Generation and UV-photolysis of N-methyleneformamide

17 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Simple imines have been detected in space and are considered as building blocks to larger heteroaromatic, cyclic and biological relevant compounds. Herein we revisited the formation of the simplest acylimine, namely N-methyleneformamide, by high-vacuum flash pyrolysis (HVFP) as well as its spectroscopic characterization by cryogenic matrix isolation infrared (IR) and UV/Vis spectroscopy. N-methyleneformamide prefers a gauche over a s-trans conformation in contrast to parent 1,3-butadiene. In UV-photolysis experiments we identified formaldehyde:HCN and formaldimine:CO complexes as the major decomposition products. As further photolysis products we observed the HCN:CO and HNC:CO complexes. All experimental findings are supported by deuterium labeling experiments and high-level ab initio coupled cluster calculations. N-methyleneformamide should be considered as a candidate for an interstellar search. The sequence R2C=N–RC=O also occurs in cytosine making the title compound highly relevant for prebiotic chemistry and the search for the molecular origins of life.

Keywords

imines
matrix isolation spectroscopy
photolysis
pyrolysis
retro-aza-Diels-Alder

Supplementary materials

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Description
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Title
SI - Generation and UV-photolysis of N-methyleneformamide
Description
The Supporting Information file to this article includes: Selected IR and UV/Vis spectra, IR and UV/Vis spectroscopic data, synthetic procedures, NMR spectra, Coordinates and energies of calculated structures
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