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Updated: May 2, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Photodissociation Dynamics of the Simplest Diazirine: Cyclo-CH2N2 → CH2 + N2
1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853-1301, United States.
Abstract:
The photodissociation of the simplest diazirine, 3H-diazirine (cyclo-CH2N2), was studied in the gas phase following excitation of S1 levels with one quantum of C-N symmetric stretching (ν6, 802 cm-1) or two quanta of C-N asymmetric stretching (2ν9, 216 cm-1). The angular and velocity distributions of the products were measured using 9.9 eV single photon vacuum ultraviolet photoionization and 70 eV electron impact ionization. Preferential scattering of products perpendicular to the laser polarization axis indicates that the transition is 1B1 ← 1A1 with dissociation occurring on subpicosecond time scales. From photofragment anisotropy measurements, initial asymmetric parent vibrational excitation results in shorter dissociation time scales as compared to symmetric stretching, suggesting that dissociation is initiated by asymmetric stepwise ring-opening. However, the final product translational energy distributions were nearly identical for each level, suggesting similar later-time dissociation dynamics. We observed no evidence for formation of ground state CH2 (X̃ 3B1). The CH2 + N2 products are formed with a most probable total internal energy of ∼2 eV. Although the translational energy distributions are consistent with production of highly vibrationally excited CH2 (ã 1A1) following passage through a conical intersection, a significant yield of CH2 (b̃ 1B1) is possible.
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