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1 Supplementary Information β-cyclodextrin-resveratrol inclusion complex and the role of geometrical and electronic effects on its electronic induced circular dichroism Eduardo Troche Pesqueira, a Ignacio Pérz-Juste, b Armando Navarro-Vázquez* a and María Magdalena Cid* a a Departamento de QuímicaOrgánica, Edificio de CienciasExperimentais, Campus Lagoas Marcosende, Vigo, Spain. Fax: ; Tel: ; E mail: mcid@uvigo.es; armando.navarro@uvigo.es b Departamento de QuímicaFísica, Edificio de CienciasExperimentais, Campus Lagoas Marcosende, Vigo, Spain. Fax: ; Tel: ; E mail: uviqpipj@uvigo.es 1
2 NMR spectra Fig. 1 1D 1 H annotated spectrum of β-cyclodextrin (D 2 O, 400 MHz). Fig. 2 1D 1 H annotated spectrum of resveratrol (D 2 O, 400 MHz). Fig. 3 2D T-ROESY spectrum (D 2 O, 600 MHz). 2
3 Fig. 4 2D T-ROESY annotated spectrum in the β-cyclodextrin region. Fig. 5 2D T-ROESY annotated spectrum in the resveratrol region. Fig. 6 2D T-ROESY annotated spectrum in the cross-peaks region between resveratrol (F2 dimension) and β-cyclodextrin (F1 dimension). 3
4 Titrations Fig. 7 a) NMR titration of the β-cyclodextrin-resveratrol inclusion complex (D 2 O, 400 MHz), and individual plots for protons b) H2, c) H3, d) H4, e) H5 and f) H6 of resveratrol, along with the equations for each fitting (error bars were estimated as a 5% of error for each measurement). 4
5 Fig. 8 a) Circular Dichroism titration of the β-cyclodextrin-resveratrol inclusion complex, b) UV-vis spectra for each solution and c) plot of the inverse of the CD intensity at 308 nm vs. the inverse of the β-cyd concentration (error bars were estimated as a 5% of error for each measurement). β-cyd crystallization Crystal data and structure refinement Identification code an14581s Empirical formula C42 H70 O45 Formula weight Temperature 293(2) K Wavelength Å Crystal system Monoclinic Space group P2(1) Unit cell dimensions a = (18) Å α= 90 b = (12) Å β= (2) c = (2) Å γ = 90 Volume (6) Å 3 Z 2 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 1364 Crystal size 0.52 x 0.48 x 0.36 mm 3 Theta range for data collection 1.43 to Index ranges -19<=h<=19, -13<=k<=13, -19<=l<=27 Reflections collected Independent reflections [R(int) = ] 5
![013 Final R indices [I>2sigma(I)] R1 = 0.0711, wr2 = 0.1980 R indices (all data) R1 = 0.0956, wr2 = 0.2280 Largest diff. peak and hole 1.593 and -0.504 e.](/docs-images/74/70366535/images/6-1.jpg "å -3 Fig. 9 β-cyd channels and the two perpendicular arrangements. Molecular Dynamics 6 Fig.")
6 Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. Transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters / 1 / 805 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 Fig. 9 β-cyd channels and the two perpendicular arrangements. Molecular Dynamics 6 Fig. 10 Comparison of the total Energy (kcal/mol) over the 20 ns of MD simulation for each of the possible inclusion modes.
7 Fig. 11 Variation of the dihedral angles of the alkene bond of resveratrol with each of the aromatic moieties where the phi angle is the one formed by atoms: 151, 152, 154 and 155 and psi is the one formed by: 157, 156, 155 and 154. Table 1 Most representative families of structures extracted from their MD runs by clustering them (in parenthesis the step number of the simulation), and their relative energies calculated at the CAM-B3LYP/SVP theory level. Shaded conformations are depicted in the manuscript (Figure 6). Structure ΔE Structure ΔE a(411) 7.1 b(436) 30.4 a(1976) 4.6 b(756) 19.2 a(2381) 14.3 b(1366) 31.2 a(2716) 21.3 b(1466) 34.9 a(3116) 23.2 b(2691) 23.3 a(3661) 6.5 b(4111) 5.8 a(4591) 50.8 b(4376) 14.3 c(336) 12.7 d(126) 13.6 c(846) 26.0 d(296) 1.5 c(2926) 0.0 d(816) 17.0 c(3236) 9.4 d(1051) 5.9 c(3551) 16.7 d(2041) 25.5 c(3816) 22.8 d(3051) 40.7 c(4641) 18.3 d(4356)
8 Details of TD-DFT electronic circular dichroism computations for the functional comparison Rotatory strengths were computed using the 6-31+G* level and the IEFPCM solvation model with water parameters on CAM-B3LYP/6-31+G* geometries. ECD spectrum was simulated by convoluting transitions with gaussian bands of 0.5 ev half-height full linewidth. CAM-B3LYP Transition λ (nm) Rotatory strength (length) a a) erg.esu.cm/gauss B3LYP Transition λ (nm) Rotatory strength (length) a
9 OPBE Transition λ (nm) Rotatory strength (length) a M05 Transition λ (nm) Rotatory strength (length) a M06L Transition λ (nm) Rotatory strength (length) a
10 M06-2X Transition λ (nm) Rotatory strength (length) a
11 Fig. 12 3D Cartesian coordinate of the DFT optimized 1 structures Planar resveratrol (PL): 29 C C C C C C C C C C C C C C O O O H H H H H H H H H H H H SCF energy= u.a. 1 Both geometry optimizations and excited states TD-DFT calculations were performed at the theory level CAM-B3LYP/6-31+G*. 11
12 Twisted resveratrol (TW): 29 C C C C C C C C C C C C C C O O O H H H H H H H H H H H H SCF energy = u.a. 12
13 Mirror twisted resveratrol (TWm): 29 C C C C C C C C C C C C C C O O O H H H H H H H H H H H H SCF energy = u.a. 13
14 Inclusion complex with planar resveratrol (CPL): 176 C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O
15 C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O H H H H H H H H H H
16 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 H H H H H H H H H H H H H H
17 H H H H C C C C C C C C C C C C C C O O O H H H H H H H H H H H H SCF energy= u.a. 17
18 Inclusion complex with twisted resveratrol (CTW): 176 C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O
19 C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O H H H H H H H H H H
20 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 H H H H H H H H H H H H H H
21 H H H H C C C C C C C C C C C C C C O O O H H H H H H H H H H H H SCF energy= u.a. 21
22 Inclusion complex with mirror twisted resveratrol (CTWm): 176 C C C C C C C C C C C C C C O O O H H H H H H H H H H H H C
23 C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O C C O C O C O C O C O C C
24 O C O C O C O C O C C O C O C O C O C O 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
25 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 SCF energy= u.a. 25
26 Details of TD-DFT electronic circular dichroism computations Planar resveratrol (PL) Transition λ (nm) Rotatory strength (length) a Twisted resveratrol (TW) Transition λ (nm) Rotatory strength (length) a
27 Mirror image of twisted resveratrol (TWm) Transition λ (nm) Rotatory strength (length) a Inclusion complex with planar resveratrol (CPL) Transition λ (nm) Rotatory strength (length) a
28 Inclusion complex with twisted resveratrol (CTW) Transition λ (nm) Rotatory strength (length) a Inclusion complex of the mirror image of twisted resveratrol (CTWm) Transition λ (nm) Rotatory strength (length) a
29 Charge comparison between PL, TW, CPL, CTW in ground and excited states Fig. 12 Labelled resveratrol Table 2. NPA (Natural Population Analysis) charges of resveratrol atoms in free resveratrol (PL and TW) and in the complexes (CPL and CTW) in their ground (S 0 ) and first excited (S 1 ) electronic states. PL TW CPL CTW S 0 S 1 S 0 S 1 S 0 S 1 S 0 S 1 C C C C C C C C C C C C C C O O O q H(2,4,6,7,16,17) q H(10,11,13,14,15) q(2oh) q(1oh) q TOTAL To help the interpretation of the charge distribution both in the ground and excited states, we have added charges dividing the molecule as represented in the figure above and according to the expressions: q(2oh) = q(c1,c2,c3,c4,c5,c7,o16,o17) + q(h,h,h,h,h,h,h,h ) C2 C4 C3 C4 C5 C7 O16 O17 q(1oh) = q(c8,c9,c10,c11,c12,c13,c14,o15) + q(h,h,h,h,h,h,h,h ) C8 C9 C10 C11 C12 C13 C14 O15 29
30 q TOTAL represents the total charge of the resveratrol unit: Zero values correspond to free resveratrol and the negative values in the complexes indicate the existence of charge transfer from the β-cyd towards resveratrol. 30
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