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 |
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1
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2
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| 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.