Gas-Phase Ionic Syntheses of Amino Acids: β versus α
Bibliographic record
Abstract
Both theoretical and experimental studies are reported for the gas-phase reactions of protonated hydroxylamine with acetic and propanoic acids which yield protonated glycine and alanine, GlyH+ and AlaH+, respectively. The key step for these reactions is an insertion of the amino group into a C-H bond. For the formation of AlaH+, the reaction barrier for insertion into a Cbeta-H bond is ca. 5 kcal.mol-1 lower than that for the insertion into a Calpha-H bond; the product beta-AlaH+ is ca. 6 kcal mol-1 lower in energy than alpha-AlaH+. Thus, both kinetics and thermodynamics favor formation of the beta-form. The energetic preference for the beta-form is due to more efficient hydrogen bonding between the amino group and the carbonyl oxygen in the limiting transition structure and in the beta-AlaH+ product. These theoretical results are in excellent accord with selected ion flow tube measurements of the gas-phase synthesis which show striking specificity for the beta-isomer according to multi-collision-induced dissociation of the AlaH+ product ion. The results suggest that Gly and beta-Ala found in carbonaceous chondrite meteorites are products of interstellar chemistry.
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How this classification was reachedexpand
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 | 0.001 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.001 | 0.000 |
| Research integrity | 0.000 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
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 itClassification
machine, unvalidatedMachine predicted; a candidate call from one teacher head, not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".