Photostimulated Reduction of Nitriles by SmI 2 Chintada Nageswara Rao and Shmaryahu Hoz * Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel E-mail: shoz@mail.biu.ac.il Supporting information Table of contents (1) Complete reference 14 S2 (2) NBO charges S3 (3) Experimental setup for irradiation S4 (4) Spectral data: 1 H, 13 C NMR and HRMS (CI/EI) S5-S14 (5) Archive files S15-S42 S1
(1) Complete reference 14 Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009. S2
(2) Table S1: NBO charges for SN; syn, clinal and anti conformations. syn C H H C H H C C N N Gas P. -0.80 0.25 0.21-0.80 0.25 0.21 0.26 0.26-0.42-0.42 THF -0.67 0.23 0.20-0.63 0.26 0.25 0.00 0.31-0.55-0.42 anti C H H C H H C C N N Gas P. -0.69 0.24 0.24-0.69 0.24 0.24 0.17 0.17-0.46-0.46 THF -0.67 0.24 0.24-0.67 0.24 0.24 0.16 0.16-0.47-0.47 S3
(3) Experimental setup for irradiation Figure S1 S4
(4) Spectral data: 1 H, 13 C NMR and HRMS (CI/EI) Crude reaction mixture, 1 H& 13 C (300&75 MHz, CDCl 3 ) NMR and HRMS (CI) of benylamine NH 2 S5
NH 2 calc.mass[m] + =107.0735 obs.mass[m] + =107.0839 S6
Crude reaction mixture, 1 H& 13 C (300&75 MHz, CDCl 3 ) NMR of 2- phenylethylamine NH 2 S7
Crude reaction mixture, 1 H& 13 C (300&75 MHz, CDCl 3 ) NMR and HRMS (CI) of octylamine NH 2 S8
NH 2 calc.mass[m+h] + =130.1596 obs.mass[m+h] + =130.1569 S9
Crude reaction mixture, 1 H& 13 C (300&75 MHz, CDCl 3 ) NMR and HRMS (CI) of isoindolone NH O S10
O NH calc.mass[m] + =133.0528 obs.mass[m] + =133.0745 S11
Crude reaction mixture, 1 H (300 MHz, CDCl 3 ) NMR and MS (EI) of α-amino-mtolunitrile NH 2 CN NH 2 CN calc.mass[m] + =132.0687 obs.mass[m] + =132.0757 S12
Crude reaction mixture, 1 H& 13 C (300&75 MHz, CDCl 3 ) NMR and HRMS (CI) of α-amino-p-tolunitrile NH 2 CN S13
NH 2 CN calc.mass[m] + =132.0687 obs.mass[m] + =132.0651 S14
(5) Archive files Gaussian Archives p-dcn In the gas phase p-dcn-b3lyp 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\22-Dec- 2011\0\\#B3LYP/6-31+G*OPTnosymm\\1,4-Ph-dCN\\0,1\C,0.1919752445,- 0.221071081,0.4026382663\C,1.507441111,- 0.4222131188,0.8575261745\C,2.2867542433,0.6668547379,1.2316744111\C,1.758 1501439,1.9677939364,1.1546948235\C,0.4427111734,2.1689353717,0.6997825992 \C,-0.3366123001,1.0798537319,0.3256338141\H,1.9101456357,- 1.4282321217,0.9150646639\H,0.0399958863,3.1749476331,0.6422014491\H,- 1.3521936769,1.2293496271,- 0.0262042472\C,2.5622413245,3.0918113936,1.5411023862\N,3.213907754,4.0033 506115,1.8544065687\H,3.3023460026,0.5173880145,1.5834947434\C,- 0.6120644868,-1.345116984,0.0162048162\N,-1.2637287455,-2.2565890723,- 0.297299119\\Version=EM64L-G09RevA.02\HF=-416.7472804\RMSD=9.852e- 09\RMSF=1.111e-04\Dipole=-0.0000241,- 0.0000164,0.0000986\Quadrupole=2.4819288,-7.0932894,4.611 3607,-15.5311701,-2.6676573,-6.7298402\PG=C01 [X(C8H4N2)]\\@ In THF p-dcn-b3lyp-thf 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\22-Dec- 2011\0\\#B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph-dcn in THF\\0,1\C,0.1947017728,-0.2171451942,0.4039985285\C,1.5096145564,- 0.4240232196,0.8580828665\C,2.2890422201,0.6649912108,1.2321587647\C,1.755 4469814,1.9638664859,1.1532899691\C,0.4405384663,2.1707439297,0.6992050478 \C,-0.3388912452,1.081726673,0.3251282815\H,1.9130416904,-1.4292199366,0.916377532\H,0.0371071331,3.1759388299,0.6409075067\H,-1.3539475503,1. 2324653108,-0.0263386544\C,2.5594235948,3.0881395033,1.5398397024\N,3. 2112037709,3.9999172151,1.8533578239\H,3.3040993754,0.514257891,1.5836 254198\C,-0.6092575672,-1.3414257414,0.0174347778\N,-1.2610538889,-2.2 53170278,-0.2961462162\\Version=EM64L-G09RevA.02\HF=-16.7579684\RMSD= 3.611e-09\RMSF=6.238e-05\Dipole=0.0000006,-0.0000173,0.0000489\Quadrup ole=2.817342,-8.6225402,5.8051982,-18.4294448,-3.3573346,-8.0422249\pg =C01 [X(C8H4N2)]\\@ Radical anion p-dcn-radical anion-b3lyp 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\22-Dec- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\1,4-ph-dcn radicalanion\\-1,2\c,0.1695 S15
31517,-0.2524584551,0.391955566\C,1.5199353649,-0.4221511424,0.8620726 841\C,2.2900247993,0.6540294458,1.2316007681\C,1.7806118792,1.99919003 97,1.1653141099\C,0.4302091475,2.1688819046,0.6951981983\C,-0.33988070 56,1.0927008011,0.3256701762\H,1.9311977337,-1.4273227326,0.9228946056 \H,0.0189454932,3.1740528203,0.6343745172\H,-1.3569747036,1.2512279947,-0.0258681811\C,2.5678535689,3.0998737745,1.5438414052\N,3.2286510616,4.0237115536,1.8617260571\H,3.3071194915,0.4955042944,1.5831381877\C, -0.6177134552,-1.353142969,0.013437398\N,-1.2784418825,-2.2770346498,- 0.3044341422\\Version=EM64L-G09RevA.02\HF=-416.7930682\S2=0.758675\S2-1=0.\S2A=0.750051\RMSD=9.329e-09\RMSF=6.150e-05\Dipole=-0.0000383,0.00 00309,-0.0000099\Quadrupole=1.5082925,-14.3742486,12.8659561,-28.15880 26,-9.810366,-14.0785204\PG=C01 [X(C8H4N2)]\\@ Radical anion in THF p-dcn-radical anion-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\22-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph-dcn radical anion in THF\\-1,2\C,0.1723802564,-0.2484527138,0.3933394068\C,1.52 25325481,-0.423944315,0.8630076666\C,2.2922099313,0.6517713487,1.23221 95937\C,1.7777627574,1.9951833585,1.1639338006\C,0.4276109024,2.170674 6766,0.6942656627\C,-0.3420665517,1.0949589348,0.3250537302\H,1.934690 8921,-1.4280944878,0.9241768326\H,0.0154526508,3.1748247423,0.63309472 32\H,-1.3585595026,1.2545054918,-0.0259540371\C,2.5632794908,3.0934354 215,1.5416693592\N,3.2244592921,4.017823443,1.859797951\H,3.3087035343,0.4922254859,1.5832258955\C,-0.6131387842,-1.3467025221,0.0156020709\ N,-1.2742481073,-2.2711461846,-0.302511306\\Version=EM64L-G09RevA.02\H F=-416.8568581\S2=0.757997\S2-1=0.\S2A=0.750043\RMSD=3.094e-09\RMSF=3. 189e-05\Dipole=-0.0000502,0.0000399,-0.0000116\Quadrupole=1.9472119,-1 5.3646468,13.4174349,-30.5298141,-10.1345136,-15.0823703\PG=C01 [X(C8H 4N2)]\\@ o-dcn In the gas phase o-dcn-b3lyp 1\1\GINC-ELA\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\30-Nov-2011\0\\# B3LYP/6-31+G* OPT nosymm\\1,2-ph-dcn-am1\\0,1\c,0.3482274133,- 0.1696465006,0.0933377072\C,1.7117458597,- 0.3932354337,0.2810521214\C,2.6277644043,0.6598181675,0.1368651225\C,2.157 9648472,1.9528636525,-0.2007635579\C,0.7830677847,2.1626230336,- 0.3865839845\C,-0.1153805216,1.1063462536,-0.2400519358\H,-0.3511998147,- 0.9925680143,0.2077033657\H,2.079949809,- 1.3807737903,0.5399335236\H,0.4313513054,3.1562572726,-0.6450859878 \H,-1.177265048,1.2809916722,-0.3862962831\C,3.0641846443,3.0533036126,-0.3561884358\C,4.0254941877,0.4072902714,0.3342317708\N,3.7717843763 S16
,3.9668195267,-0.489620546\N,5.1516152623,0.1684403462,0.5010213198\\V ersion=ibm64-g09reva.02\hf=-416.7437658\rmsd=4.554e-09\rmsf=4.798e- 05\ Dipole=-2.7274884,-1.0037061,-0.0495866\Quadrupole=-16.142517,4.932931 1,11.2095859,-11.8581992,-0.204229,0.1868877\PG=C01 [X(C8H4N2)]\\@ In THF o-dcn-b3lyp-scrf-thf 1\1\GINC-NANO02\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\01-Dec- 2011\0\\#B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,2-ph-dcn in THF\\0,1\C,0.3471984368,-0.1700225785,0.093272506\C,1.7110205976,- 0.3965723044,0.2816949441\C,2.6238220728,0.6581264899,0.137023992\C,2.1538 180995,1.9517303289,-0.2008570175\C,0.7802960549,2.1647909409,- 0.3872595344\C,-0.1164239671,1.1059969198,-0.2400667784\H,-0.3521900851,- 0.992177241,0.2073829045\H,2.0763826465,- 1.384705324,0.5401231144\H,0.4255796282,3.1568558386,-0.6456688261\H,- 1.1778026116,1.2800039824,-0.3859844616\C,3.0660957994,3.0464595111,- 0.3546272184\C,4.0225154202,0.4136387981,0.332712134\N,3.7942188145,3.9451 098624,0.4828199835\N,5.1547736035,0.1992948457,0.494628425\\Version=EM64 L-G09RevA.02\HF=-16.7551319\RMSD=4.391e-09\RMSF=1.388e-04\Dipole=- 3.4836943,-1.2818361,-0.0632532\Quadrupole=-0.6177771,6.2682812,14.3494959,- 15.1322161,-0.2668099,0.25843 87\PG=C01 [X(C8H4N2)]\\@ Radical anion o-dcn-radical anion-b3lyp 1\1\GINC-ARMON\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\30-Nov- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\1,2-ph-dcn radicalanion\\-1,2\c,0.35845 35144,-0.1862440854,0.0980571825\C,1.7111153236,-0.3942485952,0.281131 096\C,2.6707797398,0.6471389112,0.1439046074\C,2.1827562796,1.99043225 59,-0.2067734297\C,0.7819589675,2.1629717773,-0.3868034394\C,-0.118175 4394,1.1256526361,-0.2447565392\H,-0.3402288805,-1.0120966975,0.213280 1546\H,2.0759187148,-1.38648373,0.5408478036\H,0.424571337,3.158019096 1,-0.6461003221\H,-1.1814008029,1.3030819965,-0.3915590514\C,3.0352000 984,3.0978054729,-0.369066033\C,4.0318504383,0.3544194457,0.3466942232 \N,3.7155449794,4.0484831642,-0.5135765881\N,5.1609602399,0.0695984223,0.5242745357\\Version=IBM64-G09RevA.02\HF=-416.7827521\S2=0.760808\S2-1=0.\S2A=0.750097\RMSD=9.733e-09\RMSF=2.244e-05\Dipole=-2.5932224,-0. 9544207,-0.0470127\Quadrupole=-31.5131155,4.9856437,26.5274717,-23.181 2342,-0.9763801,2.5156462\PG=C01 [X(C8H4N2)]\\@ Radical anion in THF o-dcn-radical anion-b3lyp-thf 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\01-Dec- 2011 \0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,2-phdcn radical anion in THF\\-1,2\C,0.3560484201,- 0.1867601075,0.0980315968\C,1.7053808193,- 0.4017351322,0.2827999889\C,2.6631403581,0.64552674,0.1438175686\C,2.17544 04982,1.987218322,-0.2063551052\C,0.7723819147,2.1651209401,- 0.3884310394\C,-0.1203531251,1.1241997176,-0.2454440176\H,-0.3454 186552,-1.0089259504,0.212833098\H,2.0666159341,-1.3942770463,0.543189 1615\H,0.4119820508,3.1581283604,-0.6481259133\H,-1.1833752288,1.29694 74342,-0.3916156013\C,3.0435160819,3.0770254506,-0.3627446755\C,4.0251 022026,0.3763962686,0.3402899265\N,3.7694073904,3.9977102307,-0.495435 5843\N,5.1694358489,0.1419548422,0.5067447965\\Version=EM64L-G09RevA.0 S17
2\HF=-416.8502763\S2=0.759226\S2-1=0.\S2A=0.75007\RMSD=3.221e- 09\RMSF=1.920e-05\Dipole=-3.5421116,-1.3029449,-0.0632883\Quadrupole=- 36.7118766,7.1242213,29.5876554,-27.3002126,-0.9004975,2.266414\PG=C01 [X(C8H4N2)]\\@ m-dcn In the gas phase m-dcn-b3lyp 1\1\GINC-ESHEL\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\30-Nov-2011\0\\# B3LYP/6-31+G* OPT nosymm\\1,3-ph-dcn\\0,1\c,0.3342585325,-0.3766611647, 0.0053631898\C,1.7236217855,-0.4648938626,0.0863644278\C,2.504210356,0.702660004,0.0121416504\C,1.8912218505,1.9540513726,-0.1428234855\C,0. 4935429479,2.0308222881,-0.2231401429\C,-0.2861392584,0.8626935602,-0. 1487731452\H,-0.2680438787,-1.2782789316,0.0628894366\H,2.2104899806,- 1.4274973805,0.2065732121\H,-1.3672303198,0.9357853824,-0.2119130491\C,3.9352260799,0.6151575543,0.0953241206\N,5.0938705788,0.5374952457,0. 163377247\H,2.4928838596,2.8547727108,-0.2001321822\C,-0.1423923218,3. 3086305384,-0.3818000629\N,-0.6635149927,4.3406466029,-0.5102309765\\V ersion=ibm64-g09reva.02\hf=-416.7467144\rmsd=5.535e-09\rmsf=1.971e- 05\Dipole=-0.9767833,-1.4622644,0.0929041\Quadrupole=-7.7416332,-1.091615 6,8.8332488,3.5519133,-1.1327748,1.3138638\PG=C01 [X(C8H4N2)]\\@ In THF m-dcn-b3lyp-scrf-thf 1\1\GINC-NANO02\FOpt\RB3LYP\6-31+G(d)\C8H4N2\ROZENTE\01-Dec- 2011\0\\#B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,3-ph- dcn\\0,1\c,0.3335021615,-0.3776657138,0.0053564988\c,1.722645396,-.4656395308,0.0861795329\c,2.5021716815,0.7037162907,0.0119337558\c,1.8932 427002,1.9566591472,-0.1429581699\C,0.495648644,2.0294430455,- 0.2227994147\C,-0.2861606775,0.8617986165,-0.1485757163\H,-0.2686373511,- 1.2785731051,0.0628773923\H,2.2068127957,-1.4293029059,0.2061809908\H,- 1.3670631881,0.9327244637,0.2110885889\C,3.9324638464,0.6169950979,0.09510 50642\N,5.0916860966,0.5421081953,0.1629978448\H,2.4952208774,2.8568886245,-0.2001239914\C,-0.1400182938,3.3064972042,-0.3815675178\N,- 0.6595094889,4.33973449,-0.5102974404\\Version=EM64L-G09RevA.02\HF=- 416.7577091\RMSD=2.785e-09\RMSF=1.603e-04\Dipole=-1.2202419,- 1.828366,0.116644\Quadrupole=-9.5075409,-1.616131,11.1236719,3.931129,- 1.3628875,1.6520755\PG=C01[X(C8H4N2)]\\@ Radical anion m-dcn-radical anion-b3lyp S18
1\1\GINC-ESHEL\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\30-Nov- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\1,3-ph-dcn radical anion\\-1,2\c,0.32997 03081,-0.3830852767,0.0057121278\C,1.7176784152,-0.500269946,0.0891876 076\C,2.5276966392,0.7096652857,0.0124517673\C,1.8877959594,1.94887810 66,-0.1426871945\C,0.4909932756,2.0550882076,-0.2258333216\C,-0.316555 0582,0.8435434202,-0.1485022504\H,-0.2749828582,-1.2886041441,0.063673 0976\H,2.1996317994,-1.4652249721,0.2094508131\H,-1.3979641658,0.91126 32064,-0.2104787065\C,3.9384265863,0.6489313234,0.0923484326\N,5.10986 593,0.5704936256,0.1614945164\H,2.4910386704,2.8519271085,-0.200066870 9\C,-0.1123086148,3.324690802,-0.3818874025\N,-0.6392816866,4.36808717 28,-0.5116423759\\Version=IBM64-G09RevA.02\HF=-416.7818125\S2=0.762386 \S2-1=0.\S2A=0.750099\RMSD=3.242e-09\RMSF=4.506e-05\Dipole=-0.7802423, -1.1683066,0.074297\Quadrupole=-16.9229216,-4.1969449,21.1198665,2.767 6481,-1.9502136,3.0125936\PG=C01 [X(C8H4N2)]\\@ Radical anion in THF m-dcn-radical anion-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H4N2(1-,2)\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,3-ph-dcn radical anion in THF\\-1,2\C,0.3286758493,-0.3851134983,0.0061564586\C,1.71 69317935,-0.5006784716,0.0895742753\C,2.525153519,0.7110930779,0.01186 3581\C,1.8902115576,1.9527579839,-0.1434996732\C,0.4929273585,2.053123 4938,-0.2258086013\C,-0.3169075627,0.8423615339,-0.1487123793\H,-0.275 4831418,-1.2896457925,0.063943626\H,2.1985992581,-1.465419745,0.209982 261\H,-1.3980205261,0.9095470898,-0.2113047477\C,3.9331933548,0.651591 1,0.0916084099\N,5.1051544911,0.5736337829,0.1611499521\H,2.4931785456,2.8555635726,-0.2007444939\C,-0.1080866704,3.32087716,-0.3808118805\N,-0.6335226264,4.3656926326,-0.5101765479\\Version=EM64L-G09RevA.02\HF =-416.8448382\S2=0.762687\S2-1=0.\S2A=0.750097\RMSD=7.054e-09\RMSF=2.0 55e-05\Dipole=-0.9805937,-1.4689834,0.092398\Quadrupole=-17.9201876,-4.3787507,22.2989383,2.8881489,-2.0578523,3.1751979\PG=C01 [X(C8H4N2)]\ \@ In the gas phase BN-B3LYP 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C7H5N1\ROZENTE\30-Nov- 2011\0\\#B3LYP/6-31+G*OPTnosymm\\Ph-CN\\0,1\C,0.261098662,- 0.0670341127,0.3237489129\C,1.6319631862,- 0.3113898307,0.3924540793\C,2.539535897,0.7106776581,0.0617199286\C,2.0645 893551,1.9731203637,-0.3363323289\C,0.6914873425,2.2056871011,- 0.4012682051\C,-0.210611218,1.1887586435,-0.0721944853\H,-0.4389471772,- 0.8573665921,0.579554094\H,2.0063655998,-1.2833 201597,0.6988658585\H,0.3258828898,3.1813128168,-0.7088879391\H,-1.279 9910503,1.3747635127,-0.1239871203\C,3.9521120097,0.4649764531,0.13025 S19
80805\N,5.0975578765,0.265662214,0.1857369884\H,2.7715114567,2.7570544 724,-0.5901326436\\Version=EM64L-G09RevA.02\HF=-24.5051873\RMSD=9.254 e-09\rmsf=9.744e-05\dipole=-1.8468311,0.3212896,-0.0895733\quadrupole= -15.1672716,10.8555449,4.3117267,0.5001477,-1.0936827,-2.0954099\PG=C0 1 [X(C7H5N1)]\\@ In THF BN-B3LYP-SCRF-THF 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C7H5N1\ROZENTE\01-Dec- 2011\0\\#B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\ph-cn in THF\\0,1\C,0.2617058527,-0.0687431402,0.3242338412\C,1.6322074533,- 0.3142162013,0.3932976308\C,2.5374254335,0.7110295146,0.061599046\C,2.0658 665388,1.9756154304,-0.3371562537\C,0.6927050755,2.2070277109,- 0.4017621994\C,-0.2086188714,1.1884023335,-0.0721285841\H,-0.438472549,- 0.8585861092,0.579946743\H,2.0049127879,- 1.2866591842,0.7000109928\H,0.3268297696,3.1823120952,-0.7092219404\H,- 1.2777265374,1.3743855372,- 0.1237868146\C,3.9490777888,0.465625602,0.1300711426\N,5.0951936361,0.2661 198156,0.1856080347\H,2.7714484514,2.7605891358,- 0.591176419\\Version=EM64L-G09RevA.02\HF=-324.5120681\RMSD=7.442e- 09\RMSF=1.270e-04\Dipole=-2.2906742,0.3985049,-0.1109005\Quadrupole=- 18.5379608,12.9227517,5.6152091,0.4601542,-1.3045974,-2.3112775\PG=C01 [X(C7H5N1)]\\@ Radical anion BN-radical anion-b3lyp 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C7H5N1(1-,2)\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\ph-cn radical anion\\-1,2\c,0.264747692,-0.0739475682,0.3258931717\c,1.6206274076,-0.3248656639,0.3968022542\ C,2.5895011418,0.7019470123,0.0640860893\C,2.0589453778,1.9895340851,- 0.3414898118\C,0.6974614937,2.210900804,-0.4029626972\C,-0.2442693107, 1.1945727088,-0.0739714545\H,-0.4320418645,-0.8729098404,0.5844377193\ H,1.9808196057,-1.3043784768,0.7058836809\H,0.3380936236,3.1935230117, -0.7128644624\H,-1.3142846267,1.3807456967,-0.1255778948\C,3.965033295 5,0.4627412693,0.1308199968\N,5.1325537204,0.2596258593,0.1873875356\H,2.7553672737,2.7854136424,-0.5989089073\\Version=EM64L-G09RevA.02\HF= -324.5086506\S2=0.760391\S2-1=0.\S2A=0.750075\RMSD=4.830e-09\RMSF=6.90 6e-05\Dipole=-1.8249684,0.3176022,-0.0882365\Quadrupole=-32.1332164,16.476284,15.6569325,-3.0999899,-1.8588904,-1.0204514\PG=C01 [X(C7H5N1)] \\@ Radical anion in THF BN-radical anion-b3lyp-thf 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C7H5N1(1-,2)\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\ph-cn radical anion in THF\\-1,2\C,0.2651761504,- 0.0744081643,0.3263942293\C,1.621324477,- 0.3278487214,0.3970578393\C,2.5889614644,0.7022859214,0.0629929142 \C,2.060322001,1.9925169617,-0.3434025101\C,0.6975960904,2.2113812198, -0.4031402735\C,-0.2396796177,1.1941146128,-0.0724775406\H,-0.43190627 S20
31,-0.8716622533,0.5840345435\H,1.9797952934,-1.3077978909,0.705473345 4\H,0.3367551002,3.192256048,-0.7123741035\H,-1.308961122,1.379910085, -0.1244866435\C,3.958903105,0.4643735883,0.1308297857\N,5.1294814489,0.2583758455,0.1900300605\H,2.7547867121,2.7894052876,-0.6013964269\\Ve rsion=em64l-g09reva.02\hf=-324.5782705\s2=0.761681\s2-1=0.\s2a=0.75009 7\RMSD=4.245e-09\RMSF=4.448e-05\Dipole=-2.540684,0.4436137,-0.1260197\ Quadrupole=-36.63883,19.4738908,17.1649392,-3.3680825,-2.1664817,-1.45 7315\PG=C01 [X(C7H5N1)]\\@ In the gas phase SN-B3LYP 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C4H4N2\ROZENTE\25-Dec- 2011\0\\#B3LYP/6-31+G*OPT\\CN-CH2-CH2-CN\\0,1\C,- 3.5030305484,0.2429624716,-0.1876658944\H,-3.1552657414,-0.7560743643,- 0.4729029275\H,-3.0369495533,0.4891618576,0.7734666115\C,- 3.0487404797,1.2879390721,-1.2383370172\H,-3.4472268185,2.2766529167,- 0.9852980943\H,-1.955252298,1.3591480917,-1.2094537202\C,- 4.9569416922,0.2071199275,-0.0000783387\C,-3.4532219201,0.9455551963,- 2.6056333915\N,-6.1064964854,0.1933925574,0.1599822563\N,- 3.7585898832,0.6631747432,-3.6892826639\\Version=EM64L-G09RevA.0 2\State=1-A\HF=-264.3114353\RMSD=2.952e-09\RMSF=1.243e-05\Dipole=1.877 8678,0.3821884,1.1920732\Quadrupole=-0.3820974,4.8843212,-4.5022238,-0.497684,4.2945447,-0.0628931\PG=C01 [X(C4H4N2)]\\@ In THF SN-B3LYP-THF 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C4H4N2\ROZENTE\25-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\cn-ch2- CH2-CN in THF\\0,1\C,-3.4984987228,0.251557827,-0.1780058019\H,- 3.1348866557,-0.7492703269,-0.4327912172\H,- 3.056447359,0.5250586467,0.7858609502\C,-3.0360019352,1.2830678265,- 1.2369631288\H,-3.4019005376,2.283656126,-0.9842420725\H,- 1.9416742214,1.321842871,-1.2256364207\C,-4.9550475552,0.196 820658,-0.0199812677\C,-3.4725985047,0.9520135244,-2.5967634455\N,-6.1 087397045,0.1591897044,0.1068375579\N,-3.8159202241,0.6850956128,-3.67 35183335\\Version=EM64L-G09RevA.02\HF=-264.3252367\RMSD=5.537e- 09\RMSF=2.356e-05\Dipole=2.3606644,0.481087,1.4983298\Quadrupole=- 22.6907801,20.6441155,2.0466647,-1.6729514,-12.1480593,0.6880513\PG=C01 [X(C4H4N2)]\\@ Radical anion SN-radical anion-b3lyp 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C4H4N2(1-,2)\ROZENTE\25-Dec- 2011\0\\#B3LYP/6-31+G* OPT\\CN-CH2-CH2-CN radical anion\\-1,2\c,- 3.5488091083,0.2678209621,-0.1933047518\H,-3.1906520378,-0.7457238717,- S21
0.4246309778\H,-3.0789812398,0.5754932324,0.7674123365\C,- 3.0643005838,1.2505969144,-1.2716362085\H,-3.4154909659,2.2655596301,- 1.0358875223\H,-1.9524125496,1.2648400957,-1.2282783425\C,- 5.0070184522,0.2229204706,-0.0151235874\C,-3.4812555603,0.9138584737,- 2.6401736952\N,-6.0954202271,0.0703455909,0.3893729911\N,- 3.5873746954,0.8233209716,-3.8029534221\\Version=EM64L- G09RevA.02\State=2-A\HF=-264.3022037\S2=0.750516\S2-1=0.\S 2A=0.75\RMSD=5.352e-09\RMSF=2.234e-05\Dipole=-0.1017824,-0.0207151,-0. 0646116\Quadrupole=-2.9391929,9.6071776,-6.6679847,-2.5083576,3.274725 5,0.4317364\PG=C01 [X(C4H4N2)]\\@ Radical anion in THF SN-radical anion-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C4H4N2(1-,2)\ROZENTE\25-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\cn-ch2- CH2-CNradical anion in THF\\-1,2\C,-3.609783852,0.2671389551,- 0.2486656838\H,-3.265245429,-0.7441078334,-0.5044727944\H,- 3.1951159808,0.5182455083,0.7443955992\C,-3.0367382004,1.2744341083,- 1.2656241063\H,-3.4157757654,2.2800904253,-1.0447470814\H,- 1.9422526932,1.309862019,-1.1876070507\C,-5.1452924983,0.2638802094,- 0.2106370979\C,-3.3688335803,0.963797752 6,-2.6612308379\N,-5.9060459371,0.0298321956,0.7163954304\N,-3.5366314 838,0.7458591295,-3.7930095572\\Version=EM64L-G09RevA.02\HF=-264.37285 58\S2=0.753324\S2-1=0.\S2A=0.750006\RMSD=4.955e-09\RMSF=1.653e-04\Dipo le=3.4537705,1.0795433,-0.6623598\quadrupole=-73.2991734,49.4228844,23.8762889,2.0072603,-8.6776364,2.646802\pg=c01 [X(C4H4N2)]\\@ In the gas phase trans-sn-b3lyp 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C4H4N2\ROZENTE\25-Dec- 2011\0\\#B3LYP/6-31+G*OPT\\trans-CN-CH2-CH2-CN\\0,1\C,- 3.4027363999,0.0679542875,-0.5252437027\H,-3.2312220371,-0.8917860151,- 1.0249649813\H,-2.8493233828,0.0440130766,0.4199552699\C,- 2.8916590745,1.2312004866,-1.4136943253\H,-3.4450890772,1.255160811,- 2.3588827225\H,-3.0631499166,2.1909377472,-0.9139588061\C,- 4.8329734566,0.2071429222,-0.2373700471\C,-1.4614289742,1.091994671,- 1.7015943581\N,-5.9662171815,0.3325434345,-0.0190649554\N,- 0.3281913596,0.9665805785,-1.9199234513\\Version=EM64L-G09 RevA.02\State=1-A\HF=-264.3132942\RMSD=6.290e-09\RMSF=1.020e-04\Dipole =0.0000075,0.0000179,0.0000293\Quadrupole=-13.1416884,7.6427901,5.4988 983,-1.2232636,6.144648,-0.0228756\PG=C01 [X(C4H4N2)]\\@ In THF S22
trans-sn-b3lyp-thf 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C4H4N2\ROZENTE\26-Dec- 2011\0\\#B3LYP/6-31+G*OPT SCRF=(PCM, Solvent=THF) nosymm\\trans-cn- CH2-CH2-CN in THF\\0,1\C,-3.4025977894,0.0674903982,-0.5249774276\H,- 3.2400412846,-0.8939017407,-1.0234220735\H,- 2.8574189057,0.0437693276,0.4243870354\C,-2.89180055,1.2316574703,- 1.4139715825\H,-3.4369781653,1.2553779188,-2.3633367684\H,- 3.054358663,2.1930495464,-0.9155272957\C,-4.832158109,0.2075837451,-0.238034124\C,-1.462239772,1.0915652701,-1.7009132319\N,-5.9656039637,0.3260417199,-0.014857933\N,-0.3287936572,0.9731083443, -1.9240886787\\Version=EM64L-G09RevA.02\HF=-264.3256591\RMSD=8.497e- 09\RMSF=9.916e-05\Dipole=-0.0000007,-0.0000015,-0.0000016\Quadrupole=-15.5145039,9.0370213,6.4774826,-1.5246544,7.3098885,-0.0053602\PG=C01 [X (C4H4N2)]\\@ Radical anion trans-sn-radical anion-b3lyp 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C4H4N2(1-,2)\ROZENTE\26-Dec- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\trans-cn-ch2-ch2-cn radical anion\\- 1,2 \C,-3.4814094451,0.1141581194,-0.5343835191\H,-3.3583011861,-0.8757145 403,-1.0064045731\H,-2.9747364961,0.06407652,0.4447023187\C,-2.8129888 552,1.184989447,-1.4045654709\H,-3.3196600838,1.235068705,-2.383652403 6\H,-2.9360994928,2.1748625855,-0.9325461845\C,-4.931577224,0.34699142 62,-0.3018723242\C,-1.3628201049,0.9521580477,-1.637073467\N,-6.003381 1759,0.1162675997,0.1308570361\N,-0.2910167962,1.1828840897,-2.0698034 924\\Version=EM64L-G09RevA.02\HF=-264.2996497\S2=0.751118\S2-1=0.\S2A= 0.750001\RMSD=3.899e-09\RMSF=1.985e-04\Dipole=-0.0000056,-0.0000028,0. 0000005\Quadrupole=-40.65423,22.169849,18.484381,3.3343471,0.1273666,5.257255\PG=C01 [X(C4H4N2)]\\@ Radical anion in THF trans-sn-radicalanion-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C4H4N2(1-,2)\ROZENTE\26-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\trans-cn- CH2-CH2-CN radical anion in THF\\-1,2\C,-3.4780990178,0.1139693276,- 0.5350616553\H,-3.3643766832,-0.8759443943,-1.0072393811\H,- 2.9797475005,0.0660939754,0.4473349648\C,-2.816298337,1.185176679,- 1.4038852414\H,-3.3146502682,1.2330521228,-2.3862818419\H,- 2.9300207032,2.1750904603,-0.9317072468\C,-4.9341764495,0.3728093777,- 0.3177032483\C,-1.3602196393,0.9263349523,-1.6212432858\N,- 5.9923301218,0.0984716808,0.1392680472\N,-0.3020721396,1.2006878183,- 2.0782231913\\Version=EM64L-G09RevA.02\HF=-264.3653729\S2=0.751579\S2-1=0.\S2A=0.750002\RMSD=5.142e-09\RMSF=6.848e-05\Dipole=-0.0001222,- 0.0000225,0.0000475\Quadrupole=-43.6565963,24.09 79759,19.5586204,2.6937024,1.6949709,5.0478287\PG=C01 [X(C4H4N2)]\\@ In the gas phase PN-B3LYP S23
1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C8H7N1\ROZENTE\30-Nov- 2011\0\\#B3LYP/6-31+G* OPT nosymm\\ph-ch2-cn\\0,1\c,0.2903727055,- 0.06575867,0.6527294825\C,1.6154379172,- 0.4286891646,0.3988994934\C,2.4887876342,0.4680173854,- 0.2282768804\C,2.0182896099,1.7330346669,-0.6004063935\C,0.6935663272,2.0977599888,-0.3472911678\C,-0.173342077,1.1988699745,0.2 801278468\H,-0.3780432241,-0.7710588059,1.1396068331\H,1.9719583808,-1.4134863135,0.6933545458\H,0.3398902987,3.0824437323,-0.6415993163\H,- 1.2042507624,1.4816906794,0.4761607037\C,3.9370825201,0.0747192266,-0. 4945664041\H,2.6893544058,2.4376135751,-1.0870370639\H,4.3099178129,0. 5701558602,-1.3993373021\H,4.0160046055,-1.005103694,-0.6702074991\C,4.8385298719,0.4203791626,0.6154764201\N,5.5491289337,0.6938091162,1.49 25650216\\Version=EM64L-G09RevA.02\HF=-363.8164455\RMSD=8.730e- 09\RMSF=1.251e-05\Dipole=-1.1722241,-0.2978881,-1.1159401\Quadrupole=- 10.3951787,8.6590321,1.7361466,-4.7995048,-13.6004234,-3.4493905\PG=C01 [X(C8H7N1)]\\@ In THF PN-B3LYP-SCRF-THF 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C8H7N1\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\ph-ch2-cn inthf\\0,1\c,0.2850965803,-0.069860768,0.645170176\c,1.6099270883,- 0.4372928863,0.3910534637\C,2.4883536353,0.4623155537,- 0.2260874153\C,2.0253870146,1.7336494137,- 0.5893475417\C,0.7010840248,2.1020341854,-0.3354554338\C,- 0.1717459049,1.2011425518,0.28311585\H,-0.3880863753,-0.7770160356,1.1225152937\H,1.9599650896,-1.4277065304,0.6730913089\H,0.3519629582,3.0901006814,-0.6235176943\H,-1.201879818,1.4868737658,0.4787444355\C,3.9355687159,0.0636499313,-0.4946261257\H,2.6994762212,2.4375321529,-1. 0722216006\H,4.3065146529,0.5369700899,-1.4112066805\H,4.0202680383,-1.0196871049,-0.6377207416\C,4.8369139663,0.4438744194,0.60292099\N,5.5 438790723,0.7478172998,1.4737700355\\Version=EM64L-G09RevA.02\HF=-363. 8248745\RMSD=4.844e-09\RMSF=2.468e-06\Dipole=-1.3353976,-0.43213,-1.36 65668\Quadrupole=-12.0137174,9.7781175,2.2355999,-6.1834164,-16.012061 7,-4.013502\PG=C01 [X(C8H7N1)]\\@ Radical anion PN-radical anion-b3lyp 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C8H7N1(1-,2)\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\ph-ch2-cn radical anion\\-1,2\c,0.27680 10906,-0.0762898197,0.6355640786\C,1.6001292528,-0.4332768959,0.400777 9311\C,2.5118756074,0.491363683,-0.1694153985\C,2.0050077547,1.7420005 36,-0.6054396991\C,0.6809722818,2.0952592725,-0.368991033\C,-0.1904914 372,1.2169946287,0.3125994722\H,-0.4001444484,-0.8043812143,1.08400688 S24
74\H,1.9467264965,-1.4352937302,0.6580062191\H,0.320353585,3.067449358,-0.7070881593\H,-1.21379345,1.5121094231,0.5385573394\C,3.9401292069, 0.0957669031,-0.4485823208\H,2.6661567755,2.4323119488,-1.1313533823\H,4.3101016905,0.5946996408,-1.3708125644\H,4.0121808874,-0.9980505493, -0.6352871172\C,4.8750127081,0.4187590683,0.6290022455\N,5.6616669583, 0.6549744671,1.4586538211\\Version=EM64L-G09RevA.02\HF=-363.7966741\S2 =0.752498\S2-1=0.\S2A=0.750004\RMSD=4.152e-09\RMSF=1.095e-05\Dipole=-1.3610824,0.301317,0.0994206\Quadrupole=-30.3191212,16.59284,13.7262812,-5.4609578,-6.7925828,-1.2007634\PG=C01 [X(C8H7N1)]\\@ Radical anion in THF PN-radical anion-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H7N1(1-,2)\ROZENTE\01-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\ph-ch2-cn radical anion in THF\\-1,2\C,0.3461664909,-0.0602706454,0.6890508728\C,1.643 2248736,-0.4551787925,0.3546662828\C,2.5204501836,0.41136795,-0.332095 2103\C,2.0496682861,1.7068815247,-0.6364059535\C,0.753315323,2.1049027 124,-0.3030478992\C,-0.1136374907,1.2219446181,0.3563785088\H,-0.31220 64784,-0.7566029855,1.2050478745\H,1.9841650747,-1.4555630572,0.616839 0109\H,0.4137520119,3.105388296,-0.5645825523\H,-1.1246073973,1.529486 369,0.6127153284\C,3.9454462299,0.0281926609,-0.5865075502\H,2.7091870 734,2.4028660418,-1.1522622592\H,4.3355975529,0.5204580534,-1.48451792 88\H,4.0445848878,-1.0514612368,-0.7458127503\C,4.9653191297,0.3912337 295,0.5847448527\N,4.8422592088,0.9307514814,1.6659876927\\Version=EM6 4L-G09RevA.02\HF=-363.8669778\S2=0.754371\S2-1=0.\S2A=0.750014\RMSD=3.201e-09\RMSF=2.320e-05\Dipole=-4.2081485,- 0.199239,-2.0656963\Quadrupole=-50.9329301,30.0733354,20.8595947,- 12.3623526,-23.9346197,-6.2849519\PG=C01 [X(C8H7N1)]\\@ In the gas phase HC-B3LYP 1\1\GINC-NANO01\FOpt\RB3LYP\6-31+G(d)\C8H15N1\ROZENTE\05-Dec- 2011\0\\#B3LYP/6-31+G* OPT nosymm\\c7- CN\\0,1\C,0.001575893,0.0004440343,-0.06 70164992\H,1.0983623657,0.0175621464,-0.1083516296\H,-0.3476707074,1.0 401762416,-0.1111352719\H,-0.3574031863,-0.509509369,-0.9690792443\C,- 0.4943978722,-0.6977720254,1.2046694093\H,-1.5937185979,-0.7294163056, 1.1996886481\H,-0.1589608266,-1.7451711731,1.2013265129\C,-0.014440245,-0.0184084228,2.4947791058\H,1.0858472134,0.0145878537,2.4981409648\H,-0.3509735548,1.0296766626,2.49851359\C,-0.5050280446,-0.7132092847,3.7725197984\H,-0.1684197312,-1.7608011849,3.7686019583\H,-1.604878526, -0.7455604599,3.7693210723\C,-0.0229546324,-0.0320996846,5.0609463535\ H,-0.3605069614,1.0153467889,5.0666738634\H,1.0770695245,-0.0005634618,5.0658660099\C,-0.517613194,-0.7328863502,6.3325980818\H,-0.177398189 4,-1.7762457603,6.3429823197\H,-1.6146665981,-0.7606973616,6.343524220 8\C,-0.0196367268,-0.0286570776,7.6132969291\H,-0.360721651,1.01469770 81,7.6309003386\H,1.0777192083,-0.0024316682,7.6311218053\C,-0.4834244 S25
685,-0.6842855404,8.8406228871\N,-0.8599637511,-1.2164831055,9.8021929 661\\Version=EM64L-G09RevA.02\HF=-368.6505896\RMSD=5.171e- 09\RMSF=3.404e-05\Dipole=0.4637751,0.6557062,- 1.5768132\Quadrupole=17.1594156,15.7706391,-32.9300548,- 1.9621612,9.7410498,13.772346\PG=C01 [X(C8H15N1)]\\@ In THF HC-B3LYP-SCRF-THF 1\1\GINC-NANO02\FOpt\RB3LYP\6-31+G(d)\C8H15N1\ROZENTE\06-Dec- 2011\0\\#B3LYP/6-31+G* OPT SCRF=(PCM,Solvent=THF) nosymm\\c7-cn in THF\\0,1\C,0.0004573013,0.0025677538,0.0658438059\H,1.0973786508,0.0195886 055,-0.1067273513\H,-0.3494528746,1.0423066067,-0.1074275441\H,- 0.3591218236,-0.5066238835,-0.968323901\C,-0.4946438309,- 0.6972739876,1.2056855366\H,-1.5939951705,-0.7282229775,1.2013556867\H,- 0.1582854706,-1.7443770853,1.2009288536\C,-0.0139682871,- 0.0191322432,2.4961074214\H,1.0862790794,0.01305359,2.4991535694\H,- 0.3518028719,1.0284632339,2.5014278593\C,-0.5039470082,- 0.715660257,3.7731207916\H,-0.1652042921,-1.7625054312,3.7684810242\H,- 1.603759928,-0.7475840031,3.7701257244\C,-0.021791662,- 0.0340649355,5.0611236645\H,-0.3611083251,1.0122867545,5.068820025 \H,1.0777752817,-0.0041265161,5.0683899024\C,-0.5184146543,-0.73706330 51,6.3306302351\H,-0.1745777557,-1.7789182038,6.3410769846\H,-1.615219 2429,-0.7624927657,6.3399239651\C,-0.0188533177,-0.0274219874,7.608819 5063\H,-0.3602788295,1.0150490443,7.6269763969\H,1.0777635217,-0.00491 91013,7.6314607797\C,-0.4845954737,-0.6782664333,8.8366239905\N,-0.862 8362763,-1.206369272,9.8007948752\\Version=EM64L-G09RevA.02\HF=-368.65 7598\RMSD=9.560e-09\RMSF=6.034e-06\Dipole=0.5780144,0.8064279,-1.79863 5\Quadrupole=19.9641239,18.395802,-38.3599259,-2.2734087,11.8276037,16.5186812\PG=C01 [X(C8H15N1)]\\@ Radical anion HC-radical anion-b3lyp 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C8H15N1(1-,2)\ROZENTE\05-Dec- 2011\0\\# B3LYP/6-31+G* OPT nosymm\\c7-cn radical anion\\-1,2\c,0.01682761 58,0.0207764778,-0.0740211019\H,1.1146449493,0.0394703351,-0.109693282 \H,-0.3244443342,1.0643060028,-0.1123464409\H,-0.3312654948,-0.4703121 845,-0.9934391902\C,-0.4905529464,-0.6892532951,1.1861484608\H,-1.5907 699275,-0.7195074902,1.1731098487\H,-0.1599786998,-1.7391001416,1.1742 561228\C,-0.0180689838,-0.0253244119,2.4875949557\H,1.0817477263,0.009 3345306,2.4967860212\H,-0.3481525839,1.0243721805,2.4983790277\C,-0.51 49638384,-0.7271366229,3.7581845213\H,-0.1813754968,-1.7768005217,3.74 87207656\H,-1.6158025398,-0.7614344967,3.7487856389\C,-0.0365195652,-0.0511216855,5.0519138633\H,-0.3671302519,0.9974917319,5.0630377518\H,1.0622368905,-0.0109965275,5.0614697248\C,-0.5349321941,-0.7596956752,6.3187992794\H,-0.1961537606,-1.8049785989,6.3196192854\H,-1.6331481266,-0.7956107441,6.3190290855\C,-0.0583610061,-0.0798474124,7.6174673713 \H,-0.3985236713,0.9718682171,7.6424736819\H,1.0462754452,-0.039709625 9,7.6426249524\C,-0.506288279,-0.7196091853,8.8670620467\N,-0.68750418 69,-0.9788876562,9.9967417999\\Version=EM64L-G09RevA.02\HF=-368.614007 2\S2=0.750285\S2-1=0.\S2A=0.75\RMSD=6.425e-09\RMSF=9.973e-06\Dipole=-0.5433035,-0.7661345,-1.9044442\Quadrupole=71.2739681,68.4817094,-139.7 556775,-3.9235422,5.7062343,8.0547835\PG=C01 [X(C8H15N1)]\\@ S26
Radical anion in THF HC-radical anion-b3lyp-scrf-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H15N1(1-,2)\ROZENTE\06-Dec- 2011\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\c7-cn radical anion in THF\\-1,2\C,0.0179051679,0.0319034097,- 0.077372306\H,1.1153783638,0.0457308609,-0.106365347\H,- 0.3276284717,1.0733755331,-0.1149037952\H,-0.3334654352,-0.4691321252,- 0.9879486331\C,-0.4922863968,-0.6750682888,1.1844748668\H,-1.59178779,- 0.7025796411,1.1686828207\H,-0.159880644,-1.72358196,1.1745962009\C,- 0.0221692266,-0.0103844636,2.4858280 302\H,1.0784103097,0.0211471559,2.4965799939\H,-0.3579950028,1.0381382 061,2.4978085847\C,-0.519881379,-0.7169879253,3.7543848505\H,-0.189615 4356,-1.7670088793,3.7356583282\H,-1.6204416346,-0.7429573285,3.746800 589\C,-0.0377813618,-0.0613051075,5.0567169112\H,-0.373290417,0.986763 4202,5.0810516161\H,1.0629144869,-0.0288692379,5.0577259588\C,-0.52061 94568,-0.7853257803,6.3212731574\H,-0.1977957433,-1.8361417647,6.28794 67516\H,-1.621206773,-0.8057378033,6.3339907214\C,-0.0147483645,-0.158 8893768,7.6280145283\H,-0.3816738445,0.8823645462,7.7147689399\H,1.085 0396917,-0.1110982304,7.5980592126\C,-0.4064728313,-0.9527722331,8.889 9083493\N,-0.8631110716,-0.5532897861,9.9550238599\\Version=EM64L-G09R eva.02\hf=-368.6928857\s2=0.75327\s2-1=0.\s2a=0.750006\rmsd=8.882e-09\ RMSF=8.839e-06\Dipole=0.7912121,0.9542987,-9.2712234\Quadrupole=113.47 23114,109.3630958,-222.8354071,-2.15447,25.8775603,30.4122864\PG=C01 [ X(C8H15N1)]\\@ Radical in THF α-amino-p-tolunitrile-radical-b3lyp-thf 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H7N2(2)\ROZENTE\11-Jan- 2012\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph- CNCH-NH2-radical in THF\\0,2\C,0.1736243972,- 0.2662306059,0.8984459565\C,1.3817383039,- 0.0913492668,1.6491977255\C,2.2573241329,0.9378188481,1.380611881 4\C,1.9807846296,1.8619628634,0.3364568503\C,0.793647282,1.7044166256, -0.4225387877\C,-0.0838108884,0.6730894765,-0.1535276454\H,1.607307867 9,-0.7895049173,2.4516551354\H,0.5772834075,2.4032884535,-1.2253884314 \H,-0.9772019714,0.5831628575,-0.764540057\C,2.8802495147,2.9254042908,0.0549399583\N,3.6216265933,3.8000852608,-0.1748841632\H,3.1652133134,1.0480283914,1.9662430233\C,-0.689752815,-1.3282841078,1.2232442944\N,-1.8552054441,-1.6307058584,0.5836485392\H,-2.3016137889,-0.962955278,-0.0314142387\H,-0.4130465315,-2.0143207811,2.0173049328\H,-2.4789035 S27
631,-2.3079730622,1.0002650562\\Version=EM64L-G09RevA.02\HF=-418.55316 56\S2=0.768332\S2-1=0.\S2A=0.750233\RMSD=8.049e-09\RMSF=2.989e-05\Dipo le=-3.1575008,-2.9618859,0.7085771\quadrupole=-1.8009497,-8.2415004,10.0424501,-13.3195323,2.919283,-3.9142129\pg=c01 [X(C8H7N2)]\\@ Radical in THF α-amino-p-tolunitrile-radical-b3lyp-thf 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C8H7N2(2)\ROZENTE\11-Jan- 2012\0\\#B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph- CNCH2-NH-radical in THF\\0,2\C,0.2195440598,- 0.3482004976,0.5609901257\C,1.0935102246,- 0.0201395023,1.6089282411\C,1.957008722,1.0677355713,1.5053775715 \C,1.9537448834,1.8481601347,0.3352032103\C,1.0829246079,1.5292869471, -0.7221153346\C,0.2259304646,0.4379649884,-0.6019947328\H,1.1044612887,-0.6230678247,2.5134884956\H,1.0839593368,2.1307932272,-1.6256069348\ H,-0.4429934185,0.1915711395,-1.4222441171\C,2.8437610552,2.9664396612,0.2180392157\N,3.5667863842,3.874615581,0.1231147842\H,2.6345133734,1.3112182484,2.3176791268\C,-0.7547086978,-1.506971353,0.6856021039\N,- 2.0736083711,-1.1136181542,1.1551899241\H,-1.9331613653,-0.4589423614, 1.9391078747\H,-0.3548605509,-2.2455592588,1.4035368208\H,-0.866670127 2,-2.0239947267,-0.2735873552\\Version=EM64L-G09RevA.02\HF=-418.513644 3\S2=0.753834\S2-1=0.\S2A=0.750011\RMSD=9.418e-09\RMSF=1.234e-05\Dipol e=-0.5525578,-1.5948027,0.4554917\quadrupole=-9.4269121,-6.5167749,15. 943687,-16.1822922,2.8461253,-1.3454539\PG=C01 [X(C8H7N2)]\\@ Radical in THF α-amino-p-tolunitrile--radical-b3lyp-thf 1\1\GINC-NANO02\FOpt\UB3LYP\6-31+G(d)\C8H7N2(2)\ROZENTE\11-Jan- 2012\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph- CNHCH-NH-radical\\0,2\C,0.0600420982,- 0.292912674,0.5835170087\C,0.3662862429,0.5494844509,1.6847602458\C,1.2173 788251,1.6236504475,1.556193045\C,1.8348761318,1.9123664058,0.2896449607\C S28
,1.5219549567,1.0675536167,-0.8286710891\C,0.6639059351,-0.000268067,- 0.6645188136\H,- 0.0720170664,0.3528045071,2.6600106621\H,1.970802604,1.2730375625,- 1.7952935918\H,0.4457010944,-0.6384733795,- 1.5179604634\C,2.6371801899,3.0166794281,0.1383815456\N,3.6336990574,3.728 8815413,0.1012833636\H,1.4365854135,2.2573041978,2.4098448648\C,- 0.8391323617,-1.4438724137,0.6778020713\N,-1.4936682738,- 1.8988963902,1.6920557502\H,-1.3243191929,-1.3334710393,2.531503 0145\H,-0.9671592108,-1.9945365818,-0.2600037049\H,3.5266168964,4.7211 759378,-0.1411796496\\Version=EM64L-G09RevA.02\HF=-418.5057945\S2=0.77 9124\S2-1=0.\S2A=0.750604\RMSD=6.016e-09\RMSF=7.405e-06\Dipole=0.92811 41,2.0102344,-0.5666168\Quadrupole=-8.5524494,4.5462202,4.0062292,0.32 23267,0.4389079,4.3174544\PG=C01 [X(C8H7N2)]\\@ Radical in THF 1,4-Ph-CH=NCH-NH-radical-B3LYP-THF 1\1\GINC-NANO01\FOpt\UB3LYP\6-31+G(d)\C8H7N2(2)\ROZENTE\11-Jan- 2012\0\\# B3LYP/6-31+G* OPT SCRF=(PCM, Solvent=THF) nosymm\\1,4-ph- CH=NCH-NH-radical in THF\\0,2\C,0.0273403723,- 0.2771268292,0.6029669455\C,0.3713291032,0.5034288785,1.7191416007\C,1.255 9212895,1.5698141625,1.5881165757\C,1.817375491,1.8806772489,0.3381890888\ C,1.4780371741,1.1048404727,-0.7826177703\C,0.5930958271,0.0403135631,- 0.6458454775\H,- 0.0472480547,0.2854973193,2.6980562013\H,1.9070724337,1.3378262272,- 1.7524097271\H,0.3334344933,-0.5571809678,- 1.5163227138\C,2.7570060606,3.024984633,0.2386178452\N,3.3407537814,3.4298 797963,-0.8008200858\H,1.5144391375,2.1663046997,2.4590227406\C,- 0.907352608,-1.425972001,0.675959777\N,-1.5336620513,- 1.8987655351,1.6879170742\H,-1.3256733147,-1.3731443698,2.5444936091\H,- 1.0743805756,-1.9320338888,-0.2799924799\H,2.956215622, 3.5681983806,1.1778825921\\Version=EM64L-G09RevA.02\HF=-418.5146223\S2 =0.762707\S2-1=0.\S2A=0.750088\RMSD=6.259e-09\RMSF=1.647e-05\Dipole=0. 0827947,0.3351968,0.732384\Quadrupole=-5.8754144,-4.5666462,10.4420606,-8.2378939,7.6104319,11.3047684\PG=C01 [X(C8H7N2)]\\@ S29