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 -