Manuscript No ... "A new Method for Generating Nitrenium Cations, Amide Anions and Aminyl Radicals under Stable Conditions" by Krzysztof Piech, Thomas Bally,* Adam Sikora, and Andrzej Marcinek*. SUPPORTING INFORMATION ********************* Full quote of the Gaussian Program (Reference 36): M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Rev. C-01, Gaussian, Inc., Wallingford CT, 2005. Energies and geometries of all stationary points located and characterized in the course of the above study; "r" denotes: radical Note: All structures are optimized in vacuum, with energies in hartree. ------------------------------------------------------ 1 - B3LYP/6-31G* Symmetry: c1 0 1 6 -2.681174 -1.662609 -0.757227 6 -3.796159 -1.079239 -0.153133 6 -3.660066 0.147452 0.499828 6 -2.423220 0.786536 0.561467 6 -1.310205 0.202370 -0.058514 6 -1.441909 -1.025635 -0.719396 7 -0.046077 0.861008 -0.032826 6 1.189244 0.133062 0.027508 6 2.184234 0.348697 -0.930911 6 3.380255 -0.363499 -0.850637 6 3.583495 -1.289695 0.174431 6 2.585802 -1.501354 1.128242 6 1.390489 -0.787042 1.061478 7 -0.094248 2.232960 -0.018041 8 0.985118 2.792871 0.051866 1 -2.773680 -2.615664 -1.270727 1 -4.760689 -1.577631 -0.186696 1 -4.519103 0.607336 0.980620 1 -2.311957 1.731626 1.079493 1 -0.579963 -1.472678 -1.203231 1 2.021615 1.067848 -1.725530 1 4.153976 -0.194399 -1.594194 1 4.516303 -1.843802 0.230259 1 2.738399 -2.218647 1.929782 1 0.611708 -0.939001 1.802544 Electronic energy= -647.945308 Sum of electronic and zero-point Energies= -647.750164 Sum of electronic and thermal Enthalpies= -647.737352 Sum of electronic and thermal Free Energies= -647.789579 RCCSD -645.970711 ------------------------------------------------------ 1r+ - B3LYP/6-31G* Symmetry: c1 1 2 6 -2.724830 -1.722253 -0.628382 6 -3.835157 -1.010520 -0.142280 6 -3.675677 0.285339 0.381461 6 -2.427180 0.874591 0.428219 6 -1.293909 0.156333 -0.057272 6 -1.465306 -1.155240 -0.593540 7 -0.049556 0.731196 -0.045427 6 1.167927 0.055626 -0.013234 6 2.239882 0.489229 -0.825597 6 3.458024 -0.171688 -0.750102 6 3.628677 -1.244012 0.136142 6 2.569068 -1.669475 0.948978 6 1.340984 -1.029870 0.881513 7 -0.072780 2.362998 0.054319 8 0.986695 2.810462 0.189457 1 -2.857679 -2.712275 -1.052413 1 -4.822525 -1.460295 -0.177477 1 -4.536705 0.823810 0.763695 1 -2.303613 1.860358 0.857582 1 -0.610754 -1.676735 -1.009059 1 2.098725 1.294619 -1.536910 1 4.277340 0.141042 -1.389178 1 4.588907 -1.747048 0.194628 1 2.710243 -2.491426 1.643437 1 0.523831 -1.323464 1.532351 Electronic energy= -647.669296 Sum of electronic and zero-point Energies= -647.475470 Sum of electronic and thermal Enthalpies= -647.462026 Sum of electronic and thermal Free Energies= -647.515675 RCCSD -645.693120 TDDFT B3LYP/6-31G* excited state energies and transition moments: 1.3696 eV 905.25 nm f=0.0293 1.4762 eV 839.88 nm f=0.0197 1.5892 eV 780.17 nm f=0.0133 1.9801 eV 626.16 nm f=0.0572 2.2102 eV 560.96 nm f=0.0167 2.5114 eV 493.68 nm f=0.0398 2.9822 eV 415.75 nm f=0.0134 3.0856 eV 401.82 nm f=0.0049 3.1265 eV 396.56 nm f=0.0435 3.3444 eV 370.72 nm f=0.0035 3.4099 eV 363.60 nm f=0.0081 3.5288 eV 351.35 nm f=0.0103 3.6919 eV 335.82 nm f=0.0058 3.8287 eV 323.82 nm f=0.0081 3.9278 eV 315.66 nm f=0.0616 4.0640 eV 305.08 nm f=0.0019 4.1245 eV 300.61 nm f=0.0640 4.1665 eV 297.57 nm f=0.0478 ------------------------------------------------------ 1+....NOr (the most stable complex) - B3LYP/6-31G* Symmetry: c1 1 2 6 -2.155842 -1.479764 -0.799803 6 -3.156950 -1.344715 0.182263 6 -2.947646 -0.550927 1.321505 6 -1.743408 0.109006 1.482611 6 -0.672977 -0.090817 0.549110 6 -0.929545 -0.867288 -0.632653 7 0.475269 0.533045 0.855910 6 3.400865 -1.227307 -0.575881 6 4.319590 -0.161404 -0.523626 6 3.954427 1.083102 0.015063 6 2.674509 1.266583 0.501478 6 1.697925 0.224547 0.385409 6 2.104452 -1.049176 -0.136420 1 -2.359024 -2.052795 -1.699168 1 -4.112082 -1.842432 0.041998 1 -3.736605 -0.438698 2.058234 1 -1.545037 0.738806 2.343603 1 -0.180154 -0.916030 -1.414843 1 3.723042 -2.197385 -0.940822 1 5.336053 -0.316971 -0.873309 1 4.682211 1.885979 0.070300 1 2.356812 2.205851 0.941504 1 1.418022 -1.887863 -0.102879 8 -3.694065 1.501866 -1.234604 7 -2.661428 1.943464 -1.021927 Electronic energy= -647.658910 Sum of electronic and zero-point Energies= -647.466750 Sum of electronic and thermal Enthalpies= -647.452044 Sum of electronic and thermal Free Energies= -647.510598 ------------------------------------------------------ 1r- - B3LYP/6-31G* Symmetry: c1 -1 1 6 3.017104 -1.704092 0.160582 6 4.044677 -0.780929 -0.055657 6 3.703675 0.578079 -0.110921 6 2.389168 0.999298 0.035083 6 1.318596 0.078140 0.235794 6 1.692069 -1.298491 0.299018 7 0.068045 0.575022 0.465949 6 -1.087699 -0.114406 0.244847 6 -2.253992 0.319366 0.938985 6 -3.495443 -0.272535 0.735408 6 -3.652610 -1.324916 -0.173962 6 -2.527472 -1.755646 -0.888260 6 -1.280926 -1.169883 -0.696787 7 -0.287187 2.629275 -0.595187 8 -1.420626 2.927130 -0.429405 1 3.251122 -2.767357 0.228283 1 5.076598 -1.106368 -0.170079 1 4.483358 1.324053 -0.268864 1 2.137413 2.054223 0.001217 1 0.925047 -2.042052 0.493613 1 -2.134914 1.132231 1.649331 1 -4.356434 0.090839 1.296718 1 -4.623393 -1.792009 -0.327166 1 -2.627563 -2.559810 -1.618170 1 -0.435127 -1.504780 -1.289758 Electronic energy= -647.969712 Sum of electronic and zero-point Energies= -647.779867 Sum of electronic and thermal Enthalpies= -647.765649 Sum of electronic and thermal Free Energies= -647.821918 RCCSD -645.974974 TDDFT B3LYP/6-31G* excited state energies and transition moments: 0.7300 eV 1698.43 nm f=0.0000 2.0433 eV 606.79 nm f=0.0058 2.8061 eV 441.83 nm f=0.0171 2.8899 eV 429.02 nm f=0.0097 3.0613 eV 405.00 nm f=0.0004 3.1560 eV 392.85 nm f=0.0000 3.3065 eV 374.97 nm f=0.0153 3.3660 eV 368.35 nm f=0.0056 3.6308 eV 341.48 nm f=0.0216 4.0074 eV 309.39 nm f=0.3744 4.0465 eV 306.40 nm f=0.0038 ------------------------------------------------------ 1+ - B3LYP/6-31G* Symmetry: c2 1 1 6 0.383305 2.765720 -1.385985 6 -0.117237 3.804535 -0.575152 6 -0.520532 3.565886 0.748748 6 -0.424191 2.289677 1.268040 6 0.000000 1.199416 0.437587 6 0.440854 1.475616 -0.901827 7 0.000000 0.000000 1.041177 6 -0.383305 -2.765720 -1.385985 6 0.117237 -3.804535 -0.575152 6 0.520532 -3.565886 0.748748 6 0.424191 -2.289677 1.268040 6 0.000000 -1.199416 0.437587 6 -0.440854 -1.475616 -0.901827 1 0.746292 2.990637 -2.383695 1 -0.156626 4.814884 -0.972238 1 -0.879437 4.384130 1.364157 1 -0.707185 2.061179 2.290073 1 0.898493 0.688808 -1.490883 1 -0.746292 -2.990637 -2.383695 1 0.156626 -4.814884 -0.972238 1 0.879437 -4.384130 1.364157 1 0.707185 -2.061179 2.290073 1 -0.898493 -0.688808 -1.490883 Electronic energy= -517.766161 Sum of electronic and zero-point Energies= -517.579045 Sum of electronic and thermal Enthalpies= -517.568262 Sum of electronic and thermal Free Energies= -517.614473 RCCSD -516.120174 TDDFT B3LYP/6-31G* excited state energies and transition moments: 1.9791 eV 626.47 nm f=0.1008 2.4723 eV 501.50 nm f=0.0119 2.5265 eV 490.74 nm f=0.0034 3.4701 eV 357.29 nm f=0.6377 4.2533 eV 291.50 nm f=0.0056 4.6504 eV 266.61 nm f=0.0032 4.8868 eV 253.71 nm f=0.0027 4.9086 eV 252.58 nm f=0.0000 5.2738 eV 235.09 nm f=0.0034 5.4524 eV 227.39 nm f=0.0126 ------------------------------------------------------ 1r - B3LYP/6-31G* Symmetry: c2 0 2 6 0.546664 2.728404 -1.345575 6 0.005429 3.802252 -0.629436 6 -0.516655 3.586592 0.653187 6 -0.499438 2.317066 1.209853 6 0.000000 1.202602 0.481835 6 0.542133 1.445732 -0.811629 7 0.000000 0.000000 1.133080 6 -0.546664 -2.728404 -1.345575 6 -0.005429 -3.802252 -0.629436 6 0.516655 -3.586592 0.653187 6 0.499438 -2.317066 1.209853 6 0.000000 -1.202602 0.481835 6 -0.542133 -1.445732 -0.811629 1 0.982727 2.897511 -2.326873 1 0.008165 4.800415 -1.058129 1 -0.923434 4.419254 1.220817 1 -0.883475 2.131705 2.208117 1 0.999069 0.628347 -1.359125 1 -0.982727 -2.897511 -2.326873 1 -0.008165 -4.800415 -1.058129 1 0.923434 -4.419254 1.220817 1 0.883475 -2.131705 2.208117 1 -0.999069 -0.628347 -1.359125 Electronic energy= -518.014346 Sum of electronic and zero-point Energies= -517.829093 Sum of electronic and thermal Enthalpies= -517.818280 Sum of electronic and thermal Free Energies= -517.865258 RCCSD -516.365681 TDDFT B3LYP/6-31G* excited state energies and transition moments: 1.6530 eV 750.07 nm f=0.0444 2.8265 eV 438.65 nm f=0.0038 2.8877 eV 429.35 nm f=0.0014 3.1149 eV 398.03 nm f=0.0366 3.6813 eV 336.80 nm f=0.0021 4.0053 eV 309.55 nm f=0.0493 4.1361 eV 299.76 nm f=0.0079 4.1372 eV 299.68 nm f=0.3606 4.2057 eV 294.80 nm f=0.0040 4.4555 eV 278.27 nm f=0.1133 ------------------------------------------------------ 1- - B3LYP/6-31G* Symmetry: c1 -1 1 6 0.534702 2.781771 -1.345136 6 0.059067 3.873248 -0.609271 6 -0.435004 3.624372 0.680688 6 -0.460075 2.340698 1.205055 6 0.000000 1.199286 0.473396 6 0.508138 1.487151 -0.834893 7 0.000000 0.000000 1.108682 6 -0.534702 -2.781771 -1.345136 6 -0.059067 -3.873248 -0.609271 6 0.435004 -3.624372 0.680688 6 0.460075 -2.340698 1.205055 6 0.000000 -1.199286 0.473396 6 -0.508138 -1.487151 -0.834893 1 0.943384 2.943586 -2.344087 1 0.076865 4.880272 -1.020921 1 -0.806059 4.452694 1.286132 1 -0.835775 2.157498 2.209573 1 0.912921 0.673874 -1.430117 1 -0.943384 -2.943586 -2.344087 1 -0.076865 -4.880272 -1.020921 1 0.806059 -4.452694 1.286132 1 0.835775 -2.157498 2.209573 1 -0.912921 -0.673874 -1.430117 Electronic energy= -518.067063 Sum of electronic and zero-point Energies= -517.883521 Sum of electronic and thermal Enthalpies= -517.872631 Sum of electronic and thermal Free Energies= -517.919038 RCCSD -516.404724 TDDFT B3LYP/6-31G* excited state energies and transition moments: 3.4588 eV 358.46 nm f=0.0184 3.5788 eV 346.44 nm f=0.0192 3.8360 eV 323.21 nm f=0.6337 4.5480 eV 272.61 nm f=0.0017 4.7604 eV 260.45 nm f=0.0131 4.8024 eV 258.17 nm f=0.0092 5.3217 eV 232.98 nm f=0.0160 5.3579 eV 231.40 nm f=0.0004 5.4963 eV 225.58 nm f=0.0060 5.9163 eV 209.57 nm f=0.0903 ------------------------------------------------------ NOr - B3LYP/6-31G* Symmetry: c*V 0 2 7 0.000000 0.000000 -0.617973 8 0.000000 0.000000 0.540727 Electronic energy= -129.888156 Sum of electronic and zero-point Energies= -129.883620 Sum of electronic and thermal Enthalpies= -129.880315 Sum of electronic and thermal Free Energies= -129.903626 RCCSD -129.563051 ------------------------------------------------------ Attachment converted: IMac G4 HD:krzysztof.piech.vcf (TEXT/MSWD) (01CCFD22)