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A Journey from Thermally Tunable Synthesis to Spectroscopy of Phenylmethanimine in Gas Phase and Solution
Author(s) -
Melli Alessio,
Potenti Simone,
Melosso Mattia,
Herbers Sven,
Spada Lorenzo,
Gualandi Andrea,
Lengsfeld Kevin G.,
Dore Luca,
Buschmann Philipp,
Cozzi Pier Giorgio,
Grabow JensUwe,
Barone Vincenzo,
Puzzarini Cristina
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003270
Subject(s) - imine , characterization (materials science) , spectroscopy , thermal decomposition , nuclear magnetic resonance spectroscopy , chemistry , phase (matter) , decomposition , chemical physics , chemical engineering , organic chemistry , photochemistry , materials science , nanotechnology , catalysis , physics , quantum mechanics , engineering
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.