A Theoretical Study About the Hydrogen Adducts of Diamidocarbenes and Diaminocarbenes

Supplementary Materials

A Theoretical Study about the Hydrogen Adducts of Diamidocarbenes and Diaminocarbenes

The converged geometry of 4

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.362708

C 1.267335 0.000000 1.930773

C 2.130196 0.000202 0.892349

N 1.339556 0.000311 -0.249502

H -0.854746 -0.000403 1.888858

H 1.700760 -0.000339 -1.185964

H 1.444962 0.000494 2.990494

H 3.204520 0.001051 0.872981

The converged geometry of 4 in thiophene

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358670

C 1.264152 0.000000 1.921943

C 2.123865 0.000000 0.883922

N 1.334626 0.000002 -0.252873

H -0.851273 0.000000 1.892795

H 1.701001 0.000003 -1.188728

H 1.439242 0.000000 2.981757

H 3.197729 0.000000 0.858114

The converged geometry of 4 in acetonitrile

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358010

C 1.265068 0.000000 1.918005

C 2.123290 0.000000 0.878101

N 1.333085 0.000002 -0.257418

H -0.848292 0.000000 1.898139

H 1.702646 0.000003 -1.192764

H 1.439861 0.000000 2.977869

H 3.197047 0.000000 0.848214

The converged geometry of 4I

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.360076

C 1.271576 0.000000 1.901466

C 2.121691 -0.000045 0.854930

N 1.331212 -0.000048 -0.278715

H 3.196717 -0.000083 0.820562

H 1.458238 0.000025 2.960720

C 1.856234 -0.000065 -1.627655

C -1.212722 0.000084 2.150388

H 1.009475 -0.000104 -2.306609

H 2.463352 0.887771 -1.803568

H 2.463394 -0.887882 -1.803515

H -2.050788 0.000220 1.460732

H -1.260563 -0.887774 2.780636

H -1.260357 0.887879 2.780734

The converged geometry of 4II

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358272

C 1.264817 0.000000 1.938382

C 2.131543 -0.000025 0.902009

N 1.336865 -0.000019 -0.240271

H -0.854987 0.000040 1.885982

H 1.705026 -0.000046 -1.175113

C 1.478985 -0.000033 3.409409

C 3.617259 -0.000060 0.852654

H 1.036541 0.881958 3.875525

H 1.036682 -0.882130 3.875457

H 2.542527 0.000044 3.638577

H 3.997817 0.882070 0.335010

H 4.030898 -0.000276 1.858911

H 3.997750 -0.882020 0.334673

The converged geometry of 4III

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358152

C 1.272978 0.000000 1.934224

C 2.130610 -0.017166 0.906387

N 1.336244 -0.005277 -0.242966

H 3.203808 -0.028340 0.877820

H 1.436814 0.004819 2.995268

C 1.858169 -0.108239 -1.570426

C -1.212160 0.103799 2.109728

F -0.985776 -0.304755 3.357615

F -1.637429 1.360198 2.166562

F -2.164196 -0.635918 1.583123

F 1.172850 0.636610 -2.410916

F 3.128213 0.294616 -1.570474

F 1.832317 -1.363375 -2.002259

The converged geometry of 4IV

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358093

C 1.258102 0.000000 1.929753

C 2.123793 0.000425 0.892066

N 1.336004 0.000368 -0.243270

H -0.851702 -0.000661 1.895595

H 1.712304 0.000030 -1.177465

C 1.365388 -0.000086 3.418662

C 3.607823 0.000885 0.730833

F 0.742600 1.073149 3.923013

F 0.742203 -1.073234 3.922821

F 2.609862 -0.000462 3.863680

F 3.992157 1.075019 0.028947

F 4.268604 -0.000504 1.875468

F 3.992550 -1.071345 0.026260

The converged geometry of 4V

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358087

C 1.270642 0.000000 1.884880

C 2.123508 -0.014598 0.831300

N 1.328988 -0.005964 -0.298818

C 1.775578 0.011213 -1.687328

C -1.231277 0.008254 2.135422

C 1.527756 0.019510 3.353829

C 3.622766 -0.037381 0.846302

H 0.876735 0.100580 -2.287508

H 2.430295 0.860228 -1.868576

H 2.300526 -0.906905 -1.937347

H -2.040194 -0.177720 1.437355

H -1.203792 -0.773649 2.891787

H -1.371801 0.972454 2.618470

F 4.134596 1.135021 1.228614

F 4.091486 -0.970785 1.674058

F 4.117193 -0.304476 -0.367153

F 2.805518 0.250689 3.631031

F 1.185404 -1.139849 3.930363

F 0.803812 0.974431 3.953290

The converged geometry of 4VI

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.357543

C 1.281608 0.000000 1.945721

C 2.143417 -0.000219 0.913295

N 1.335693 -0.000197 -0.242581

C -1.200304 0.000839 2.126066

C 1.877362 -0.001034 -1.560894

C 1.524380 0.000129 3.413370

C 3.630826 -0.000436 0.889886

F -1.245093 1.074349 2.920765

F -1.245002 -1.070876 2.923176

F -2.265094 -0.000064 1.361557

F 2.653553 1.070739 -1.747404

F 0.934890 -0.000273 -2.471935

F 2.651371 -1.074486 -1.746874

H 4.018338 -0.881447 0.379735

H 4.010472 -0.000701 1.908244

H 4.018606 0.880615 0.380025

H 2.594191 0.001102 3.604915

H 1.092649 -0.881304 3.885883

H 1.091080 0.880759 3.885956

The converged geometry of 4VII

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.358545

C 1.275752 0.000000 1.911616

C 2.130249 0.000020 0.862472

N 1.330431 0.000020 -0.274945

C -1.213531 -0.000070 2.144098

C 1.854124 0.000113 -1.622350

C 1.518119 0.000033 3.378610

C 3.615937 -0.000019 0.802924

H -2.047880 -0.000140 1.449861

H -1.268528 -0.886630 2.777033

H -1.268663 0.886501 2.777010

H 1.005389 0.000052 -2.298926

H 2.462716 0.886747 -1.804339

H 2.462889 -0.886385 -1.804409

H 3.996255 -0.880607 0.281610

H 3.996323 0.880502 0.281547

H 4.034160 -0.000007 1.807348

H 2.586401 0.000422 3.584891

H 1.084229 0.880426 3.856617

H 1.084856 -0.880682 3.856598

The converged geometry of 4VIII

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.357301

C 1.279856 0.000000 1.915783

C 2.131464 0.038277 0.873612

N 1.330251 0.012131 -0.269598

C -1.245075 0.029735 2.096165

C 1.807487 -0.024179 -1.636253

C 1.597665 -0.110269 3.386724

C 3.634609 0.168537 0.891608

F -2.219921 0.428649 1.316433

F -1.543272 -1.167707 2.573382

F -1.128373 0.876935 3.111286

F 0.855507 -0.444936 -2.432578

F 2.198666 1.175100 -2.035361

F 2.837658 -0.857447 -1.715079

F 4.235284 -1.016255 0.883764

F 4.059015 0.857099 -0.165109

F 4.026568 0.828989 1.976999

F 1.694016 1.081998 3.964376

F 0.655176 -0.804277 4.019925

F 2.747696 -0.754173 3.562363

The converged geometry of 5

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.342360

C 1.323541 0.000000 1.979166

C 2.221550 -0.342196 0.784142

N 1.295179 -0.119223 -0.333708

H -0.838385 0.184804 1.860272

H 1.572342 -0.258002 -1.287287

H 1.389595 -0.738020 2.776140

H 1.557681 0.982832 2.393394

H 3.095793 0.302681 0.720700

H 2.555741 -1.381364 0.813136

The converged geometry of 6

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.365841

C 1.257214 0.000000 1.959626

C 2.207647 -0.000001 0.739296

N 1.324512 -0.000001 -0.334279

H -0.854867 0.000000 1.898399

H 1.631610 -0.000003 -1.293482

H 1.543913 0.000000 3.114097

H 3.397219 -0.000002 0.735053

The converged geometry of 7

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.352819

C 1.073721 0.000000 2.248620

C 2.439921 -0.000009 1.615414

C 2.488824 -0.000003 0.109943

N 1.245814 -0.000005 -0.528953

H -0.904356 0.000003 1.804033

H 1.307234 -0.000009 -1.537677

H 2.988107 0.870367 1.978320

H 2.988089 -0.870401 1.978311

O 0.898011 0.000006 3.434812

O 3.512975 -0.000001 -0.514068

The converged geometry of 8

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.351759

C 0.962138 0.000000 2.388058

C 2.401713 0.176501 2.006766

C 2.616855 1.357310 1.065943

C 2.340059 1.009221 -0.366234

N 1.127348 0.344568 -0.661519

H -0.906504 -0.223887 1.742520

H 1.031760 0.262173 -1.665831

H 2.752843 -0.749418 1.542949

H 2.948255 0.310749 2.935669

H 1.971713 2.193367 1.349746

H 3.645362 1.704452 1.101399

O 3.077998 1.287488 -1.271837

O 0.589954 -0.166527 3.517594

The converged geometry of 4H

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.467475

C 1.377739 0.000000 1.818515

C 2.102561 0.410321 0.784697

N 1.247507 0.707001 -0.311920

H -0.522328 -0.771193 1.857040

H 1.628337 0.447317 -1.210207

H 1.690598 -0.181285 2.831977

H 3.151818 0.646078 0.748013

H 0.015818 -1.030141 -0.398174

H -0.865892 0.526208 -0.398145

The converged geometry of 4H in thiophene

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.473326

C 1.393256 0.000000 1.795685

C 2.142654 0.228250 0.723133

N 1.343039 0.407471 -0.448793

H -0.165318 -1.026934 -0.333277

H -0.779592 0.636389 -0.409928

H 3.218110 0.269392 0.660719

H 1.718985 -0.186615 2.806247

H -0.464125 0.810961 1.871056

H 1.380118 1.370378 -0.769314

The converged geometry of 4H in acetonitrile

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.474116

C 1.393910 0.000000 1.796800

C 2.143868 0.226286 0.724183

N 1.344680 0.404342 -0.449116

H -0.168793 -1.026479 -0.333853

H -0.777107 0.639316 -0.408966

H 3.219332 0.273429 0.663980

H 1.719621 -0.178584 2.808965

H -0.459745 0.815937 1.867567

H 1.380455 1.369063 -0.765278

The converged geometry of 4IH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.457220

C 1.373182 0.000000 1.794134

C 2.095650 -0.392626 0.747350

N 1.243611 -0.676868 -0.344588

C 1.735292 -0.373929 -1.669969

C -0.831473 1.023630 2.049634

H 1.687608 0.182833 2.807696

H 3.148497 -0.611577 0.690993

H 0.026435 1.050818 -0.376482

H -0.873883 -0.503866 -0.413903

H 1.033031 -0.744629 -2.416430

H 2.690489 -0.872183 -1.827063

H 1.869937 0.707265 -1.822475

H -1.876050 0.839704 1.798996

H -0.559191 2.030073 1.698487

H -0.732741 0.991382 3.133400

The converged geometry of 4IIH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.465826

C 1.381597 0.000000 1.828891

C 2.112833 -0.405142 0.791577

N 1.253301 -0.693279 -0.311707

H -0.509534 0.783557 1.852424

H 1.642342 -0.407909 -1.200660

C 1.753936 0.254087 3.243290

C 3.554565 -0.743194 0.688121

H 1.450022 1.255191 3.559674

H 1.254920 -0.460234 3.901934

H 2.828288 0.167977 3.389205

H 4.038186 -0.177232 -0.112174

H 4.077719 -0.525409 1.616450

H 3.680675 -1.803527 0.458166

H -0.861276 -0.534246 -0.398723

H 0.003141 1.028949 -0.398851

The converged geometry of 4IIIH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.472365

C 1.365389 0.000000 1.876943

C 2.135394 0.320245 0.851304

N 1.331206 0.552597 -0.300693

C 1.864462 0.177732 -1.542757

C -0.846183 -0.947491 2.067271

F 1.016922 0.504212 -2.517302

F 2.094028 -1.144321 -1.661723

F 3.026577 0.788415 -1.751448

F -2.091410 -0.785938 1.622524

F -0.507657 -2.224232 1.802803

F -0.833834 -0.814249 3.389779

H 1.625061 -0.145214 2.910084

H 3.193794 0.506678 0.820652

H -0.788944 0.631599 -0.395472

H -0.097081 -1.022353 -0.391559

The converged geometry of 4IVH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.468678

C 1.360808 0.000000 1.833090

C 2.107456 0.381111 0.798097

N 1.275574 0.660743 -0.300462

H -0.538357 -0.749244 1.881658

H 1.670966 0.443151 -1.203726

C 1.715281 -0.183792 3.264758

C 3.570561 0.694646 0.722362

F 1.275973 0.828447 4.016971

F 1.138327 -1.297457 3.749201

F 3.027305 -0.289957 3.448056

F 3.919713 1.707972 1.514874

F 4.329882 -0.350561 1.050513

F 3.891422 1.037864 -0.533561

H -0.023265 -1.025654 -0.400929

H -0.839893 0.565370 -0.397027

The converged geometry of 4VH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.451649

C 1.361480 0.000000 1.811016

C 2.099547 -0.389179 0.757322

N 1.249320 -0.660568 -0.331813

C 1.681079 -0.437757 -1.700825

C -0.934849 0.946697 2.034807

C 1.675833 0.286571 3.245994

C 3.550955 -0.702139 0.569105

H 1.887436 0.621359 -1.898370

H 2.567632 -1.023335 -1.923571

H 0.881142 -0.769668 -2.360884

H -1.926580 0.717226 1.648089

H -0.961437 0.843665 3.115158

H -0.684119 1.982738 1.775774

F 4.105191 0.159152 -0.303555

F 4.278392 -0.657514 1.672274

F 3.695740 -1.925209 0.039435

F 2.927534 0.050458 3.600454

F 0.885423 -0.442184 4.047000

F 1.421977 1.576775 3.531329

H -0.861912 -0.528082 -0.408234

H 0.001580 1.045014 -0.385906

The converged geometry of 4VIH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.475543

C 1.382262 0.000000 1.850001

C 2.132537 -0.370181 0.813798

N 1.294179 -0.583377 -0.348804

C -0.854523 0.947809 2.048961

C 1.224177 -1.918544 -0.799590

C 1.793444 0.329290 3.240134

C 3.604423 -0.565917 0.724576

F -0.425709 2.222841 1.916932

F -1.015074 0.741318 3.354806

F -2.049591 0.888047 1.460769

F 2.426518 -2.343729 -1.184165

F 0.394962 -2.012343 -1.839234

F 0.782323 -2.792764 0.123896

H 3.875770 -1.621673 0.706878

H 4.100928 -0.100256 1.572189

H 3.981352 -0.113446 -0.192294

H 2.868901 0.222350 3.346566

H 1.303590 -0.342485 3.945191

H 1.514882 1.348956 3.508195

H -0.827209 -0.577891 -0.399718

H -0.041566 1.025774 -0.377722

The converged geometry of 4VIIH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.464779

C 1.386486 0.000000 1.780569

C 2.102678 -0.403650 0.726813

N 1.232406 -0.667783 -0.392690

C 3.558234 -0.674974 0.597169

C 1.827289 0.351782 3.156370

C 1.057872 -2.104553 -0.613228

C -0.816144 1.048171 2.035077

H 0.027497 1.042045 -0.360231

H -0.877013 -0.501189 -0.409397

H 3.756476 -1.736514 0.429358

H 4.095489 -0.375972 1.494638

H 3.969934 -0.129344 -0.253306

H 2.894374 0.184306 3.277647

H 1.296915 -0.263220 3.886645

H 1.616543 1.396666 3.393585

H 0.375727 -2.260168 -1.447946

H 0.668319 -2.621561 0.273121

H 2.016036 -2.546512 -0.881450

H -1.851637 0.902008 1.728149

H -0.497369 2.049536 1.705211

H -0.782417 1.009624 3.122385

The converged geometry of 4VIIIH

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.460994

C 1.387521 0.000000 1.816641

C 2.128218 0.352818 0.765643

N 1.302818 0.617760 -0.341382

C 3.633752 0.491297 0.736697

C 1.841312 -0.434694 3.184617

C -0.763912 1.053862 2.040139

C 1.730931 0.531129 -1.689239

F 4.082890 0.934288 1.906431

F 4.008046 1.360555 -0.197118

F 4.224693 -0.672143 0.481236

F 2.975755 -1.133999 3.104549

F 0.923903 -1.215212 3.746202

F 2.063299 0.595601 4.000219

F -0.364221 2.275958 1.656007

F -0.676720 1.004553 3.359384

F -2.036050 0.930009 1.677738

F 2.625886 -0.442346 -1.886441

F 2.270045 1.659194 -2.126268

F 0.667645 0.268160 -2.450050

H -0.831956 0.570489 -0.398976

H -0.035023 -1.029636 -0.362600

The converged geometry of 5H

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.462034

C 1.429047 0.000000 1.800859

C 2.167892 -0.546744 0.537039

N 1.118697 -0.825628 -0.452231

H -0.411408 -0.870641 1.777715

H 0.845068 -1.798197 -0.374040

H 1.610389 -0.598798 2.691178

H 2.848139 0.208087 0.142236

H -0.947638 -0.350629 -0.402622

H 0.169830 1.023724 -0.342180

H 1.751588 1.019206 2.014325

H 2.749394 -1.443851 0.739986

The converged geometry of 6H

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.444110

C 1.240149 0.000000 2.006960

C 2.214888 -0.000001 0.812561

N 1.414563 -0.000001 -0.289497

H -0.839948 0.000001 1.996485

H 1.787417 -0.000002 -1.223106

O 1.525426 0.000000 3.171182

O 3.412640 0.000000 0.858385

H -0.491842 -0.889593 -0.401264

H -0.491840 0.889594 -0.401264

The converged geometry of 7H

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.444450

C 1.156227 0.000000 2.166782

C 2.403806 -0.082667 1.306289

C 2.255991 -0.966966 0.081511

N 1.018576 -0.901111 -0.487065

O 1.184363 0.058292 3.372539

O 3.145687 -1.662381 -0.346081

H 3.236597 -0.430842 1.906897

H 2.633098 0.930056 0.957416

H -0.969825 -0.343228 -0.351271

H 0.161824 1.012847 -0.387015

H 0.866867 -1.445739 -1.320040

H -0.862325 0.075051 1.958430

The converged geometry of 8H

C 0.000000 0.000000 0.000000

N 0.000000 0.000000 1.438234

C 1.153304 0.000000 2.177235

C 2.423258 -0.145219 1.366712

C 2.757733 1.148453 0.617364

C 1.827315 1.698685 -0.455586

N 0.566014 1.190926 -0.604197

H -0.827762 0.288464 1.936595

H 0.035170 1.662978 -1.319756

H 2.356328 -0.989164 0.679719

H 3.219023 -0.354610 2.076352

H 2.861375 1.962029 1.338582

H 3.726933 1.056411 0.129739

O 2.198334 2.627431 -1.139352

O 1.147532 0.149329 3.376838

H 0.514172 -0.893071 -0.356356

H -1.029898 -0.070778 -0.338027