3.4.2. γ-CD with EFV in the 1:1 Stoichiometry

A solution of γ-CD (142.0 mg, 0.10 mmol) in ultrapure water (1.5 mL) at 40 ◦C was treated with another solution of EFV (31.5 mg, 0.10 mmol) in ethanol (0.2 mL). The mixed solution was stirred for 3 min and then subjected to snap-freezing in liquid nitrogen. Solvents were subsequently removed by freeze-drying to obtain a white solid.

FT-IR: ν(tilde) (cm−<sup>1</sup> ) = 3390 s, 2932 m, 2893 sh, 2252 w, 1746 m, 1637 m, 1499 m, 1458 m, 1414 m, 1383 m, 1372 m, 1335 m, 1302 m, 1249 m, 1198 m, 1187 m, 1159 s, 1099 sh, 1079 s, 1052 sh, 1025 vs, 1000 s, 942 m, 931 sh, 861 w, 838 vw, 760 m, 742 w, 706 m, 691 w, 674 vw, 671 vw, 655 w, 608 w, 580 m, 566 sh, 528 w, 480 w

<sup>13</sup>C{1H} CP-MAS NMR: δ (ppm) = 149.2, 147.3 (EFV C1), 134.5 (EFV C3), 133.1 (EFV C6), 130.2 (EFV C7), 128.4 (EFV C14), 126.8 (EFV C8), 118.7 (EFV C5), 114.9, 114.2 (EFV C4), 103.1 (γ-CD C1), 96.8, 95.6 (EFV C10), 82.2 (γ-CD, C), 79.1 (EFV C2), 73.0 (γ-CD C2,3,5), 66.1, 64.9 (EFV C9), 60.8 (γ-CD C), 8.8, 7.5 (EFV C12,13), −0.1, −0.8, −1.7 (EFV C11) ppm.

For comparison, the data for efavirenz is as follows:

FT-IR data of efavirenz: ν(tilde) (cm−<sup>1</sup> ) = 3255 s, 3183 s, 3094 m, 3020 w, 2951 w, 2876 w, 2253 s, 1894 vw, 1741 vs, 1705 s, 1602 s, 1498 vs, 1457 m, 1428 w, 1403 m, 1134 m, 1060 m, 1333 vs, 1280 s, 1251 vs, 1184 vs, 1168 vs, 1096 s, 1073 s, 1028 s, 976 s, 948 s, 931 s, 884 m, 866 m, 835 m, 824 s, 755 m, 742 m, 711 s, 689 s, 668 w, 656 m, 568 m, 556 m, 541 m, 518 w, 484 m, 460 w, 417 w.

<sup>13</sup>C{1H} CP-MAS NMR of efavirenz: δ (ppm) = 149.3, 147.5 (C1), 134.5 (C3), 133.2 (C6), 130.7, 130.2 (C7), 128.4 (C14), 126.8 (C8), 118.8 (C5), 114.8, 114.2 (C4), 96.8, 95.5 (C10), 79.0 (C2), 66.0, 64.9 (C9), 9.4, 8.9, 8.1, 7.5 (EFV C12,13), −0.1, −0.8, −1.0, −1.8 (EFV C11).
