A Comparative Study of Two Quantum Chemical Descriptors in Predicting Toxicity of Aliphatic Compounds towards Tetrahymena pyriformis

Table 1

Electrophilicity (𝜔, eV), energy of lowest unoccupied molecular orbital (𝐸_{𝐿𝑈𝑀𝑂}, au), log𝑃, and observed and calculated values of pIGC₅₀ for the complete set of aliphatic acceptor compounds with Tetrahymena pyriformis.

Molecule	𝜔	𝐸LUMO	log 𝑃^∗	pIGC50
				Observed^∗	Cal.(𝜔, log𝑃)	Cal.(𝐸LUMO, log𝑃)
Diols
1,2-butanediol	0.4500	0.1504	−0.53	−2.048	−1.954	−1.892
1,3-butanediol	0.4643	0.1491	−1.38	−2.301	−2.483	−2.574
1,4-butanediol	0.4458	0.1573	−0.83	−2.236	−2.328	−2.154
1,2-pentanediol	0.4453	0.1506	0.00	−1.627	−1.537	−1.464
1,5-pentanediol	0.4566	0.1548	−0.64	−1.934	−1.926	−1.994
2-methyl-2,4-pentanediol	0.4600	0.1448	−0.68	−1.953	−1.896	−1.996
1,2-hexanediol	0.4443	0.1505	0.53	−1.267	−1.047	−1.036
1,6-hexanediol	0.4514	0.1564	−0.11	−1.495	−1.522	−1.570
1,2-decanediol	0.4320	0.1507	2.64	0.764	0.735	0.667
1,10-decanediol	0.4298	0.1562	2.01	0.224	0.085	0.141
Halogenated alcohol
2-bromoethanol	0.4711	0.1301	0.18	−0.846	−0.990	−1.071
2-chloroethanol	0.5211	0.1398	−0.06	−1.417	−1.536	−1.541
1-chloro-2-propanol	0.5087	0.1364	0.14	−1.492	−1.320	−1.282
3-chloro-1-propanol	0.5053	0.1403	0.50	−1.399	−1.084	−1.091
4-chloro-1-butanol	0.4787	0.1453	0.85	−0.759	−0.665	−0.939
3-chloro-2,2-dimethyl-1-propanol	0.4923	0.1406	0.81	−0.782	−0.800	−0.843
6-chloro-1-hexanol	0.4711	0.1447	1.59	−0.272	−0.176	−0.309
8-chloro-1-octanol	0.4641	0.1448	2.65	0.488	0.492	0.566
6-bromo-1-hexanol	0.4320	0.1348	1.73	0.007	0.223	0.083
8-bromo-1-octanol	0.4281	0.1353	2.79	1.042	0.867	0.950
2,3-dibromopropanol	0.4953	0.1209	0.63	−0.486	−0.928	−0.440
Saturated alcohol
methyl alcohol	0.4744	0.1555	−0.77	−2.665	−2.609	−2.497
ethyl alcohol	0.4595	0.1547	−0.31	−1.991	−2.285	−2.164
1-propanol	0.4491	0.1570	0.25	−1.746	−1.864	−1.690
2-propanol	0.4752	0.1468	0.05	−1.882	−1.939	−2.051
1-butanol	0.4482	0.1571	0.88	−1.431	−1.355	−1.209
2-butanol	0.4615	0.1503	0.61	−1.542	−1.530	−1.554
2-methyl-1-propanol	0.4535	0.1550	0.76	−1.372	−1.435	−1.344
2-pentanol	0.4524	0.1510	1.19	−1.159	−1.088	−1.099
3-pentanol	0.4474	0.1476	1.21	−1.244	−1.089	−1.153
3-methyl-2-butanol	0.4469	0.1529	1.28	−0.996	−1.034	−0.991
tert-amyl alcohol	0.4679	0.1453	0.89	−1.173	−1.281	−1.444
2-methyl-1-butanol	0.4519	0.1550	1.22	−0.953	−1.066	−0.993
3-methyl-1-butanol	0.4611	0.1526	1.16	−1.036	−1.084	−1.087
2,2-dimethyl-1-propanol	0.4710	0.1497	1.31	−0.870	−0.928	−1.035
2-methyl-2-propanol	0.4782	0.1442	0.35	−1.791	−1.685	−1.876
1-hexanol	0.4479	0.1569	2.03	−0.379	−0.420	−0.338
3,3-dimethyl-1-butanol	0.4681	0.1511	1.62	−0.737	−0.686	−0.770
4-methyl-1-pentanol	0.4679	0.1519	1.75	−0.637	−0.581	−0.653
1-heptanol	0.4481	0.1568	2.72	0.105	0.142	0.184
2,4-dimethyl-3-pentanol	0.4261	0.1496	1.93	−0.705	−0.575	−0.564
1-octanol	0.4387	0.1568	3.00	0.583	0.338	0.397
2-octanol	0.4391	0.1511	2.90	0.001	0.258	0.203
3-octanol	0.4282	0.1503	2.72	0.031	0.075	0.050
1-nonanol	0.4282	0.1568	3.77	0.855	0.930	0.982
2-nonanol	0.4331	0.1511	3.25	0.618	0.523	0.470
3-ethyl-2,2-dimethyl-3-pentanol	0.4112	0.1458	2.86	−0.169	0.132	0.065
1-decanol	0.4195	0.1568	4.57	1.335	1.551	1.591
4-decanol	0.4093	0.1528	3.78	0.850	0.874	0.909
3,7-dimethyl-3-octanol	0.4331	0.1440	3.52	0.340	0.743	0.530
1-undecanol	0.4126	0.1568	4.53	1.955	1.495	1.560
1-dodecanol	0.4068	0.1568	5.13	2.161	1.964	2.017
1-tridecanol	0.4019	0.1568	5.58	2.450	2.314	2.359
Carboxylic acid
Propanoic acid	0.4952	0.1524	0.33	−0.512	−0.593	−0.607
Butyric acid	0.5028	0.1500	0.79	−0.572	−0.474	−0.476
Valeric acid	0.4922	0.1517	1.39	−0.267	−0.303	−0.304
Hexanoic acid	0.4868	0.1519	1.92	−0.208	−0.155	−0.153
Heptanoic acid	0.4793	0.1522	2.41	−0.113	−0.016	−0.013
Octanoic acid	0.4700	0.1522	3.05	0.081	0.165	0.170
Nonanoic acid	0.4594	0.1522	3.47	0.351	0.287	0.290
Decanoic acid	0.4495	0.1523	4.09	0.506	0.464	0.468
Undecanoic acid	0.4408	0.1523	4.53	0.898	0.590	0.594
iso-Butyric acid	0.4814	0.1509	0.60	−0.333	−0.509	−0.530
Isovalerianic acid	0.5038	0.1441	1.16	−0.341	−0.375	−0.369
Trimethylacetic acid	0.4789	0.1482	1.47	−0.254	−0.271	−0.281
3-Methylvaleric acid	0.4831	0.1517	1.75	−0.233	−0.198	−0.201
4-Methylvaleric acid	0.4984	0.1499	1.75	−0.272	−0.210	−0.201
2-Ethylbutyric acid	0.4679	0.1478	1.68	−0.152	−0.205	−0.221
2-Propylpentanoic acid	0.4454	0.1547	2.75	0.026	0.103	0.084
2-Ethylhexanoic acid	0.4563	0.1538	2.64	0.075	0.065	0.053
Succinic acid	0.5258	0.1500	−0.59	−0.939	−0.867	−0.870
Glutaric acid	0.5380	0.1425	−0.29	−0.639	−0.795	−0.784
Adipic acid	0.5175	0.1474	0.08	−0.606	−0.679	−0.678
Pimelic acid	0.5170	0.1457	0.42	−0.584	−0.586	−0.581
3,3-Dimethylglutaric acid	0.5309	0.1375	0.16	−0.664	−0.667	−0.654
Suberic acid	0.4998	0.1484	0.95	−0.512	−0.428	−0.430
Sebacic acid	0.4802	0.1496	2.01	−0.268	−0.125	−0.127
1,10-Decanedicarboxylic acid	0.4592	0.1505	3.07	−0.086	0.179	0.176
Crotonic acid	0.5022	0.1131	0.72	−0.545	−0.493	−0.491
trans-2-Pentenoic acid	0.5129	0.1101	1.41	−0.277	−0.314	−0.293
trans-2-Hexenoic acid	0.4982	0.1124	1.94	−0.128	−0.158	−0.142
Halogenated acid
4-Bromobutyric acid	0.3372	0.1609	0.68	−0.771	−0.623	−0.524
5-Bromovaleric acid	0.3239	0.1634	1.21	−0.693	−0.560	−0.362
4-Chlorobutyric acid	0.3394	0.1844	0.54	−0.677	−0.644	−0.693
3-Chloropropionic acid	0.3668	0.1792	0.41	−0.332	−0.582	−0.709
5-Chlorovaleric acid	0.3211	0.1875	1.07	−0.286	−0.597	−0.533
2-Bromobutyric acid	0.5256	0.1205	1.42	0.122	0.128	−0.070
2-Bromoisobutyric acid	0.3590	0.1550	0.86	−0.584	−0.517	−0.434
2-Bromoisovaleric acid	0.3782	0.1515	1.48	−0.549	−0.332	−0.211
2-Bromovaleric acid	0.5213	0.1208	1.61	−0.042	0.152	−0.008
2-Bromooctanoic acid	0.5175	0.1213	3.19	0.491	0.456	0.512
2-Bromohexanoic acid	0.5193	0.1210	2.14	0.455	0.252	0.165
Monoester
Ethyl acetate	0.4712	0.1543	0.73	−1.297	−1.400	−1.413
Propyl acetate	0.4783	0.1520	1.24	−1.238	−1.089	−1.104
Isopropyl acetate	0.4834	0.1502	1.02	−1.590	−1.274	−1.338
Butyl acetate	0.4734	0.1525	1.78	−0.486	−0.683	−0.675
Amyl acetate	0.4706	0.1527	2.30	0.163	−0.304	−0.271
Hexyl acetate	0.4666	0.1530	2.83	−0.009	0.090	0.143
Octyl acetate	0.4559	0.1532	3.88	1.057	0.886	0.951
Decyl acetate	0.4403	0.1533	4.94	1.879	1.721	1.762
Ethyl propionate	0.4723	0.1522	1.21	−0.945	−1.073	−1.119
Butyl propionate	0.4692	0.1518	2.30	0.170	−0.295	−0.304
Isobutyl propionate	0.4862	0.1485	2.17	−0.693	−0.491	−0.521
Propyl propionate	0.4753	0.1510	1.77	−0.815	−0.702	−0.738
tert-Butyl propionate	0.4646	0.1468	1.95	−0.409	−0.510	−0.751
Ethyl butyrate	0.4745	0.1511	1.77	−0.490	−0.697	−0.734
Ethyl isobutyrate	0.4705	0.1483	1.55	−1.271	−0.825	−0.999
Ethyl valerate	0.4675	0.1521	2.30	−0.358	−0.285	−0.294
Propyl butyrate	0.4744	0.1506	2.30	−0.414	−0.327	−0.348
Butyl butyrate	0.4689	0.1513	2.83	0.515	0.076	0.081
Propyl valerate	0.4692	0.1511	2.83	0.009	0.073	0.076
Amyl propionate	0.4661	0.1521	2.83	−0.043	0.093	0.111
Ethyl hexanoate	0.4626	0.1524	2.83	0.064	0.115	0.120
Methyl butyrate	0.4761	0.1525	1.29	−1.246	−1.041	−1.048
Methyl valerate	0.4692	0.1535	1.96	−0.845	−0.532	−0.503
Methyl hexanoate	0.4638	0.1538	2.30	−0.561	−0.261	−0.232
Methyl heptanoate	0.4581	0.1541	2.83	0.104	0.143	0.182
Methyl octanoate	0.4515	0.1541	3.36	0.536	0.552	0.585
Methyl nonanoate	0.4436	0.1541	3.88	1.042	0.963	0.983
Methyl decanoate	0.4357	0.1541	4.41	1.378	1.380	1.387
Methyl undecanoate	0.4283	0.1542	4.79	1.425	1.691	1.679
Methyl formate	0.4808	0.1638	0.03	−1.498	−1.946	−1.606
tert-Butyl formate	0.4799	0.1522	0.97	−1.372	−1.287	−1.303
Diester
Diethyl malonate	0.3493	0.1881	0.96	−0.997	−0.735	−0.674
Diethyl sebacate	0.2748	0.2011	3.90	1.354	1.274	1.192
Diethyl suberate	0.2854	0.2000	2.84	0.702	0.688	0.564
Diethyl succinate	0.3383	0.1896	1.19	−0.851	−0.534	−0.522
Dimethyl malonate	0.3685	0.1856	−0.05	−1.287	−1.371	−1.291
Dibutyl adipate	0.2920	0.1988	3.90	0.792	1.129	1.163
Dimethyl succinate	0.3544	0.1872	0.35	−1.057	−1.064	−1.038
Diethyl adipate	0.2996	0.1979	1.79	−0.126	0.075	−0.071
Dimethyl brassylate	0.2682	0.1998	4.43	1.654	1.579	1.482
Dimethyl sebacate	0.2853	0.1994	2.84	1.011	0.689	0.556
Dimethyl suberate	0.2977	0.1982	1.79	0.296	0.091	−0.066
Diethyl pimelate	0.2880	0.2002	2.31	0.407	0.417	0.259
Dibutyl suberate	0.2788	0.2009	4.96	1.656	1.737	1.803
Diethyl butylmalonate	0.3399	0.1860	3.02	0.557	0.311	0.492
Diethyl ethyl malonate	0.3460	0.1850	1.96	−0.242	−0.238	−0.134
Diethyl 3-oxopimelate	0.3614	0.1624	1.49	−0.378	−0.589	−0.690
Diethyl 4-oxopimelate	0.3731	0.1614	1.54	−0.638	−0.664	−0.673
Diethyl methylmalonate	0.3504	0.1850	1.44	−0.511	−0.519	−0.435
Diethyl propylmalonate	0.3420	0.1857	2.49	0.134	0.044	0.182
Dibutyl succinate	0.3302	0.1907	3.60	0.512	0.664	0.888
Aldehyde
Propionaldehyde	0.4454	0.1436	0.59	−0.485	−0.536	−0.607
Butyraldehyde	0.4363	0.1447	0.88	−0.380	−0.412	−0.492
Isobutyraldehyde	0.4649	0.1368	0.61	−0.433	−0.615	−0.499
Valeraldehyde	0.4312	0.1452	1.36	−0.022	−0.250	−0.282
2-Methyl-butyraldehyde	0.4249	0.1454	1.14	−0.311	−0.287	−0.385
Hexylaldehyde	0.4194	0.1474	1.78	−0.173	−0.077	−0.123
2-Methylvaleraldehyde	0.4179	0.1464	1.67	−0.474	−0.103	−0.158
2-Ethylbutyraldehyde	0.4216	0.1439	1.67	−0.054	−0.119	−0.122
3,3-Dimethylbutyraldehyde	0.4559	0.1371	1.63	−0.374	−0.279	−0.042
Heptaldehyde	0.4260	0.1456	2.42	−0.002	0.080	0.192
2-Ethylhexanal	0.4136	0.1455	2.73	0.161	0.224	0.334
trans-4-Decen-1-al	0.3360	0.1341	4.05	1.208	0.944	1.097
cis-7-Decen-1-al	0.2795	0.1452	3.52	0.948	1.036	0.695
Ketones
Acetone	0.4356	0.1425	−0.24	−2.204	−2.250	−2.201
2-Butanone	0.4274	0.1402	0.29	−1.746	−1.828	−1.903
2-Pentanone	0.4089	0.1440	0.91	−1.222	−1.309	−1.285
3-Pentanone	0.4159	0.1430	0.85	−1.456	−1.374	−1.369
4-Methyl-2-pentanone	0.4159	0.1415	1.31	−1.208	−1.028	−1.093
2-Heptanone	0.3989	0.1453	1.98	−0.487	−0.476	−0.437
5-Methyl-2-hexanone	0.4028	0.1444	1.88	−0.646	−0.563	−0.547
4-Heptanone	0.4056	0.1438	1.91	−0.669	−0.548	−0.553
2-Octanone	0.3976	0.1453	2.37	−0.145	−0.179	−0.146
2-Nonanone	0.3965	0.1454	3.14	0.660	0.402	0.427
2-Decanone	0.3957	0.1454	3.73	0.582	0.847	0.866
3-Decanone	0.3997	0.1429	3.49	0.626	0.656	0.580
2-Undecanone	0.3952	0.1455	4.09	1.535	1.119	1.134
2-Dodecanone	0.3948	0.1455	4.55	1.670	1.466	1.476
7-Tridecanone	0.3907	0.1453	5.08	1.521	1.876	1.860

∗Taken from [1].