Supporting Information
for
Stable α-heteroatom-free dialkylcarbenes: A DFT study
M.Z. Kassaee,[(] M.R. Momeni
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
XYZ Coordinates for all the structures studied in this work
B3LYP/6-311+G**
************************************************************************
1(S) (C2v)
HF = -272.6720454
1 6 0 2.422224 -0.733500 -0.182215
2 6 0 2.422249 0.733487 -0.182172
3 6 0 1.207655 0.000015 0.455704
4 6 0 0.000000 -0.000002 -0.313250
5 1 0 3.047985 -1.260725 0.527423
6 1 0 2.213278 1.253147 -1.106830
7 1 0 1.207133 0.000002 1.550662
8 6 0 -1.207655 -0.000019 0.455704
9 6 0 -2.422251 -0.733485 -0.182175
10 6 0 -2.422222 0.733503 -0.182211
11 1 0 2.213218 -1.253077 -1.106912
12 1 0 3.048055 1.260617 0.527498
13 1 0 -1.207133 -0.000009 1.550662
14 1 0 -3.048058 -1.260617 0.527492
15 1 0 -2.213282 -1.253141 -1.106836
16 1 0 -3.047982 1.260726 0.527428
17 1 0 -2.213214 1.253084 -1.106906
1(T) (C2)
HF = -272.647704
1 6 0 -2.360275 -0.544256 0.594689
2 6 0 -2.543111 0.627320 -0.320524
3 6 0 -1.261879 -0.185126 -0.426340
4 6 0 0.000000 0.365921 -0.000053
5 1 0 -2.931285 -1.446259 0.406579
6 1 0 -2.454256 1.619990 0.103706
7 1 0 -1.219501 -0.853971 -1.288756
8 6 0 1.261859 -0.185115 0.426308
9 6 0 2.543094 0.627331 0.320547
10 6 0 2.360313 -0.544264 -0.594652
11 1 0 -2.140621 -0.347464 1.636601
12 1 0 -3.253404 0.542257 -1.134275
13 1 0 1.219431 -0.853944 1.288735
14 1 0 3.253342 0.542288 1.134339
15 1 0 2.454260 1.619993 -0.103709
16 1 0 2.931315 -1.446261 -0.406491
17 1 0 2.140715 -0.347495 -1.636580
2(S) (C2)
HF = -350.1080087
1 6 0 1.137842 -0.068595 0.118499
2 6 0 0.000005 -0.960636 -0.000191
3 6 0 -1.137848 -0.068580 -0.118523
4 6 0 -0.720943 1.405301 -0.272894
5 6 0 0.720909 1.405278 0.272926
6 6 0 2.473851 -0.594910 0.637337
7 6 0 2.311921 -0.480273 -0.827398
8 6 0 -2.473891 -0.594865 -0.637275
9 6 0 -2.311847 -0.480365 0.827455
10 1 0 2.460960 -1.582409 1.080113
11 1 0 3.092166 0.139550 1.141675
12 1 0 2.170404 -1.379814 -1.410195
13 1 0 2.773441 0.351794 -1.346049
14 1 0 -2.461032 -1.582325 -1.080138
15 1 0 -3.092221 0.139644 -1.141521
16 1 0 -2.170254 -1.379952 1.410163
17 1 0 -2.773378 0.351636 1.346202
18 1 0 -1.377788 2.107011 0.248504
19 1 0 0.731585 1.676814 1.334416
20 1 0 -0.731627 1.676902 -1.334369
21 1 0 1.377755 2.107024 -0.248422
2(T) (C2)
HF = -350.075519
1 6 0 -0.416581 1.159754 0.108401
2 6 0 0.000000 0.000000 0.891287
3 6 0 0.416581 -1.159754 0.108401
4 6 0 0.000000 -0.774376 -1.326840
5 6 0 0.000000 0.774376 -1.326840
6 6 0 -1.712606 1.924821 0.387540
7 6 0 -0.378846 2.589749 0.601823
8 6 0 1.712606 -1.924821 0.387540
9 6 0 0.378846 -2.589749 0.601823
10 1 0 -2.285057 1.630502 1.258971
11 1 0 -2.305427 2.228650 -0.468614
12 1 0 -0.047651 2.759244 1.619680
13 1 0 -0.068579 3.350512 -0.106929
14 1 0 2.285057 -1.630502 1.258971
15 1 0 2.305427 -2.228650 -0.468614
16 1 0 0.047651 -2.759244 1.619680
17 1 0 0.068579 -3.350512 -0.106929
18 1 0 -1.010966 -1.148375 -1.518602
19 1 0 -0.665831 1.196568 -2.083911
20 1 0 0.665831 -1.196568 -2.083911
21 1 0 1.010966 1.148375 -1.518602
3(S) (C2v)
HF = -348.8807301
1 6 0 -0.669816 1.405464 0.000048
2 6 0 0.669816 1.405464 0.000079
3 6 0 1.133966 -0.015275 -0.000214
4 6 0 0.000000 -0.928177 -0.000413
5 6 0 -1.133966 -0.015275 -0.000047
6 6 0 2.427846 -0.471141 0.733475
7 6 0 2.428214 -0.470849 -0.733251
8 1 0 -1.316405 2.275577 0.000208
9 6 0 -2.428117 -0.470888 -0.733312
10 1 0 2.350253 -1.413608 1.257948
11 1 0 2.943613 0.323021 1.259655
12 1 0 2.350957 -1.413135 -1.258107
13 1 0 2.944319 0.323485 -1.258844
14 6 0 -2.427943 -0.471102 0.733415
15 1 0 1.316404 2.275577 0.000213
16 1 0 -2.350747 -1.413188 -1.258121
17 1 0 -2.944106 0.323438 -1.259029
18 1 0 -2.350464 -1.413555 1.257933
19 1 0 -2.943826 0.323069 1.259470
3(T) (C2v)
HF = -348.8455495
1 6 0 0.669841 1.331619 0.000119
2 6 0 -0.669843 1.331618 0.000016
3 6 0 -1.222155 -0.062795 -0.000017
4 6 0 0.000001 -0.871887 -0.000148
5 6 0 1.222156 -0.062792 -0.000036
6 6 0 -2.503017 -0.431416 -0.749486
7 6 0 -2.502922 -0.431541 0.749520
8 1 0 1.304397 2.210686 0.000198
9 6 0 2.502921 -0.431558 0.749492
10 1 0 -2.506838 -1.383488 -1.266480
11 1 0 -3.020201 0.368643 -1.267380
12 1 0 -2.506661 -1.383746 1.266277
13 1 0 -3.020079 0.368361 1.267684
14 6 0 2.503019 -0.431399 -0.749514
15 1 0 -1.304401 2.210683 0.000025
16 1 0 2.506640 -1.383769 1.266237
17 1 0 3.020082 0.368332 1.267670
18 1 0 2.506856 -1.383465 -1.266520
19 1 0 3.020206 0.368669 -1.267391
************************************************************************
MP2/6-31+G*
1(S) (C2v)
MP2 = -271.6366018
1 6 0 -2.408128 -0.733394 0.180219
2 6 0 -2.408155 0.733369 0.180251
3 6 0 -1.200248 0.000035 -0.457189
4 6 0 0.000000 -0.000001 0.326299
5 1 0 -3.037550 -1.260144 -0.529982
6 1 0 -2.196155 1.252554 1.107203
7 1 0 -1.195315 0.000046 -1.553021
8 6 0 1.200248 -0.000039 -0.457189
9 6 0 2.408157 -0.733367 0.180254
10 6 0 2.408126 0.733396 0.180216
11 1 0 -2.196098 -1.252619 1.107141
12 1 0 -3.037606 1.260122 -0.529922
13 1 0 1.195315 -0.000055 -1.553021
14 1 0 3.037610 -1.260121 -0.529917
15 1 0 2.196159 -1.252548 1.107208
16 1 0 3.037546 1.260145 -0.529987
17 1 0 2.196095 1.252625 1.107135
1(T) (C2)
MP2 = -271.6128511
1 6 0 -2.293593 -0.587804 0.580604
2 6 0 -2.550391 0.607684 -0.286190
3 6 0 -1.248115 -0.147921 -0.443597
4 6 0 0.000000 0.453943 -0.000020
5 1 0 -2.837493 -1.504954 0.374424
6 1 0 -2.491270 1.588774 0.174002
7 1 0 -1.182361 -0.780684 -1.331920
8 6 0 1.248105 -0.147922 0.443581
9 6 0 2.550384 0.607686 0.286207
10 6 0 2.293610 -0.587801 -0.580595
11 1 0 -2.058203 -0.416678 1.626191
12 1 0 -3.281433 0.519943 -1.083884
13 1 0 1.182330 -0.780687 1.331901
14 1 0 3.281407 0.519945 1.083919
15 1 0 2.491273 1.588776 -0.173984
16 1 0 2.837506 -1.504951 -0.374403
17 1 0 2.058244 -0.416674 -1.626188
2(S) (C2)
MP2 = -348.8075177
1 6 0 -1.122092 -0.074475 -0.161883
2 6 0 0.000013 -0.979166 -0.000378
3 6 0 1.122074 -0.074516 0.161826
4 6 0 0.692357 1.383081 0.331337
5 6 0 -0.692442 1.383141 -0.331258
6 6 0 -2.475497 -0.586365 -0.608149
7 6 0 -2.248415 -0.453738 0.850441
8 6 0 2.475428 -0.586455 0.608269
9 6 0 2.248571 -0.453527 -0.850334
10 1 0 -2.497850 -1.585687 -1.030623
11 1 0 -3.112193 0.149243 -1.093160
12 1 0 -2.101236 -1.352587 1.438449
13 1 0 -2.672022 0.396522 1.377753
14 1 0 2.497735 -1.585862 1.030545
15 1 0 3.112100 0.149048 1.093477
16 1 0 2.101529 -1.352265 -1.438547
17 1 0 2.672146 0.396881 -1.377434
18 1 0 1.391483 2.103978 -0.110666
19 1 0 -0.609222 1.614548 -1.402138
20 1 0 0.609122 1.614336 1.402246
21 1 0 -1.391570 2.103965 0.110865
2(T) (C2)
MP2 = -348.7749508
1 6 0 -0.474026 1.131444 0.113373
2 6 0 0.000000 0.000000 0.922399
3 6 0 0.474026 -1.131444 0.113373
4 6 0 0.000000 -0.770955 -1.298479
5 6 0 0.000000 0.770955 -1.298479
6 6 0 -1.826394 1.785749 0.345287
7 6 0 -0.554906 2.553941 0.599863
8 6 0 1.826394 -1.785749 0.345287
9 6 0 0.554906 -2.553941 0.599863
10 1 0 -2.402008 1.453389 1.204121
11 1 0 -2.413911 2.045773 -0.531965
12 1 0 -0.274733 2.750130 1.630810
13 1 0 -0.282464 3.336114 -0.104733
14 1 0 2.402008 -1.453389 1.204121
15 1 0 2.413911 -2.045773 -0.531965
16 1 0 0.274733 -2.750130 1.630810
17 1 0 0.282464 -3.336114 -0.104733
18 1 0 -1.022223 -1.143602 -1.447599
19 1 0 -0.639207 1.202604 -2.078092
20 1 0 0.639207 -1.202604 -2.078092
21 1 0 1.022223 1.143602 -1.447599
3(S) (C2v)
MP2 = -347.6145394
1 6 0 -0.676541 1.403265 0.000350
2 6 0 0.676541 1.403265 0.000282
3 6 0 1.124480 -0.014378 -0.000277
4 6 0 0.000000 -0.931269 -0.000631
5 6 0 -1.124480 -0.014378 -0.000075
6 6 0 2.415720 -0.470458 0.732640
7 6 0 2.416202 -0.469878 -0.732489
8 1 0 -1.329936 2.273748 0.000722
9 6 0 -2.416069 -0.469904 -0.732603
10 1 0 2.335938 -1.415895 1.256806
11 1 0 2.927865 0.329307 1.259095
12 1 0 2.336824 -1.414922 -1.257427
13 1 0 2.928783 0.330263 -1.257952
14 6 0 -2.415853 -0.470432 0.732527
15 1 0 1.329936 2.273748 0.000555
16 1 0 -2.336561 -1.414955 -1.257506
17 1 0 -2.928503 0.330241 -1.258202
18 1 0 -2.336202 -1.415862 1.256726
19 1 0 -2.928145 0.329330 1.258846
3(T) (C2v)
MP2 = -347.5788083
1 6 0 -0.675945 1.325975 -0.000116
2 6 0 0.675945 1.325975 -0.000081
3 6 0 1.222111 -0.063322 0.000015
4 6 0 0.000000 -0.884611 0.000113
5 6 0 -1.222112 -0.063320 0.000026
6 6 0 2.492279 -0.426605 0.750619
7 6 0 2.492242 -0.426745 -0.750596
8 1 0 -1.311773 2.209558 -0.000204
9 6 0 -2.492242 -0.426748 -0.750581
10 1 0 2.500191 -1.383501 1.264202
11 1 0 3.009919 0.377975 1.266219
12 1 0 2.500122 -1.383746 -1.263984
13 1 0 3.009862 0.377724 -1.266388
14 6 0 -2.492280 -0.426602 0.750634
15 1 0 1.311774 2.209557 -0.000143
16 1 0 -2.500110 -1.383748 -1.263971
17 1 0 -3.009864 0.377719 -1.266375
18 1 0 -2.500202 -1.383498 1.264216
19 1 0 -3.009920 0.377979 1.266230
************************************************************************
B3LYP/6-31+G*
1(S) (C2v)
HF = -272.6092639
1 6 0 -2.428617 -0.734997 0.177172
2 6 0 -2.428820 0.734812 0.177445
3 6 0 -1.208440 0.000154 -0.449450
4 6 0 0.000000 -0.000001 0.326582
5 1 0 -3.050868 -1.264844 -0.538817
6 1 0 -2.231601 1.256901 1.107404
7 1 0 -1.200194 0.000321 -1.547863
8 6 0 1.208440 -0.000161 -0.449450
9 6 0 2.428824 -0.734808 0.177447
10 6 0 2.428613 0.735001 0.177169
11 1 0 -2.230965 -1.257193 1.106975
12 1 0 -3.051088 1.264807 -0.538445
13 1 0 1.200194 -0.000335 -1.547863
14 1 0 3.051098 -1.264801 -0.538439
15 1 0 2.231606 -1.256896 1.107408
16 1 0 3.050858 1.264850 -0.538823
17 1 0 2.230960 1.257198 1.106971
1(T) (C2)
HF = -272.5848552
1 6 0 -2.365263 -0.544791 0.595929
2 6 0 -2.548858 0.627282 -0.321549
3 6 0 -1.265481 -0.185489 -0.425730
4 6 0 0.000000 0.369040 -0.000074
5 1 0 -2.937540 -1.450656 0.409286
6 1 0 -2.463296 1.624252 0.102405
7 1 0 -1.222357 -0.857406 -1.290019
8 6 0 1.265452 -0.185478 0.425684
9 6 0 2.548833 0.627297 0.321586
10 6 0 2.365318 -0.544798 -0.595881
11 1 0 -2.148294 -0.347625 1.642048
12 1 0 -3.261326 0.542223 -1.138206
13 1 0 1.222257 -0.857377 1.289983
14 1 0 3.261238 0.542260 1.138299
15 1 0 2.463299 1.624257 -0.102397
16 1 0 2.937586 -1.450656 -0.409173
17 1 0 2.148431 -0.347655 -1.642020
1H2 (C2)
HF = -273.917241
1 6 0 -2.594674 0.428998 0.345198
2 6 0 -2.175811 -0.647542 -0.632942
3 6 0 -1.200502 -0.147849 0.408997
4 6 0 0.000000 0.687994 0.000000
5 1 0 -3.302852 0.168215 1.127990
6 1 0 -2.009038 -0.354102 -1.667744
7 1 0 -1.006948 -0.829520 1.237084
8 6 0 1.200496 -0.147863 -0.408984
9 6 0 2.175822 -0.647520 0.632956
10 6 0 2.594668 0.428989 -0.345224
11 1 0 -2.707512 1.442809 -0.033900
12 1 0 -2.598875 -1.642591 -0.518204
13 1 0 1.006930 -0.829563 -1.237044
14 1 0 2.598888 -1.642572 0.518245
15 1 0 2.009065 -0.354044 1.667751
16 1 0 3.302836 0.168183 -1.128016
17 1 0 2.707511 1.442812 0.033843
18 1 0 -0.287778 1.349569 -0.831483
19 1 0 0.287783 1.349576 0.831474
2(S) (C2)
HF = -350.0300397
1 6 0 1.140279 -0.070706 0.111759
2 6 0 0.000014 -0.966151 -0.000135
3 6 0 -1.140273 -0.070700 -0.111682
4 6 0 -0.724181 1.405511 -0.266994
5 6 0 0.724158 1.405512 0.266951
6 6 0 2.476119 -0.593157 0.642276
7 6 0 2.323052 -0.479145 -0.824991
8 6 0 -2.476080 -0.593205 -0.642221
9 6 0 -2.323083 -0.479122 0.825038
10 1 0 2.465740 -1.583352 1.087590
11 1 0 3.089833 0.144910 1.154255
12 1 0 2.191460 -1.382291 -1.411105
13 1 0 2.789058 0.354447 -1.344349
14 1 0 -2.465705 -1.583440 -1.087442
15 1 0 -3.089649 0.144868 -1.154361
16 1 0 -2.191433 -1.382206 1.411235
17 1 0 -2.789280 0.354433 1.344287
18 1 0 -1.378720 2.107638 0.263687
19 1 0 0.744975 1.682200 1.330189
20 1 0 -0.745014 1.682156 -1.330244
21 1 0 1.378707 2.107620 -0.263741
2(T) (C2)
HF = -349.997794
1 6 0 0.000000 1.234981 0.109017
2 6 0 0.000000 0.000000 0.893618
3 6 0 0.000000 -1.234981 0.109017
4 6 0 -0.262463 -0.729387 -1.327396
5 6 0 0.262463 0.729387 -1.327396
6 6 0 -0.959485 2.396149 0.387859
7 6 0 0.522348 2.569194 0.601155
8 6 0 0.959485 -2.396149 0.387859
9 6 0 -0.522348 -2.569194 0.601155
10 1 0 -1.600665 2.316175 1.261963
11 1 0 -1.417876 2.884444 -0.470135
12 1 0 0.894336 2.619431 1.621678
13 1 0 1.075345 3.180906 -0.109619
14 1 0 1.600665 -2.316175 1.261963
15 1 0 1.417876 -2.884444 -0.470135
16 1 0 -0.894336 -2.619431 1.621678
17 1 0 -1.075345 -3.180906 -0.109619
18 1 0 -1.343220 -0.738826 -1.520699
19 1 0 -0.221862 1.353193 -2.087851
20 1 0 0.221862 -1.353193 -2.087851
21 1 0 1.343220 0.738826 -1.520699
2H2 (C1)
HF = -351.3359547
1 6 0 -1.223464 -0.051447 -0.160808
2 6 0 0.004391 -0.915193 -0.452367
3 6 0 1.200020 -0.045059 -0.010452
4 6 0 0.658274 1.359632 0.318013
5 6 0 -0.747140 1.389375 -0.316420
6 6 0 -2.620676 -0.491005 -0.495678
7 6 0 -2.177960 -0.418244 0.954154
8 6 0 2.344058 -0.626491 0.784233
9 6 0 2.551729 -0.227220 -0.660774
10 1 0 -2.759866 -1.475708 -0.938080
11 1 0 -3.325915 0.257647 -0.851922
12 1 0 -2.016180 -1.353491 1.486348
13 1 0 -2.583551 0.381035 1.571733
14 1 0 2.319548 -1.687844 1.024597
15 1 0 2.797131 -0.006549 1.556219
16 1 0 2.661677 -1.019961 -1.398984
17 1 0 3.150099 0.658432 -0.867098
18 1 0 1.310301 2.159375 -0.053358
19 1 0 -0.677675 1.645613 -1.384113
20 1 0 0.573169 1.484191 1.406379
21 1 0 -1.418144 2.117610 0.154338
22 1 0 -0.030637 -1.881854 0.065358
23 1 0 0.064650 -1.124582 -1.530825
2NH2(S) (C2)
HF = -571.4286067
1 6 0 -1.120798 0.527438 0.169948
2 6 0 -0.000006 -0.343168 0.000385
3 6 0 1.121047 0.527220 -0.169889
4 6 0 0.722316 2.009104 -0.277921
5 6 0 -0.722117 2.009403 0.276467
6 6 0 -2.504959 0.161445 -0.686679
7 6 0 -2.440142 0.009573 0.777232
8 6 0 2.505023 0.162132 0.686309
9 6 0 2.439976 0.008698 -0.777494
10 1 0 -2.892444 1.097833 -1.086013
11 1 0 -2.975154 0.745637 1.376783
12 1 0 2.893191 1.098745 1.084490
13 1 0 2.974747 0.744182 -1.377970
14 1 0 0.738453 2.329836 -1.330276