Azabenzenes (azines) The nitrogen derivatives of benzene with one to six N atoms: Stability, homodesmotic stabilization energy, electron distribution, and magnetic ring current; a computational study
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Bibliographic record
Abstract
The twelve azabenzenes the species formed by replacing CH groups of benzene by N were examined computationally (with emphasis on the six contiguous-nitrogen species). MP2(fc)/6-31G*, B3LYP/6-31G*, CCSD(T)/6-31G*//MP2(fc)/6-31G*, and G3(MP2) calculations were used to probe kinetic and thermodynamic stabilities, homodesmotic ring-opening energies, electron distribution (bond orders and lengths, Bird index), and NICS values, primarily to discern where the transition occurs from reasonably stable to highly fragile species. Some azabenzenes with three and those with four or more nitrogens are thermodynamically unstable, but kinetic stabilities indicated that, with the possible exception of hexaazabenzene, all the azabenzenes should be isolable, although some with four nitrogens might decompose at room temperature, and pentaazabenzene would require matrix isolation techniques. Although homodesmotic ring-opening reactions showed an almost monotonic decrease in the stability of the cyclic relative to the open-chain species (in appropriate ring-opening reactions) on going from benzene to hexaazabenzene, bond-order variation and NICS suggested this may be because of increasing destabilization by nitrogen lone pairs rather than because of a decrease in electron delocalization (in aromaticity). Key words: azines, azabenzenes, pentazine, hexazine, ab initio, DFT, aromaticity.
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Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.000 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
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Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it