The ω rotamers are estimated to be accurate to about +-5%, but the error in
θ is larger since 1) the relationship between 2JH6R,H6S
is less reliable and 2) the ω rotamer populations are required. An error of at
least +-10% is to be expected.
[1] R. Stenutz, I. Carmichael, G. Widmalm and A.S. Serianni,
Rotamer distribution
|
|
Coupling constants |
Rotamers |
| Compound |
δH6R-δH6S |
3JH5,H6R |
3JH5,H6S |
2JH6R,H6S |
Pgt |
Pgg |
Ptg |
θtrans |
| α-D-glucopyranose
| -0.09 | 5.80 | 1.00 | |
57 | 48 | -4 |
| β-D-glucopyranose
| -0.18 | 6.00 | 2.10 | |
54 | 39 | 7 |
| penta-O-acetyl-α-D-glucopyranose (CDCl3)
| 0.20 | 4.30 | 2.10 | |
35 | 57 | 8 |
| methyl α-D-glucopyranoside
| -0.13 | 5.40 | 2.30 | |
47 | 44 | 10 |
| methyl α-D-glucopyranoside (DMSO:D2O 19:1)
| -0.20 | 5.90 | 1.50 | |
56 | 43 | 1 |
| methyl α-D-glucopyranoside (DMSO)
| -0.16 | 6.10 | 1.00 | |
60 | 44 | -4 |
| methyl β-D-glucopyranoside
| -0.21 | 5.80 | 2.00 | -12.30 |
52 | 41 | 6 |
11 |
| methyl tetra-O-acetyl-α-D-glucopyranoside (C6D6)
| 0.17 | 4.60 | 2.40 | |
37 | 52 | 11 |
| methyl tetra-O-benzoyl-α-D-glucopyranoside (CDCl3)
| -0.12 | 5.10 | 2.90 | |
41 | 43 | 16 |
| methyl tetra-O-benzoyl-α-D-glucopyranoside (C6D6:CDCl3 1:1)
| -0.13 | 5.00 | 2.90 | |
40 | 44 | 16 |
| methyl per-O-methyl-β-D-glucopyranoside
| -0.07 | 4.90 | 2.10 | -10.80 |
42 | 50 | 8 |
60 |
| methyl 2,3,4,6-tetra-O-trimethylsilyl-α-D-glucopyranoside
| -0.09 | 5.20 | 2.20 | -11.40 |
45 | 47 | 9 |
40 |
| methyl 2,3,4,6-tetra-O-trimethylsilyl-β-D-glucopyranoside
| -0.12 | 5.10 | 1.90 | -11.40 |
45 | 50 | 5 |
41 |
| methyl 2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside
| -0.11 | 4.60 | 2.50 | -11.60 |
37 | 51 | 12 |
32 |
| methyl 2-O-benzyl-α-D-glucopyranoside (CDCl3)
| | 4.80 | 2.20 | -12.00 |
40 | 51 | 9 |
20 |
| methyl 2-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.08 | 4.70 | 3.30 | -11.80 |
35 | 45 | 20 |
22 |
| methyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside (CDCl3)
| 0.23 | 4.40 | 2.00 | -12.40 |
37 | 57 | 7 |
7 |
| methyl 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.18 | 4.80 | 2.40 | -12.00 |
40 | 50 | 11 |
19 |
| methyl 3-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.11 | 4.90 | 3.60 | -11.80 |
36 | 41 | 23 |
21 |
| methyl 2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranoside (CDCl3)
| 0.13 | 4.80 | 2.40 | -12.40 |
40 | 50 | 11 |
6 |
| methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.11 | 4.80 | 2.40 | -12.00 |
40 | 50 | 11 |
19 |
| methyl 2,3-di-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.11 | 5.00 | 3.60 | -11.80 |
37 | 40 | 23 |
21 |
| methyl 4,6-di-O-acetyl-2,3-di-O-benzyl-α-D-glucopyranoside (CDCl3)
| 0.21 | 5.00 | 2.20 | -12.30 |
43 | 49 | 9 |
10 |
| methyl 4,6-di-O-acetyl-2,3-di-O-benzyl-β-D-glucopyranoside (CDCl3)
| 0.16 | 4.90 | 2.40 | -12.20 |
41 | 49 | 11 |
12 |
| methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.16 | 4.60 | 2.70 | -12.00 |
36 | 50 | 14 |
18 |
| methyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (CDCl3)
| -0.11 | 4.20 | 1.60 | -12.40 |
36 | 61 | 2 |
9 |
| methyl 2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranoside (CDCl3)
| -0.35 | 3.60 | 2.00 | -10.00 |
28 | 65 | 7 |
87 |
| methyl 6-O-acetyl-β-D-glucopyranoside
| -0.13 | 4.90 | 2.30 | -12.30 |
41 | 49 | 10 |
9 |
| methyl 4-O-acetyl-β-D-glucopyranoside
| -0.20 | 5.90 | 2.20 | -12.50 |
53 | 39 | 8 |
3 |
| methyl 4-O-acetyl-β-D-glucopyranoside (CDCl3)
| -0.16 | 3.60 | 2.10 | -12.50 |
28 | 65 | 8 |
4 |
| methyl 4,6-di-O-acetyl-β-D-glucopyranoside
| 0.18 | 3.80 | 2.10 | -12.60 |
30 | 62 | 8 |
0 |
| methyl tetra-O-acetyl-β-D-glucopyranoside (CDCl3)
| 0.14 | 4.60 | 2.50 | -12.30 |
37 | 51 | 12 |
9 |
| methyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside (CDCl3)
| -0.09 | 4.60 | 2.00 | -12.00 |
39 | 54 | 7 |
21 |
| methyl 4-O-acetyl-6-O-trityl-β-D-glucopyranoside (CDCl3)
| -0.13 | 5.10 | 2.10 | -10.30 |
44 | 48 | 7 |
77 |
| methyl 4-O-acetyl-2,3-di-O-benzyl-6-O-trityl-β-D-glucopyranoside (CDCl3)
| -0.07 | 4.90 | 2.10 | -10.30 |
42 | 50 | 8 |
77 |
| methyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (CDCl3)
| -0.15 | 4.60 | 3.30 | -12.10 |
33 | 46 | 20 |
12 |
| methyl 2,3,4-tri-O-acetyl-6-O-benzoyl-β-D-glucopyranoside (CDCl3)
| -0.18 | 4.60 | 3.10 | -12.10 |
34 | 47 | 18 |
13 |
| methyl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranoside (CDCl3)
| 0.06 | 4.60 | 3.10 | -12.20 |
34 | 47 | 18 |
9 |
| methyl 2,3,4,6-tetra-O-o-nitrobenzoyl-β-D-glucopyranoside (CDCl3)
| -0.14 | 4.50 | 2.50 | -12.60 |
36 | 52 | 12 |
-1 |
| α-D-mannopyranose
| -0.13 | 5.80 | 2.00 | |
52 | 41 | 6 |
| β-D-mannopyranose
| -0.17 | 6.40 | 2.30 | |
58 | 33 | 9 |
| methyl α-D-mannopyranoside
| -0.15 | 6.00 | 2.00 | |
55 | 39 | 6 |
| methyl α-D-mannopyranoside
| -0.16 | 5.60 | 1.70 | -12.00 |
51 | 45 | 3 |
22 |
| methyl β-D-mannopyranoside
| -0.21 | 6.60 | 2.30 | |
60 | 31 | 9 |
| methyl tetra-O-acetyl-α-D-mannopyranoside (CDCl3)
| 0.16 | 5.40 | 2.20 | |
47 | 44 | 8 |
| methyl tetra-O-acetyl-α-D-mannopyranoside (CDCl3)
| 0.18 | 4.50 | 2.40 | -12.20 |
36 | 53 | 11 |
12 |
| methyl tetra-O-benzoyl-α-D-mannopyranoside (CDCl3)
| -0.21 | 4.60 | 2.70 | |
36 | 50 | 14 |
| methyl 2,4-di-O-benzyl-3,6-di-O-benzoyl-α-D-mannopyranoside (CDCl3)
| -0.03 | 4.40 | 2.00 | |
37 | 57 | 7 |
| methyl 2,4-di-O-benzyl-6-O-TBDMS-α-D-mannopyranoside (CDCl3)
| -0.01 | 5.40 | 1.00 | |
52 | 52 | -4 |
| methyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside (CDCl3)
| -0.05 | 5.40 | 2.00 | |
48 | 46 | 6 |
| methyl 2,3,4,6-tetra-O-trimethylsilyl-α-D-mannopyranoside
| -0.09 | 6.00 | 2.00 | -11.50 |
55 | 39 | 6 |
38 |
| methyl 2,3,4-tri-O-trimethylsilyl-α-D-mannopyranoside
| -0.08 | 5.50 | 2.90 | -11.50 |
45 | 39 | 16 |
34 |
| methyl α-D-galactopyranoside
| 0.00 | 7.80 | 6.00 | |
57 | -6 | 48 |
| methyl β-D-galactopyranoside
| 0.04 | 8.00 | 4.30 | -11.50 |
67 | 3 | 30 |
28 |
| penta-O-acetyl-α-D-galactopyranose (CDCl3)
| -0.05 | 6.40 | 6.40 | |
40 | 7 | 53 |
| methyl tetra-O-acetyl-β-D-galactopyranoside (CDCl3)
| -0.06 | 7.20 | 6.50 | -11.50 |
48 | -2 | 54 |
19 |
| methyl tetra-O-benzoyl-α-D-galactopyranoside (C6D6:CDCl3 1:1)
| 0.27 | 7.10 | 5.70 | |
51 | 4 | 45 |
| methyl 2,3,4-tri-O-methyl-α-D-galactopyranoside 6-(dimethylphosphate) (CCl4)
| -0.06 | 6.72 | 5.97 | |
45 | 6 | 48 |
| methyl 2,3,4-tri-O-methyl-α-D-galactopyranoside 6-(dimethylphosphate)
| -0.11 | 8.09 | 4.15 | |
68 | 3 | 29 |
| methyl 2,3,4-tri-O-methyl-β-D-galactopyranoside 6-(dimethylphosphate) (CCl4)
| -0.07 | 6.12 | 6.52 | |
36 | 9 | 54 |
| methyl 2,3,4-tri-O-methyl-β-D-galactopyranoside 6-(dimethylphosphate)
| -0.06 | 8.11 | 4.66 | |
67 | -0 | 34 |
| methyl α-D-galactopyranoside 6-(diphenylphosphate) (methanol-d4)
| 0.04 | 8.22 | 3.91 | -10.59 |
71 | 3 | 26 |
60 |
| methyl β-D-galactopyranoside 6-(diphenylphosphate) (methanol-d4)
| 0.05 | 7.83 | 4.13 | -10.72 |
66 | 6 | 28 |
55 |
| methyl 6-O-trityl-α-D-galactopyranoside (methanol-d4)
| 0.17 | 7.00 | 4.98 | -9.68 |
53 | 10 | 38 |
86 |
| methyl 6-O-trityl-α-D-galactopyranoside (acetone-d6)
| 0.12 | 6.86 | 5.13 | -9.33 |
51 | 10 | 39 |
97 |
| methyl 6-O-trityl-β-D-galactopyranoside (methanol-d4)
| 0.16 | 6.68 | 5.26 | -9.56 |
48 | 11 | 41 |
88 |
| methyl 6-O-trityl-β-D-galactopyranoside (acetone-d6)
| 0.15 | 6.70 | 5.35 | -9.26 |
48 | 10 | 42 |
98 |
| methyl 3,4-O-isopropylidene-α-D-galactopyranoside (CDCl3)
| 0.13 | 6.27 | 4.45 | -11.60 |
47 | 21 | 32 |
24 |
| methyl 3,4-O-isopropylidene-β-D-galactopyranoside (CDCl3)
| 0.17 | 6.68 | 3.90 | -11.40 |
54 | 20 | 26 |
33 |
| methyl 4-deoxy-4-fluoro-6-O-trityl-α-D-galactopyranoside
| -0.06 | 6.50 | 6.50 | -9.00 |
41 | 5 | 54 |
102 |
| methyl 2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-α-D-galactopyranoside
| -0.08 | 6.50 | 7.00 | -11.50 |
39 | 2 | 59 |
16 |
| methyl 6-O-pivaloyl-α-D-galactopyranoside
| 0.06 | 8.00 | 5.00 | -12.00 |
64 | -1 | 38 |
8 |
| glycerol
| | 6.50 | 4.30 | -11.70 |
50 | 19 | 31 |
21 |
| erythritol
| | 6.50 | 3.30 | -12.00 |
55 | 26 | 20 |
15 |
| threitol
| | 7.20 | 4.20 | -11.80 |
58 | 12 | 29 |
18 |
| arabinitol (1,2)
| | 7.60 | 5.00 | -11.60 |
59 | 3 | 38 |
22 |
| arabinitol (4,5)
| | 6.50 | 3.10 | -12.00 |
55 | 27 | 18 |
16 |
| ribitol
| | 7.30 | 3.00 | -12.00 |
65 | 19 | 17 |
17 |
| xylitol
| | 6.80 | 4.40 | -11.70 |
53 | 15 | 32 |
21 |
| methyl α-D-arabinofuranoside
| | 6.10 | 3.10 | -12.20 |
51 | 31 | 18 |
10 |
| methyl α-D-ribofuranoside
| | 4.80 | 3.10 | -12.40 |
37 | 45 | 18 |
3 |
| methyl α-D-xylofuranoside
| | 6.00 | 3.80 | -12.20 |
47 | 28 | 25 |
7 |
| methyl β-D-arabinofuranoside
| | 7.40 | 3.20 | -12.10 |
65 | 16 | 19 |
13 |
| methyl β-D-lyxofuranoside
| | 7.60 | 4.50 | -11.90 |
62 | 6 | 32 |
14 |
| methyl β-D-ribofuranoside
| | 6.60 | 3.10 | -12.20 |
57 | 26 | 18 |
10 |
| methyl β-D-xylofuranoside
| | 7.60 | 4.40 | -11.90 |
62 | 7 | 31 |
14 |
| β-D-Glc(1->3)-β-D-Glc (red)
| -0.16 | 5.00 | 2.00 | -12.00 |
44 | 50 | 6 |
21 |
| β-D-Glc(1->3)-β-D-Glc (nonred)
| -0.20 | 5.40 | 2.00 | -12.00 |
48 | 46 | 6 |
21 |
| β-D-Glc(1->3)-β-D-Glc (per OAc, red, CDCl3)
| 0.09 | 4.20 | 1.60 | -12.20 |
36 | 61 | 2 |
16 |
| β-D-Glc(1->3)-β-D-Glc (per OAc, nonred, CDCl3)
| 0.32 | 4.80 | 2.20 | -12.30 |
40 | 51 | 9 |
10 |
| α-D-Glc(1->4)-β-D-Glc (red)
| -0.15 | 5.00 | 2.00 | -12.00 |
44 | 50 | 6 |
21 |
| α-D-Glc(1->4)-β-D-Glc (nonred)
| -0.09 | 5.00 | 2.00 | -12.00 |
44 | 50 | 6 |
21 |
| α-D-Glc(1->4)-β-D-GlcOMe (red)
| -0.21 | 5.00 | 1.80 | -12.00 |
44 | 51 | 4 |
22 |
| α-D-Glc(1->4)-β-D-GlcOpClPh (per OAc, red, CDCl3)
| -0.22 | 5.10 | 2.00 | -12.00 |
45 | 49 | 6 |
21 |
| α-D-Glc(1->4)-β-D-GlcOpClPh (per OAc, nonred, CDCl3)
| 0.16 | 4.60 | 2.00 | -12.00 |
39 | 54 | 7 |
21 |
| β-D-Glc(1->4)-β-D-Glc (red)
| -0.15 | 5.60 | 2.00 | -12.00 |
50 | 44 | 6 |
21 |
| β-D-Glc(1->4)-β-D-Glc (nonred)
| -0.17 | 4.40 | 2.00 | -12.00 |
37 | 57 | 7 |
21 |
| β-D-Glc(1->4)-β-D-GlcOoClPh (per OAc, red, CDCl3)
| -0.42 | 5.60 | 1.50 | -12.00 |
52 | 47 | 1 |
23 |
| β-D-Glc(1->4)-β-D-GlcOoClPh (per OAc, nonred, CDCl3)
| 0.32 | 4.40 | 1.60 | -12.40 |
39 | 59 | 2 |
9 |
| α-D-Glc(1->6)-α-DGlc (red)
| 0.28 | 4.30 | 1.80 | |
37 | 59 | 4 |
| α-D-Glc(1->6)-α-DGlc (per OAc, red, CDCl3)
| 0.19 | 5.80 | 2.30 | |
51 | 39 | 9 |
| α-D-Glc(1->6)-α-DGlc (per OBz, red, CDCl3)
| 0.33 | 6.40 | 2.00 | |
59 | 35 | 6 |
| α-D-Glc(1->6)-β-D-Glc (red)
| 0.31 | 4.00 | 2.00 | -11.40 |
32 | 61 | 7 |
41 |
| α-D-Glc(1->6)-β-D-Glc (nonred)
| -0.08 | 4.80 | 2.00 | -12.00 |
41 | 52 | 6 |
21 |
| α-D-Glc(1->6)-β-D-Glc (per OAc, red, CDCl3)
| 0.06 | 4.10 | 2.90 | -11.30 |
30 | 54 | 16 |
40 |
| α-D-Glc(1->6)-β-D-Glc (per OAc, non, CDCl3)
| 0.19 | 4.50 | 2.10 | -12.40 |
38 | 55 | 8 |
7 |
| β-D-Glc(1->6)-α-D-Glc (red)
| -0.36 | 5.70 | 2.00 | |
51 | 42 | 6 |
| β-D-Glc(1->6)-α-D-Glc (per OAc, red, CDCl3)
| -0.26 | 7.30 | 1.80 | |
70 | 26 | 4 |
| β-D-Glc(1->6)-α-D-Glc (per OBz, red, CDCl3)
| -0.23 | 8.20 | 1.90 | |
79 | 16 | 5 |
| α-D-Glc(1->6)-β-D-GlcOMe (red)
| 0.22 | 4.30 | 1.80 | -11.00 |
37 | 59 | 4 |
55 |
| α-D-Man(1->6)-β-DManOMe (red)
| 0.14 | 5.60 | 1.90 | |
51 | 44 | 5 |
| β-D-Man(1->6)-β-DManOMe (red)
| -0.37 | 5.80 | 1.90 | |
53 | 42 | 5 |
| α-D-Gal(1->6)α-D-Gal (red)
| 0.17 | 7.40 | 4.90 | |
58 | 6 | 37 |
| α-D-Gal(1->6)α-D-Gal (per OAc, red, CDCl3)
| 0.31 | 6.20 | 6.20 | |
39 | 11 | 51 |
| α-D-Gal(1->6)α-D-Gal (per OBz, red, CDCl3)
| 0.25 | 7.70 | 3.90 | |
65 | 9 | 26 |
| β-D-Gal(1->6)α-D-Gal (red)
| -0.20 | 8.20 | 4.30 | |
69 | 1 | 30 |
| β-D-Gal(1->6)α-D-Gal (per OAc, red, CDCl3)
| -0.19 | 7.70 | 3.70 | |
66 | 10 | 24 |
| β-D-Gal(1->6)α-D-Gal (per OBz, red, CDCl3)
| -0.38 | 8.20 | 3.80 | |
71 | 4 | 25 |
| α-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe
| 0.06 | 5.20 | 1.80 | |
47 | 49 | 4 |
| α-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe
| 0.05 | 5.80 | 2.20 | -11.60 |
52 | 40 | 8 |
33 |
| α-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe (per OAc, CDCl3)
| 0.04 | 4.50 | 2.10 | |
38 | 55 | 8 |
| α-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe (per OBz, CDCl3)
| 0.00 | 5.60 | 1.80 | |
51 | 45 | 4 |
| β-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe
| -0.35 | 5.40 | 1.80 | |
49 | 47 | 4 |
| β-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe (per OAc, CDCl3)
| -0.25 | 6.20 | 2.00 | |
57 | 37 | 6 |
| β-D-Glc(1->6)[α-D-Glc(1->4)]β-D-GlcOMe (per OBz, CDCl3)
| -0.36 | 6.70 | 1.60 | |
64 | 34 | 2 |
| α-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe
| 0.11 | 4.80 | 1.80 | |
42 | 53 | 4 |
| α-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe (per OAc, CDCl3)
| 0.21 | 2.90 | 1.60 | |
22 | 75 | 3 |
| α-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe (per OBz, CDCl3)
| 0.08 | 3.50 | 1.50 | |
29 | 69 | 1 |
| β-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe
| -0.35 | 3.80 | 2.10 | |
30 | 62 | 8 |
| β-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe (per OAc, CDCl3)
| -0.23 | 5.70 | 1.80 | |
52 | 44 | 4 |
| β-D-Glc(1->6)[β-D-Glc(1->4)]β-D-GlcOMe (per OBz, CDCl3)
| -0.29 | 4.90 | 1.70 | |
44 | 53 | 3 |
| per-O-acetyl-α-Cyclodextrin (C6D6)
| -0.05 | 4.20 | 2.10 | -12.20 |
34 | 58 | 8 |
14 |
::
::
