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. Author manuscript; available in PMC: 2022 Sep 10.
Published in final edited form as: J Org Chem. 2022 Jun 8;87(12):7934–7944. doi: 10.1021/acs.joc.2c00587

Table 2.

Nonequivalent Chemical Shifts (ΔΔδ, ppm) of Other Split Protons of (±)-G1–14 in the Presence of TAMCSAs 1a–1c in CDCl3 (400 or 600 MHz) at 25 °Ca

guest/TAMCSA proton ΔΔδ guest/TAMCSA proton ΔΔδ
  (±)-G1/1a PhCH 0.030   (±)-G9/1bb 4-PhCH2CH 0.024
  (±)-G1/1bb PhCH 0.041   (±)-G9/1ce PhCH3 0.007
  (±)-G1/1c PhCH 0.029 4-PhCH2CH 0.052
  (±)-G2/1a PhCH2 0.091   (±)-G10/1ac CH 2 0.070
0.049 α-H(trp unit) 0.036
PhCH2CH 0.042 ArH 0.012
  (±)-G2/1bb PhCH2 0.061 ArH 0.119
0.040 C═CHNH 0.031
PhCH2CH 0.031   (±)-G10/1bf CH 2 0.051
  (±)-G2/1cc PhCH2 0.111 α-H(trp unit) 0.027
0.054 ArH 0.067
PhCH2CH 0.051 ArH 0.013
  (±)-G3/1ac,i CH 3 0.049   (±)-G10/1cb CH 2 0.045
  (±)-G3/1bb CH 3 0.020 α-H(trp unit) 0.029
  (±)-G3/1cd,i CH 3 0.029 ArH 0.078
  (±)-G4/1a (CH3)2CHCH 0.014 C═CHNH 0.030
0.042   (±)-G11/1ac PhCH2 0.153
(CH3)2CHCH 0.031 0.100
  (±)-G4/1b (CH3)2CHCH 0.007 PhCH2CH 0.086
0.022 ArH 0.061
(CH3)2CHCH 0.024 ArH 0.014
  (±)-G4/1cb (CH3)2CHCH 0.013   (±)-G11/1bb PhCH2 0.095
0.044 0.068
(CH3)2CHCH 0.037 PhCH2CH 0.077
  (±)-G5/1ae CH 3 0.018 ArH 0.058
0.007 ArH 0.012
(CH3)2CHCH2CH 0.039   (±)-G11/1cc PhCH2 0.154
  (±)-G5/1bc CH 3 0.022 0.087
0.008 PhCH2CH 0.080
(CH3)2CHCH2CH 0.059 ArH 0.061
  (±)-G5/1c CH 3 0.020 ArH 0.013
0.008   (±)-G12/1ah CH 3 0.034
(CH3)2CHCH2CH 0.045 ArH 0.016
  (±)-G6/1ab SCH3 0.030   (±)-G12/1bd CH 3 0.017
  (±)-G6/1bb SCH3 0.021 ArH 0.032
  (±)-G6/1cb SCH3 0.025   (±)-G12/1cb CH 3 0.032
  (±)-G7/1ac PhCH3 0.038 ArH 0.019
  (±)-G7/1bc PhCH3 0.023   (±)-G13/1ab ArH 0.026
  (±)-G7/1cc PhCH3 0.033 ArH 0.012
  (±)-G8/1ab CH 3 0.040   (±)-G13/1bb ArH 0.014
PhCH3 0.037 ArH 0.040
CH3(OH)CHCH 0.027   (±)-G13/1cc ArH 0.022
  (±)-G8/1bf CH 3 0.050 ArH 0.029
PhCH3 0.025   (±)-G14/1ab,j CH 3 0.024
CH3(OH)CHCH 0.024 CH3(OH)CHCH 0.028
  (±)-G8/1cb CH 3 0.038   (±)-G14/1bb,j CH 3 0.009
PhCH3 0.035 CH3(OH)CHCH 0.022
CH3(OH)CHCH 0.027   (±)-G14/1cj CH 3 0.018
  (±)-G9/1ag PhCH3 0.005 CH3(OH)CHCH 0.021
4-PhCH2CH 0.030
a

5.0 mM.

b

7.5 mM.

c

10.0 mM.

d

6.0 mM.

e

4.0 mM.

f

12.5 mM.

g

2.0 mM.

h

3.0 mM.

i

600 MHz.

j

CDCl3 (10% CD3COCD3).