Supporting Information
Theoretical Investigations on 4,4’,5,5’-tetranitro-2,2’-1H,1’H2,2’-biimidazole derivatives as potential nitrogen-rich high
energy materials
Qing Maa,b, Tao Jiangb, Xiaoyu Zhangb, Guijuan Fanb, Jun Wangb* and Jinglun
Huangb*
a
School of Chemical Engineering, Nanjing University of Science and Technology,
Nanjing 210094, China
b
Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang
621900, China
E-mail: wangjun01@caep.cn; jinglunhuang@caep.cn
A List of Contents ......................................................................................................S1
1. Cartesian coordinates of optimized geometries and the corresponding absolute
energies……………………………………………………………………………….……...………………………………………………………………………………………….……. S2
2. Thermodynamic properties of the title molecules at different
temperatures…………………………………………………………………………………………………………………….……...…………………………………………….. S8
Table S1. Thermodynamic properties of the title molecules at different
temperatures…………………………………………………………………………………………………………………………………………….………. S8
Total: 9 pages
S1
1. Cartesian coordinates of optimized geometries and the corresponding absolute
energies
Structure T1
N
C
C
N
C
C
N
C
C
N
N
N
N
N
O
O
O
O
O
O
O
O
H
H
1.4700870
2.7433400
2.7881360
1.4794940
0.7224220
-0.7224190
-1.4700860
-2.7433420
-2.7881320
-1.4794890
3.8577920
3.8559140
-3.8577810
-3.8559070
4.5650100
3.9577880
3.5270310
4.9940240
-3.9577020
-4.5651500
-4.9940090
-3.5270180
1.1640760
-1.1640700
-1.1134120
-0.6729860
0.7118200
1.1183820
-0.0078780
0.0078890
1.1134200
0.6729900
-0.7118140
-1.1183740
-1.6261930
1.6623070
1.6262070
-1.6623040
-1.5966240
-2.3777500
2.8505460
1.2229920
2.3778500
1.5964720
-1.2229900
-2.8505430
2.0840470
-2.0840380
-0.0090710
-0.0056850
0.0162250
0.0228850
0.0033820
-0.0033690
0.0091010
0.0057090
-0.0162210
-0.0228600
-0.0440170
0.0747940
0.0440590
-0.0748000
-1.0396150
0.9136010
0.0239480
0.1789180
-0.9135000
1.0395450
-0.1790140
-0.0239990
0.0425550
-0.0425180
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
Structure T2
N
C
-1.4327460
-2.7185580
1.1652170
0.7918580
0.0080010
-0.0162500
S2
0.131776 (Hartree/Particle)
0.149914
0.150858
0.080706
-1269.286492
-1269.268355
-1269.267410
-1269.337562
C
N
C
C
N
C
C
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
H
H
H
H
-2.8263500
-1.5344090
-0.7212300
0.7212710
1.4328800
2.7186540
2.8263300
1.5343650
-1.1479300
1.1477250
-3.7782540
-3.9581010
3.7784420
3.9579150
-3.5506230
-4.7962480
-3.8191780
-4.9576640
4.7962450
3.5510710
4.9575640
3.8188070
-1.6979080
-0.1414550
0.1414010
1.6982650
-0.5971920
-1.0699660
0.0311090
-0.0312940
-1.1653630
-0.7918980
0.5971570
1.0698250
-2.3962580
2.3960550
1.7885650
-1.4834800
-1.7884880
1.4835570
2.8856910
1.4475380
-2.5820620
-1.0910390
-1.4473720
-2.8855880
1.0908710
2.5824780
-2.9862690
-2.4584860
2.4583330
2.9862010
-0.0414720
-0.0173510
0.0001280
-0.0001010
-0.0081970
0.0159180
0.0415290
0.0172480
-0.2252620
0.2251420
0.0900420
-0.0891460
-0.0906460
0.0898670
-0.4011900
0.6805700
0.4601740
-0.6673490
-0.6814460
0.4007600
0.6677600
-0.4587730
0.3977760
-0.0483490
0.0474030
-0.3972720
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
Structure T3
N
C
C
N
C
C
-1.2700780
-2.6271190
-2.8207640
-1.6398240
-0.7148900
0.7141100
-1.3578630
-1.1783410
0.1950770
0.8436990
-0.1179130
0.1162750
0.1557130
0.1687950
0.1926680
0.1889270
0.1718470
0.1718760
S3
0.168859 (Hartree/Particle)
0.189004
0.189948
0.117535
-1379.580630
-1379.560485
-1379.559541
-1379.631955
N
C
C
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
O
O
O
O
H
H
1.2689800
2.6260970
2.8200490
1.6393190
-1.2399490
1.2432350
-3.5192200
-4.0724990
3.5184100
4.0722330
-4.7056480
-2.9998800
-4.8633390
-4.1988420
2.9992270
4.7051600
4.8600440
4.2017860
-2.1078250
-0.2646450
0.2635750
2.1119140
-0.7879670
0.7865990
1.3563250
1.1771000
-0.1961740
-0.8451680
3.9236860
-3.9180680
-2.3009410
0.9529090
2.2993560
-0.9533510
-2.0666010
-3.4123370
0.6331070
1.8596830
3.4110770
2.0643390
-0.6371810
-1.8559620
4.7125200
3.9352330
-3.9356430
-4.7055530
-2.2612970
2.2596100
0.1552010
0.1686090
0.1931900
0.1895860
-0.7806070
-0.7797130
0.0966340
0.2588840
0.0964950
0.2595230
-0.0907040
0.2159620
1.1337460
-0.5525680
0.2133890
-0.0883060
1.1383930
-0.5560210
-0.9815340
-0.0669960
-0.0721320
-0.9824060
0.1136830
0.1133260
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
Structure T4
N
C
C
N
C
C
N
C
1.2774780
2.6188990
2.8860290
1.6636530
0.7105170
-0.7105600
-1.2774960
-2.6189290
-1.3063290
-1.0768930
0.2652310
0.8844650
-0.1261780
0.1259660
1.3061160
1.0767100
-0.4956050
-0.5089410
-0.3887870
-0.2959210
-0.3563680
-0.3564360
-0.4958100
-0.5090140
S4
0.150734 (Hartree/Particle)
0.178626
0.179570
0.080910
-1679.437204
-1679.409312
-1679.408368
-1679.507028
C
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
N
H
H
N
O
O
O
O
-2.8860900
-1.6637320
1.5076210
-1.5077580
3.5931810
4.1255540
-3.5931970
-4.1256320
4.7699370
3.1735520
4.5151770
4.6261560
-3.1736130
-4.7698980
-4.6292100
-4.5122920
1.2365420
0.6933120
-0.6936840
-1.2363860
0.8076530
1.5224600
-1.5225940
-0.8070310
-0.2653850
-0.8846240
2.2357980
-2.2358660
-2.1416220
1.0458840
2.1413690
-1.0460220
-1.7850240
-3.2818340
1.4049100
1.2783920
3.2817440
1.7845450
-1.2738570
-1.4096660
2.5344800
2.6017750
-2.6022280
-2.5339310
3.6488300
1.6724520
-1.6717300
-3.6480450
-0.3886580
-0.2956650
-0.0693640
-0.0684750
-0.6537300
-0.3957400
-0.6544140
-0.3955480
-0.6455620
-0.7718500
-1.4948690
0.6904620
-0.7711010
-0.6482070
0.6902380
-1.4942320
1.3696330
-0.5723150
-0.5715140
1.3705310
1.5404760
2.1657400
2.1663690
1.5417620
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
Structure T5
N
C
C
N
C
C
N
C
-0.0064700
0.9994650
2.0333960
1.6184250
0.3740980
-0.3796070
0.1497430
-0.8837260
1.8128410
2.7007600
2.1626880
0.8769830
0.7248400
-0.5129920
-1.7122600
-2.5706450
-1.1089560
-0.9609480
-0.2256090
0.0966880
-0.4654190
-0.4562000
-0.5323050
-0.6919620
S5
0.167818 (Hartree/Particle)
0.193938
0.194882
0.104714
-1788.901301
-1788.875181
-1788.874237
-1788.964405
C
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
C
H
H
C
N
N
N
N
N
N
O
O
O
O
O
O
O
O
O
O
O
O
-2.0856000
-1.7597850
2.2331390
-2.6230930
0.8640230
3.3071830
-0.6187120
-3.4369890
1.4815280
0.1326400
3.7170870
3.8726900
0.4104810
-1.4429550
-3.7711110
-4.1105140
3.1316600
2.5839630
-2.4272840
-3.2756590
2.8628750
4.6084040
3.1211560
-3.6897460
-2.4580210
-4.5597000
3.7800710
1.8108720
5.4795150
4.7035290
3.0322490
3.2506710
-4.0905270
-3.5706520
-3.0762880
-1.2704210
-4.3238610
-5.6309880
-1.9007390
-0.5641880
-0.0374230
0.5117780
4.0578810
2.6840900
-3.9952300
-2.3601480
4.9332180
4.1962740
2.2816370
3.4627230
-4.4236010
-4.6225310
-3.4129430
-1.6392590
-1.0240670
0.4179350
1.2227060
0.9715230
-2.3884540
-0.7090630
-1.2647540
2.4531190
0.9976560
0.1531690
-3.1835940
-2.4861820
-0.8311520
-0.3698170
-2.4051970
-0.2417760
3.0422500
2.8656470
0.8122150
1.2542730
-1.0065010
0.7042140
-0.7472390
-0.5609160
0.9370060
-0.5651780
-1.4838200
0.1930420
-0.8747500
-1.0127790
-0.8865990
-2.4538280
1.2900310
-0.5535640
-0.3720770
-1.5309890
-0.4972750
-1.7466710
0.4740970
1.7810580
-1.2688790
0.5744790
1.2341330
0.8885800
-1.0362990
0.3317920
1.9142450
0.8964860
1.1598310
1.8240380
0.0564480
2.0585200
-1.4284420
-1.6974790
1.3117810
-0.8096830
2.9377540
1.7802260
1.1961910
0.7695170
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
0.231768 (Hartree/Particle)
0.270898
0.271842
0.152527
-2685.068643
S6
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
Structure T6
N
C
C
N
C
C
N
C
C
N
N
N
N
N
N
N
O
O
O
O
O
O
O
O
C
H
H
C
N
N
F
N
F
N
O
O
O
O
0.0038130
-1.0297810
-2.1099340
-1.6974270
-0.3999660
0.4377430
0.0392320
1.1289240
2.2355060
1.8102050
-2.4156870
2.6551030
-0.8783720
-3.3775240
1.0804730
3.6179860
-1.1503360
-0.4703330
-3.9460970
-3.7806160
-0.0063920
2.1620560
3.8084890
4.4449880
-3.1973250
-2.9051600
2.3407900
3.0538330
-3.6391940
-4.5353070
-2.5334800
3.2510470
2.2063570
4.4612670
-3.8329000
-3.7642190
-4.3562930
-5.5785740
-1.6846940
-2.5289700
-1.8789930
-0.5553450
-0.4972290
0.6896750
1.9310230
2.7146440
1.9569880
0.6514320
0.5218330
-0.4196830
-3.9538390
-2.3709250
4.1607990
2.2999640
-4.7433560
-4.2109470
-1.7005310
-3.4111610
4.6740210
4.7365530
2.7278160
2.1035840
1.2622830
0.2927090
-1.0079890
-1.2041800
2.5800890
0.5495920
1.5194060
-2.6813030
-1.1999650
-0.7808870
3.5167670
2.5186830
-0.3739420
0.9412300
-0.5729300
-0.3816250
0.1721160
0.3215780
-0.1340310
-0.1413490
0.0407020
-0.1259450
-0.4267970
-0.4197720
0.8170870
-0.6798430
-0.6996190
0.6324340
0.0161990
-0.7580500
0.1928080
-1.8206750
1.5032670
0.1440230
0.2232150
-0.0860270
-1.8826220
0.1191020
-0.1087270
1.6799300
-1.4537630
0.4340770
0.5803170
-0.5691530
-1.2275870
-0.0347820
1.4678560
0.9877320
-0.1593520
1.7904710
-1.3453420
-0.0941020
S7
-2685.029514
-2685.028569
-2685.147884
O
O
O
O
3.5540320
3.0708380
4.4949610
5.3710420
-3.4498840
-2.9160020
-0.3360070
-0.9494950
0.8508130
-1.2154700
2.1120860
0.1992790
Zero-point correction=
Thermal correction to Energy=
Thermal correction to Enthalpy=
Thermal correction to Gibbs Free Energy=
Sum of electronic and zero-point Energies=
Sum of electronic and thermal Energies=
Sum of electronic and thermal Enthalpies=
Sum of electronic and thermal Free Energies=
0.211565 (Hartree/Particle)
0.247064
0.248008
0.136187
-2475.031374
-2474.995874
-2474.994930
-2475.106752
2. Thermodynamic properties of the title molecules at different temperatures
Table S1. Thermodynamic properties of the title molecules at different temperatures
T/K
T1
500.0
600.0
700.0
800.0
C p ,m /J·mol-1·K-1 213.49 282.31 341.76
389.42
426.10
454.02
475.41
S m / J·mol-1·K-1
787.04
861.43
929.31
991.40
82.98
119.64
160.50
204.57
251.08
C p ,m /J·mol-1·K-1 244.39 324.18 391.54
445.67
487.73
520.16
545.39
S m / J·mol-1·K-1
846.56
931.70 1009.43 1080.61
93.65
135.62
182.38
232.84
286.17
C p ,m /J·mol-1·K-1 313.33 388.91 455.79
510.21
552.48
584.84
609.71
H m / kJ·mol-1
T2
H m / kJ·mol-1
T3
S m / J·mol-1·K-1
H m / kJ·mol-1
T4
200.0
300.0
400.0
516.00 615.81 705.43
26.83
51.68
535.76 650.34 753.14
29.23
57.76
731.04 872.56 993.87 1101.67 1198.59 1286.30 1366.09
78.23 120.56
168.97
222.20
279.14
338.92
C p ,m /J·mol-1·K-1 288.95 381.42 459.18
520.90
568.24
604.24
631.77
S m / J·mol-1·K-1
973.19 1072.54 1162.97 1245.53
H m / kJ·mol-1
43.07
607.96 743.05 863.81
35.16
68.79 110.95
S8
160.09
214.65
273.36
335.22
T5
C p ,m /J·mol-1·K-1 467.91 541.65 602.73
S m / J·mol-1·K-1
H m / kJ·mol-1
T6
653.59
706.93
751.00
794.30
794.56 901.24 994.75 1082.78 1168.97 1249.84 1335.80
54.30 108.54 175.74
252.98
337.71
427.97
522.34
C p ,m /J·mol-1·K-1 447.27 502.34 554.50
600.77
645.96
690.61
729.20
S m / J·mol-1·K-1
H m / kJ·mol-1
793.56 882.57 962.73 1040.71 1119.47 1201.13 1280.10
51.91 102.34 164.34
S9
235.31
312.95
395.51
481.72