{"id":"W1972537745","doi":"10.1039/c4ce00981a","title":"<i>O</i>-<i>vs. N</i>-protonation of 1-dimethylaminonaphthalene-8-ketones: formation of a<i>peri</i>N–C bond or a hydrogen bond to the pi-electron density of a carbonyl group","year":2014,"lang":"en","type":"article","venue":"CrystEngComm","topic":"Crystallography and molecular interactions","field":"Chemistry","cited_by":19,"is_retracted":false,"has_abstract":true,"ca_institutions":"","funders":"European Regional Development Fund; Engineering and Physical Sciences Research Council; Office of Science; University of Edinburgh; Trent University; Advantage West Midlands; Diamond Light Source; University of Warwick; Nottingham Trent University","keywords":"Protonation; Chemistry; Hydrogen bond; Medicinal chemistry; Electron; Pi; Ion; Electron density; Crystallography; Physics; Organic chemistry; Molecule","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":[],"consensus_categories":[],"category_scores_codex":[0.0004603542,0.0002347107,0.0004481903,0.0001810841,0.0001078476,0.00001529394,0.0004025697,0.0001545483,0.00004246346],"category_scores_gemma":[0.0002129626,0.0001820073,0.0003096561,0.0004500715,0.0001208207,0.0001631123,0.0001149782,0.0002183793,0.000001683484],"about_ca_system_candidate":false,"about_ca_system_consensus":false,"about_ca_system_score_codex":0.00004923316,"about_ca_system_score_gemma":0.00005050374,"about_ca_topic_candidate":false,"about_ca_topic_consensus":false,"about_ca_topic_score_codex":0.000292889,"about_ca_topic_score_gemma":0.0003960258,"domain_scores_codex":[0.9982208,0.0000894847,0.0007329601,0.0002680287,0.0004158334,0.0002729205],"domain_scores_gemma":[0.9980772,0.0002481137,0.000537784,0.0007505139,0.0003020941,0.0000843161],"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":[0.0004387437,0.0002357479,0.0006936306,0.0006670504,0.00009604907,0.000001583575,0.001347248,0.00009181035,0.994127,0.0006786002,0.0003580549,0.001264458],"study_design_scores_gemma":[0.0006912143,0.0003483875,0.0004545806,0.0002096602,0.0001328149,0.00004731601,0.000630818,0.0006597629,0.980267,0.0002274335,0.01612555,0.000205481],"study_design_candidate":"bench_or_experimental","study_design_consensus":"bench_or_experimental","genre_codex":"empirical","genre_gemma":"empirical","genre_scores_codex":[0.9912713,0.0001847413,0.002622829,0.0001652982,0.00006599173,0.0005123555,0.00007527274,0.00003929884,0.005062922],"genre_scores_gemma":[0.9988809,0.00002013114,0.0005862127,0.000114675,0.00005574343,0.0001525867,0.00006672955,0.00002994472,0.00009313047],"genre_candidate":"empirical","genre_consensus":"empirical","teacher_disagreement_score":0.0157675,"threshold_uncertainty_score":0.7422042,"prediction_status":"machine_predicted_unvalidated"},"machine_scores":{"provisional":true,"baseline":true,"maturity_gate_passed":false,"score_opus":0.01020315359288444,"score_gpt":0.239303278156254,"score_spread":0.2291001245633696,"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."}}