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. 2019 May 16;10(23):5943–5951. doi: 10.1039/c9sc00721k

Table 3. Association constants (K/M–1) for 1 : 1 complexes formed with cations measured by UV/Vis absorption and 31P NMR titration experiments at 298 K a .

Anion Cation HBD HBA/solvent
1
2
MeCN Acetone MeCN Acetone
BPh4 Guanidinium 8 33 800 ± 2000 b 198 ± 61 225 ± 40
BPh4 2-Ethylhexyl ammonium 9 c c 147 ± 25 123 ± 34
BPh4 Triethyl ammonium 10 c c 85 ± 6 203 ± 50
BPh4 N-Methyl imidazolium 11 c c 102 ± 12 156 ± 18
BPh4 Li+ d 27 400 ± 5900 b b
BPh4 Na+ 13 390 ± 51 1700 ± 160 e 73 ± 5
BPh4 K+ 14 e 270 ± 75 e 13 ± 3
BPh4 Rb+ 15 e 220 ± 50 e e
BPh4 Cs+ 16 e 210 ± 35 e e
BF4 Ag+ 17 f b 8 ± 1 966 ± 40
PF6 +I(4-tBuPh)2 18 38 300 ± 1100 48 000 ± 3000 62 ± 3 83 ± 12
PF6 MOIM+ 19 23 ± 9 200 ± 60 e e
PF6 N-Butyl-4-methyl pyridinium 20 12 ± 2 180 ± 40 e e
PF6 Tetra(n-butyl) ammonium 21 e 10 ± 2 e e
PF6 Na+ 22 391 ± 35 1700 ± 140 e 55 ± 13
BF4 Na+ 23 300 ± 90 1900 ± 100 57 ± 6 57 ± 2
BArF4 Na+ 24 400 ± 160 1400 ± 400 53 ± 3 72 ± 2
N(SO2CF3)2 Na+ 25 410 ± 30 1500 ± 200 56 ± 5 78 ± 12
I Na+ 26 320 ± 120 1000 ± 300 45 ± 1 59 ± 6

aAverage of at least two titrations. Errors are quoted at the 95% confidence limit. Unless otherwise stated greater than 50% saturation of the binding isotherm was achieved.

bAssociation constant was too high to be measured using UV/Vis spectroscopy.

cProtonation of the H-bond acceptor was observed upon addition of guest.

dLi salt is LiBPh4 tris(1,2-dimethyoxyethane).

eAssociation constant was too low to be measured, because the salt was not sufficiently soluble to obtain 50% saturation of the binding isotherm.

fPoor fit to a 1 : 1 binding isotherm.