Gas-Phase Generation and Characterization of Nitrileimine, HCNNH: A new, stable isomer of diazomethane

✍ Scribed by Norman Goldberg; Andreas Fiedler; Helmut Schwarz

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: German
• Weight: 420 KB
• Volume: 77
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19940770822

✦ Synopsis

Abstract

A new isomer of diazomethane 1, the nitrile imine, HCNNH (2) is reported to be a stable molecule in the gas phase. Upon neutralizing the α‐distonic HCNNH^+^ cation in a beam experiment, this long‐time predicted ylide can be generated. The experiments are supported by theoretical calculations (DFT/HF hybride method) on the neutral and cationic diazomethane 1, nitrile imine 2, and N‐isocyano amine 3 as well as the transition states for their interconversion.