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-rw-r--r--paper/functional-groups.csv169
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diff --git a/paper/functional-groups.csv b/paper/functional-groups.csv
index 414c28c..0e2b4ca 100644
--- a/paper/functional-groups.csv
+++ b/paper/functional-groups.csv
@@ -4,11 +4,9 @@ Tertiary_carbon, 91, 73
Quaternary_carbon, 58, 60
Alkene, 39, 30
Alkyne, 5, 8
-Allene, 0, 0
Alkylchloride, 71, 41
Alkylfluoride, 52, 74
Alkylbromide, 5, 3
-Alkyliodide, 0, 0
Alcohol, 44, 27
Primary_alcohol, 12, 2
Secondary_alcohol, 23, 10
@@ -18,8 +16,6 @@ Dialkylthioether, 14, 6
Alkylarylether, 62, 90
Diarylether, 35, 47
Alkylarylthioether, 11, 10
-Diarylthioether, 3, 0
-Oxonium, 0, 0
Amine, 66, 41
Primary_aliph_amine, 8, 3
Secondary_aliph_amine, 2, 2
@@ -27,74 +23,31 @@ Tertiary_aliph_amine, 16, 9
Quaternary_aliph_ammonium, 1, 6
Primary_arom_amine, 26, 15
Secondary_arom_amine, 2, 1
-Tertiary_arom_amine, 19, 0
-Quaternary_arom_ammonium, 0, 0
Secondary_mixed_amine, 8, 3
Tertiary_mixed_amine, 14, 7
-Quaternary_mixed_ammonium, 0, 0
Ammonium, 1, 6
-Alkylthiol, 0, 0
Dialkylthioether, 10, 4
Alkylarylthioether, 10, 10
Disulfide, 4, 2
-1,2-Aminoalcohol, 5, 0
1,2-Diol, 12, 3
-1,1-Diol, 1, 0
-Hydroperoxide, 0, 0
-Peroxo, 0, 0
-Organolithium_compounds, 0, 0
-Organomagnesium_compounds, 0, 0
Organometallic_compounds, 1, 5
Aldehyde, 3, 1
Ketone, 21, 25
-Thioaldehyde, 0, 0
-Thioketone, 0, 0
-Imine, 0, 0
-Immonium, 0, 0
-Oxime, 0, 0
Oximether, 7, 15
Acetal, 13, 13
-Hemiacetal, 1, 0
-Aminal, 1, 0
-Hemiaminal, 0, 0
-Thioacetal, 0, 0
-Thiohemiacetal, 0, 0
Halogen_acetal_like, 13, 14
Acetal_like, 34, 30
-Halogenmethylen_ester_and_similar, 1, 0
NOS_methylen_ester_and_similar, 18, 19
Hetero_methylen_ester_and_similar, 19, 19
-Cyanhydrine, 0, 0
Chloroalkene, 39, 21
-Fluoroalkene, 0, 1
Bromoalkene, 1, 2
-Iodoalkene, 1, 0
Enol, 4, 5
-Endiol, 2, 0
Enolether, 2, 4
-Enolester, 0, 6
-Enamine, 0, 1
-Thioenol, 0, 0
Thioenolether, 1, 1
-Acylchloride, 0, 0
-Acylfluoride, 0, 0
-Acylbromide, 0, 0
-Acyliodide, 0, 0
-Acylhalide, 0, 0
Carboxylic_acid, 33, 38
-Carboxylic_ester, 0, 0
Lactone, 11, 10
-Carboxylic_anhydride, 1, 0
Carboxylic_acid_derivative, 215, 227
-Carbothioic_acid, 0, 0
Carbothioic_S_ester, 1, 1
-Carbothioic_S_lactone, 0, 0
-Carbothioic_O_ester, 0, 0
-Carbothioic_O_lactone, 0, 0
-Carbothioic_halide, 0, 0
-Carbodithioic_acid, 0, 0
-Carbodithioic_ester, 0, 0
-Carbodithiolactone, 0, 0
Amide, 38, 60
Primary_amide, 2, 1
Secondary_amide, 22, 36
@@ -102,78 +55,33 @@ Tertiary_amide, 15, 23
Lactam, 12, 18
Alkyl_imide, 5, 4
N_hetero_imide, 6, 3
-Imide_acidic, 0, 0
-Thioamide, 0, 0
-Thiolactam, 0, 0
-Oximester, 0, 0
Amidine, 3, 4
-Hydroxamic_acid, 0, 0
Hydroxamic_acid_ester, 1, 1
-Imidoacid, 0, 0
-Imidoacid_cyclic, 0, 2
-Imidoester, 0, 0
Imidolactone, 13, 32
-Imidothioacid, 0, 0
-Imidothioacid_cyclic, 0, 0
-Imidothioester, 0, 0
Imidothiolactone, 1, 1
Amidine, 3, 5
Imidolactam, 3, 2
-Imidoylhalide, 0, 0
Imidoylhalide_cyclic, 10, 19
-Amidrazone, 0, 0
Alpha_aminoacid, 1, 1
-Alpha_hydroxyacid, 0, 0
-Peptide_middle, 0, 0
-Peptide_C_term, 0, 0
-Peptide_N_term, 1, 0
-Carboxylic_orthoester, 0, 0
-Ketene, 0, 0
-Ketenacetal, 0, 0
Nitrile, 35, 39
-Isonitrile, 0, 0
Vinylogous_carbonyl_or_carboxyl_derivative, 70, 97
Vinylogous_acid, 9, 8
Vinylogous_ester, 113, 120
Vinylogous_amide, 19, 24
Vinylogous_halide, 11, 27
-Carbonic_acid_dieester, 0, 2
-Carbonic_acid_esterhalide, 0, 0
-Carbonic_acid_monoester, 0, 0
Carbonic_acid_derivatives, 109, 131
-Thiocarbonic_acid_dieester, 0, 0
-Thiocarbonic_acid_esterhalide, 0, 0
-Thiocarbonic_acid_monoester, 0, 0
Urea, 23, 21
Thiourea, 4, 4
-Isourea, 0, 1
Isothiourea, 1, 3
Guanidine, 6, 7
-Carbaminic_acid, 0, 0
Urethan, 34, 35
Biuret, 1, 4
-Semicarbazide, 0, 0
-Carbazide, 0, 0
Semicarbazone, 1, 3
-Carbazone, 0, 0
-Thiosemicarbazide, 1, 0
-Thiocarbazide, 0, 0
-Thiosemicarbazone, 0, 0
-Thiocarbazone, 0, 0
-Isocyanate, 0, 0
-Cyanate, 0, 0
-Isothiocyanate, 0, 0
-Thiocyanate, 0, 0
-Carbodiimide, 0, 0
-Orthocarbonic_derivatives, 0, 0
Phenol, 27, 9
-1,2-Diphenol, 2, 0
Arylchloride, 142, 163
Arylfluoride, 22, 41
Arylbromide, 4, 8
Aryliodide, 1, 4
-Arylthiol, 0, 0
-Iminoarene, 0, 1
Oxoarene, 32, 29
Thioarene, 1, 2
Hetero_N_basic_H, 17, 11
@@ -182,114 +90,38 @@ Hetero_N_nonbasic, 127, 191
Hetero_O, 10, 12
Hetero_S, 17, 18
Heteroaromatic, 147, 205
-Nitrite, 0, 0
-Thionitrite, 0, 0
-Nitrate, 0, 0
Nitro, 42, 31
-Nitroso, 0, 0
-Azide, 0, 0
-Acylazide, 0, 0
-Diazo, 0, 0
-Diazonium, 0, 0
-Nitrosamine, 0, 0
-Nitrosamide, 0, 0
-N-Oxide, 0, 1
-Hydrazine, 1, 0
-Hydrazone, 1, 0
-Hydroxylamine, 3, 0
Sulfon, 3, 14
Sulfoxide, 2, 3
-Sulfonium, 0, 0
-Sulfuric_acid, 0, 0
-Sulfuric_monoester, 0, 0
-Sulfuric_diester, 0, 0
-Sulfuric_monoamide, 1, 0
-Sulfuric_diamide, 0, 0
-Sulfuric_esteramide, 0, 1
Sulfuric_derivative, 5, 8
-Sulfonic_acid, 4, 0
Sulfonamide, 6, 9
-Sulfonic_ester, 1, 0
-Sulfonic_halide, 0, 0
Sulfonic_derivative, 24, 29
-Sulfinic_acid, 0, 0
-Sulfinic_amide, 0, 0
-Sulfinic_ester, 0, 0
-Sulfinic_halide, 0, 0
-Sulfinic_derivative, 0, 0
-Sulfenic_acid, 0, 0
-Sulfenic_amide, 0, 0
-Sulfenic_ester, 0, 0
-Sulfenic_halide, 0, 0
Sulfenic_derivative, 48, 34
-Phosphine, 0, 0
-Phosphine_oxide, 0, 0
-Phosphonium, 0, 0
-Phosphorylen, 0, 0
Phosphonic_acid, 5, 5
Phosphonic_monoester, 1, 1
Phosphonic_diester, 2, 1
-Phosphonic_monoamide, 0, 0
-Phosphonic_diamide, 0, 0
-Phosphonic_esteramide, 0, 0
Phosphonic_acid_derivative, 10, 7
-Phosphoric_acid, 0, 0
-Phosphoric_monoester, 0, 0
-Phosphoric_diester, 0, 0
Phosphoric_triester, 10, 3
-Phosphoric_monoamide, 0, 0
-Phosphoric_diamide, 0, 0
-Phosphoric_triamide, 0, 0
-Phosphoric_monoestermonoamide, 0, 0
Phosphoric_diestermonoamide, 3, 2
-Phosphoric_monoesterdiamide, 0, 0
Phosphoric_acid_derivative, 70, 44
Phosphinic_acid, 1, 1
-Phosphinic_ester, 0, 0
-Phosphinic_amide, 0, 0
Phosphinic_acid_derivative, 1, 1
-Phosphonous_acid, 0, 0
-Phosphonous_monoester, 0, 0
-Phosphonous_diester, 0, 0
-Phosphonous_monoamide, 0, 0
-Phosphonous_diamide, 0, 0
-Phosphonous_esteramide, 0, 0
-Phosphonous_derivatives, 0, 0
-Phosphinous_acid, 0, 0
-Phosphinous_ester, 0, 0
-Phosphinous_amide, 0, 0
-Phosphinous_derivatives, 0, 0
Quart_silane, 1, 2
-Non-quart_silane, 0, 0
-Silylmonohalide, 0, 0
-Het_trialkylsilane, 0, 0
-Dihet_dialkylsilane, 0, 0
-Trihet_alkylsilane, 0, 0
-Silicic_acid_derivative, 0, 0
-Trialkylborane, 0, 0
-Boric_acid_derivatives, 0, 0
-Boronic_acid_derivative, 0, 0
-Borohydride, 0, 0
-Quaternary_boron, 0, 0
Aromatic, 402, 396
Heterocyclic, 228, 272
Epoxide, 11, 2
-NH_aziridine, 0, 0
Spiro, 3, 10
Annelated_rings, 97, 73
Bridged_rings, 8, 4
Sugar_pattern_1, 10, 9
Sugar_pattern_2, 6, 7
Sugar_pattern_combi, 4, 5
-Sugar_pattern_2_reducing, 1, 0
Sugar_pattern_2_alpha, 1, 1
Sugar_pattern_2_beta, 1, 1
Conjugated_double_bond, 207, 213
Conjugated_tripple_bond, 10, 19
Cis_double_bond, 31, 19
Trans_double_bond, 31, 19
-Mixed_anhydrides, 1, 0
-Halogen_on_hetero, 0, 0
Halogen_multi_subst, 1, 6
Trifluoromethyl, 44, 63
C_ONS_bond, 520, 484
@@ -301,7 +133,6 @@ Salt, 26, 45
1,5-Tautomerizable, 124, 148
Rotatable_bond, 488, 462
Michael_acceptor, 33, 33
-Dicarbodiazene, 0, 0
CH-acidic, 60, 73
CH-acidic_strong, 1, 4
Chiral_center_specified, 1, 2