suppmat1120. 27KB Jun 05 2011 09:30:55 PM
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table A.
The difference between the infrared OH-stretching frequencies for the non-bonded
and bonded O-H in various diols, calculated at the MPW1PW91/6-311+G(2d,p)
level. Frequencies have not been scaled (see text).
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
12EG(B)
2.338
3915
3857
58
12EG(D)
2.328
3881
3839
42
12PG(A)
2.244
3912
3843
69
12PG(B)
2.295
3916
3841
75
12PG(C)
2.273
3900
3849
52
12PG(D)
2.319
3896
3850
46
12PG(M)
2.248
3885
3828
57
12PG(N)
2.288
3895
3829
65
12PG(O)
2.251
3859
3829
30
12PG(P)
2.309
3880
3834
46
23BD(E)
2.263
3903
3835
68
23BD(F)
2.151
3904
3840
64
23BD(B)
2.248
3898
3843
55
23BD(X)
2.244
3906
3838
68
12BD(D)
2.306
3896
3852
44
12PD(D)
2.310
3896
3852
44
12HD(D)
2.309
3895
3852
43
Average (1,2)
2.278
3896
3842
54
±
0.046
14
9
12
13PG
2.015
3904
3812
92
1
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
2M13PG(A)
2.009
3904
3806
98
2M13PG(B)
1.976
3901
3804
97
13BD(A)
1.970
3904
3796
108
13BD(B)
2.014
3858
3790
68
24PD-meso
1.950
3888
3789
99
24PD-dl(A)
1.985
3887
3797
90
24PD-dl(B)
1.949
3887
3790
97
Average (1,3)
1.984
3892
3798
94
±
0.025
16
9
12
14BD(A)
1.849
3890
3707
183
25HD-dl(A)
1.821
3877
3692
185
25HD-meso(A)
1.859
3877
3702
175
Average (1,4)
1.843
3881
3700
181
±
0.020
7
8
5
15PD(A)
1.903
3906
3754
152
16HD(A)
1.982
3890
3725
164
12EG(B)s
1.890
3901
3693
208
12EG(B)as
1.853
3901
3640
261
12EG(D)s
1.890
3877
3688
190
12EG(D)as
1.870
3877
3635
242
Complexes
TIP3 1:1
2
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
12EG(C)s
2.051
3901
3825
76
12EG(C)s
2.051
3900
3810
91
Cooperative B/D
1.876
3889
3664
225
±
0.018
14
31
32
3
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table B.
The difference between the 1H nuclear shielding tensors (ppm downfield shift) for
the non-bonded and bonded O-H protons in various diols, calculated at the
MPW1PW91/6-311+G(2d,p) level. Non-bonded H2O gave a value of 31.71 ppm.
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
12EG(B)
2.338
31.72
30.35
1.37
12EG(D)
2.328
32.48
30.22
2.26
12PG(A)
2.244
31.65
29.66
2.00
12PG(B)
2.295
31.87
30.23
1.64
12PG(C)
2.273
31.52
30.36
1.16
12PG(D)
2.319
31.96
30.80
1.15
12PG(M)
2.248
32.19
29.56
2.63
12PG(N)
2.288
31.89
30.11
1.78
12PG(O)
2.251
32.80
30.19
2.61
12PG(P)
2.309
32.07
30.64
1.42
23BD(E)
2.263
32.07
30.74
1.33
23BD(F)
2.151
31.57
29.44
2.13
23BD(B)
2.248
31.83
30.22
1.61
23BD(X)
2.244
31.74
30.18
1.56
12BD(D)
2.306
30.98
30.78
0.19
12PD(D)
2.310
31.04
30.77
0.26
12HD(D)
2.309
31.02
30.77
0.24
Average (1,2)
2.278
31.79
30.30
1.49
±
0.046
0.49
0.44
0.75
13PG
2.015
31.65
29.51
2.14
DIOL
4
) ppm
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
2M13PG(A)
2.009
31.78
29.92
1.87
2M13PG(B)
1.976
31.64
29.12
2.52
13BD(A)
1.970
31.65
28.72
2.93
13BD(B)
2.014
32.25
28.95
3.30
24PD-meso
1.950
31.50
28.47
3.03
24PD-dl(A)
1.985
31.64
29.14
2.51
24PD-dl(B)
1.949
31.73
28.71
3.02
Average (1,3)
1.984
31.73
29.07
2.67
±
0.025
0.22
0.47
0.46
14BD(A)
1.849
31.33
28.00
3.33
25HD-dl(A)
1.821
31.36
27.28
4.08
25HD-meso(A)
1.859
31.40
28.19
3.21
Average (1,4)
1.843
31.36
27.82
3.54
±
0.020
0.04
0.48
0.47
15PD(A)
1.903
31.51
28.61
2.90
16HD(A)
1.982
31.52
28.75
2.77
12EG(B)
1.890
31.37
27.24
4.13
H2O
1.853
31.49
27.35
4.15
12EG(D)
1.890
31.75
27.17
4.57
H2O
1.870
31.42
27.30
4.12
) ppm
Complexes
TIP3 1:1
5
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
12PG tGga
1.880
31.34
26.86
4.48
H2O
1.846
31.47
27.36
4.10
12PG tGgb
1.880
31.27
27.21
4.06
H2O
1.840
31.49
27.31
4.17
23BD-dl-tGg
1.910
31.70
28.15
3.55
H2O
1.848
31.60
27.28
4.33
23BD-meso
1.887
31.57
27.47
4.10
H2O
1.830
31.52
27.19
4.33
Average (1:1)
1.869
31.50
27.32
4.17
±
0.025
0.14
0.30
0.25
6
) ppm
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table C.
The difference in the O-H bond length for the non-bonded and bonded O-H in
various diols, calculated at the MPW1PW91/6-311+G(2d,p) level.
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
12EG(B)
2.338
0.9581
0.9621
4.0
12EG(D)
2.328
0.9601
0.9630
2.9
12PG(A)
2.244
0.9580
0.9629
4.9
12PG(B)
2.295
0.9578
0.9630
5.2
12PG(C)
2.273
0.9588
0.9625
3.7
12PG(D)
2.319
0.9591
0.9624
3.3
12PG(M)
2.248
0.9600
0.9637
3.7
12PG(N)
2.288
0.9593
0.9638
4.5
12PG(O)
2.251
0.9617
0.9637
2.0
12PG(P)
2.309
0.9603
0.9634
3.1
23BD(E)
2.263
0.9588
0.9635
4.7
23BD(F)
2.151
0.9588
0.9632
4.4
23BD(B)
2.248
0.9591
0.9631
4.0
23BD(X)
2.244
0.9586
0.9633
4.7
12BD(D)
2.306
0.9590
0.9624
3.4
12PD(D)
2.310
0.9590
0.9624
3.4
12HD(D)
2.309
0.9590
0.9624
3.4
Average (1,2)
2.278
0.9591
0.9630
3.8
±
0.046
0.0010
0.0005
0.4
13PG
2.015
0.9588
0.9640
5.2
2M13PG(A)
2.009
0.9588
0.9643
5.5
2M13PG(B)
1.976
0.9589
0.9643
5.4
7
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
13BD(A)
1.970
0.9610
0.9670
6.0
13BD(B)
2.014
0.9618
0.9651
3.3
24PD-meso
1.950
0.9597
0.9651
5.4
24PD-dl(A)
1.985
0.9596
0.9647
5.1
24PD-dl(B)
1.949
0.9597
0.9649
5.2
Average (1,3)
1.984
0.9598
0.9649
5.1
±
0.025
0.0011
0.0009
0.6
14BD(A)
1.849
0.9596
0.9684
8.8
25HD-dl(A)
1.821
0.9605
0.9691
8.6
25HD-meso(A)
1.859
0.9605
0.9689
8.4
Average (1,4)
1.843
0.9602
0.9688
8.6
±
0.020
0.0005
0.0004
0.2
15PD(A)
1.903
0.9587
0.9665
7.8
16HD(A)
1.982
0.9597
0.9677
8.0
12EG(B)
1.890
0.9590
0.9704
11.4
12EG(B)h2o
1.853
0.9587
0.9722
13.5
12EG(D)
1.890
0.9607
0.9712
10.5
12EG(D)h2o
1.870
0.9590
0.9725
13.5
12EG(C)
2.051
0.9600
0.9635
3.5
12EG(C)h2o
2.051
0.9600
0.9635
3.5
Complexes
TIP3 1:1
8
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
Cooperative B/D
1.876
0.9594
0.9716
12.2
± (excl. symm.)
0.018
0.0009
0.0010
1.5
9
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table A.
The difference between the infrared OH-stretching frequencies for the non-bonded
and bonded O-H in various diols, calculated at the MPW1PW91/6-311+G(2d,p)
level. Frequencies have not been scaled (see text).
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
12EG(B)
2.338
3915
3857
58
12EG(D)
2.328
3881
3839
42
12PG(A)
2.244
3912
3843
69
12PG(B)
2.295
3916
3841
75
12PG(C)
2.273
3900
3849
52
12PG(D)
2.319
3896
3850
46
12PG(M)
2.248
3885
3828
57
12PG(N)
2.288
3895
3829
65
12PG(O)
2.251
3859
3829
30
12PG(P)
2.309
3880
3834
46
23BD(E)
2.263
3903
3835
68
23BD(F)
2.151
3904
3840
64
23BD(B)
2.248
3898
3843
55
23BD(X)
2.244
3906
3838
68
12BD(D)
2.306
3896
3852
44
12PD(D)
2.310
3896
3852
44
12HD(D)
2.309
3895
3852
43
Average (1,2)
2.278
3896
3842
54
±
0.046
14
9
12
13PG
2.015
3904
3812
92
1
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
2M13PG(A)
2.009
3904
3806
98
2M13PG(B)
1.976
3901
3804
97
13BD(A)
1.970
3904
3796
108
13BD(B)
2.014
3858
3790
68
24PD-meso
1.950
3888
3789
99
24PD-dl(A)
1.985
3887
3797
90
24PD-dl(B)
1.949
3887
3790
97
Average (1,3)
1.984
3892
3798
94
±
0.025
16
9
12
14BD(A)
1.849
3890
3707
183
25HD-dl(A)
1.821
3877
3692
185
25HD-meso(A)
1.859
3877
3702
175
Average (1,4)
1.843
3881
3700
181
±
0.020
7
8
5
15PD(A)
1.903
3906
3754
152
16HD(A)
1.982
3890
3725
164
12EG(B)s
1.890
3901
3693
208
12EG(B)as
1.853
3901
3640
261
12EG(D)s
1.890
3877
3688
190
12EG(D)as
1.870
3877
3635
242
Complexes
TIP3 1:1
2
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OH-stretch
(cm-1)
Bonded HD
OH-stretch
(cm-1)
red-shift
(cm-1)
12EG(C)s
2.051
3901
3825
76
12EG(C)s
2.051
3900
3810
91
Cooperative B/D
1.876
3889
3664
225
±
0.018
14
31
32
3
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table B.
The difference between the 1H nuclear shielding tensors (ppm downfield shift) for
the non-bonded and bonded O-H protons in various diols, calculated at the
MPW1PW91/6-311+G(2d,p) level. Non-bonded H2O gave a value of 31.71 ppm.
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
12EG(B)
2.338
31.72
30.35
1.37
12EG(D)
2.328
32.48
30.22
2.26
12PG(A)
2.244
31.65
29.66
2.00
12PG(B)
2.295
31.87
30.23
1.64
12PG(C)
2.273
31.52
30.36
1.16
12PG(D)
2.319
31.96
30.80
1.15
12PG(M)
2.248
32.19
29.56
2.63
12PG(N)
2.288
31.89
30.11
1.78
12PG(O)
2.251
32.80
30.19
2.61
12PG(P)
2.309
32.07
30.64
1.42
23BD(E)
2.263
32.07
30.74
1.33
23BD(F)
2.151
31.57
29.44
2.13
23BD(B)
2.248
31.83
30.22
1.61
23BD(X)
2.244
31.74
30.18
1.56
12BD(D)
2.306
30.98
30.78
0.19
12PD(D)
2.310
31.04
30.77
0.26
12HD(D)
2.309
31.02
30.77
0.24
Average (1,2)
2.278
31.79
30.30
1.49
±
0.046
0.49
0.44
0.75
13PG
2.015
31.65
29.51
2.14
DIOL
4
) ppm
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
2M13PG(A)
2.009
31.78
29.92
1.87
2M13PG(B)
1.976
31.64
29.12
2.52
13BD(A)
1.970
31.65
28.72
2.93
13BD(B)
2.014
32.25
28.95
3.30
24PD-meso
1.950
31.50
28.47
3.03
24PD-dl(A)
1.985
31.64
29.14
2.51
24PD-dl(B)
1.949
31.73
28.71
3.02
Average (1,3)
1.984
31.73
29.07
2.67
±
0.025
0.22
0.47
0.46
14BD(A)
1.849
31.33
28.00
3.33
25HD-dl(A)
1.821
31.36
27.28
4.08
25HD-meso(A)
1.859
31.40
28.19
3.21
Average (1,4)
1.843
31.36
27.82
3.54
±
0.020
0.04
0.48
0.47
15PD(A)
1.903
31.51
28.61
2.90
16HD(A)
1.982
31.52
28.75
2.77
12EG(B)
1.890
31.37
27.24
4.13
H2O
1.853
31.49
27.35
4.15
12EG(D)
1.890
31.75
27.17
4.57
H2O
1.870
31.42
27.30
4.12
) ppm
Complexes
TIP3 1:1
5
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
shielding tensor
(ppm)
Bonded HD
shielding tensor
(ppm)
downfield
shift
12PG tGga
1.880
31.34
26.86
4.48
H2O
1.846
31.47
27.36
4.10
12PG tGgb
1.880
31.27
27.21
4.06
H2O
1.840
31.49
27.31
4.17
23BD-dl-tGg
1.910
31.70
28.15
3.55
H2O
1.848
31.60
27.28
4.33
23BD-meso
1.887
31.57
27.47
4.10
H2O
1.830
31.52
27.19
4.33
Average (1:1)
1.869
31.50
27.32
4.17
±
0.025
0.14
0.30
0.25
6
) ppm
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
Table C.
The difference in the O-H bond length for the non-bonded and bonded O-H in
various diols, calculated at the MPW1PW91/6-311+G(2d,p) level.
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
12EG(B)
2.338
0.9581
0.9621
4.0
12EG(D)
2.328
0.9601
0.9630
2.9
12PG(A)
2.244
0.9580
0.9629
4.9
12PG(B)
2.295
0.9578
0.9630
5.2
12PG(C)
2.273
0.9588
0.9625
3.7
12PG(D)
2.319
0.9591
0.9624
3.3
12PG(M)
2.248
0.9600
0.9637
3.7
12PG(N)
2.288
0.9593
0.9638
4.5
12PG(O)
2.251
0.9617
0.9637
2.0
12PG(P)
2.309
0.9603
0.9634
3.1
23BD(E)
2.263
0.9588
0.9635
4.7
23BD(F)
2.151
0.9588
0.9632
4.4
23BD(B)
2.248
0.9591
0.9631
4.0
23BD(X)
2.244
0.9586
0.9633
4.7
12BD(D)
2.306
0.9590
0.9624
3.4
12PD(D)
2.310
0.9590
0.9624
3.4
12HD(D)
2.309
0.9590
0.9624
3.4
Average (1,2)
2.278
0.9591
0.9630
3.8
±
0.046
0.0010
0.0005
0.4
13PG
2.015
0.9588
0.9640
5.2
2M13PG(A)
2.009
0.9588
0.9643
5.5
2M13PG(B)
1.976
0.9589
0.9643
5.4
7
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
13BD(A)
1.970
0.9610
0.9670
6.0
13BD(B)
2.014
0.9618
0.9651
3.3
24PD-meso
1.950
0.9597
0.9651
5.4
24PD-dl(A)
1.985
0.9596
0.9647
5.1
24PD-dl(B)
1.949
0.9597
0.9649
5.2
Average (1,3)
1.984
0.9598
0.9649
5.1
±
0.025
0.0011
0.0009
0.6
14BD(A)
1.849
0.9596
0.9684
8.8
25HD-dl(A)
1.821
0.9605
0.9691
8.6
25HD-meso(A)
1.859
0.9605
0.9689
8.4
Average (1,4)
1.843
0.9602
0.9688
8.6
±
0.020
0.0005
0.0004
0.2
15PD(A)
1.903
0.9587
0.9665
7.8
16HD(A)
1.982
0.9597
0.9677
8.0
12EG(B)
1.890
0.9590
0.9704
11.4
12EG(B)h2o
1.853
0.9587
0.9722
13.5
12EG(D)
1.890
0.9607
0.9712
10.5
12EG(D)h2o
1.870
0.9590
0.9725
13.5
12EG(C)
2.051
0.9600
0.9635
3.5
12EG(C)h2o
2.051
0.9600
0.9635
3.5
Complexes
TIP3 1:1
8
Dr. R.A. Klein, Institute for Physiological Chemistry, University of Bonn, Germany
ref: Klein, R.A.; J. Comp, Chem. 2002, 23, 585-599. and Journal of Computational Chemistry (2002) MS #JCC 10448
DIOL
O-HD...OA-H
distance Å
Non-bonded
OA-H
Bonded O-HD
Difference
Å x 103
Cooperative B/D
1.876
0.9594
0.9716
12.2
± (excl. symm.)
0.018
0.0009
0.0010
1.5
9