Table 1 Anion association constants (Ka, in M−1) for tri- and tetradentate [2]rotaxanes with TBA halide salts in acetone-d6 or 2% D2O/acetone-d6 determined by 1H NMR titrationsa

From: Amphoteric chalcogen-bonding and halogen-bonding rotaxanes for anion or cation recognition

 

Acetone-d6

2% D2O/acetone-d6

[2]Rotaxane

Cl

Br

I

Cl

10·XB3

>105

/

/

/

8·XB2ChBMe

4,090 (351)

2,330 (41)

977 (24)

89 (1)

10·XB2HB

4,380 (322)

2,140 (68)

902 (57)

/

8·ChB3

130 (1)

80 (1)

46 (<1)

/

10·ChB2HB

127 (2)

110 (2)

34 (3)

/

10·HB3

81 (3)

65 (5)

43 (1)

/

8·XB2ChBPh

/

/

/

69 (1)

8·XB2ChBpCF3

/

/

/

173 (3)

9·XB3ChB

>105

>105

3,080 (153)

/

9·XB2ChB2

10,600 (394)

4,220 (137)

1,090 (21)

/

9·ChB3XB

557 (13)

253 (4)

99 (2)

/

9·ChB4

172 (2)

100 (1)

56 (1)

/

  1. aKa values calculated using Bindfit58,59 with a 1:1 host–guest binding model. Errors (±) are in parentheses and are all <5%. Solvent: acetone-d6 or 2% D2O/acetone-d6. T = 298 K. The rotaxane concentration was 1.0 mM, except for [9·ChB4] = [9·XB2ChB2] = 0.5 mM. Data for 10·XB3, 10·XB2HB, 10·ChB2HB and 10·HB3 are adopted from refs. 56,57.
  2. The solidus indicates that the titration experiment was not performed.