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1 Electronic Supporting Information Locked Chromophores as CD Probes for the Helical Conformation of Tetraamidic Macrocycles Carmine Coluccini, a Andrea Mazzanti, b and Dario Pasini*,a a) Department of Organic Chemistry, University of Pavia, Viale Taramelli, Pavia - Italy. b) Department of Organic Chemistry "A. Mangini", University of Bologna, Viale Risorgimento, Bologna - Italy dario.pasini@unipv.it Content: Tables S1-S2 (page S2-S3) Figures S1-S3 (Page S3-S5) Additional NMR spectra of macrocycles 13 and 15 (pages S6-S15) Copies of 1 H NMR and 13 C NMR Spectra of precursors (pages S16 S29) Copies of Mass spectra of macrocycles (pages S30-S32) Calculated geometries of 13 and 15 (pages S33-S36) Calculated UV transitions and CD rotational strength of 13 and 15 (pages S38-S55) S1
2 Table S1. Selected 1 H NMR chemical shifts for precursors 7-9 and macrocycles a D E F H N A O O Entry Compound NHCO NHCOOtBu BINOL-E BINOL-A BINOL-F BINOL-D CH 2 Solvent b - b 7.96 (d) - c 7.87 (d) - c 4.26 (s) CDCl broad 6.45 (s) 8.12 (d) 7.19 (d) 7.99 (d) 7.45 (d) 4.60 (dd) CDCl (s) 9.08 (s) 8.12 (d) - c 8.00 (d) 7.75 (d) 4.71 (dd) DMSO-d broad 6.60 (s) 8.15 (d) 6.86 (d) 8.02 (d) - c 4.66 (bs) CDCl broad (d) 8.07 (d) 7.24 (d) 7.83 (d) 7.54 (d) 4.67 (s) CDCl (s) - b 8.11 (d) 6.95 (d) 7.98 (d) 7.59 (d) 4.69 (dd) DMSO-d (s) - b 8.08 (d) 7.10 (d) 7.55 (d) 7.90 (d) (dd) THF-d (s) - b 8.02 (d) 7.25 (d) 7.78 (d) 7.76 (d) 4.80 (dd) CDCl (s) - b 7.90 (d) 7.09 (d) 7.71 (d) 7.69 (d) 4.70 (dd) THF-d 8 a) Concentrations were in the range 5-10 mm (200, 300 or 600 MHz). Peak multiplicity as follows: s singlet, bs broad singlet, d doublet, dd double doublet (AB system). b) Not applicable. c) Not clearly assigned. S2
3 Table S2. Optical rotations and Molar Optical Rotations for precursors and macrocycles. Entry Compound [α] 25 D α m (c=0.002, THF) (c=0.0017, THF) (c=0.006, THF) (c=0.0008, THF) (c = , THF) (c=0.001, THF) (c=0.003, CH 2 Cl 2 ) Figure S1. UV/Vis spectrum of macrocycles and precursors in EtOH ( M) S3
4 Simulated UV and CD spectra. Calculation of the Electronic Circular Dichroism spectra was carried out using the TD-DFT method at the B3LYP/6-31G(d) level. 1 Rotational strength were calculated in both length and velocity representation. Since the resulting values are quite similar, errors due to basis set incompleteness are consequently small. 2 The simulated ECD spectra were obtained by applying a 0.4 ev Gaussian shaped line width. 3 Due the molecular size, 500 transition had to be calculated in order to simulate the nm range in the case of 15, and 300 in the case of 13. Figure S2. Experimental and theoretical UV (top) and CD (bottom) spectra for macrocycles 13 (left) and 15 (right). Black traces: experimental spectra. Red traces: calculated spectra ε ε λ (nm) λ (nm) Δε λ (nm) Δε λ (nm) S4
5 Figure S3. Variable temperature CD spectra of (RR)-13 (top) and (RR)-15 (bottom) in EtOH (5 to 55 C at 5 C interval). S5
6 Compound 13 S6
7 Compound 13 S7
8 Compound 13 - HSQC spectrum S8
9 Compound 13 - HMBC spectrum S9
10 Compound 15 S10
11 Compound 15 S11
12 Compound 13 - HSQC spectrum S12
13 Compound 15 - HMBC spectrum S13
14 NOE traces for irradiation on selected signals of macrocycle 15 (600 MHz, CDCl 3 ) CH 2 - system AB CH- aryl NH C D E F E F A -NH- B C D I G H L B A O O H N H G I L Spectra registered in CDCl S14
15 COSY spectra for macrocycle 15. S15
16 Compound 2 S16
17 1 H NMR Compound 3. S17
18 Compound 5. S18
19 Compound 6. S19
20 1 H NMR (200 MHz, CDCl 3 ) Compound 7. 1 H NMR (200 MHz, DMSO-d 6 ) S20
21 13 C NMR (75 MHz, CD 3 COCD 3 ) 13 C NMR DEPT (75 MHz, CD 3 COCD 3 ) S21
22 Compound 8. 1 H NMR (200 MHz, CDCl 3 ) S22
23 13 C NMR (75 MHz, CDCl 3 ) S23
24 Compound 9. 1 H NMR (200 MHz, CDCl 3 ) 13 C NMR (75 MHz, CDCl 3 ) S24
25 13 C NMR DEPT (75 MHz, CDCl 3 ) S25
26 Compound H NMR (200 MHz, CDCl 3 ) S26
27 Compound H NMR (200 MHz, CDCl 3 ) S27
28 Compound H NMR (200 MHz, CDCl 3 ) S28
29 Compound 14. S29
30 Mass Spectra (ESI) Compound 13. S30
31 Compound 14.. S31
32 Compound 15. S32
33 Compound 13, global minimum Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 1 cycles Convg = D-08 -V/T = S**2 = Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S33
34 S34
35 Compound 15, global minimum Method: B3LYP/6-31G(d) SCF Done: E(RB+HF-LYP) = A.U. after 10 cycles Convg = D-08 -V/T = S**2 = Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S35
36 S36
37 S37
38 Compound 13, UV and CD data, TD-DFT B3LYP/6-31G(d) (Rotatory strengths in erg esu cm/gauss) state Energy (ev) nm osc. strength Rotatory Strengths (velocity) Rotatory Strengths (length) f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S38
39 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S39
40 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S40
41 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S41
42 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S42
43 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S43
44 f= f= f= f= f= f= f= f= S44
45 Compound 15, UV and CD data, TD-DFT B3LYP/6-31G(d) (Rotatory strengths in erg esu cm/gauss) state Energy (ev) nm osc. strength Rotatory Strengths (velocity) Rotatory Strengths (length) f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S45
46 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S46
47 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S47
48 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S48
49 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S49
50 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S50
51 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S51
52 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S52
53 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S53
54 f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= f= S54
55 f= f= f= f= f= f= f= The use of a relatively small basis set is dictated by the very large molecular size and by the need to limit the computational work into reasonable times (about 15 days on 8 cores servers). For the same reason we had to avoid to include the presence of the solvent in the calculations. 2 P.J. Stephens, D.M. McCann, F.J. Devlin, J. R. Cheeseman and M.J. Frisch, J. Am. Chem. Soc., 2004, 126, Gaussview 4.1.2, Semichem Inc., S55
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