{"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":"metacan-v3-hybrid-931329e0061c","candidate_categories":[],"consensus_categories":[],"category_scores_codex":[0.0001447875,0.0001543516,0.0001116789,0.0002016872,0.0005061318,0.0003100164,0.0002199062,0.0002013913,0.004395881],"category_scores_gemma":[0.0003050486,0.0001137699,0.00007987986,0.0001468484,0.0005189187,0.0003173823,0.000367517,0.000307354,0.0005183069],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.000160445,"about_ca_system_score_gemma":0.0001721838,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.0003010443,"about_ca_topic_score_gemma":0.0006739342,"domain_scores_codex":[0.9998987,0.00001867582,0.000003162144,0.00001051552,0.00003419806,0.00003468397],"domain_scores_gemma":[0.999842,0.00005537545,0.00003512738,0.00001864429,0.0000157632,0.0000329627],"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":[0.0003182017,0.00009212235,0.001896399,0.00009991646,0.0000109615,0.0009691918,0.0002441042,0.001647436,0.9352046,0.0381517,0.001439999,0.01992558],"study_design_scores_gemma":[0.00008692582,0.0006152074,0.007242507,0.00003050429,0.00002474394,0.001342241,0.0005689093,0.009036102,0.9460327,0.01930876,0.01565491,0.00005652057],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9716191,0.0001696225,0.003256385,0.0001976628,0.00004053502,0.000007144342,0.00004050279,0.00006321082,0.0246058],"genre_scores_gemma":[0.9982186,0.00007522411,0.0007710909,0.00005604915,0.000008768909,0.000004655697,0.00002037765,0.000006765594,0.0008384185],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.004395881,"threshold_uncertainty_score":0.01470566,"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."}}