Palladium, [ <i>N</i> , <i>N</i> ′‐1,2‐ethanediylidenebis[2,6‐dimethylbenzenamine‐κN]][(3,4‐ <i>η</i> )‐2,5‐furandione] ( <sup>DMP</sup> DAB–Pd–MAH)
Bibliographic record
Abstract
image [2721487‐84‐7] C 22 H 22 N 2 O 3 Pd (MW 468.85) InChI = 1S/C18H20N2.C4H2O3.Pd/c1‐13‐7‐5‐8‐14(2)17(13)19‐11‐12‐20‐18‐15(3)9‐6‐10‐16(18)4;5‐3‐1‐2‐4(6)7‐3;/h5‐12H,1‐4H3;1‐2H;/b19‐11+,20‐12+;; InChiKey = WHOQNDZHEHSRKP‐GAMUHHASSA‐N (palladium(0) compound used as a precursor to phosphine palladium(0) complexes, 1–5 and as a catalyst precursor for cross‐coupling reactions, 1,6 CH activation reactions, 7 and enantioselective allylation reactions 4,8 ) Alternative Names : (1 E ,2 E )‐ N 1, N 2‐bis(2,6‐dimethylphenyl)ethane‐1,2‐diimine 2,5‐dihydrofuran‐2,5‐dione palladium, [κ 2 ‐ N , N ′‐bis(2,6‐dimethylphenyl)ethan‐1,2‐diimine][ η 2 ‐maleic anhydride]palladium(0). Physical Data : m.p. 121 °C (dec). Solubility : fully soluble (≥20 mg mL −1 ) in acetone, dichloromethane, tetrahydrofuran (THF), 2‐methyltetrahydrofuran (MeTHF); partially soluble in toluene (5 mg mL −1 ), ethyl acetate (2.5 mg mL −1 ); poorly soluble (≤2 mg mL −1 ) in pentane, n ‐hexane, n ‐heptane, diethyl ether, tert ‐butylmethyl ether (TBME); insoluble in isopropanol (<1 mg mL −1 ); soluble but decomposes in acetonitrile, chloroform; poorly soluble and decomoposes in dimethylsulfoxide (DMSO), N,N ‐dimethylformamide (DMF), methanol, ethanol; insoluble in water. Form Supplied in : red/purple crystalline solid. Preparative Methods : commercially available. There are two reported procedures 1 for preparing DMP DAB–Pd–MAH by reacting N , N ′‐1,2‐ethanediylidenebis(2,6‐dimethylbenzenamine) ( DMP DAB) and maleic anhydride (MAH) 9 with either Pd 2 dba 3 ·CHCl 3 10 or “Pd(dba) 2 ” (actually Pd 2 dba 3 ·dba). 11 These palladium sources can be prepared from a variety of palladium(II) starting materials according to the method of Zalesskiy and Ananikov, 12 or purchased from commercial sources. Recystallization of crude “Pd(dba) 2 ” is not required, since purification of DMP DAB–Pd–MAH removes residual dba and colloidal palladium(0) (see below). N , N ′‐1,2‐ethanediylidenebis(2,6‐dimethylbenzenamine) ( DMP DAB) is prepared from glyoxal (40% wt/wt solution in water) and 2,6‐dimethylaniline in methanol with 13 or without 14 formic acid as a catalyst. Purification : colloidal palladium(0) can be removed from DMP DAB–Pd–MAH by dissolving the solid in a minimum amount of acetone, dichloromethane, or THF, followed by filtration through a bed of Celite ™ and subsequent solvent removal from the filtrate. Uncoordinated N , N ′‐1,2‐ethanediylidenebis(2,6‐dimethylbenzenamine) ( DMP DAB), maleic anhydride, and/or residual dibenzylideneacetone (dba) from the synthesis can be removed by slurrying solid DMP DAB–Pd–MAH in TBME (∼30 mL g −1 of solid), followed by filtration and washing with TBME. Analysis of Reagent Purity : 1 H NMR spectroscopic analysis is suitable for routine purity determination. In d 6 ‐acetone (solvent residual peak at 2.05 ppm), DMP DAB–Pd–MAH has diagnostic resonances at 8.55 ppm (s, 2 H ) for the N=CH–CH=N protons, 3.57 ppm (s, 2 H ) for the coordinated male
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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 | 0.001 | 0.004 |
| Meta-epidemiology (narrow) | 0.002 | 0.002 |
| Meta-epidemiology (broad) | 0.002 | 0.001 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.002 | 0.000 |
| Research integrity | 0.002 | 0.001 |
| Insufficient payload (model declined to judge) | 0.075 | 0.003 |
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; both teacher heads agree on what is shown here.
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".