Andriy A. Koblik, Oleksandra V. Shvek, Bohdan V. Vashchenko, Dmytro S. Lesyk, Petro O. Borysko, Oleksandr V. Stryzhak, Oleksandr O. Grygorenko. “Bridgehead-functionalized bicyclo[2.1.1]hexanes – promising saturated isosteres of monosubstituted benzene.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007511/v1

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Experimental LogP values (1-octanol–H2O, 23 °C)
Bicyclo[1.1.1]pentane derivative 50 2.26
Bicyclo[1.1.1]pentane derivative 58 2.24
Cyclopentane 48 2.23
Gem-demethylated compound 47b 3.58
Gem-demethylated compound 58b 3.78
Bicyclo[2.1.1]hexane derivative 46a 2.57
Bicyclo[2.1.1]hexane derivative 54a 2.44
N-phenylbenzamide 53 2.58
Cyclohexane analog 49 2.64
Main, p. 10
Experimental pKa(H) and pKa values at 23 °C, 3 replicates
Bicyclo[1.1.1]pentane amine derivative 63, pKa(H) 8.60
Bicyclo[1.1.1]pentane acid derivative 68, pKa 4.10
Bicyclo[2.1.1]hexane amine derivative 16a, pKa(H) 9.65
Bicyclo[2.1.1]hexane acid derivative 2a, pKa 4.60
Cyclohexylamine 62, pKa(H) 10.50
Cyclohexane reference 67, pKa 4.87
Bicyclo[2.2.1]heptane amine derivative 64, pKa(H) 10.27
Bicyclo[2.2.1]heptane acid derivative 69, pKa 5.08
Bicyclo[2.2.2]octane amine derivative 65, pKa(H) 10.76
Bicyclo[2.2.2]octane acid derivative 70, pKa 5.42
Gem-dimethyl bicyclo[2.1.1]hexane amine 16b, pKa(H) 9.40
Gem-dimethyl bicyclo[2.1.1]hexane acid 2b, pKa 4.84
Homologated bicyclo[2.1.1]hexane amines 3a and 3b, pKa(H) 10.47–10.54
Homologated bicyclo[2.1.1]hexane carboxylic acids 5a and 5b, pKa 4.87–5.35