Details
| Original language | English |
|---|---|
| Pages (from-to) | 15016-15022 |
| Number of pages | 7 |
| Journal | Chemistry - A European Journal |
| Volume | 26 |
| Issue number | 65 |
| Early online date | 27 Jul 2020 |
| Publication status | Published - 26 Nov 2020 |
Abstract
Phenylmethanimine is an aromatic imine with a twofold relevance in chemistry: organic synthesis and astrochemistry. To tackle both aspects, a multidisciplinary strategy has been exploited and a new, easily accessible synthetic approach to generate stable imine-intermediates in the gas phase and in solution has been introduced. The combination of this formation pathway, based on the thermal decomposition of hydrobenzamide, with a state-of-the-art computational characterization of phenylmethanimine laid the foundation for its first laboratory observation by means of rotational electric resonance spectroscopy. Both E and Z isomers have been accurately characterized, thus providing a reliable basis to guide future astronomical observations. A further characterization has been carried out by nuclear magnetic resonance spectroscopy, showing the feasibility of this synthetic approach in solution. The temperature dependence as well as possible mechanisms of the thermolysis process have been examined.
Keywords
- astrochemistry, computational chemistry, NMR spectroscopy, rotational spectroscopy
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 26, No. 65, 26.11.2020, p. 15016-15022.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A Journey from Thermally Tunable Synthesis to Spectroscopy of Phenylmethanimine in Gas Phase and Solution
AU - Melli, Alessio
AU - Potenti, Simone
AU - Melosso, Mattia
AU - Herbers, Sven
AU - Spada, Lorenzo
AU - Gualandi, Andrea
AU - Lengsfeld, Kevin G.
AU - Dore, Luca
AU - Buschmann, Philipp
AU - Cozzi, Pier Giorgio
AU - Grabow, Jens Uwe
AU - Barone, Vincenzo
AU - Puzzarini, Cristina
N1 - Funding Information: This work has been supported by MIUR “PRIN 2015” (Grant Number 2015F59J3R), “PRIN 2017” (Grant Number 2017A4XRCA) and by the University of Bologna (RFO funds). Partial support by the Italian Space Agency (ASI; “Life in Space“ project, N. 2019‐3‐U.0) is also acknowledged. Further support was obtained by the Deutsche Forschungsgemeinschaft (DFG, GR‐1344) and the Land Niedersachsen. KGL acknowledges a Fonds der Chemie (FCI) scholarship. The authors gratefully thank Dr. A. Petroli and Prof. A. Mazzanti for their assistance in the variable temperature NMR experiment and the SMART@SNS Laboratory ( http://smart.sns.it ) for providing high‐performance computing facility. Open access funding enabled and organized by Projekt DEAL.
PY - 2020/11/26
Y1 - 2020/11/26
N2 - Phenylmethanimine is an aromatic imine with a twofold relevance in chemistry: organic synthesis and astrochemistry. To tackle both aspects, a multidisciplinary strategy has been exploited and a new, easily accessible synthetic approach to generate stable imine-intermediates in the gas phase and in solution has been introduced. The combination of this formation pathway, based on the thermal decomposition of hydrobenzamide, with a state-of-the-art computational characterization of phenylmethanimine laid the foundation for its first laboratory observation by means of rotational electric resonance spectroscopy. Both E and Z isomers have been accurately characterized, thus providing a reliable basis to guide future astronomical observations. A further characterization has been carried out by nuclear magnetic resonance spectroscopy, showing the feasibility of this synthetic approach in solution. The temperature dependence as well as possible mechanisms of the thermolysis process have been examined.
AB - Phenylmethanimine is an aromatic imine with a twofold relevance in chemistry: organic synthesis and astrochemistry. To tackle both aspects, a multidisciplinary strategy has been exploited and a new, easily accessible synthetic approach to generate stable imine-intermediates in the gas phase and in solution has been introduced. The combination of this formation pathway, based on the thermal decomposition of hydrobenzamide, with a state-of-the-art computational characterization of phenylmethanimine laid the foundation for its first laboratory observation by means of rotational electric resonance spectroscopy. Both E and Z isomers have been accurately characterized, thus providing a reliable basis to guide future astronomical observations. A further characterization has been carried out by nuclear magnetic resonance spectroscopy, showing the feasibility of this synthetic approach in solution. The temperature dependence as well as possible mechanisms of the thermolysis process have been examined.
KW - astrochemistry
KW - computational chemistry
KW - NMR spectroscopy
KW - rotational spectroscopy
UR - http://www.scopus.com/inward/record.url?scp=85092581699&partnerID=8YFLogxK
U2 - 10.1002/chem.202003270
DO - 10.1002/chem.202003270
M3 - Article
C2 - 32717136
AN - SCOPUS:85092581699
VL - 26
SP - 15016
EP - 15022
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 65
ER -