Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Supplementary Material (ESI) for Chemical Communications
First linear alignment of five C–Se---O---Se–C atoms in anthraquinone and
9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions
Warô Nakanishi,* Satoko Hayashi and Norio Itoh
Department of Material Science and Chemistry, Faculty of Systems Engineering, Wakayama
University, 930 Sakaedani, Wakayama 640-8510, Japan. Fax: +81 73 457 8253; Tel: +81 73 457
8252; E-mail: nakanisi@sys.wakayama-u.ac.jp
The results of ab initio MO calculations performed on 1–3 are shown in Table 1, together with
the optimized conformers. The B3LYP/Gen method is employed: 6-311+G(d) basis sets for Se
and O and 6-31G(d) basis sets for C and H.[S1] The optimized conformers are given below.
Table 1 Energies of the Conformers in 1, 2 and 3
1
2
3
---------------------------------------------------------------------------------E/au (E/kJ mol–1) E/au (E/kJ mol–1) E/au (E/kJ mol–1)
conformation
AA-trans
AA-cis
AB
BB
–5953.9764
(0.0)
–5919.2120 (0.0)
–5953.9884 (–31.5) –5919.2213 (–24.4)
–5953.9995 (–60.6) –5919.2259 (–36.5)
–5804.6946
–5804.6938
–5804.6944
–5804.6932
(0.0)
(2.1)
(0.5)
(3.7)
Me
Se
O
Se
1 (AA-trans )
Se
Se
O
2 (AA-cis)
Se
Se
Se
3 (AA-trans )
3 (AA-cis )
Me
Se
O
Se
Se
O
1 (AB)
Se
Se
2 (AB)
Se
3 (AB)
Me
Se
O
Se
1 (BB)
Se
O
Se
2 (BB)
– S1 –
Se
Se
Se
3 (BB)
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
The optimized structures for 1, 2 and 3, are as follows:
1: Optimized conformers, 1 (AA-trans), 1 (AB) and 1 (BB).
Conformer: 1 (AA-trans) (type A-type A pairing for the PhSe moieties)
Symmetry: C1
E = –5953.9764 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
34
6
6
6
6
6
6
6
8
6
6
6
6
6
6
34
6
6
6
6
6
6
1
1
1
1
1
1
1
1
6
8
1
1
1
6
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
-2.653348
-2.293992
-3.281369
-3.192577
-2.118345
-1.117345
-1.165107
0.000280
-0.000180
1.166223
1.119259
2.120706
3.194624
3.282665
2.294808
2.653168
2.672301
1.951478
2.030155
2.802554
3.510393
3.459540
4.030960
4.117165
2.853094
1.471657
1.317072
4.143948
3.975799
2.031013
0.001181
0.001567
-2.028047
-3.973404
-4.142879
-2.673450
-1.953389
-2.032776
-2.805122
-3.512199
-3.460639
-4.031470
-4.118926
-2.856212
-1.474864
-1.319009
– S2 –
-1.094290
0.816327
1.583960
2.973119
3.622973
2.879322
1.466736
0.707200
-0.510735
1.466105
2.878719
3.621830
2.971395
1.582189
0.815090
-1.095709
-1.579684
-2.704251
-3.127217
-2.415805
-1.284595
-0.872348
-0.007928
-0.729315
-2.740365
-4.003592
-3.229626
1.073410
3.537184
4.702426
3.641074
4.865323
4.703519
3.539331
1.075643
-1.578201
-2.703146
-3.126030
-2.414173
-1.282593
-0.870412
-0.005690
-0.726962
-2.738673
-4.002696
-3.228882
Z
1.208680
1.132001
1.768129
1.846934
1.254445
0.621381
0.567687
-0.000210
-0.000485
-0.567808
-0.621448
-1.254440
-1.846863
-1.768042
-1.132018
-1.208626
0.665715
1.080014
2.409203
3.329004
2.914231
1.581751
1.256505
3.624790
4.364705
2.727163
0.373449
-2.189968
-2.346553
-1.265216
-0.000002
0.000099
1.265250
2.346690
2.190148
-0.665669
-1.080262
-2.409435
-3.328936
-2.913872
-1.581398
-1.255921
-3.624194
-4.364628
-2.727624
-0.373943
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 1 (AB) (type A-type B pairing for the PhSe moieties)
Symmetry: C1
E = –5953.9884 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
1
6
1
6
6
6
6
6
6
1
8
34
6
8
6
6
34
6
6
1
1
6
1
6
6
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
3.318136
2.496404
0.950154
1.186017
1.735088
0.145661
2.766733
0.398421
-1.242498
3.793716
-0.464631
2.143315
-2.353141
-1.472420
-3.634415
-2.121967
-3.223633
-0.717975
-4.710246
-3.756062
-5.708552
-4.506967
-5.351420
-3.234042
4.086661
-2.550450
6.876257
4.686086
4.891022
6.282372
6.077744
4.064001
4.428291
6.900794
6.536620
7.958717
-1.660533
-1.477291
-3.180277
-2.723367
-1.044438
-0.970990
-4.024088
-3.209695
-0.212791
-1.314780
– S3 –
3.919751
3.279582
4.751339
3.749762
1.127572
2.914780
1.988960
1.599688
3.444221
1.645438
-0.426320
-0.667466
2.564276
4.575344
3.122695
1.229751
-1.381609
0.716165
2.366989
4.148878
2.794168
1.043039
0.439808
0.453763
-0.631422
-2.356341
-0.772692
-1.062871
-0.280628
-0.349517
-1.129591
-1.344719
0.044384
-0.075755
-1.463872
-0.828432
-3.910251
-3.236099
-2.252557
-3.019978
-4.021391
-3.286458
-1.581346
-2.932675
-4.706820
-4.514758
Z
1.251146
0.941857
1.332546
0.990773
0.089118
0.586500
0.496438
0.133185
0.636924
0.466531
-0.648660
-0.516987
0.163562
1.044600
0.134336
-0.250234
-1.319871
-0.277762
-0.313041
0.463193
-0.345520
-0.700098
-1.018568
-0.668723
-0.329264
0.212980
-0.127151
0.862123
-1.422177
-1.318410
0.961923
1.707046
-2.349801
-2.169194
1.888711
-0.049136
2.357105
0.037647
1.458597
2.531325
1.109182
-0.920707
1.589127
3.499459
0.969265
3.191241
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 1 (BB) (type B-type B pairing for the PhSe moieties)
Symmetry: C2
E = –5953.9995 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
1
6
1
6
6
6
6
6
6
1
8
34
6
8
6
6
34
6
6
1
1
6
1
6
6
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0.000534
0.000403
0.000311
0.000285
0.000165
0.000138
0.000343
0.000101
0.000000
0.000420
0.000000
0.000000
-0.000138
0.000000
-0.000285
-0.000101
0.000000
0.000000
-0.000403
-0.000311
-0.000534
-0.000343
-0.000420
-0.000165
-0.000584
0.000584
-0.001486
1.210888
-1.212511
-1.210612
1.208089
2.151130
-2.152405
-2.153569
2.150696
-0.001838
0.001486
1.212511
-1.210888
-1.208089
1.210612
2.152405
-2.151130
-2.150696
2.153569
0.001838
– S4 –
4.625479
3.685658
2.437873
2.475852
2.513900
1.279508
3.705089
1.279786
0.000000
4.658123
0.000000
2.565297
-1.279508
0.000000
-2.475852
-1.279786
-2.565297
0.000000
-3.685658
-2.437873
-4.625479
-3.705089
-4.658123
-2.513900
4.498399
-4.498399
7.240360
5.187466
5.186799
6.555196
6.555863
4.653245
4.652062
7.083702
7.084887
8.304248
-7.240360
-5.186799
-5.187466
-6.555863
-6.555196
-4.652062
-4.653245
-7.084887
-7.083702
-8.304248
Z
3.389540
2.844047
4.619766
3.536133
0.708571
2.821785
1.452300
1.406077
3.588229
0.937058
-0.564425
-1.229672
2.821785
4.812353
3.536133
1.406077
-1.229672
0.671892
2.844047
4.619766
3.389540
1.452300
0.937058
0.708571
-1.493390
-1.493390
-2.061523
-1.641975
-1.641330
-1.921754
-1.922403
-1.538418
-1.537283
-2.034498
-2.035651
-2.282983
-2.061523
-1.641330
-1.641975
-1.922403
-1.921754
-1.537283
-1.538418
-2.035651
-2.034498
-2.282983
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
2: Optimized conformers, 2 (AA-cis), 2 (AB) and 2 (BB).
Conformer: 2 (AA-cis) (type A-type A pairing for the PhSe moieties)
Symmetry:
E = –5919.2120 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
6
6
6
6
6
6
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
6
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
6
6
1
8
6
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
1.346032
1.991992
3.181024
3.691731
3.068766
1.886780
1.560532
3.652574
4.583110
-0.262652
-1.656993
-1.464915
-2.537256
-3.804865
-3.992980
-2.921855
-0.487843
-2.379795
-4.637839
-4.973100
-3.069619
1.346032
1.991992
3.181024
3.691731
3.068766
1.886780
1.560532
3.652574
4.583110
-0.262652
-1.656993
-1.464915
-2.537256
-3.804865
-3.992980
-2.921855
-0.487843
-2.379795
-4.637839
-4.973100
-3.069619
1.370029
3.623618
4.522577
0.332754
0.724896
-0.199011
1.308940
1.308940
– S5 –
-0.258618
0.182323
0.957767
1.320981
0.898034
0.058212
-0.053259
1.274993
1.939127
-1.285428
-0.030189
1.355233
2.207590
1.689007
0.305943
-0.555089
1.768015
3.283193
2.357365
-0.109278
-1.631067
-0.258618
0.182323
0.957767
1.320981
0.898034
0.058212
-0.053259
1.274993
1.939127
-1.285428
-0.030189
1.355233
2.207590
1.689007
0.305943
-0.555089
1.768015
3.283193
2.357365
-0.109278
-1.631067
-0.385659
1.277779
1.889604
-1.272571
-2.647477
-3.226845
-2.886726
-2.886726
Z
2.559405
3.696814
3.647799
2.435754
1.221874
1.248186
4.664078
4.573420
2.364728
2.960933
2.481961
2.507111
2.238788
1.966813
1.946753
2.190405
2.738254
2.253594
1.767303
1.726576
2.146764
-2.559405
-3.696814
-3.647799
-2.435754
-1.221874
-1.248186
-4.664078
-4.573420
-2.364728
-2.960933
-2.481961
-2.507111
-2.238788
-1.966813
-1.946753
-2.190405
-2.738254
-2.253594
-1.767303
-1.726576
-2.146764
0.000000
0.000000
0.000000
0.000000
0.000000
0.000000
0.896884
-0.896884
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 2 (AB) (type A-type B pairing for the PhSe moieties)
Symmetry: C1
E = –5919.2213 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
1
6
1
6
6
6
6
6
6
1
8
34
6
6
6
34
6
6
1
1
6
1
6
6
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
1
1
1
1
1
1
6
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
3.223101
2.396944
0.872686
1.104854
1.680929
0.027225
2.681605
0.300047
-1.296324
3.716801
-0.506240
2.130895
-2.378207
-3.711290
-2.145841
-3.306729
-0.797255
-4.784012
-3.847241
-5.797429
-4.576226
-5.438869
-3.313760
4.024126
-2.469094
6.751593
4.436383
4.984609
6.344964
5.796443
3.692312
4.666702
7.084822
6.109473
7.809739
-1.314682
-1.305321
-3.056674
-2.470806
-0.736954
-0.835611
-3.965400
-2.925501
0.166317
-0.866324
-1.491886
-0.572203
-1.578007
0.163954
-0.337784
– S6 –
3.930190
3.328118
4.666501
3.737827
1.286528
2.945709
2.096498
1.707901
3.366194
1.787789
-0.066263
-0.466977
2.606259
3.089179
1.343031
-1.274673
0.994722
2.359919
4.051778
2.728766
1.072962
0.459517
0.557561
-0.536558
-2.180773
-0.809836
-1.004598
-0.212217
-0.349495
-1.136334
-1.263190
0.146809
-0.097015
-1.498830
-0.917223
-3.596646
-2.926140
-2.141834
-2.840094
-3.642163
-2.924768
-1.568842
-2.803109
-4.222182
-4.147242
4.319709
0.246535
0.581789
1.019584
-0.677341
Z
1.528703
1.159882
1.849417
1.335072
0.023638
0.838302
0.512731
0.139546
0.986750
0.427998
-1.221455
-0.713874
0.536989
0.713428
-0.137937
-1.158033
-0.396595
0.285391
1.199917
0.416309
-0.280486
-0.520968
-0.484299
-0.274348
0.341219
0.301380
0.981449
-1.241549
-0.952413
1.267599
1.729319
-2.216184
-1.707531
2.243319
0.524674
2.455981
0.128669
1.611595
2.668097
1.186295
-0.849056
1.771084
3.654745
1.016662
3.278676
1.471844
-2.620404
-2.894854
-2.872401
-3.151069
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 2 (BB) (type A-type A pairing for the PhSe moieties)
Symmetry: Cs
E = –5919.2259 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
6
6
6
6
6
6
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
6
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
6
6
1
8
6
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0.866506
1.606835
3.018193
3.682393
2.969279
1.538814
1.110834
3.557606
4.757184
-1.087289
-1.337031
-1.531820
-1.795696
-1.868178
-1.678173
-1.415973
-1.476026
-1.946407
-2.075823
-1.738089
-1.272590
0.866506
1.606835
3.018193
3.682393
2.969279
1.538814
1.110834
3.557606
4.757184
-1.087289
-1.337031
-1.531820
-1.795696
-1.868178
-1.678173
-1.415973
-1.476026
-1.946407
-2.075823
-1.738089
-1.272590
0.899458
3.636130
4.714817
-0.414478
-0.557342
-1.630195
-0.098909
-0.098909
– S7 –
-0.122246
-0.011831
0.148484
0.231219
0.114868
-0.111437
-0.017279
0.229661
0.387683
-0.148665
0.161962
-0.919416
-0.691606
0.614235
1.694660
1.471761
-1.934273
-1.534530
0.790179
2.712355
2.310030
-0.122246
-0.011831
0.148484
0.231219
0.114868
-0.111437
-0.017279
0.229661
0.387683
-0.148665
0.161962
-0.919416
-0.691606
0.614235
1.694660
1.471761
-1.934273
-1.534530
0.790179
2.712355
2.310030
-0.307243
0.194632
0.333688
-0.732734
-2.165812
-2.362618
-2.592445
-2.592445
Z
2.524574
3.680065
3.648422
2.456485
1.225771
1.242774
4.643561
4.588384
2.420649
2.616109
4.517883
5.387392
6.740384
7.229576
6.364407
5.011178
5.004464
7.409764
8.281707
6.741245
4.335703
-2.524574
-3.680065
-3.648422
-2.456485
-1.225771
-1.242774
-4.643561
-4.588384
-2.420649
-2.616109
-4.517883
-5.387392
-6.740384
-7.229576
-6.364407
-5.011178
-5.004464
-7.409764
-8.281707
-6.741245
-4.335703
0.000000
0.000000
0.000000
0.000000
0.000000
0.000000
0.898957
-0.898957
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
3: Optimized conformers, 3 (AA-trans), 3 (AA-cis), 3 (AB) and 3 (BB).
Conformer: 3 (AA-trans) (type A-type A pairing for the PhSe moieties)
Symmetry: C1
E = –5804.6946 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
6
6
6
6
6
6
6
6
6
6
6
6
6
6
1
1
1
1
1
1
1
1
34
34
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
3.166479
2.170026
1.061192
1.056364
2.114765
3.136443
0.001737
0.007373
-1.044423
-1.055072
-2.166963
-3.161006
-3.125151
-2.100234
-0.000335
3.995970
2.088739
3.939281
0.009561
-3.993051
-3.926105
-2.069698
2.282025
-2.286569
2.676129
2.179607
2.492974
3.281618
3.766558
3.476925
1.541885
2.105965
3.514761
4.382661
3.869404
-2.681654
-3.457229
-3.747756
-3.288654
-2.525094
-2.211116
-3.829841
-4.344162
-3.522222
-2.158254
-1.593090
– S8 –
1.650249
0.924471
1.595662
3.042667
3.749531
3.074538
0.921158
3.721326
3.046239
1.599274
0.931982
1.661183
3.085296
3.756717
-0.161423
1.130828
4.836529
3.614991
4.809461
1.144631
3.628511
4.843597
-1.008590
-1.000506
-1.453466
-2.661004
-3.051334
-2.232182
-1.023133
-0.635787
-3.289199
-3.991207
-2.532048
-0.380110
0.297850
-1.444631
-0.612358
-0.999893
-2.222759
-3.056156
-2.666543
0.332522
-0.345545
-2.522451
-4.007098
-3.306877
Z
1.869198
1.258017
0.621129
0.628359
1.278484
1.888478
-0.000258
-0.001678
-0.630910
-0.622233
-1.257912
-1.868979
-1.889815
-1.281281
0.000338
2.338813
1.278022
2.382045
-0.002247
-2.337222
-2.383400
-1.282064
1.373152
-1.372193
-0.476972
-0.981437
-2.285634
-3.095473
-2.590611
-1.281409
-0.365246
-2.670674
-4.113349
-3.214010
-0.889830
0.477766
1.291755
2.600770
3.096189
2.276778
0.972625
0.907859
3.231495
4.114011
2.654320
0.348832
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 3 (AA-cis) (type A-type A pairing for the PhSe moieties)
Symmetry: C1
E = –5804.6938 au
Center
Atomic
Coordinates (Angstroms)
Number
Number
X
Y
Z
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
1
6
1
6
6
6
6
6
6
1
1
34
6
1
6
6
6
6
1
1
6
1
6
6
6
6
6
6
6
1
1
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
-5.967125
-4.916591
-4.549755
-4.134311
-3.032248
-2.753241
-4.357139
-2.175834
-1.944853
-4.988973
-0.396570
-2.399281
-0.596947
-2.379380
0.212257
-0.018503
-0.827770
1.525100
-0.240196
2.135655
2.102917
3.141533
1.368472
-1.295335
-1.829287
-1.028708
0.296037
0.822577
0.031456
-2.861981
-1.444902
0.915639
1.856898
0.451142
2.241030
3.100958
4.059492
4.704336
4.405342
3.450929
2.794103
4.310588
5.450287
4.913951
3.206924
2.047540
– S9 –
0.908705
0.945154
2.819988
2.000744
-0.126039
2.055174
-0.128413
0.980339
3.134706
-0.966120
0.271512
-1.617872
3.217438
3.939872
4.328928
2.153958
1.066385
4.407591
5.115002
5.256742
3.377742
3.460987
2.280505
-2.528517
-2.921392
-3.606542
-3.918402
-3.536489
-2.835711
-2.690096
-3.905428
-4.454405
-3.758434
-2.515827
0.966315
-0.161392
-1.068411
-1.926791
-1.882184
-0.975016
-0.117078
-1.100871
-2.623369
-2.545618
-0.933636
0.576225
1.027675
0.753038
1.715101
1.133357
-0.368125
0.769258
0.001096
-0.009638
1.140680
-0.277179
-0.976755
-1.442062
0.772742
1.729656
1.159552
-0.021720
-0.381136
0.780243
1.759305
1.073955
-0.014791
-0.318710
-0.401935
-0.123648
1.109165
2.023904
1.706017
0.471520
-0.443517
1.352758
2.982650
2.419824
0.224793
-1.392679
-1.534774
-0.208534
-0.679933
0.211753
1.575894
2.039630
1.154624
-1.737665
-0.162588
2.269821
3.098089
1.527407
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 3 (AB) (type A-type B pairing for the PhSe moieties)
Symmetry: C1
E = –5804.6944 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
6
6
6
6
6
6
6
6
6
6
6
6
6
6
1
1
1
1
1
1
1
1
34
34
6
6
6
6
6
6
1
1
1
1
1
6
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
4.497326
3.228279
2.109113
2.373778
3.709733
4.741345
0.789938
1.308394
-0.008389
-0.277724
-1.640467
-2.643211
-2.362368
-1.084147
0.601353
5.329744
3.887442
5.755621
1.510123
-3.666302
-3.182613
-0.865818
3.012242
-1.986276
2.507338
1.593402
1.252651
1.803010
2.707001
3.070351
1.140206
0.544799
1.528237
3.140808
3.783975
-3.920828
-4.578430
-5.971971
-6.710927
-6.055496
-4.661143
-4.000554
-6.479219
-7.795308
-6.626897
-4.147768
– S10 –
1.135045
0.603244
1.385147
2.727695
3.234499
2.464319
0.914484
3.508072
3.035068
1.691338
1.219134
2.036054
3.360615
3.848746
-0.086933
0.531216
4.247685
2.853033
4.520077
1.678291
3.978064
4.857311
-1.175954
-0.609376
-2.173914
-3.224209
-4.006645
-3.731525
-2.675497
-1.902917
-3.424042
-4.822734
-4.333994
-2.455728
-1.092247
-0.593044
-0.121277
-0.167498
-0.690456
-1.165744
-1.117531
0.278253
0.200104
-0.729438
-1.574052
-1.482869
Z
-0.721790
-0.715788
-0.246248
0.222567
0.191991
-0.271199
-0.219386
0.685190
0.715621
0.252135
0.298859
0.761245
1.200497
1.184748
-0.588374
-1.069541
0.544408
-0.291808
1.030620
0.802137
1.556972
1.526154
-1.457447
-0.273469
0.131706
-0.013358
1.093148
2.346169
2.487517
1.383541
-0.980655
0.973879
3.207524
3.459690
1.496200
-0.346711
-1.490555
-1.559412
-0.495052
0.642309
0.720154
-2.318293
-2.447440
-0.553779
1.471659
1.604403
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Conformer: 3 (BB) (type B-type B pairing for the PhSe moieties)
Symmetry: C2
E = –5804.6932 au
Center
Atomic
Atomic
Coordinates (Angstroms)
Number
Number
Type
X
Y
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
6
6
1
1
6
6
6
6
6
6
1
1
1
6
6
6
6
6
6
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
34
6
6
6
6
6
6
1
1
1
1
1
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0
0.000000
0.000000
0.000000
0.000000
-0.021655
-0.019028
-0.007423
-0.002901
0.000000
-0.007801
-0.000957
-0.024942
-0.029704
0.021655
0.019028
0.007423
0.002901
0.000000
0.007801
0.000957
0.024942
0.029704
0.037077
-0.220407
-1.515446
-1.696655
0.888158
0.699301
-0.591045
-2.702209
-2.372027
1.561383
1.889754
-0.735607
-0.037077
0.220407
-0.888158
-0.699301
1.515446
1.696655
0.591045
-1.561383
-1.889754
2.702209
2.372027
0.735607
– S11 –
0.000000
0.000000
0.000000
0.000000
3.653005
2.468233
1.227215
1.230328
2.504818
3.673631
4.631403
2.449682
4.598216
-3.653005
-2.468233
-1.227215
-1.230328
-2.504818
-3.673631
-4.631403
-2.449682
-4.598216
2.493891
4.376194
4.903665
6.249807
5.196087
6.541340
7.068499
6.656660
4.262734
7.174995
4.782334
8.114796
-2.493891
-4.376194
-5.196087
-6.541340
-4.903665
-6.249807
-7.068499
-7.174995
-4.782334
-6.656660
-4.262734
-8.114796
Z
0.894047
3.684712
4.772922
-0.191209
3.034352
3.718847
3.012061
1.565833
0.890078
1.610790
1.101989
4.805605
3.570683
3.034352
3.718847
3.012061
1.565833
0.890078
1.610790
1.101989
4.805605
3.570683
-1.057265
-1.427183
-1.514093
-1.837297
-1.672609
-1.999153
-2.080610
-1.903275
-1.329355
-2.189642
-1.606203
-2.336017
-1.057265
-1.427183
-1.672609
-1.999153
-1.514093
-1.837297
-2.080610
-2.189642
-1.606203
-1.903275
-1.329355
-2.336017
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
Experimental Section
Chemicals were used without further purification unless otherwise noted. Solvents were purified
by standard methods. 1H NMR spectra were measured at 300 MHz. The 1H chemical shifts are
given in ppm relative to those of internal TMS in CDCl3 solvent. Column chromatography was
performed on silica gel that covered with basic alumina layer on the top.
1,8-Bis(phenylselanyl)anthraquinone (1). To 3.00 g (9.61 mmol) of diphenyl diselenide in 40
ml of ethanol, was added 1.10 g (29.10 mmol) of NaBH4 under Ar atmosphere. The solution was
added 40 ml of benzene and distilled until solution was ca 25 ml. Then 80 ml of DMF was added to
the solution and distilled until temperature of solution was 110 °C. After the solution was cooled to
45 °C, 2.40 g (8.66 mmol) of 1,8-dichloroanthraquionone and 4.30 g (22.58 mmol) of CuI were
added to the solution. The mixture was refluxed over 20 hrs and cooled to room temperature. After
usual work-up, the crude product was chromatographed on silica gel that covered with basic
alumina layer on the top and recrystallized from ethanol–chloroform. 1 gave 78 % yield as dark red
prisms: mp 199.0 °C (DSC), 1H NMR  7.30 (d, J = 8.1 Hz, 2H), 7.41 (t, J = 7.8 Hz, 2H), 7.42–7.52
(m, 6H), 7.73–7.80 (m, 4H), 8.11 (d, J = 7.5 Hz, 2H). Anal. Calcd for C26H16O2Se2: C, 60.25; H,
3.11. Found: C, 60.32; H, 3.15.
1,8-Bis(phenylselanyl)-9-(methoxyl)anthracene (2). To a solution of 2.00 g (5.45mmol) of
1,8-dibromo-9-methoxyanthracene (6) in 30 ml of dry THF at –78 °C was added dropwise 7 ml of
n-BuLi (1.6 M in hexane) via syringe, and the mixture was stirred at the same temperature for 2 hrs.
Freshly prepared 2.84 g (12.02 mmol) of phenylselanylbromide in 10 ml of dry THF was added to
the orange suspension at –78 °C dropwise using canuula. The reaction mixture was maintained with
stirring at –78 °C for 1.2 hrs, and then temperature of the one was raised to 65 °C slowly for 1 hr.
After usual work-up, the crude product was chromatographed on silica gel with benzene: hexane =
1:1–4:1 eluent and recrystallization from ethanol–chloroform. 2 gave 41 % yield as yellow needle:
mp 221.6 °C (DSC), 1H NMR (CDCl3)  4.03 (s, 3H), 6.88 (dd, J = 0.7 and 7.3 Hz, 2H), 7.11 (t, J =
7.7 Hz, 2H), 7.41–7.50 (m, 6H), 7.70 (d, J = 8.3 Hz, 2H), 7.77–7.84 (m, 4H), 8.18 (s, 1H). Anal.
Calcd for C27H20OSe2: C, 62.56; H, 3.89. Found: C, 62.61; H, 3.88.
1,8-Bis(phenylselanyl)anthracene (3).[S2] To 2.00 g (3.86 mmol) of 1 in 60 ml of 1,4-Dioxane,
added 2.52 g (38.6 mmol) of Zinc powder and 0.096 g (0.39 mmol) of CuSO4•5H2O and then added
120 ml of 28 % NH3aq, slowly. The solution was heated to reflux over 4 hrs. The solvent was
removed in vacuo. The residue was dissolved in 80 ml of ethanol and 1 ml of 36 % HClaq. The
solution was heated to reflux during 1 hr. The reaction mixture was concentrated in vacuo. The
crude product was chromatographed on silica gel and recrystallized from ethanol. 3 gave 86 % yield
as bright yellow prisms: mp 126.8 °C (DSC), 1H NMR  7.13–7.24 (m, 6H), 7.38–7.49 (m, 4H),
7.35 (t, J = 7.6 Hz, 2H), 7.76 (dd, J = 1.1 and 6.8 Hz, 2H), 7.97 (d, J = 8.5 Hz, 2H), 8.42 (s, 1H),
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9.48 (s, 1H). Anal. Calcd for C26H18Se2: C, 63.95; H, 3.72. Found: C, 63.89; H, 3.64.
1,8-Dibromo-9-methoxyanthracene (6).[S2] To a solution of 77.74 g (1943.61 mmol) of NaOH
and 3.82 g (11.84 mmol) of (n-Bu)4NBr in 250 ml of H2O, was added, dropwise and with
vigorously stirring during 45min, a solution of 13.29 g (37.74 mmol) of 1,8-dibromo-9-anthrone (7)
and 19.92 g (157.92 mmol) of dimethyl sulfate in 215 ml of CH2Cl2. The resulting mixture was
stirred at 25 °C for additional 1.5 hrs. After usual work-up, the crude product was recrystallized
from chloroform–acetone to give 6.45 g of 6 as orange prisms (47 % yield): mp 178.6 °C (DSC), 1H
NMR (CDCl3)3.86 (s, 3H), 7.24 (t, J = 7.7 Hz, 2H), 7.85 (d, J = 7.2 Hz, 2H), 7.91 (d, J = 8.3 Hz,
2H), 8.23 (s, 1H).
1,8-Dibromo-9-anthrone (7).[S2] 17.00 g (46.45 mmol) of 1,8-dibromoanthraquinone (8) was
dissolved in 155 ml of concentrated sulfuric acid with vigorously stirring. Then 4.01 g (148.63
mmol) of Al powder was added and the mixture was stirred for 42 hrs, while the temperature of the
mixture was maintained at 30–40 °C. The resulting yellow suspension was poured onto 500 ml of
ice water and after standing for 20 min, was filtered. After usual work-up, the crude product was
recrystallized from CH2Cl2–ethanol to give 13.54 g of 7 as tan needles (83 % yield): 1H NMR
(CDCl3)  4.17 (s, 2H), 7.29 (d, J = 7.7 Hz, 2H), 7.34 (t, J = 7.7 Hz, 2H), 7.64 (d, J = 7.7 Hz, 2H).
1,8-Dibromoanthraquinone (8).[S3] To a suspension of 10.00 g (36.09 mmol) of
1,8-dichloroanthraquinone, 21.47 g (180.44 mmol) of KBr, and 0.43 g (2.53 mmol) of CuCl2･2H2O
in 87 ml of nitrobenzene, was added 11 ml of 85 % H3PO4 with vigorously stirring, and then
refluxed for 42 hrs. After one-thirds of the solution was steam distilled, cooling and filtration, the
residue was recrystallized from chloroform–ethanol to give 7.81 g of 8 as yellow prisms (59 %
yield): mp 235.9 °C (DSC), 1H NMR (CDCl3)  7.55 (t, J = 7.9 Hz, 2H), 8.03 (d, J = 7.9 Hz, 2H),
8.24 (dd, J = 1.3 and 7.7 Hz, 2H).
Reference
[S1] Gaussian 98, Revision A.9; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.;
Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant,
J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi,
J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski,
J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.;
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G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.;
Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.;
Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.
Gaussian, Inc., Pittsburgh PA, 1998.
[S2] H. O. House, J. A. Hrabie, D. VanDerveer, J. Org. Chem., 1986, 51, 921.
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[S3] I. G. Farbenindustrie, D.R.P. 1931, 597259; Frdl. 21, 1112.
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