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. Author manuscript; available in PMC: 2021 Sep 22.

Published in final edited form as: J Chem Inf Model. 2020 Mar 10;60(3):1090–1100. doi: 10.1021/acs.jcim.9b01156

Table 6.

Distribution of Some Common Tautomeric Pairs in Different Prevalence Categories

	Prevalence_Category						Prevalence_Category
Tautomer_1	0	1	2	3	4	Tautomer_2	0	1	2	3	4
Azo	39	73	99	79	43	Hydrazone	54	127	80	38	34
Enol	63	35	20	14	5	Keto	20	34	10	43	30
Oxo-enamine	9	2	37	44	21	Oxo-imine	25	70	7	2	9
Diketo	27	41	9	25	6	Keto-enol	6	37	22	39	4
Enol-imine	6	53	0	29	16	Oxo-enamine	16	29	2	51	6
Keto-enethiol	0	59	19	3	0	Thioketo-enol	0	4	19	58	0
Amine	10	32	5	28	8	Imine	18	33	5	24	3
Enamine	19	13	26	9	5	Imine	5	14	26	8	19
Oxo-enamine	16	15	34	0	0	Phenol-imine	0	0	34	15	16
Pyridol	3	38	8	8	0	Pyridone	2	15	12	27	2
Enethiol	0	6	3	1	16	Thioketo	18	1	4	3	0
Enol-imine	6	53	0	29	16	Oxo-enamine	16	29	2	51	6
Lactam	10	1	4	15	1	Lactim	4	11	5	9	1
5H-2-one	2	4	2	13	6	3H-2-one	6	13	2	4	2
Cyclohexadienone	9	1	5	4	8	Phenol	9	3	5	0	10
Isoindole	1	8	5	10	0	Isoindolenine	0	10	5	8	1
N-hydroxide	1	3	5	9	1	N-oxide	1	10	5	2	1
Keteneimine	5	11	0	0	0	Nitrile	0	6	0	9	1
Ring^a	28	125	114	64	7	Chain^a	11	65	171	65	26
Benzoxazaphospholine^a	0	11	17	10	1	Iminophosphorane^a	1	10	17	11	0
Diazaphosphazole^b	2	4	1	17	1	Phosphinoimine^b	1	17	1	4	2
Phosphine^b	3	9	5	8	0	phosphonium salt^b	4	4	5	12	0
Ring^b	6	22	8	26	15	Chain^b	18	28	8	17	6
Tetrazole^b	5	29	8	35	5	Azide^b	4	70	1	3	4

^a

Ring-chain tautomerism type.

^b

Valence tautomerism type.