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A Journey from Thermally Tunable Synthesis to Spectroscopy of Phenylmethanimine in Gas Phase and Solution
Authors:Alessio Melli  Simone Potenti  Dr Mattia Melosso  Dr Sven Herbers  Dr Lorenzo Spada  Dr Andrea Gualandi  Kevin G Lengsfeld  Prof Luca Dore  Philipp Buschmann  Prof Pier Giorgio Cozzi  Prof Jens-Uwe Grabow  Prof Vincenzo Barone  Prof Cristina Puzzarini
Institution:1. Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy

Dipartimento di Chimica “Giacomo Ciamician”, Universitá di Bologna, Via Selmi 2, 40126 Bologna, Italy;2. Dipartimento di Chimica “Giacomo Ciamician”, Universitá di Bologna, Via Selmi 2, 40126 Bologna, Italy;3. Institut für Physikalische Chemie und Elektrochemie, Gottfried Wilhelm Leibniz Universität Hannover, Callinstraße 3A, 30167 Hannover, Germany;4. Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy

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
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