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1 Electronic Supplementary Information Cucurbit[7]uril host-guest complexes of the histamine H 2 -receptor antagonist ranitidine Ruibing Wang and Donal H. Macartney* Department of Chemistry, Queen s University, 90 Bader Lane, Kingston, ON K7L 3N6 Canada donal@chem.queensu.ca Contents Figure S1 Electrospray mass spectra of {RH 2 CB[7]} 2+ (top) and {RH CB[7]} + (bottom) in aqueous solution Figure S2 1 H NMR spectra of (a) ranitidine at pd 1.5, (b) ranitidine at pd 1.5 with 0.7 equivalents of CB[7], and (c) ranitidine at pd 1.5 with 1.4 equivalents of CB[7], in D 2 O. Page S3 S4 Figure S3 1 H NMR spectra of (a) ranitidine at pd 4.8 and (b) raniditine at pd 4.8 in the presence of 1.4 equivalents of CB[7] in D 2 O. S4 Figure S4 1 H NMR spectra of (a) ranitidine at pd 12 and (b) raniditine at pd 12 in the presence of 0.5 equivalents of CB[7] and (c) raniditine at pd 12 in the presence of 1.2 equivalents of CB[7] in D 2 O. Figure S5 UV-visible Job s plot of ΔA against [RH + ]/([RH + ]+[CB[7]]) for rantitidine and cucurbit[7]uril (total concentration is 5.0 x 10-5 M), monitored at 312 nm. Figure S6 1 H NMR competition binding study of diprotonated ranitidine with cucurbit[7]uril in the presence of the competing TSP guest at pd = 1.5 Figure S7 1 H NMR competition binding study of monoprotonated ranitidine with cucurbit[7]uril in the presence of the competing TSP guest at pd = 4.7 Figure S8 UV titration (monitored at 312 nm) of ranitidine (5 x 10-5 M) with CB[7] in aqueous solution (ph = 13.0) at 25 C. Figure S9. Structures of the diprotonated ranitidine (bottom) and the main thermal decomposition products (top). S5 S5 S6 S6 S7 S7 Figure S10 1 H NMR spectra of ranitidine (pd = 1.5) at 50 C after (a) 0 days, (b) 2 days, (c) 4 days, (d) 6 days, (e) 10 days, and (f) 13 days. S8 S1

2 Figure S11 1 H NMR spectra of ranitidine in the presence of 1.x equivalents of CB[7] at 50 C (pd = 1.5) after (a) 0 days, (b) 2 days, (c) 4 days, (d) 6 days, (e) 10 days, and (f) 13 days. Figure S12. Figure S12. Dependence of absorbance at 226 nm (normalized) on irradiation (254 nm) time for ranitidine ( ) and {RH 2 CB[7]} 2+ at ph 1.5. S9 S10 Figure S13 Energy-minimized structure of {(E)-RH 2 CB[7]} 2+ with atomic labeling S11 Table S1 Cartesian coordinates of {(E)-RH 2 CB[7]} 2+ S11 Figure S14 Energy-minimized structure of {(E)-RH 2 CB[7]} 2+ with atomic labeling S15 Table S2 Cartesian coordinates of {(E)-RH CB[7]} + S15 S2

3 Figure S1 Electrospray mass spectra of {RH 2 CB[7]} 2+ (top) and {RH CB[7]} + (bottom) in aqueous solution. S3

4 Figure S2 1 H NMR spectra of (a) ranitidine at pd 1.5, (b) ranitidine at pd 1.5 with 0.7 equivalents of CB[7], and (c) ranitidine at pd 1.5 with 1.4 equivalents of CB[7], in D 2 O. Figure S3 1 H NMR spectra of (a) ranitidine at pd 4.8 and (b) raniditine at pd 4.8 in the presence of 1.4 equivalents of CB[7] in D 2 O. S4

5 Figure S4 1 H NMR spectra of (a) ranitidine at pd 12, (b) ranitidine at pd 12 with 0.5 equivalents of CB[7], and (c) ranitidine at pd 12 with 1.2 equivalents of CB[7], in D 2 O ΔA [CB[7]]/([CB[7]] + [RH + ]) Figure S5 UV-visible Job s plot of ΔA against [RH]/([RH]+[CB[7]]) for rantitidine and cucurbit[7]uril (total concentration is 5.0 x 10-5 M), monitored at 228 nm. S5

6 Figure S6 1 H NMR competition binding study of diprotonated ranitidine with cucurbit[7]uril in the presence of the competing TSP guest Figure S7 1 H NMR competition binding study of monoprotonated ranitidine with cucurbit[7]uril in the presence of the competing TSP guest S6

7 0.58 Absorbance at 312 nm [CB[7]], M Figure S8 UV titration (monitored at 312 nm) of ranitidine (5 x 10-5 M) with CB[7] in aqueous solution (ph = 13.0) at 25 C. The solid curve corresponds to a non-linear least squares fit with a stability constant of K CB[7] 3 = 1.2 x 10 3 M ' 13' S N 8' H 3 C 9' CH 3 N H + 6' C H 2 4' 3' O 10' C H2 OH N HN CH 3 OH 17' 5-N,N-dimethylaminomethyl-2-furylmethanol 3-methylamino-5,6-dihydro-2H- 1,4-thiazin-2-one 8 H 3 C 9 CH N 6 10 H + S + H 2 N C C H 2 O H2 18 H NO 2 HN CH 3 17 diprotonated ranitidine Figure S9. Structures of the diprotonated ranitidine (bottom) and the main thermal decomposition products (top). S7

8 Figure S10 1 H NMR spectra of ranitidine (pd 1.5) at 50 C after (a) 0 days, (b) 2 days, (c) 4 days, (d) 6 days, (e) 10 days, and (f) 13 days. S8

9 Figure S11 1 H NMR spectra of the CB[7]-ranitidine host-guest complex at 50 C in D 2 O (pd 1.5) after (a) 0 days, (b) 2 days, (c) 4 days, (d) 6 days, (e) 10 days, and (f) 13 days. S9

10 1.0 Normalized absorbance Time, min Figure S12. Dependence of absorbance at 226 nm (normalized) on irradiation (254 nm) time for ranitidine ( ) and {RH 2 CB[7]} 2+ at ph 1.5. S10

11 Figure S13 Energy-minimized structure of {(E)-RH 2 CB[7]} 2+ with atomic labeling Table S1. Cartesian coordinates of {(E)-RH 2 CB[7]} 2+ Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z C C N C N N C N O O C C N C N N C N S11

12 19 8 O O C C C C N C N N C N O O C C N C N N C O C C C C C N H C C C S C C N H H C C N O O N H C H H H H H H H H H H H S12

13 76 1 H H H H H H H H H N O O C C C C C C N C N N C N O O C C N C N N C N O O C C C C C C C C C C N N N C N C O O H H H S13

14 133 1 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S14

15 Figure S14. Energy-minimized structure of {(E)-RH CB[7]} + with atomic labeling Table S2. Cartesian coordinates for {E-RH CB[7]} + Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z C C N C N N C N O O C C N C S15

16 15 7 N N C N O O C C C C N C N N C N O O C C N C N N C O C C C C C N H C C C S C C N H C C N O O N H C H H H H H H H H S16

17 72 1 H H H H H H H H H H H H N O O C C C C C C N C N N C N O O C C N C N N C N O O C C C C C C C C C C N N N C N C O O S17

18 129 1 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H S18

Figure S12. Kinetic plots for the C(2)-H/D exchange reaction of 2 CB[7] as a function

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