Experimental identification of aminomethanol (NHCHOH)-the key intermediate in the Strecker Synthesis.

The Strecker Synthesis of (a)chiral α-amino acids from simple organic compounds, such as ammonia (NH), aldehydes (RCHO), and hydrogen cyanide (HCN) has been recognized as a viable route to amino acids on primordial earth. However, preparation and isolation of the simplest hemiaminal intermediate - the aminomethanol (NHCHOH)- formed in the Strecker Synthesis to even the simplest amino acid glycine (HNCHCOOH) has been elusive. Here, we report the identification of aminomethanol prepared in low-temperature methylamine (CHNH) - oxygen (O) ices upon exposure to energetic electrons.

Gas phase identification of the elusive oxaziridine (cyclo-HCONH) - an optically active molecule.

The hitherto elusive oxaziridine molecule (cyclo-HCONH) - an optically active, high energy isomer of nitrosomethane (CHNO) - is prepared in processed methane-nitrogen monoxide ices and detected upon sublimation in the gas phase. Electronic structure calculations reveal likely routes via addition of carbene (CH) to the nitrogen-oxygen double bond of nitrosyl hydride (HNO). Our findings provide a fundamental framework to explore the preparation and stability of racemic oxaziridines exploited in chiral substrate-controlled diastereoselective preparation such as Sharpless asymmetric epoxidation, thus advancing our fundamental understanding of the preparation and chemical bonding of strained rings in small organic molecules.

The Elusive Ketene (H CCO) Channel in the Infrared Multiphoton Dissociation of Solid 1,3,5-Trinitro-1,3,5-Triazinane (RDX).

Understanding of the fundamental mechanisms involved in the decomposition of 1,3,5-trinitro-1,3,5-triazinane (RDX) still represents a major challenge for the energetic materials and physical (organic) chemistry communities mainly because multiple competing dissociation channels are likely involved and previous detection methods of the products are not isomer selective. In this study we exploited a microsecond pulsed infrared laser to decompose thin RDX films at 5 K under mild conditions to limit the fragmentation channels. The subliming decomposition products during the temperature programed desorption phase are detected using isomer selective single photoionization time-of-flight mass spectrometry (PI-ReTOF-MS).