# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S1-
A Theoretical Analysis of a Classic Example of
Supramolecular Catalysis
Peter Carlqvist and Feliu Maseras
Institute of Chemical Research of Catalonia (ICIQ), Avgda. Països Catalans 16,
43007 Tarragona, Catalonia, Spain; and
Unitat de Química Física, Edifici Cn, Universitat Autònoma de Barcelona, 08193
Bellaterra, Catalonia, Spain
E-mail: [email protected]
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S2Table S1. Absolute energies for the uncatalyzed reaction (values in a.u.), see text for the
structures.
ΔE
ΔZPE
-172.3487806143
0.08903458
1
-299.1038262243
0.11189162
2
-471.3670863975
0.20260905
3TS
-471.3537330490
0.20242897
4TS
-471.5029680651
0.20951572
5
-471.4674052724
0.20890696
6
H 2N
H2N
N N N
1a+2a
NH 2
N N
N
RCa
NH 2
H 2N
N N
N
NH 2
H 2N
N N
N
NH 2
3TSa
Scheme S1. The model reaction.
Table S2. Absolute energies and thermal corrections for the model reaction as depicted
in Scheme S1 (values in a.u.)[a].
ΔΔGg
ΔE
ΔZPE
ΔΔHg
-171.99217789
0.07412
0.08041
0.04576
1a
-298.75031925
0.09717
0.10546
0.06403
2a
-470.74646595
0.17243
0.18706
0.12828
RCa
-470.71531384
0.17265
0.18668
0.12963
3TSa
[a] ΔΔHg and ΔΔGg are calculated at 298.15 K and 1 atm.
Table S3. Absolute energies for the CB6-catalyzed reaction (values in a.u.) see text for
the structures.
ΔE
-3610.49754819216
CB6
-4082.12788486174
7
-4082.09351690946
8TS
-4082.23975826210
9
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S3Table S4. Cartesian coordinates for the uncatalyzed reaction.
1 [NH3CH2CCH]+
N
H
H
C
H
H
C
C
H
H
-1.496248
-1.357184
-2.470440
-0.489753
-0.715240
-0.715652
0.859269
1.981759
2.981524
-1.357113
-0.469045
-1.063924
-0.138593
0.698426
1.292753
1.293382
0.172167
-0.268540
-0.649786
-1.063429
-0.000157
0.827016
-0.000116
0.000225
0.890880
-0.889881
-0.000242
0.000083
0.000288
-0.827688
3.578048
2.745388
1.465627
2.806298
1.493797
1.493712
2.806213
0.234013
0.233090
0.233330
-0.887608
-2.018586
-3.102384
0.313399
-0.289702
0.535880
-0.895820
1.167264
1.166908
-0.896169
-0.370055
-1.017278
-1.017092
0.567870
0.043175
-0.295080
-0.000198
-0.000027
-0.000132
0.828556
0.889815
-0.890335
-0.828361
0.000124
-0.891066
0.891454
0.000197
0.000013
-0.000157
0.003306
0.005078
2.142122
2.642357
0.843912
3.338809
2.193780
1.966786
3.167591
0.489396
1.441297
-0.110741
-0.237439
-1.204331
0.367938
-0.525411
-1.014500
0.335759
-1.122465
1.153207
0.225679
-0.008586
-0.008204
0.000698
0.021803
0.089826
0.065582
-0.169965
-1.201684
0.106268
-0.369335
-0.607649
-1.286860
0.749007
0.985286
1.656402
0.338561
1.089445
0.133735
-0.498250
0.700048
0.534262
-0.000299
1.167277
1.512941
0.383270
-0.938239
-0.427839
2.970294
3.254800
3.383822
-2.281549
-2.768349
-2.247974
-3.050185
-2.600307
-3.098504
-4.492291
-4.999663
-5.017627
-4.546308
3.675156
3.256745
2 [NH3CH2CH2N3]+
H
N
C
H
H
H
H
C
H
H
N
N
N
3TS
N
N
C
C
N
H
C
H
H
C
H
H
C
H
H
N
H
H
H
N
H
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S4H
H
1.108753
1.366138
0.493844
1.700066
4.681821
3.568612
-0.027351
0.134874
2.045443
2.600496
0.704787
2.041766
0.120766
0.937671
-0.268918
-0.986195
-1.777106
-0.590955
-1.664842
-2.411855
-1.009492
-2.100930
3.691390
3.637105
3.775598
5.036051
5.835874
5.052078
5.181727
0.041578
0.024278
-0.039623
-0.005669
0.148532
-0.084990
-0.322504
-0.332322
-1.346036
0.650201
0.717841
1.649192
0.187685
0.840583
0.129997
-0.738762
0.067833
0.952938
-0.823951
0.175848
0.234295
1.010925
-0.639964
-0.004486
1.157875
1.383206
0.272141
-1.039892
2.456819
-2.302076
-3.030238
-2.212653
-2.750549
-2.000332
-2.944684
-4.038277
-4.314780
-4.829264
-3.933069
-0.689932
-1.329098
-1.317758
0.061252
-0.585043
0.662373
0.671205
-0.450355
-0.160549
1.158758
1.728793
0.690712
2.728093
1.689600
1.672177
2.699642
0.641631
1.670680
0.179130
-0.167776
-1.151861
0.349434
-0.398150
-0.947724
0.479142
-0.924188
0.754387
-0.212189
0.797807
0.963412
0.192144
0.255551
-0.028850
-0.280255
-0.131924
-0.548256
-0.082682
-1.099094
0.317989
-0.386120
-0.422061
-1.366733
0.728027
0.831983
1.689247
0.403460
1.148369
0.316105
-0.472712
0.742285
0.619868
0.466254
1.746945
-0.140027
1.124661
1.309073
0.079945
-0.788559
-0.231043
2.713367
3.118169
2.819654
-2.227669
-2.596195
-2.393685
-2.913155
-2.453752
-2.880427
-4.382236
-4.834380
-4.914126
-4.509854
3.584963
3.230554
4.573729
3.528469
4TS
N
N
C
C
N
H
C
H
H
C
H
H
N
H
H
H
C
H
H
N
H
H
H
5
N
N
C
C
N
H
C
H
H
C
H
H
C
H
H
N
H
H
H
N
H
H
H
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S56
N
N
C
C
N
H
C
H
H
C
H
H
N
H
H
H
C
H
H
N
H
H
H
-0.209304
0.153823
1.500356
2.003347
0.896474
1.993881
0.723682
1.324248
1.071405
-0.771679
-1.389918
-1.138329
-1.008416
-2.010570
-0.505385
-0.742702
3.397799
3.764342
3.513562
4.358041
5.325487
4.350843
4.116824
0.490071
0.645458
0.466130
0.180615
0.203620
0.557259
-0.015002
0.715689
-1.022689
0.144641
-0.582121
1.144478
-0.074776
0.035498
0.602585
-1.018630
-0.100842
0.633272
-1.100894
-0.040151
-0.230218
0.887521
-0.733639
-0.032089
1.194242
1.286502
0.032215
-0.776489
2.245248
-2.212689
-2.769847
-2.474758
-2.554134
-2.026866
-2.321090
-4.044300
-4.258012
-4.634005
-4.357591
-0.438252
-1.163810
-0.869767
0.737715
0.439659
1.185634
1.460300
Table S5. Cartesian coordinates for the model reaction.
1a [NH2H2CCH]
N
H
C
H
H
C
C
H
H
-1.533480
-1.391620
-0.514170
-0.690840
-0.688740
0.885290
2.020640
3.022160
-1.379310
-0.431240
-1.027230
0.629280
1.263840
1.267660
0.169430
-0.244940
-0.611030
-1.034660
-0.002050
0.813080
0.001080
0.878560
-0.874140
0.001130
-0.000390
-0.002120
-0.809440
-0.274930
0.501590
-0.880250
1.156330
1.157280
-0.884100
-0.335790
-0.984400
-0.984910
0.585400
0.046440
-0.335810
-0.000420
0.000030
0.818030
0.878870
-0.878130
-0.816170
-0.000090
-0.888420
0.887850
0.000130
0.000110
0.000110
2a [NH2H2CH2N3]
N
C
H
H
H
H
C
H
H
N
N
N
2.758140
1.522120
2.801560
1.520280
1.519910
2.798810
0.237510
0.209000
0.209160
-0.924770
-2.035010
-3.112410
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
-S6RCa
N
N
C
C
N
H
C
H
H
C
H
H
C
H
H
N
H
H
N
H
H
0.370180
-0.163900
2.986140
3.485080
1.070110
3.898590
2.340810
2.016740
3.085030
0.419490
1.237800
-0.148690
-0.481380
-1.281640
0.109480
-1.089180
-0.372910
-1.667960
1.171570
0.478310
1.460920
0.364340
0.508030
-0.155680
0.015850
0.251040
0.171780
-0.331250
-1.374230
-0.153740
-0.366560
-0.691220
-1.262110
0.622040
0.964160
1.511810
0.086380
-0.220350
-0.730720
0.529340
0.385730
1.512210
-0.303130
0.694110
2.329240
1.244600
-1.310950
0.278810
3.645050
3.762580
4.441570
-2.499720
-3.140670
-2.208080
-3.270090
-2.608110
-3.537920
-4.484190
-5.137620
-4.267460
3.894100
3.147630
3.817140
0.026890
-0.036120
2.216090
2.684010
0.839010
3.347600
2.157940
1.930420
3.154910
0.502160
1.460120
-0.089940
-0.229430
-1.152260
0.396180
-0.579600
0.255250
-1.179700
1.199930
0.270770
1.413030
-0.054370
-0.145800
-0.025750
0.011930
0.131550
0.091040
-0.101630
-1.134410
0.124360
-0.308820
-0.545950
-1.234180
0.776410
1.056240
1.674600
0.387210
0.139950
-0.436240
0.773310
0.596790
1.744120
-0.027550
1.132820
1.565810
0.428400
-0.965870
-0.403020
3.051270
3.340460
3.448450
-2.324110
-2.801980
-2.305830
-3.140210
-2.618690
-3.186120
-4.506360
-5.035660
-4.502040
3.736630
3.358680
3.510310
3TSa
N
N
C
C
N
H
C
H
H
C
H
H
C
H
H
N
H
H
N
H
H
Table S5. Cartesian coordinates for the CB6-catalyzed reaction.
CB6
O
C
N
N
0.213642
0.168175
1.254907
-0.983373
-0.205071
-0.069571
-0.055358
0.039854
-0.078192
1.125764
1.997793
1.902572
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
C
2.601155
-0.285095
1.518136
-S7C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
N
C
C
N
C
C
N
H
H
-0.710700
3.481160
3.819336
4.691214
3.460151
5.321435
4.165967
3.630145
4.020667
3.803673
4.823265
3.099033
5.266203
0.095601
0.092134
1.205924
-1.030727
2.540461
0.858478
3.322838
3.713642
4.631908
3.375158
5.262082
5.038333
3.588049
3.996773
3.803791
4.801632
-2.298339
4.558227
2.514452
3.068603
6.405228
5.120777
3.699139
2.991403
3.044219
2.427030
6.350203
5.025006
-2.153036
-2.889731
-1.198642
4.767785
6.365070
1.234046
6.120410
5.267771
1.766368
-2.367373
3.062098
-3.038801
1.456944
0.637407
-3.067570
-2.966966
-2.267555
-0.008650
1.167137
1.499959
2.536435
0.877699
3.337157
1.404865
4.348923
5.068382
6.440138
4.690004
7.171797
5.813903
2.694914
1.775542
1.083015
1.171454
1.410505
-0.072491
4.174178
3.422161
3.723771
2.077906
5.024152
2.561359
7.346577
6.984222
7.634405
5.875618
-0.057068
7.042804
-0.620320
-1.071323
3.371653
2.839086
8.046469
6.493016
0.490461
2.098124
4.889653
5.542196
-0.391729
-0.799678
-0.890277
0.609635
5.879393
-0.987851
2.396178
7.779775
7.609272
1.600864
8.873187
1.183258
8.800544
7.006952
2.342695
0.721016
2.269204
3.323094
-0.804074
0.311690
0.637203
1.505101
-0.389258
2.652179
-2.480924
-1.586617
-1.473851
-0.512539
-2.504720
0.283806
5.448745
4.657825
4.188210
4.096471
4.637392
3.389773
4.671493
3.804559
2.801065
3.661142
2.727818
2.041694
2.987202
1.904727
0.688162
1.653210
1.306600
-0.395268
0.481727
2.129290
-0.204505
-1.340910
-2.796263
-3.354195
4.969366
5.478993
2.639134
3.660255
0.276552
1.862705
3.767206
3.119198
0.258956
3.873195
2.162274
-0.802455
-2.153371
4.443951
0.608135
1.238308
-1.392813
-2.704890
3.417460
4.720185
5.302653
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
N
1.741385
8.768725
0.025743
-S8H
H
C
C
C
H
O
N
C
C
O
N
C
H
N
H
C
O
N
O
C
H
C
N
H
H
C
N
H
H
N
H
H
C
C
N
H
H
C
C
H
O
H
O
2.926826
3.648805
-3.251831
-3.808538
-0.112342
1.944755
0.624613
-0.470712
-3.275456
0.596208
-2.844326
-4.073827
-4.519991
-4.515693
-0.496843
-0.488684
-1.806444
-2.889401
-4.061618
0.560560
-4.534760
-5.618724
-1.841727
-2.656441
-2.295728
-1.696803
-4.563182
-3.895377
-5.621143
-4.308061
-2.688209
-1.750161
-2.322626
-3.420781
-2.993133
-3.942442
-5.648235
-4.356093
-4.294907
-3.048664
-4.022022
-2.614029
-5.376849
-2.694702
9.223813
9.606217
1.831458
1.751998
8.868892
9.674928
6.083431
7.706596
3.715320
8.887831
1.478786
2.925593
2.985348
1.003308
8.867371
9.780516
7.398013
4.426677
4.105387
9.035425
3.787799
2.924400
9.078540
6.734365
8.326687
6.714195
5.458323
5.084369
3.928999
3.274805
7.905946
9.406457
9.864756
7.402018
5.389706
6.266267
5.424675
5.949923
6.246471
7.284411
8.210360
4.640567
6.415407
7.605129
1.634201
0.035026
0.023828
2.324000
-1.448387
-1.851388
-3.490733
-2.232123
3.534630
0.810495
-1.062245
0.282738
1.657392
2.713744
-0.053183
-1.938270
-2.693066
4.437333
2.452101
2.013358
-0.782733
1.697182
0.436258
-1.728581
-3.022356
-3.538249
2.341736
-0.851740
-0.684982
-1.720459
0.444599
1.474627
-0.164669
-0.697027
-1.868833
1.315756
2.164279
3.295370
-0.087059
1.638268
-1.141760
-2.743472
-0.202871
2.752656
7
O
C
N
N
C
C
O
C
N
N
0.313200
0.251700
1.325900
-0.907600
2.682300
-0.646500
3.354300
3.771200
4.644500
3.516100
-0.445800
-0.360400
-0.393700
-0.265100
-0.588400
-0.226300
1.102200
1.335300
2.362800
0.601300
-0.152000
1.057700
1.942500
1.820200
1.474200
3.238400
-0.764800
0.352700
0.698000
1.502600
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
C
C
5.191400
4.302600
3.244300
1.044200
-0.306400
2.633800
-S9O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
C
C
N
N
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
N
C
C
N
C
C
N
H
H
3.330100
3.833400
3.732400
4.647400
3.151100
5.112200
0.391700
0.299800
1.334600
-0.859800
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-0.673700
-0.980100
-1.007300
0.232500
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-1.360100
2.141100
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6.750700
7.723200
1.587900
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0.751500
2.297900
-2.210200
-1.326400
-1.197300
-0.307600
-2.224400
0.560600
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4.441400
4.144400
3.897800
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3.329100
4.886800
3.956500
2.951300
3.755700
2.927100
2.066900
3.296900
2.219400
1.080800
1.933200
1.209000
-0.002900
5.516600
4.185700
3.134000
1.983400
0.432000
2.067400
-0.181600
-1.278000
-2.358300
-3.147800
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2.757000
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2.989800
0.528700
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-0.248300
3.989900
4.180000
-1.976600
4.247700
1.085400
1.098900
-1.111300
-2.563400
3.186300
4.593900
5.064300
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
N
H
1.513500
2.473500
8.566100
8.775600
0.319600
2.121000
-S10H
C
C
C
H
O
N
C
C
O
N
C
H
N
H
C
O
N
O
C
H
C
N
H
H
C
N
H
H
N
H
H
C
C
N
H
H
C
C
H
O
H
O
N
C
C
H
C
N
H
H
H
H
H
N
H
H
3.409300
-2.961600
-3.639600
-0.129400
1.976600
0.765200
-0.417200
-3.161200
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1.466900
-1.400500
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-1.828700
-1.894100
-2.576400
-2.588500
-3.637000
5.432600
4.751100
6.302300
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
H
-0.651000
5.057700
5.781100
-S11H
H
1.896500
1.333800
5.224800
4.247200
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0.246000
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1.202000
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-0.809300
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-1.248600
-2.364800
-3.118700
4.976600
5.421000
2.786400
3.869900
0.107700
8TS
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
C
C
N
N
H
H
H
H
H
H
H
H
H
H
H
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
H
H
H
-2.930600
-1.272500
4.609300
-1.136900
-1.224900
0.480100
1.661600
3.632100
3.223200
-S12H
H
H
H
H
H
N
C
C
N
C
C
N
H
H
N
H
H
C
C
C
H
O
N
C
C
O
N
C
H
N
H
C
O
N
O
C
H
C
N
H
H
C
N
H
H
N
H
H
C
C
N
H
H
C
C
6.421000
1.159200
6.023100
5.402200
-0.726000
-1.289000
1.873600
-2.582300
3.128500
-3.093500
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6.270600
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9.620400
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5.038200
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1.023100
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-0.551400
-1.737600
1.302300
1.851900
3.184400
-0.136300
1.783400
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
H
O
H
-3.919500
-2.031900
-5.297400
8.115000
4.635800
6.152100
-0.923000
-2.520400
-0.413300
-S13O
N
C
C
H
C
N
H
H
H
H
H
N
H
H
H
H
H
-2.915900
1.310900
-0.278900
0.191800
-0.836300
0.463700
0.602100
-0.364100
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1.853300
1.922500
4.153400
4.177000
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6.454300
7.215400
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4.623200
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2.948800
0.192700
1.082000
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3.720600
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3.198700
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-0.192200
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2.897800
3.611200
2.874200
2.094300
3.300700
2.180200
1.026200
1.866000
9
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
C
C
O
C
N
N
# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
C
C
C
C
-2.326400
4.665600
0.306400
-0.510400
-0.384100
7.019100
5.496300
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1.105400
-0.112500
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3.303600
-S14N
N
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
N
C
C
N
C
C
N
H
H
N
H
H
C
C
C
H
O
N
C
C
O
N
C
H
N
H
C
O
N
O
C
H
C
0.145800
1.336800
2.536600
3.060900
6.352200
5.035000
3.805000
3.119700
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2.432500
-1.004500
1.210200
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# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006
N
H
H
C
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-S15N
H
H
N
H
H
C
C
N
H
H
C
C
H
O
H
O
N
C
C
H
C
N
H
H
H
H
H
N
H
H
H
H
H
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