Conjugate base of a cyclic hydrazine: Formation and energetics of N-diaziridyl anion

Katherine M. Broadus, Steven R Kass

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N-Diaziridyl anion (1), the conjugate base of a simple hydrazine, has been generated in a Fourier transform mass spectrometer (FTMS) by reduction of the nitrogen-nitrogen double bond in diazirine. The acidity of its conjugate acid (390 ± 3 kcal mol-1) and the electron affinity of its corresponding radical (0.50 ± 0.10 eV) were measured. These data are combined in a thermodynamic cycle to afford the N-H bond strength in trans-diaziridine (2, 88 ± 4 kcal mol-1). This value represents one of the few such bond energies reported for a hydrazine. High-level ab initio complete basis set-quadratic configuration interaction/atomic pair natural orbital (CBS-QCI/APNO) calculations on 1 and the parent hydrazyl anion (NH2NH-) are presented. These results provide strong confirming evidence for Berkowitz's recent determination of the N-H bond strength in hydrazine.

Original languageEnglish (US)
Pages (from-to)179-187
Number of pages9
JournalInternational Journal of Mass Spectrometry
StatePublished - Jan 1 1999


  • Diaziridine
  • Hydrazine
  • Ion cyclotron resonance (ICR)
  • Thermochemistry

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