, has been captured and characterized in pulsed jets by Fourier transform microwave spectroscopy for the first time. The observed species is stabilized by the π-π* interaction between the two moieties, which connects to the endo channel of the cycloaddition. The secondary interactions between the C=C and C=O in the observed isomer are accountable for its lower energy with respect to the one with the exo channel. The present study tries to fill the significant void of the experimental information on prereactive intermediates as the first stage of Diels-Alder cycloadditions, by outlining the stability of the prereactive intermediate and its accurate molecular structure and by emphasizing the role of the π-π* interaction in governing the stereochemical outcome of the reaction.
UR - http://www.scopus.com/inward/record.url?scp=85146396563&partnerID=8YFLogxK
U2 - 10.1021/acs.jpclett.2c03560
DO - 10.1021/acs.jpclett.2c03560
M3 - Article
C2 - 36633594
AN - SCOPUS:85146396563
VL - 14
SP - 604
EP - 608
JO - Journal of Physical Chemistry Letters
JF - Journal of Physical Chemistry Letters
SN - 1948-7185
IS - 2
ER -