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. 2011 Mar 14;16(3):2414–2430. doi: 10.3390/molecules16032414

Table 1.

Comparison of calculated lipophilicities (log P/Clog P) with determined log k values, Hammett's parameter (σ) and bulk parameter (MR, reflecting bulkiness).

graphic file with name molecules-16-02414-i001.jpg
Comp. R1 R2 R3 log k log P/Clog P ChemOffice log P ACD/LogP σR2[33] MRR3[33]
GROUP 1 8a 5-Cl 3-Cl H 0.2439 2.42 / 4.33156 4.36 ± 0.47 0.373 0
8b 5-Cl 3-Cl (S)-CH3 0.4166 2.91 / 4.64056 4.71 ± 0.48 0.373 4.7
8c 5-Cl 3-Cl (R)-CH3 0.4153 2.91 / 4.64056 4.71 ± 0.48 0.373 4.7
8d 5-Cl 3-Cl (S)-CH(CH3)2 0.6124 3.80 / 5.56856 5.59 ± 0.48 0.373 14.0
8e 5-Cl 3-Cl (R)-CH(CH3)2 0.6114 3.80 / 5.56856 5.59 ± 0.48 0.373 14.0
8f 5-Cl 3-Cl (S)-CH2C6H5 0.7098 4.58 / 6.05856 6.64 ± 0.49 0.373 29.0
8g 5-Cl 3-Cl (R)-CH2C6H5 0.7066 4.58 / 6.05856 6.64 ± 0.49 0.373 29.0
GROUP 2 8h 5-Cl 4-Cl (R)-CH3 0.4308 2.91 / 4.64056 4.64 ± 0.47 0.227 4.7
8i 5-Cl 4-Cl (S)-CH(CH3)2 0.6371 3.80 / 5.56856 5.52 ± 0.48 0.227 14.0
8j 5-Cl 4-Cl (R)-CH(CH3)2 0.6125 3.80 / 5.56856 5.52 ± 0.48 0.227 14.0
8k 5-Cl 4-Cl (S)-CH2C6H5 0.7394 4.58 / 6.05856 6.57 ± 0.49 0.227 29.0
8l 5-Cl 4-Cl (R)-CH2C6H5 0.7329 4.58 / 6.05856 6.57 ± 0.49 0.227 29.0
GROUP 3 8m 5-Cl 3,4-Cl H 0.4971 2.98 / 5.01472 5.20 ± 0.49 0.600 0
8n 5-Cl 3,4-Cl (S)-CH3 0.6698 3.47 / 5.32372 5.55 ± 0.50 0.600 4.7
8o 5-Cl 3,4-Cl (S)-CH(CH3)2 0.8623 4.35 / 6.25172 6.43 ± 0.50 0.600 14.0
8p 5-Cl 3,4-Cl (R)-CH(CH3)2 0.8614 4.35 / 6.25172 6.43 ± 0.50 0.600 14.0
8q 5-Cl 3,4-Cl (S)-CH2C6H5 0.9485 5.14 / 6.74172 7.48 ± 0.51 0.600 29.0
8r 5-Cl 3,4-Cl (R)-CH2C6H5 0.9408 5.14 / 6.74172 7.48 ± 0.51 0.600 29.0
GROUP 4 8s 5-Cl 4-Br (S)-CH(CH3)2 0.6709 4.07 / 5.71856 5.76 ± 0.54 0.232 14.0
8t 5-Cl 4-Br (R)-CH(CH3)2 0.6646 4.07 / 5.71856 5.76 ± 0.54 0.232 14.0
8u 5-Cl 4-Br (S)-CH2C6H5 0.7779 4.86 / 6.20856 6.81 ± 0.55 0.232 29.0
8v 5-Cl 4-Br (R)-CH2C6H5 0.7673 4.86 / 6.20856 6.81 ± 0.55 0.232 29.0
GROUP 5 9a 4-Cl 4-Cl (S)-CH3 0.4934 2.91 / 4.64056 4.54 ± 0.47 0.227 4.7
9b 4-Cl 4-Cl (R)-CH3 0.4921 2.91 / 4.64056 4.54 ± 0.47 0.227 4.7
9c 4-Cl 4-Cl (S)-CH(CH3)2 0.6839 3.80 / 5.56856 5.41 ± 0.48 0.227 14.0
9d 4-Cl 4-Cl (R)-CH(CH3)2 0.6832 3.80 / 5.56856 5.41 ± 0.48 0.227 14.0
9e 4-Cl 4-Cl (S)-CH2C6H5 0.7540 4.58 / 6.05856 6.47 ± 0.49 0.227 29.0
9f 4-Cl 4-Cl (R)-CH2C6H5 0.7479 4.58 / 6.05856 6.47 ± 0.49 0.227 29.0
GROUP 6 9g 4-Cl 4-Br (R)-CH(CH3)2 0.7353 4.07 / 5.71856 5.65 ± 0.54 0.232 14.0
9h 4-Cl 4-CF3 (S)-CH(CH3)2 0.7892 4.16 / 5.93176 5.46 ± 0.51 0.740 14.0
9i 4-Cl 4-CH3 (S)-CH(CH3)2 0.5902 3.72 / 5.09696 4.91 ± 0.46 -0.170 14.0
9j 4-Cl 4-OCH3 (S)-CH(CH3)2 0.3623 3.11 / 4.67336 4.46 ± 0.48 -0.270 14.0