Supporting Information

for

Theoretical Study on the Reaction of Hydrogen atoms with Aniline

Marwan Bateha, Mohammednoor Altarawneh*, Abdullah Alsofi,

Ibrahim Altarawneh, Saleh Rawadieh

Department of Chemical Engineering, Al-Hussein Bin Talal University, Ma’an-Jordan

*Corresponding authors

E-mail:

Tel: +962 3 2179000

Aniline

Coordinates (Angstrom)

Atom X Y Z

C -1.8609 0.0001 0.0090

C -1.1586 -1.1879 0.0038

C 0.2188 -1.1929 -0.0064

C 0.9275 -0.0001 -0.0101

C 0.2190 1.1928 -0.0063

C -1.1584 1.1880 0.0037

H -2.9379 0.0002 0.0173

H -1.6879 -2.1273 0.0082

H 0.7558 -2.1291 -0.0154

H 0.7561 2.1290 -0.0151

H -1.6876 2.1275 0.0082

N 2.3116 -0.0002 -0.0754

H 2.7481 0.8288 0.2805

H 2.7480 -0.8283 0.2821

Moment of Inertia (AMU): 313.8526 682.4668 994.6827

Frequencies (cm**-1):

215 271 365 406 491 517 598 611 688 749 813 818

873 951 966 989 1033 1048 1110 1145 1171 1284 1325 1335

1479 1511 1614 1625 1647 3098 3100 3115 3120 3138 3512 3609

Zero-Point Energy (au): 0.1195051

Energies (au): -287.5370748

Spin Multiplicity: 1

------

Reactant: H 2

FORMULA: H 2

Coordinates (Angstrom)

Atom X Y Z

H 0.0000 0.0000 0.0000

Moment of Inertia (AMU): 0.0000 0.0000 0.0000

------

TS5

Coordinates (Angstrom)

Atom X Y Z

C 1.9120 0.0554 0.0666

C 1.1729 1.2232 -0.0049

C -0.1970 1.1761 -0.0953

C -0.8600 -0.0480 -0.0959

C -0.1111 -1.2171 -0.0028

C 1.2631 -1.1632 0.0607

H 2.9868 0.0964 0.1279

H 1.6745 2.1773 -0.0001

H -0.7777 2.0810 -0.1702

H -0.6189 -2.1696 0.0093

H 1.8302 -2.0781 0.1177

N -2.2345 -0.0614 -0.2453

H -2.5862 -1.0080 -0.1693

H -2.7874 0.4898 0.6706

H -3.1587 0.6823 1.5602

Moment of Inertia (AMU): 330.6756 727.5285 1030.1295

Frequencies (cm**-1):

154 194 336 394 406 506 529 607 682 704 759 815

823 897 960 975 979 1000 1029 1072 1127 1147 1163 1257

1320 1327 1424 1479 1497 1523 1610 1622 3101 3112 3121 3129

3138 3438

Imaginary Frequency (cm**-1): -1814i

Zero-Point Energy (au): 0.1171734

Energies (au): -288.0180503

Spin Multiplicity: 2

------

Anilino

Coordinates (Angstrom)

Atom X Y Z

C -1.7869 0.0371 -0.0001

C -1.1242 -1.1836 0.0000

C 0.2423 -1.2265 0.0001

C 1.0056 -0.0340 0.0001

C 0.3032 1.1964 0.0001

C -1.0641 1.2232 -0.0000

H -2.8642 0.0645 -0.0003

H -1.6912 -2.1002 0.0001

H 0.7806 -2.1598 0.0002

H 0.8703 2.1148 0.0005

H -1.5850 2.1670 -0.0000

N 2.3281 -0.1363 -0.0002

H 2.7376 0.7930 -0.0002

Moment of Inertia (AMU): 318.7058 641.1573 959.8632

Frequencies (cm**-1):

193 377 402 471 515 595 653 668 760 812 820 897

961 967 974 1011 1069 1135 1139 1154 1287 1316 1334 1448

1467 1562 1575 3103 3114 3123 3134 3141 3395

Zero-Point Energy (au): 0.1058149

Energies (au): -286.8843019

Spin Multiplicity: 2

------

H2

Coordinates (Angstrom)

Atom X Y Z

H 0.0000 0.0000 0.3700

H 0.0000 0.0000 -0.3700

Moment of Inertia (AMU): 0.0000 0.9855 0.9855

Frequencies (cm**-1):

4306

Zero-Point Energy (au): 0.0102205

Energies (au): -1.1672900

Spin Multiplicity: 1

------

TS1

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C -1.1804 1.2053 0.0435

C -1.8715 0.0081 -0.0395

C -1.1652 -1.1671 -0.1058

C 0.2262 -1.1674 -0.0340

C 0.9220 0.0500 -0.0313

C 0.1973 1.2281 0.0375

H -1.7214 2.1363 0.0954

H -2.9482 0.0010 -0.0630

H -1.6830 -2.1095 -0.1793

H 0.7221 2.1701 0.0804

H 0.5225 -1.6123 1.7334

H 0.7681 -2.0796 -0.2279

N 2.2975 0.0578 -0.0004

H 2.7369 0.9071 -0.2963

H 2.7490 -0.7592 -0.3622

Moment of Inertia (AMU): 335.9128 696.0957 1006.7616

Frequencies (cm**-1):

200 281 309 357 384 445 493 517 539 607 708 743

813 835 908 954 975 988 1028 1036 1101 1145 1165 1289

1321 1332 1463 1507 1601 1610 1631 3101 3102 3117 3124 3139

3524 3625

Imaginary Frequency (cm**-1): -794i

Zero-Point Energy (au): 0.1211110

Energies (au): -288.0291575

Spin Multiplicity: 2

------

ORTHO-(C6H5NH2)H

Coordinates (Angstrom)

Atom X Y Z

C 1.8752 0.0218 -0.0048

C 1.2261 -1.1607 -0.0042

C -0.2568 -1.2489 0.0092

C -0.9310 0.0772 0.0009

C -0.2255 1.2367 -0.0036

C 1.1749 1.2391 -0.0026

H 2.9538 0.0347 -0.0088

H 1.7780 -2.0869 -0.0059

H -0.6013 -1.8135 0.8842

H -0.7601 2.1753 -0.0049

H 1.7093 2.1733 -0.0071

N -2.3039 0.0350 0.0733

H -2.7804 0.8880 -0.1506

H -2.7371 -0.7678 -0.3434

H -0.6125 -1.8395 -0.8461

Moment of Inertia (AMU): 340.9890 700.7931 1029.5180

Frequencies (cm**-1):

122 264 332 367 449 479 515 566 571 645 721 772

858 918 921 937 959 987 1072 1111 1152 1166 1260 1303

1333 1411 1416 1441 1534 1600 1626 2859 2881 3091 3102 3120

3140 3498 3602

Zero-Point Energy (au): 0.1284314

Energies (au): -288.0828940

Spin Multiplicity: 2

------

TS2

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C -1.0831 1.2639 -0.0100

C -1.8325 0.1152 -0.0963

C -1.1805 -1.1196 -0.0730

C 0.2119 -1.1705 -0.0921

C 0.9584 -0.0114 0.0012

C 0.2947 1.2101 0.0554

H -1.5727 2.2245 0.0022

H -2.9072 0.1585 -0.1441

H -1.7358 -2.0191 -0.2835

H 0.8673 2.1212 0.1336

H -1.5187 -1.5510 1.6427

H 0.7111 -2.1259 -0.1354

N 2.3396 -0.0577 0.0850

H 2.8093 0.7634 -0.2457

H 2.7565 -0.8939 -0.2768

Moment of Inertia (AMU): 334.8497 703.5647 1014.5772

Frequencies (cm**-1):

208 276 285 362 396 441 513 531 596 610 674 761

818 826 858 957 982 1017 1022 1042 1106 1142 1163 1279

1320 1331 1462 1502 1598 1607 1629 3102 3104 3117 3121 3140

3513 3610

Imaginary Frequency (cm**-1): -897i

Zero-Point Energy (au): 0.1211231

Energies (au): -288.0273676

Spin Multiplicity: 2

------

Product: Meta-(C6H5NH2)H

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C 1.8752 0.0218 -0.0048

C 1.2261 -1.1607 -0.0042

C -0.2568 -1.2489 0.0092

C -0.9310 0.0772 0.0009

C -0.2255 1.2367 -0.0036

C 1.1749 1.2391 -0.0026

H 2.9538 0.0347 -0.0088

H 1.7780 -2.0869 -0.0059

H -0.6013 -1.8135 0.8842

H -0.7601 2.1753 -0.0049

H 1.7093 2.1733 -0.0071

N -2.3039 0.0350 0.0733

H -2.7804 0.8880 -0.1506

H -2.7371 -0.7678 -0.3434

H -0.6125 -1.8395 -0.8461

Moment of Inertia (AMU): 340.9890 700.7931 1029.5180

Frequencies (cm**-1):

122 264 332 367 449 479 515 566 571 645 721 772

858 918 921 937 959 987 1072 1111 1152 1166 1260 1303

1333 1411 1416 1441 1534 1600 1626 2859 2881 3091 3102 3120

3140 3498 3602

Zero-Point Energy (au): 0.1284314

Energies (au): -288.0828940

Spin Multiplicity: 2

------

Transition State: TS3

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C -1.1041 1.1968 -0.0905

C -1.8231 0.0001 -0.0457

C -1.1042 -1.1967 -0.0906

C 0.2647 -1.1966 -0.0331

C 0.9740 -0.0000 0.0126

C 0.2649 1.1966 -0.0333

H -1.6331 2.1347 -0.1343

H -2.8802 0.0001 -0.2489

H -1.6332 -2.1347 -0.1345

H 0.8047 2.1313 -0.0321

H -2.3523 -0.0004 1.6861

H 0.8045 -2.1313 -0.0318

N 2.3483 -0.0001 0.1340

H 2.8093 0.8324 -0.1787

H 2.8093 -0.8320 -0.1804

Moment of Inertia (AMU): 328.2698 712.3039 1015.9347

Frequencies (cm**-1):

189 293 346 358 376 422 491 524 555 606 705 788

804 813 908 946 983 1004 1011 1039 1103 1140 1170 1294

1315 1333 1479 1495 1591 1611 1634 3100 3101 3119 3126 3138

3516 3616

Imaginary Frequency (cm**-1): -852i

Zero-Point Energy (au): 0.1211734

Energies (au): -288.0282961

Spin Multiplicity: 2

------

Product: Para-(C6H5NH2)H

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C -1.0845 -1.2371 0.0004

C -1.9109 -0.0000 0.0119

C -1.0845 1.2371 0.0004

C 0.2617 1.2094 -0.0076

C 0.9837 -0.0000 -0.0021

C 0.2617 -1.2094 -0.0076

H -1.5966 -2.1861 0.0000

H -2.5768 0.0000 0.8835

H -1.5966 2.1861 -0.0001

H 0.8116 -2.1398 -0.0205

H -2.6016 -0.0000 -0.8397

H 0.8116 2.1398 -0.0204

N 2.3669 0.0000 -0.0759

H 2.8080 -0.8283 0.2779

H 2.8080 0.8283 0.2780

Moment of Inertia (AMU): 334.9613 718.9891 1041.6348

Frequencies (cm**-1):

103 242 259 345 380 480 516 587 618 698 699 769

876 917 928 931 953 961 1033 1141 1165 1165 1273 1294

1326 1400 1418 1465 1533 1607 1626 2872 2880 3084 3085 3114

3116 3496 3596

Zero-Point Energy (au): 0.1280696

Energies (au): -288.0787124

Spin Multiplicity: 2

------

Transition State: TS4

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C 1.8792 0.0000 -0.0003

C 1.1781 1.1967 -0.0286

C -0.1944 1.2084 -0.0392

C -0.9199 -0.0000 0.0634

C -0.1944 -1.2084 -0.0392

C 1.1781 -1.1967 -0.0286

H 2.9566 0.0000 0.0088

H 1.7140 2.1325 -0.0567

H -0.7365 2.1408 -0.0726

H -0.7365 -2.1408 -0.0726

H 1.7140 -2.1325 -0.0567

N -2.2926 -0.0000 -0.1941

H -2.7594 -0.8215 0.1448

H -2.7593 0.8217 0.1444

H -0.9058 -0.0001 1.7538

Moment of Inertia (AMU): 331.7796 700.2259 1005.3973

Frequencies (cm**-1):

190 269 346 398 476 500 510 598 602 665 726 777

801 811 887 960 974 979 1023 1048 1116 1141 1164 1265

1317 1330 1471 1481 1583 1613 1630 3109 3112 3124 3129 3144

3503 3594

Imaginary Frequency (cm**-1): -1069i

Zero-Point Energy (au): 0.1219335

Energies (au): -288.0151376

Spin Multiplicity: 2

------

Product: Ipso-(C6H5NH2)H

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C -1.8486 0.0000 -0.1694

C -1.1489 -1.2123 -0.0557

C 0.1769 -1.2355 0.1880

C 0.9806 -0.0000 0.3893

C 0.1770 1.2354 0.1880

C -1.1488 1.2123 -0.0557

H -2.9070 0.0001 -0.3663

H -1.6831 -2.1417 -0.1768

H 0.7002 -2.1773 0.2579

H 0.7003 2.1773 0.2581

H -1.6830 2.1417 -0.1766

N 2.1431 -0.0001 -0.5020

H 2.7160 0.8089 -0.3165

H 2.7168 -0.8082 -0.3153

H 1.3095 0.0000 1.4433

Moment of Inertia (AMU): 361.5318 679.6113 975.3276

Frequencies (cm**-1):

85 159 286 382 419 508 565 589 672 725 773 802

906 949 951 952 975 976 1078 1083 1134 1169 1170 1275

1310 1343 1412 1429 1530 1589 1612 2786 3093 3094 3113 3115

3140 3435 3517

Zero-Point Energy (au): 0.1284296

Energies (au): -288.0627464

Spin Multiplicity: 2

------

TS8

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C 2.0726 0.0557 0.0004

C 1.4338 -1.1684 0.0001

C 0.0512 -1.2296 -0.0005

C -0.6518 -0.0516 -0.0007

C -0.0436 1.1774 -0.0004

C 1.3394 1.2257 0.0002

H 3.1497 0.0979 0.0009

H 2.0105 -2.0798 0.0004

H -0.4604 -2.1787 -0.0007

H -0.6213 2.0879 -0.0007

H 1.8435 2.1790 0.0004

N -3.2008 -0.1310 0.0004

H -3.3727 0.4627 0.8064

H -3.3753 0.4658 -0.8028

H -1.9776 -0.1721 -0.0013

Moment of Inertia (AMU): 319.7762 1044.9499 1355.4057

Frequencies (cm**-1):

64 93 109 355 393 405 585 590 640 681 729 750

827 896 959 980 985 1019 1051 1064 1146 1160 1248 1305

1316 1352 1449 1478 1532 1598 1622 3103 3108 3118 3124 3133

3375 3467

Imaginary Frequency (cm**-1): -1734i

Zero-Point Energy (au): 0.1206129

Energies (au): -288.0267142

Spin Multiplicity: 2

------

TS11

FORMULA: C6H8N 2

Coordinates (Angstrom)

Atom X Y Z

C 2.0726 0.0557 0.0004

C 1.4338 -1.1684 0.0001

C 0.0512 -1.2296 -0.0005

C -0.6518 -0.0516 -0.0007

C -0.0436 1.1774 -0.0004

C 1.3394 1.2257 0.0002

H 3.1497 0.0979 0.0009

H 2.0105 -2.0798 0.0004

H -0.4604 -2.1787 -0.0007

H -0.6213 2.0879 -0.0007

H 1.8435 2.1790 0.0004

N -3.2008 -0.1310 0.0004

H -3.3727 0.4627 0.8064

H -3.3753 0.4658 -0.8028

H -1.9776 -0.1721 -0.0013

Moment of Inertia (AMU): 319.7762 1044.9499 1355.4057

Frequencies (cm**-1):

64 93 109 355 393 405 585 590 640 681 729 750

827 896 959 980 985 1019 1051 1064 1146 1160 1248 1305

1316 1352 1449 1478 1532 1598 1622 3103 3108 3118 3124 3133

3375 3467

Imaginary Frequency (cm**-1): -1734i

Zero-Point Energy (au): 0.1206129

Energies (au): -288.0267142

Spin Multiplicity: 2

………………………………………………………………………………………………………………………………………………………….

TS10

C -0.137297 0.291800 0.007008

C 0.066374 -0.107810 1.378419

C 0.987973 0.381882 2.180562

C 2.125733 2.057643 0.962551

C 2.000629 1.481099 -0.263408

C 0.782653 0.932371 -0.744610

H -1.018941 -0.089498 -0.483911

H -0.546803 -0.937065 1.723227

H 2.873124 1.429769 -0.901522

H 0.621008 0.957732 -1.813313

N 3.312424 2.449520 1.517524

H 4.134899 2.327321 0.959525

H 3.307618 3.290228 2.058800

H 1.277352 0.156649 3.192686

H 1.249240 2.438431 1.458486

------

Frequencies

-327.5752 132.9850 232.5594

261.8935 343.7938 367.5421

420.5632 455.7888 499.3145

547.1560 665.5581 732.8660

770.4573 817.7273 866.0584

914.4049 943.1002 985.0469

1000.1884 1047.2621 1132.2815

1226.9544 1278.9120 1288.8334

1311.1788 1391.4694 1486.2073

1561.4919 1655.9677 1678.1860

1697.5621 3125.6774 3193.3406

3208.0835 3241.3335 3255.4791

3275.6447 3669.6939 3784.7421

Rotational constants (GHZ): 4.68003 2.20877 1.55687

Sum of electronic and zero-point Energies= -287.852797

TS7

------

C -1.888923 -0.024257 -0.048776

C -1.212119 -1.189260 -0.055451

C 0.200475 -1.235970 0.080417

C 0.967325 0.065865 0.133560

C 0.175513 1.254662 0.028955

C -1.167132 1.230512 -0.010983

H -2.962506 -0.018398 -0.127397

H -1.741127 -2.123863 -0.157542

H 0.764274 -2.143518 -0.042996

H 0.712307 2.188065 -0.034342

H -1.716631 2.155451 -0.066015

N 2.334384 0.073525 -0.185961

H 2.962818 0.167937 0.590624

H 2.615126 -0.696046 -0.768531

H 0.574214 -0.653607 1.141604

------

Frequencies

-2700.9133 148.2745 173.4180

314.8981 354.1858 415.3541

482.0202 589.9442 623.8821

657.2193 680.8978 737.4538

773.7063 799.4988 959.1896

978.4183 988.1245 991.1961

1033.2373 1134.8881 1185.4005

1197.5330 1225.8788 1298.4892

1332.3579 1360.0570 1446.2165

1492.6662 1599.5671 1640.7995

1681.6308 2263.1152 3236.7331

3241.3313 3258.2011 3270.1624

3277.4753 3616.0765 3700.2035

Rotational constants (GHZ): 5.30631 2.52190 1.74671

Sum of electronic and zero-point Energies= -287.867434

------

TS9

------

C -1.876843 0.087312 -0.050631

C -1.237741 -1.178725 -0.005791

C 0.265748 -1.203696 -0.000190

C 0.960409 0.040033 -0.003033

C 0.277750 1.216748 0.050658

C -1.157870 1.227708 -0.003643

H -2.951980 0.121483 -0.116545

H -1.753759 -2.096271 -0.219542

H 0.769441 -2.119164 -0.254984

H 0.820041 2.147587 0.082702

H -1.665342 2.178214 -0.012538

N 2.329289 -0.009206 -0.116761

H 2.808703 0.841666 0.106744

H 2.767139 -0.817803 0.281162

H -0.487980 -1.327544 1.026111

------

Frequencies

-2285.8053 204.4546 245.7813

350.2525 384.8919 481.7429

525.5099 553.7433 570.4962

597.9324 658.6185 714.9487

783.7775 790.0894 830.6769

942.7592 963.4348 1010.3446

1024.4796 1126.9164 1145.0020

1194.5238 1226.9385 1289.6113

1356.2029 1375.3781 1461.7929

1487.0696 1596.7736 1638.0754

1685.7899 2279.2301 3238.3171

3248.3085 3263.6999 3266.6854

3288.6452 3657.8845 3763.9808

Rotational constants (GHZ): 5.42849 2.54022 1.74870

Sum of electronic and zero-point Energies= -287.880388