{"id":"W2329842457","doi":"10.1021/ol5012967","title":"<i>n</i>→π* Interactions Engender Chirality in Carbonyl Groups","year":2014,"lang":"en","type":"article","venue":"Organic Letters","topic":"Crystallography and molecular interactions","field":"Chemistry","cited_by":49,"is_retracted":false,"has_abstract":true,"ca_institutions":"","funders":"National Institute of General Medical Sciences; National Institutes of Health; National Institute of Arthritis and Musculoskeletal and Skin Diseases; York University; University of Wisconsin-Madison","keywords":"Antibonding molecular orbital; Delocalized electron; Chemistry; Diastereomer; Chirality (physics); Electron delocalization; Planar chirality; Carbonyl group; Group (periodic table); Stereochemistry; Crystallography; Electron; Atomic orbital; Organic chemistry; Catalysis; Enantioselective synthesis; Physics; Chiral symmetry","routes":{"ca_aff":false,"ca_fund":true,"ca_venue":false,"about_ca":false,"invisible_to_affiliation_only":true},"retraction":null,"screen":null,"direct_labels":[],"prediction":{"model_version":"codex-gemma-dda1882f352a","candidate_categories":["insufficient_payload"],"consensus_categories":[],"category_scores_codex":[0.00008112484,0.0001390631,0.0001311855,0.00009198654,0.0000660135,0.00003510462,0.0001588068,0.00005528916,0.001825609],"category_scores_gemma":[0.0000533096,0.0001484797,0.0001152909,0.0001821276,0.0000404589,0.0001119597,0.00004479319,0.0003700444,0.00004016125],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.00009205986,"about_ca_system_score_gemma":0.00001155172,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0001717926,"about_ca_topic_score_gemma":0.0006232199,"domain_scores_codex":[0.9991312,0.00003521192,0.0002082955,0.0002689867,0.0001150104,0.0002412663],"domain_scores_gemma":[0.9994428,0.00006248963,0.00005682224,0.0003594087,0.00001381213,0.00006463173],"domain_codex":null,"domain_gemma":null,"domain_candidate":null,"domain_consensus":null,"study_design_codex":"bench_or_experimental","study_design_gemma":"bench_or_experimental","study_design_scores_codex":[0.000006389124,0.00007090302,0.002861343,0.00001680524,0.00003150649,0.000009513241,0.0003258,0.00001158595,0.9947109,0.0002345225,0.001343142,0.0003776336],"study_design_scores_gemma":[0.002283465,0.00003035566,0.01496914,0.0001399975,0.000123873,0.0001833526,0.001031462,0.0004138567,0.7720813,0.0006475961,0.2069406,0.001154987],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9807866,0.00001920829,0.001679845,0.002508159,0.0003123736,0.00003847567,0.000006870402,0.0001027601,0.01454574],"genre_scores_gemma":[0.9971354,0.000003795179,0.00009928099,0.002411061,0.0001773453,0.00001756263,0.00003062984,0.00002552249,0.00009939693],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.2226295,"threshold_uncertainty_score":0.9990869,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.007708989577121138,"score_gpt":0.2203600960960453,"score_spread":0.2126511065189242,"validation_status":"score_only:v0-immature-baseline","note":"Baseline scores from an immature model (maturity gate not passed). Scores rank; they never assert a category."}}