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• W2019481413 abstract "Ab initio molecular orbital calculations optimized at the 6-31G * level have been performed for aziridinone, 2-azetidinone and acetamide and their O- and N-protonated structures. Aziridinone is calculated to have a strongly pyramidal nitrogen and only 12.7 kcal molt of “operational” resonance energy compared with the 20.5 kcal mol−1 of “operational” resonance energy in acetamide. The very low N-inversion barrier for aziridinone is associated with the 27.9 kcal mol1 of “pure” resonance energy calculated in planar aziridinone, the N-inversion transition state. This is further supported by the exceedingly short C-N bond (1.302 Å) which is reminiscent of cyclopropene. For comparison, the “operational” and “pure” resonance energies of 2-azetidinone are 19.2 and 24.9 kcal mol−1 respectively and the “pure” resonance energy of acetamide is 26.5 kcal mol−1. 2-Azetidinone is O-protonated (anti to N) but aziridinone protonates at nitrogen to generate a ring-opened acylium ion. It appears that ring-closed and -opened N-protonated aziridinones exist as isomers and this is consistent with mass spectral determinations of the corresponding phenyl derivatives. Structural and energy data and core eigenvalues (N, O and carbonyl C) are given for aziridinone, 2-azetidinone, acetamide, two earlier-studied bridgehead bicyclic lactams (l-azabicyclo[2.2.2]octan-2-one (“2-quinuclidone”) and 1-azabicyclo[3.3.1]nonan-2-one) and their protonated derivatives." @default.
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• W2019481413 date "1995-08-01" @default.
• W2019481413 modified "2023-09-25" @default.
• W2019481413 title "Aziridinone and 2-azetidinone and their protonated structures. An ab initio molecular orbital study making comparisons with bridgehead bicyclic lactams and acetamide" @default.
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• W2019481413 doi "https://doi.org/10.1016/0166-1280(94)04050-3" @default.
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