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. 2014 Mar 6;57(6):2704–2713. doi: 10.1021/jm500022q

Table 1. Preferred Activity Order for Halide Matched Series.

series enrichment p (corrected)a observations
F > H 1.06 0.000 (0.000) 8250
H > F 0.94 0.000 (0.000) 7338
Cl > F > H 1.85 0.000 (0.000) 1185
H > F > Cl 1.08 0.038 (0.189) 690
F > Cl > H 0.88 0.001 (0.005) 566
Cl > H > F 0.79 0.000 (0.000) 504
F > H > Cl 0.78 0.000 (0.000) 503
H > Cl > F 0.63 0.000 (0.000) 401
Br > Cl > F > H 5.62 0.000 (0.000) 230
Cl > Br > F > H 2.79 0.000 (0.000) 114
H > F > Cl > Br 1.69 0.000 (0.001) 69
F > Cl > Br > H 1.47 0.004 (0.090) 60
Br > Cl > H > F 1.39 0.013 (0.302) 57
Cl > Br > H > F 0.88 0.473 (10.873) 36
F > Cl > H > Br 0.86 0.380 (8.738) 35
Cl > F > Br > H 0.83 0.299 (6.880) 34
Br > H > Cl > F 0.81 0.231 (5.304) 33
H > Br > Cl > F 0.76 0.128 (2.954) 31
H > F > Br > Cl 0.73 0.093 (2.132) 30
Br > F > Cl > H 0.68 0.038 (0.865) 28
F > Br > Cl > H 0.66 0.025 (0.574) 27
F > H > Cl > Br 0.61 0.008 (0.191) 25
Cl > F > H > Br 0.56 0.003 (0.069) 23
Cl > H > F > Br 0.49 0.000 (0.009) 20
H > Br > F > Cl 0.49 0.000 (0.009) 20
Cl > H > Br > F 0.46 0.000 (0.004) 19
Br > F > H > Cl 0.44 0.000 (0.002) 18
H > Cl > Br > F 0.44 0.000 (0.002) 18
F > H > Br > Cl 0.42 0.000 (0.001) 17
H > Cl > F > Br 0.37 0.000 (0.000) 15
F > Br > H > Cl 0.34 0.000 (0.000) 14
Br > H > F > Cl 0.22 0.000 (0.000) 9
a

The p-value measured the likelihood of the observed enrichment occurring by chance. This was measured using a two-tailed binomial test. The p-value was corrected for multiple testing using the Bonferroni correction. This is a conservative correction that involves multiplying the original p-value by the degrees of freedom. Here there were N! – 1 degrees of freedom, and so the values for N = 4 were corrected by multipling by 23. Values are considered to be significant if the corrected p-value is ≤0.05.