Supporting Information
The Addition Reactions Between N-Heterocyclic Carbenes and Fullerenes (C60 and C70).
A Density Functional Study.
Ming-Chung Li1 and Ming-Der Su1,2*
1Department of Applied Chemistry, National Chiayi University, Chiayi 60004, Taiwan
2Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan
Email:
M062X/LANL2DZ+dp
Rea_IDipp
------
Atomic Coordinates (Angstroms)
Number X Y Z
------
7 0.000000 1.059840 -0.385712
6 0.000000 0.000000 0.484183
7 0.000000 -1.059840 -0.385712
6 0.000000 -0.679449 -1.723300
6 0.000000 0.679449 -1.723300
1 0.000000 -1.395178 -2.535004
1 0.000000 1.395178 -2.535004
6 0.000000 2.430564 0.036524
6 1.232364 3.078294 0.229535
6 1.209080 4.427201 0.605810
6 0.000000 5.098130 0.789160
6 -1.209080 4.427201 0.605810
6 -1.232364 3.078294 0.229535
6 0.000000 -2.430564 0.036524
6 1.232364 -3.078294 0.229535
6 1.209080 -4.427201 0.605810
6 0.000000 -5.098130 0.789160
6 -1.209080 -4.427201 0.605810
6 -1.232364 -3.078294 0.229535
1 2.148408 4.956880 0.760663
1 0.000000 6.147072 1.082786
1 -2.148408 4.956880 0.760663
1 2.148408 -4.956880 0.760663
1 0.000000 -6.147072 1.082786
1 -2.148408 -4.956880 0.760663
6 2.553488 2.361216 0.006614
6 3.538821 2.592302 1.157506
6 3.168836 2.790673 -1.333026
1 2.483485 2.589277 -2.166724
1 4.106948 2.251343 -1.520097
1 3.388073 3.867858 -1.329075
1 3.860071 3.641744 1.209816
1 4.438899 1.981358 1.009026
1 3.091183 2.321183 2.121579
6 2.553488 -2.361216 0.006614
6 3.538821 -2.592302 1.157506
6 3.168836 -2.790673 -1.333026
1 2.483485 -2.589277 -2.166724
1 4.106948 -2.251343 -1.520097
1 3.388073 -3.867858 -1.329075
1 3.860071 -3.641744 1.209816
1 4.438899 -1.981358 1.009026
1 3.091183 -2.321183 2.121579
6 -2.553488 -2.361216 0.006614
6 -3.538821 -2.592302 1.157506
6 -3.168836 -2.790673 -1.333026
1 -2.483485 -2.589277 -2.166724
1 -4.106948 -2.251343 -1.520097
1 -3.388073 -3.867858 -1.329075
1 -3.860071 -3.641744 1.209816
1 -4.438899 -1.981358 1.009026
1 -3.091183 -2.321183 2.121579
6 -2.553488 2.361216 0.006614
6 -3.538821 2.592302 1.157506
6 -3.168836 2.790673 -1.333026
1 -2.483485 2.589277 -2.166724
1 -4.106948 2.251343 -1.520097
1 -3.388073 3.867858 -1.329075
1 -3.860071 3.641744 1.209816
1 -4.438899 1.981358 1.009026
1 -3.091183 2.321183 2.121579
1 2.345973 1.285146 -0.041139
1 -2.345973 1.285146 -0.041139
1 2.345973 -1.285146 -0.041139
1 -2.345973 -1.285146 -0.041139
------
------
Rea_C60
------
Atomic Coordinates (Angstroms)
Number X Y Z
------
6 1.423016 -1.958614 2.591647
6 0.696899 -2.958028 1.828162
6 1.423016 -3.193958 0.592818
6 2.597899 -2.340356 0.592818
6 2.597899 -1.576871 1.828162
6 0.726117 -0.999415 3.324410
6 1.174882 0.381742 3.324410
6 0.000000 1.235344 3.324410
6 -1.174882 0.381742 3.324410
6 -0.726117 -0.999415 3.324410
6 3.028606 -0.251291 1.828162
6 3.477371 0.366381 0.592818
6 3.028606 1.747538 0.592818
6 2.302489 1.983468 1.828162
6 2.302489 0.748124 2.591647
6 3.028606 -1.747538 -0.592818
6 2.302489 -1.983468 -1.828162
6 2.302489 -0.748124 -2.591647
6 3.028606 0.251291 -1.828162
6 3.477371 -0.366381 -0.592818
6 0.726117 -3.420394 -0.592818
6 -0.726117 -3.420394 -0.592818
6 -1.174882 -2.802722 -1.828162
6 0.000000 -2.420980 -2.591647
6 1.174882 -2.802722 -1.828162
6 -0.696899 -2.958028 1.828162
6 -1.423016 -1.958614 2.591647
6 -2.597899 -1.576871 1.828162
6 -2.597899 -2.340356 0.592818
6 -1.423016 -3.193958 0.592818
6 -1.423016 1.958614 -2.591647
6 -2.597899 1.576871 -1.828162
6 -2.597899 2.340356 -0.592818
6 -1.423016 3.193958 -0.592818
6 -0.696899 2.958028 -1.828162
6 -0.726117 0.999415 -3.324410
6 0.726117 0.999415 -3.324410
6 1.174882 -0.381742 -3.324410
6 0.000000 -1.235344 -3.324410
6 -1.174882 -0.381742 -3.324410
6 0.696899 2.958028 -1.828162
6 1.423016 3.193958 -0.592818
6 2.597899 2.340356 -0.592818
6 2.597899 1.576871 -1.828162
6 1.423016 1.958614 -2.591647
6 -0.726117 3.420394 0.592818
6 -1.174882 2.802722 1.828162
6 0.000000 2.420980 2.591647
6 1.174882 2.802722 1.828162
6 0.726117 3.420394 0.592818
6 -3.028606 1.747538 0.592818
6 -3.477371 0.366381 0.592818
6 -3.028606 -0.251291 1.828162
6 -2.302489 0.748124 2.591647
6 -2.302489 1.983468 1.828162
6 -3.028606 0.251291 -1.828162
6 -2.302489 -0.748124 -2.591647
6 -2.302489 -1.983468 -1.828162
6 -3.028606 -1.747538 -0.592818
6 -3.477371 -0.366381 -0.592818
------
------
Precursor_IDipp-C60
------
Atomic Coordinates (Angstroms)
Number X Y Z
------
6 0.136683 -3.976677 0.000000
6 -0.007923 -0.908866 0.000000
6 0.792638 -0.611935 -1.177378
6 2.088661 -0.125676 -0.728133
6 2.088661 -0.125676 0.728133
6 0.792638 -0.611935 1.177378
6 -1.370960 -0.639058 0.000000
6 -1.993856 -0.053522 1.176272
6 -3.007169 0.889143 0.727555
6 -3.007169 0.889143 -0.727555
6 -1.993856 -0.053522 -1.176272
6 0.195460 -0.053528 2.304437
6 0.865366 1.015035 3.029215
6 -0.147137 1.958663 3.479532
6 -1.443512 1.473569 3.029095
6 -1.232793 0.228213 2.307963
6 2.731155 0.896277 1.422787
6 3.401542 1.964709 0.695655
6 3.188820 3.207515 1.422477
6 2.387743 2.906906 2.598878
6 2.105842 1.479374 2.599381
6 2.731155 0.896277 -1.422787
6 2.105842 1.479374 -2.599381
6 2.387743 2.906906 -2.598878
6 3.188820 3.207515 -1.422477
6 3.401542 1.964709 -0.695655
6 0.195460 -0.053528 -2.304437
6 -1.232793 0.228213 -2.307963
6 -1.443512 1.473569 -3.029095
6 -0.147137 1.958663 -3.479532
6 0.865366 1.015035 -3.029215
6 -0.018068 6.194276 0.000000
6 -0.819368 5.895075 -1.177980
6 -2.115541 5.410296 -0.727782
6 -2.115541 5.410296 0.727782
6 -0.819368 5.895075 1.177980
6 1.347660 5.923394 0.000000
6 1.973654 5.340299 1.177636
6 2.986057 4.396942 0.727536
6 2.986057 4.396942 -0.727536
6 1.973654 5.340299 -1.177636
6 -0.220243 5.335271 2.303989
6 -0.890195 4.268401 3.031650
6 0.123132 3.324448 3.479781
6 1.419758 3.809664 3.031127
6 1.207105 5.052044 2.303878
6 -2.755562 4.387186 1.423011
6 -3.426013 3.319707 0.695917
6 -3.212686 2.077105 1.423604
6 -2.413748 2.376565 2.601020
6 -2.129548 3.803584 2.599617
6 -2.755562 4.387186 -1.423011
6 -2.129548 3.803584 -2.599617
6 -2.413748 2.376565 -2.601020
6 -3.212686 2.077105 -1.423604
6 -3.426013 3.319707 -0.695917
6 -0.220243 5.335271 -2.303989
6 1.207105 5.052044 -2.303878
6 1.419758 3.809664 -3.031127
6 0.123132 3.324448 -3.479781
6 -0.890195 4.268401 -3.031650
7 0.165643 -4.839299 -1.061727
7 0.165643 -4.839299 1.061727
6 0.208141 -6.176535 0.678768
6 0.208141 -6.176535 -0.678768
1 0.230992 -6.989195 1.392974
1 0.230992 -6.989195 -1.392974
6 0.050868 -4.419985 -2.430208
6 1.220632 -4.172889 -3.168299
6 1.077869 -3.836045 -4.520676
6 -0.185403 -3.738573 -5.103511
6 -1.331818 -3.949799 -4.337758
6 -1.236948 -4.287055 -2.982013
6 0.050868 -4.419985 2.430208
6 1.220632 -4.172889 3.168299
6 1.077869 -3.836045 4.520676
6 -0.185403 -3.738573 5.103511
6 -1.331818 -3.949799 4.337758
6 -1.236948 -4.287055 2.982013
1 1.963324 -3.641632 -5.123561
1 -0.277608 -3.480196 -6.157393
1 -2.312864 -3.844190 -4.797979
1 1.963324 -3.641632 5.123561
1 -0.277608 -3.480196 6.157393
1 -2.312864 -3.844190 4.797979
6 2.593138 -4.296319 -2.527630
6 3.578550 -3.243881 -3.043949
6 3.156421 -5.708815 -2.744883
1 2.491262 -6.474083 -2.326554
1 4.139733 -5.812310 -2.267292
1 3.273486 -5.911102 -3.819015
1 3.852306 -3.428155 -4.091486
1 4.503679 -3.277553 -2.454997
1 3.159413 -2.232253 -2.970967
6 2.593138 -4.296319 2.527630
6 3.578550 -3.243881 3.043949
6 3.156421 -5.708815 2.744883
1 2.491262 -6.474083 2.326554
1 4.139733 -5.812310 2.267292
1 3.273486 -5.911102 3.819015
1 3.852306 -3.428155 4.091486
1 4.503679 -3.277553 2.454997
1 3.159413 -2.232253 2.970967
6 -2.484947 -4.524172 2.146903
6 -3.613478 -3.544576 2.482230
6 -2.971803 -5.972655 2.297400
1 -2.197763 -6.689019 1.996877
1 -3.858586 -6.147299 1.673196
1 -3.242052 -6.179667 3.342569
1 -4.038622 -3.739941 3.476027
1 -4.427179 -3.652765 1.753546
1 -3.262182 -2.505620 2.456783
6 -2.484947 -4.524172 -2.146903
6 -3.613478 -3.544576 -2.482230
6 -2.971803 -5.972655 -2.297400
1 -2.197763 -6.689019 -1.996877
1 -3.858586 -6.147299 -1.673196
1 -3.242052 -6.179667 -3.342569
1 -4.038622 -3.739941 -3.476027
1 -4.427179 -3.652765 -1.753546
1 -3.262182 -2.505620 -2.456783
1 2.465465 -4.137447 -1.448460
1 -2.209158 -4.361874 -1.097589
1 2.465465 -4.137447 1.448460
1 -2.209158 -4.361874 1.097589
------
------
TS_IDipp-C60(OP)
------
Atomic Coordinates (Angstroms)
Number X Y Z
------
7 4.212748 -1.104403 -0.009917
6 3.398491 0.001027 -0.010444
7 4.208972 1.108605 -0.012004
6 5.572474 0.693490 -0.031067
6 5.574599 -0.684517 -0.030416
1 6.387626 1.394022 -0.043844
1 6.391860 -1.381989 -0.041460
6 3.829196 -2.499612 0.008424
6 3.687930 -3.187722 -1.218502
6 3.401669 -4.558761 -1.175375
6 3.238140 -5.215910 0.044003
6 3.354147 -4.515923 1.245123
6 3.639901 -3.143676 1.252999
6 3.822205 2.504403 0.002921
6 3.675822 3.187299 -1.224716
6 3.390407 4.559267 -1.185690
6 3.234821 5.221131 0.032573
6 3.355935 4.524117 1.235510
6 3.638873 3.152350 1.246433
1 3.301580 -5.117634 -2.106478
1 3.013464 -6.283014 0.059703
1 3.217638 -5.044172 2.189654
1 3.286440 5.114394 -2.118426
1 3.012481 6.288032 0.044686
1 3.223613 5.055870 2.177865
6 3.858880 -2.485045 -2.554898
6 2.833296 -2.967984 -3.586681
6 5.292561 -2.695085 -3.058935
1 6.027063 -2.273733 -2.365648
1 5.440955 -2.213944 -4.031937
1 5.526201 -3.758434 -3.182779
1 3.014668 -4.000168 -3.906282
1 2.856308 -2.341626 -4.484941
1 1.811919 -2.923065 -3.183844
6 3.835895 2.477962 -2.559706
6 2.811445 2.966040 -3.589393
6 5.270407 2.673902 -3.069368
1 6.004533 2.257257 -2.373692
1 5.413465 2.180051 -4.037571
1 5.509685 3.734521 -3.206665
1 3.005440 3.991838 -3.919971
1 2.820358 2.331397 -4.482953
1 1.791972 2.937982 -3.181201
6 3.761717 2.400795 2.561692
6 2.820066 2.952521 3.638128
6 5.219200 2.445778 3.039759
1 5.893903 1.959351 2.328339
1 5.330246 1.934779 4.002538
1 5.567477 3.476589 3.175924
1 3.128804 3.940210 3.996398
1 2.789912 2.287043 4.508323
1 1.791642 3.042260 3.262229
6 3.759559 -2.388230 2.566052
6 2.821748 -2.939500 3.645075
6 5.218160 -2.426253 3.042488
1 5.891176 -1.943689 2.327086
1 5.329445 -1.907256 4.002096
1 5.567926 -3.454428 3.186050
1 3.135942 -3.923799 4.009507
1 2.787590 -2.269984 4.511736
1 1.794456 -3.036759 3.269969
1 3.686861 -1.384601 -2.418379
1 3.462566 -1.317126 2.395863
1 3.655558 1.380400 -2.418517
1 3.468390 1.328899 2.395304
6 1.399173 0.000809 0.038542
6 0.981689 -1.198772 -0.764277
6 0.487458 -0.755416 -2.063246
6 0.486681 0.714535 -2.078237
6 0.981412 1.184152 -0.787960
6 0.997487 0.014118 1.410237
6 0.375172 1.189044 1.988353
6 -0.591295 0.760554 3.018010
6 -0.590524 -0.701397 3.032968
6 0.375418 -1.149880 2.011856
6 0.400037 2.293125 -0.205365
6 -0.668492 3.025536 -0.901196
6 -1.628947 3.491954 0.102998
6 -1.150299 3.047667 1.421519
6 0.104402 2.324783 1.233416
6 -0.517579 1.397101 -2.746956
6 -1.585182 0.657541 -3.432786
6 -2.841921 1.393427 -3.243796
6 -2.550409 2.589907 -2.443685
6 -1.113803 2.588172 -2.138122
6 -0.516031 -1.451809 -2.719345
6 -1.110987 -2.631662 -2.086847
6 -2.548615 -2.639924 -2.391399
6 -2.841399 -1.459481 -3.215198
6 -1.584437 -0.726415 -3.419146
6 0.401496 -2.296727 -0.159688
6 0.106885 -2.300068 1.279266
6 -1.147029 -3.020139 1.481250
6 -1.625205 -3.490820 0.172457
6 -0.665221 -3.043270 -0.841462
6 -5.870407 -0.002705 -0.049141
6 -5.578623 -1.183148 0.774628
6 -5.104442 -0.716471 2.083319
6 -5.105248 0.752484 2.069332
6 -5.579895 1.193774 0.750941
6 -5.586231 -0.016034 -1.405298
6 -4.990189 1.165807 -2.040773
6 -4.027619 0.702375 -3.048919
6 -4.026814 -0.765580 -3.034935
6 -4.989887 -1.210120 -2.018119
6 -5.015884 2.307741 0.151811
6 -3.949165 3.051284 0.833597
6 -2.984148 3.491834 -0.181145
6 -3.458270 3.025148 -1.491835
6 -4.715292 2.294090 -1.285896
6 -4.098409 1.452831 2.713508
6 -3.029883 0.725420 3.409319
6 -1.773774 1.459465 3.200340
6 -2.065765 2.639937 2.383568
6 -3.499309 2.634667 2.076122
6 -4.096857 -1.402080 2.741144
6 -3.497514 -2.596164 2.128412
6 -2.062938 -2.594896 2.434903
6 -1.772220 -1.397445 3.227984
6 -3.029137 -0.660535 3.422967
6 -5.014376 -2.309115 0.196599
6 -4.712785 -2.323765 -1.241075
6 -3.455989 -3.057658 -1.432072
6 -2.981402 -3.496941 -0.111691
6 -3.946879 -3.037523 0.893384
------
------
TS_IDipp-C60(65)
------
Atomic Coordinates (Angstroms)
Number X Y Z
------
6 3.204186 0.006666 -0.060400
6 1.490854 -0.087063 0.865636
6 1.335358 0.036884 -1.117111
6 0.935952 -1.417975 1.024191
6 0.577667 -2.086362 -0.231378
6 0.785586 -1.243457 -1.426425
6 0.954271 1.040817 1.473061
6 0.418258 2.195607 0.746033
6 -0.674674 2.759994 1.565623
6 -0.872631 1.893465 2.727328
6 0.104109 0.801724 2.624119
6 0.763335 1.194088 -1.537491
6 -0.191773 1.134188 -2.649355
6 -1.161401 2.216253 -2.490677
6 -0.825588 2.931871 -1.250543
6 0.343316 2.296221 -0.634803
6 -0.114017 -1.330024 -2.491503
6 -1.217846 -2.291168 -2.473734
6 -2.386531 -1.670289 -3.108755
6 -2.007234 -0.309190 -3.505859
6 -0.601620 -0.105381 -3.129750
6 -0.462024 -3.012347 -0.237172
6 -1.247403 -3.264284 0.974045
6 -2.646833 -3.495000 0.589006
6 -2.728045 -3.402435 -0.870690
6 -1.379778 -3.118964 -1.379155
6 0.141973 -1.615903 2.152492
6 -0.254338 -0.489241 3.007094
6 -1.607379 -0.747471 3.496218
6 -2.043114 -2.052512 2.975236
6 -0.959634 -2.578690 2.139906
6 -5.783347 0.029091 -0.481361
6 -5.702764 -0.063522 0.982411
6 -5.270659 1.241605 1.496698
6 -5.081312 2.140972 0.350244
6 -5.403402 1.393105 -0.871458
6 -5.406772 -1.047348 -1.267252
6 -4.625631 -0.825250 -2.491495
6 -3.658076 -1.922695 -2.618031
6 -3.834103 -2.818121 -1.468739
6 -4.917744 -2.279919 -0.635258
6 -4.664027 1.602449 -2.025724
6 -3.562605 2.571391 -2.026102
6 -2.482956 2.029193 -2.859264
6 -2.918687 0.726152 -3.380222
6 -4.265910 0.460547 -2.860590
6 -4.039207 3.055027 0.349645
6 -3.122159 3.121599 1.495226
6 -1.769990 3.370201 0.974932
6 -1.849746 3.463706 -0.479866
6 -3.251736 3.271073 -0.871238
6 -4.408641 1.310038 2.579079
6 -3.923325 0.075434 3.214404
6 -2.528626 0.284988 3.613683
6 -2.145535 1.643108 3.214185
6 -3.307218 2.279980 2.578713
6 -5.245063 -1.227605 1.578952
6 -4.840787 -2.368536 0.745538
6 -3.672482 -2.996366 1.376493
6 -3.362880 -2.249549 2.604354
6 -4.333708 -1.157064 2.728119
7 3.902803 1.131107 -0.455644
7 3.944147 -1.092009 -0.466268
6 5.034424 -0.646514 -1.269375
6 5.011365 0.727515 -1.259663
1 5.708439 -1.338121 -1.751616
1 5.663481 1.447922 -1.730834
6 3.631995 2.512811 -0.126739
6 3.725245 2.908481 1.230295
6 3.479875 4.253347 1.541346
6 3.166703 5.175923 0.542909
6 3.110684 4.775910 -0.791496
6 3.341343 3.440679 -1.153297
6 3.718446 -2.480624 -0.134870
6 3.847025 -2.874058 1.220408
6 3.659847 -4.227528 1.533617
6 3.364662 -5.161182 0.540187
6 3.259395 -4.760079 -0.791034
6 3.428930 -3.415983 -1.153950
1 3.538563 4.584894 2.578405
1 2.970935 6.215235 0.806524
1 2.882445 5.510615 -1.564018
1 3.752029 -4.557082 2.569634
1 3.219478 -6.208134 0.805029
1 3.040274 -5.501539 -1.560164
6 4.145587 1.952429 2.334951
6 3.405342 2.223208 3.649770
6 5.666022 2.055292 2.519487
1 6.198370 1.800244 1.596613
1 6.014978 1.376206 3.304658
1 5.970445 3.069360 2.806005
1 3.683424 3.183399 4.097748
1 3.621506 1.444911 4.389735
1 2.317193 2.233208 3.491043
6 4.235852 -1.903911 2.325163
6 3.463410 -2.168899 3.622405
6 5.751704 -1.996521 2.548933
1 6.304588 -1.748705 1.637282
1 6.076677 -1.304457 3.333824
1 6.055254 -3.003834 2.855261
1 3.747995 -3.116128 4.092901
1 3.647187 -1.375946 4.356247
1 2.380314 -2.201661 3.442609
6 3.327566 -3.019314 -2.617149
6 2.190392 -3.756622 -3.333776
6 4.671550 -3.291692 -3.308704
1 5.488218 -2.726787 -2.842825
1 4.632481 -3.010978 -4.367279
1 4.940900 -4.353824 -3.264022
1 2.414585 -4.816202 -3.495806
1 1.993746 -3.312493 -4.316599
1 1.253974 -3.703624 -2.761770
6 3.313063 3.052223 -2.622688
6 2.188653 3.758579 -3.388301
6 4.677280 3.375115 -3.252662
1 5.491856 2.831574 -2.755814
1 4.693730 3.102715 -4.314007
1 4.909197 4.443958 -3.186780
1 2.377601 4.829817 -3.516279
1 2.065994 3.328709 -4.388518
1 1.226157 3.655245 -2.869012
1 3.901552 0.890217 2.050321
1 3.126048 1.949584 -2.713203
1 3.997327 -0.843811 2.026539
1 3.102791 -1.921923 -2.690620
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TS_IDipp-C60(66)
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Atomic Coordinates (Angstroms)
Number X Y Z
------
6 3.125230 0.002562 -0.032484
6 1.322496 0.000816 0.710895
6 1.360294 0.002095 -0.648522
6 0.826885 1.191236 1.470759
6 0.093814 0.733368 2.646877
6 0.094870 -0.737631 2.644628
6 0.828756 -1.191763 1.468345
6 0.809120 -1.166267 -1.369127
6 0.068811 -0.727714 -2.560052
6 0.067635 0.733286 -2.558797
6 0.807291 1.169731 -1.366721
6 0.386102 -2.301034 0.775891
6 -0.794469 -3.043173 1.236038
6 -1.532082 -3.494618 0.051762
6 -0.800834 -3.030749 -1.138237
6 0.384052 -2.302770 -0.695298
6 -1.022076 -1.428711 3.090394
6 -2.208662 -0.696855 3.553440
6 -3.399148 -1.431838 3.106192
6 -2.949917 -2.619304 2.369547
6 -1.480502 -2.614989 2.361677
6 -1.024365 1.422288 3.092893
6 -1.484782 2.609008 2.365596
6 -2.954073 2.610693 2.374459
6 -3.401438 1.421160 3.108691
6 -2.209769 0.687145 3.554681
6 0.382507 2.300964 0.780689
6 0.379461 2.304227 -0.690369
6 -0.806595 3.031247 -1.132053
6 -1.537679 3.493379 0.057983
6 -0.799388 3.040825 1.241104