Support Information
Table S1. Calculated geometrical and topological as well as NBO parameters of the H-bonded dimers (∆
refers to the change in the indicated quantity as a result of the formation of the dimer.)
sym
metry
RX···Y
RH···Y
∆RXH
dC-O-C=O
ρH···Y
▽2ρH··Y
E(2)
EDT
∆νX-H
FA-1
C2h
2.696
1.699
0.02729
0.09482
0.0287
0.2179
26.13
51.34
-480
FA-2
C2h
3.201
2.218
0.02415
0.33946
0.0163
0.1091
24.97
78.84
-457
FA-3
C2h
3.433
2.074
0.00923
0.56266
0.0162
0.0775
6.92
20.76
-96
FFA-1
C2h
2.671
1.680
0.02850
0.09345
0.0298
0.2286
27.27
51.53
-499
FFA-2
C2h
3.127
2.136
0.03368
0.35535
0.0184
0.1306
32.74
102.23
-634
FFA-3
C2h
3.458
2.107
0.00606
0.56970
0.0153
0.0703
5.46
13.65
-55
BA-1
C2h
2.666
1.667
0.03103
0.09296
0.0308
0.2375
29.6
58.17
-565
BA-2
C2
3.197
2.23
0.02268
0.34926
0.0163
0.1082
24.29
74.48
-443
BA-3
Ci
3.415
2.063
0.00929
0.58438
0.0169
0.0786
6.71
20.16
-93
CA-1
C2h
2.633
1.631
0.03614
0.09127
0.03253
0.2626
34.06
63.96
-645
CA-2
C2h
3.138
2.161
0.02914
0.36635
0.0177
0.1234
29.59
87.59
-558
CA-3
Ci
3.343
1.988
0.0130
0.58615
0.0193
0.0968
9.25
26.03
-140
Table S2. Interaction energy Eint and the energy barrier EPT (kcal/mol) of proton transfer reaction (The right
is the ZPE corrected value a)
FA-1
FA-2
FA-3
FFA-1
FFA-2
FFA-3
10.21/9.36
6.28/5.02
16.01/14.76
12.14/11.85
6.41/5.51
12.56/5.92
12.99/10.70
7.26/3.00
7.34/1.34
19.84/17.27
BA-1
BA-2
BA-3
CA-1
CA-2
CA-3
Eint
16.37/15.38
9.98/9.42
5.81/4.96
18.40/17.11
12.64/12.26
7.27/6.27
EPT
6.48/1.99
13.48/6.54
12.62/9.58
5.67/1.58
11.72/5.30
9.69/3.28
Eint
EPT
15.07/13.26 a
7.33/3.22
a
The captions are listed in the following:
Fig. S1 The correlation between the interaction energy Eint and H-bond distance RH···Y for each form. (The
symbols ●, ○ and ♦ are for the form1, form 2 and form 3, respectively. Hereafter as so.)
Fig. S2 The correlation between the difference in length of C-O and C=O bond and H-bond length of form 1.
Fig. S3 The correlations between electron density transfer and (a) the changes in bond length of X-H bond
and (b) H-bond length. Also shown is the correlation between the stabilization energy and H-bond length (c).
Fig. S4 The energy barrier for proton transfer against H-bond distance.