Content
Protonated BINOL
Diprotonated BINOL
Transition states of racemization of BINOL
Rotations in 1,1'-diprotonated BINOLs

Protonated BINOL

The geometries of all the protonated forms were optimized by DFT (Priroda program, PBE functional, L1 basis (Λ01, cc-pVDZ analog)).


On figure(s) below click on the level title to download xyz file ==>
Click on energy level to view 3D structure in browser (run JSmol) ==>

0.00 0.00 0.93 0.93 1.24 1.24 1.97 1.97 2.55 2.55 4.45 4.45 4.69 4.69 4.94 4.94 5.29 5.29 5.67 5.67 6.24 6.24 7.12 7.12 7.13 7.13 7.52 7.52 7.81 7.81 8.18 8.18 8.36 8.36 8.44 8.44 8.81 8.81 9.80 9.80 9.96 9.96 10.31 10.31 10.43 10.43 10.92 10.92 11.29 11.29 11.40 11.40 11.53 11.53 11.75 11.75 11.85 11.85 12.20 12.20 12.81 12.81 13.20 13.20 13.26 13.26 13.38 13.38 14.20 14.20 14.63 14.63 15.41 15.41 16.66 16.66 16.84 16.84 19.43 19.43 23.23 23.23 23.61 23.61 24.09 24.09 24.14 24.14 25.46 25.46 25.95 25.95 26.61 26.61 26.73 26.73 28.50 28.50

Diprotonated BINOL

The geometries of all the protonated forms were optimized by DFT (Priroda program, PBE functional, L1 basis (Λ01, cc-pVDZ analog)).


On figure(s) below click on the level title to download xyz file ==>
Click on energy level to view 3D structure in browser (run JSmol) ==>

Yellow highlighted are structures from Chem. Eur. J. 2014, 20, 14816 (SI)
0.00 0.00 0.79 0.79 1.31 1.31 1.35 1.35 1.60 1.60 2.16 2.16 2.22 2.22 3.15 3.15 3.37 3.37 3.37 3.37 3.58 3.58 3.86 3.86 3.91 3.91 4.61 4.61 4.64 4.64 4.76 4.76 5.39 5.39 5.52 5.52 5.55 5.55 5.70 5.70 5.83 5.83 5.95 5.95 6.10 6.10 6.11 6.11 6.18 6.18 6.25 6.25 6.40 6.40 6.55 6.55 6.61 6.61 6.76 6.76 6.97 6.97 7.31 7.31 7.43 7.43 7.78 7.78 7.83 7.83 8.21 8.21 8.25 8.25 8.53 8.53 8.60 8.60 8.80 8.80 8.96 8.96 9.11 9.11 9.12 9.12 9.39 9.39 9.51 9.51 9.79 9.79 9.89 9.89 10.13 10.13 10.20 10.20 10.21 10.21 10.26 10.26 10.28 10.28 10.28 10.28 10.30 10.30 10.37 10.37 10.37 10.37 10.39 10.39 10.41 10.41 10.47 10.47 10.62 10.62 10.67 10.67 10.73 10.73 10.76 10.76 10.84 10.84 10.86 10.86 10.88 10.88 10.96 10.96 11.20 11.20 11.30 11.30 11.36 11.36 11.61 11.61 11.74 11.74 11.76 11.76 11.88 11.88 11.89 11.89 12.00 12.00 12.00 12.00 12.81 12.81 12.90 12.90 12.92 12.92 12.96 12.96 13.08 13.08 13.24 13.24 13.33 13.33 13.37 13.37 13.58 13.58 13.62 13.62 13.72 13.72 13.76 13.76 13.79 13.79 13.91 13.91 14.06 14.06 14.07 14.07 14.25 14.25 14.38 14.38 14.57 14.57 14.58 14.58 14.79 14.79 14.81 14.81 15.01 15.01 15.01 15.01 15.17 15.17 15.18 15.18 15.28 15.28 15.55 15.55 16.18 16.18 16.23 16.23 16.40 16.40 16.41 16.41 16.46 16.46 16.51 16.51 16.63 16.63 16.65 16.65 16.75 16.75 16.92 16.92 17.12 17.12 17.20 17.20 17.45 17.45 17.72 17.72 17.82 17.82 17.85 17.85 17.98 17.98 18.10 18.10 18.27 18.27 18.46 18.46 18.47 18.47 18.67 18.67 18.70 18.70 18.84 18.84 18.91 18.91 18.97 18.97 19.06 19.06 19.56 19.56 19.79 19.79 19.80 19.80 19.88 19.88 19.89 19.89 19.99 19.99 20.10 20.10 20.12 20.12 20.31 20.31 20.99 20.99 21.05 21.05 21.08 21.08 21.11 21.11 21.42 21.42 21.86 21.86 21.99 21.99 22.04 22.04 22.24 22.24 22.37 22.37 22.59 22.59 22.94 22.94 23.22 23.22 23.68 23.68 23.86 23.86 23.94 23.94 23.99 23.99 24.09 24.09 24.39 24.39 24.50 24.50 24.52 24.52 24.53 24.53 24.58 24.58 24.91 24.91 25.04 25.04 25.08 25.08 25.28 25.28 25.30 25.30 25.78 25.78 25.87 25.87 26.11 26.11 26.15 26.15 26.31 26.31 26.41 26.41 26.44 26.44 26.46 26.46 26.51 26.51 26.58 26.58 26.64 26.64 26.78 26.78 26.85 26.85 26.89 26.89 26.90 26.90 26.96 26.96 27.09 27.09 27.15 27.15 27.39 27.39 27.70 27.70 27.74 27.74 28.04 28.04 28.49 28.49 28.56 28.56 28.59 28.59 28.72 28.72 28.86 28.86 28.88 28.88 29.04 29.04 29.58 29.58 29.58 29.58 29.59 29.59 29.67 29.67 29.89 29.89 29.92 29.92 29.95 29.95 30.06 30.06 30.12 30.12 30.14 30.14 30.15 30.15 30.21 30.21 30.52 30.52 30.73 30.73 30.84 30.84 30.89 30.89 30.93 30.93 31.00 31.00 31.12 31.12 31.19 31.19 31.32 31.32 31.37 31.37 31.38 31.38 31.53 31.53 31.56 31.56 31.76 31.76 32.98 32.98 33.00 33.00 33.02 33.02 33.60 33.60 33.64 33.64 33.87 33.87 34.27 34.27 34.42 34.42 34.87 34.87 34.89 34.89 35.09 35.09 35.38 35.38 35.40 35.40 35.72 35.72 35.76 35.76 35.76 35.76 36.01 36.01 36.04 36.04 36.04 36.04 36.19 36.19 36.35 36.35 36.81 36.81 36.95 36.95 37.03 37.03 37.30 37.30 37.34 37.34 38.00 38.00 38.92 38.92 39.09 39.09 39.26 39.26 39.97 39.97 42.12 42.12 42.20 42.20 42.86 42.86 44.62 44.62 48.16 48.16 48.18 48.18 49.15 49.15 52.51 52.51 53.17 53.17


Relaxation of 247.OO into 010.88



IRC (concatenated xyz)

Transition states of racemization of BINOL

The geometries of all the protonated forms and transition states were optimized by DFT (Priroda program, PBE functional, L1 basis (Λ01, cc-pVDZ analog)).


On figure(s) below click on the level title to download xyz file ==>
Click on energy level to view 3D structure in browser (run JSmol) ==>

Energy level titles:
first digit — charge of the structure
second letter "l" — structure from Chem. Eur. J. 2014, 20, 14816 (SI) optimized by DFT/PBE/L1
suffix "TS" — transition state of racemization

 0.00 0.00 29.59 29.59 34.16 34.16 35.11 35.11 36.11 36.11 40.20 40.20 40.56 40.56 43.15 43.15 45.49 45.49 47.15 47.15 47.29 47.29 57.47 57.47 9.00 9.00 17.47 17.47 13.44 13.44 14.86 14.86 0.00 0.00 23.28 23.28 23.87 23.87 25.20 25.20 30.42 30.42 34.77 34.77 36.96 36.96 37.95 37.95 38.77 38.77 39.86 39.86 0.00 0.00 3.15 3.15 3.58 3.58 4.61 4.61 8.25 8.25 10.20 10.20 10.37 10.37 15.92 15.92 15.97 15.97 20.33 20.33 38.27 38.27 45.81 45.81 46.79 46.79

Zero energy levels: 0-00 — ZZ-BINOL, 1-00 — 01.1, 2-00 — 001.88

IRC (concatenated xyz): 0-11_b-a, 1-11_d-a (not racemization), 2l-1 (not racemization), 2-88_a

Rotations in 1,1'-diprotonated BINOLs

The geometries of all the protonated forms and transition states were optimized by DFT (Priroda program, PBE functional, L1 basis (Λ01, cc-pVDZ analog)).


On figure(s) below click on the level title to download xyz file ==>
Click on energy level to view 3D structure in browser (run JSmol) ==>

Correspondence with previous diagram:
11R and 11S are 008.11, 9R is 011.11, 9S is 014.11

 0.00 0.00 0.01 0.01 0.74 0.74 1.46 1.46 7.01 7.01 7.98 7.98 9.70 9.70 9.70 9.70 9.74 9.74 10.95 10.95 14.54 14.54 16.31 16.31


IRC (concatenated xyz): 11R-11S, 9R-9S