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Supporting Information rigin of the Regio- and Stereoselectivity of Allylic Substitution of rganocopper Reagents Naohiko Yoshikai, Song-Lin Zhang, and Eiichi Nakamura* Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan Contents 1. Computational thods.... 2 2. Reaction Pathways, Energetics and Representative Structures of Homocuprate Reactions.... 3 2-1. [ 2 ] + Allyl Acetate... 3 2-2. [ 2 Li] 2 + Allyl Acetate... 4 2-3. [ 2 Li] 2 2 2 + Allyl Acetate... 5 3. Reaction Pathways, Energetics and Representative Structures of Heterocuprate Reactions.... 6 3-1. [X] + Allyl Acetate (X = CN, Cl, S, N 2 )... 6 3-2. [(CN)Li][ 2 Li] + Allyl Acetate... 8 3-3. [(CN)Li][ 2 Li] 2 2 + Allyl Acetate... 10 4. Energies and Cartesian Coordinates of Stationary Points.... 11 S1

1. Computational thods. All calculations were performed with a Gaussian 03 package. 1 The density functional theory (DFT) method was employed using the B3LYP hybrid functional. 2 Structures were optimized with a basis set consisting of Stuttgart-Dresden effective core potential 3 for and 6-31+G(d) 4 for the rest. For the lithium-free models, geometry optimization was carried out with self-consistent reaction field (SCRF) method based on the conductor calculation model (CPCM, ε = 7.58 for THF). 5 For the lithium cuprate models, the geometry optimization was carried out in the gas phase. Each stationary point was adequately characterized by normal coordinate analysis (no imaginary frequencies for an equilibrium structure and one imaginary frequency for a transition structure). The intrinsic reaction coordinate (IRC) analysis 6 was carried out to confirm that stationary points are smoothly connected to each other. The effect of coordination of one 2 molecule on each lithium atom was also examined for the oxidative addition step. The method and basis sets used here have been applied to other cuprate reactions and known to give reliable results. 7 S2

2. Reaction Pathways, Energetics and Representative Structures of Homocuprate Reactions. 2-1. [ 2 ] + Allyl Acetate Scheme S1. Reaction of 2 and Allyl Acetate + Ac Ac RT CP' TS' Ac Ac PD Ac Ac + PD TS RE E rel (kcal/mol) +20 +10 0 10 20 RT 0.0 CP' 11.0 TS' 16.1 1.2 PD Ac 2.4 PD + Ac TS RE 11.3 + butene 21.7 Reaction coordinate Figure S1. Energy diagram (ZPE corrected) for the reaction of 2 and allyl acetate. 2.03 2.05 1.41 1.49 2.01 2.10 2.71 1.43 1.42 1.50 1.90 CP' TS' Figure S2. Structures of π-complex and oxidative addition TS in the reaction of 2 and allyl acetate. Bond lengths are in Å. S3

2-2. [ 2 Li] 2 + Allyl Acetate Scheme S2. Reaction of [ 2 Li] 2 and Allyl Acetate " Li 1 + Ac! Li 2 1 2 RT Li 1 Li 2 1 2 CP Li anti path syn path Li 1 1 2 Li 2! " CP Li 1 Li 2 1 2! " 1 " Li 1 2! TS Li 2 Li 1 2 1 "! Li 2 Li 2 Li 1 1 2 2 Li LiAc 1 2 "! CP syn TS syn + "! PD TS RE PD Li +20 E rel (kcal/mol) TS syn 15.2 +10 0 10 20 30 RT 0.0 10.0 CP Li CP 5.7 10.5 TS 0.2 CP syn 19.3 PD Li 17.0 TS RE + 2 Li LiAc 2.1 PD + 2 Li 2 Ac + butene + 2 Li LiAc 33.4 Reaction coordinate Figure S3. Energy diagram (ZPE corrected) for the reaction of [ 2 Li] 2 and allyl acetate. S4

2.28 2.22 Li 1 1 2 2.04 2.05 1.41 1.48 1.51 Li 2 1.83 2.38 1 Li 1 2 2.02 2.59 2.10 1.42 1.42 1.97 2.20 Li 2 1.76 CP TS Li 1 2.12 2.35 2 1 2.02 2.13 1.40 1.51 CP syn Li 2 1.88 1.46 Li 1 Li 2 2.12 2.33 1.75 2 1 3.07 1.96 2.22 2.07 1.44 1.40 TS syn Figure S4. Structures of π-complexes and oxidative addition TSs in the reaction of [ 2 Li] 2 and allyl acetate. Bond lengths are in Å. 2-3. [ 2 Li] 2 2 2 + Allyl Acetate 2.01 Li 1 2.37 1 2.34 2 Li 2 2.04 2.05 1.90 1.40 1.49 1.50 1.94 +7.5 2.05 Li 1 1 2.51 2.27 2 2.52 1.94 2.03 2.12 Li 2 1.80 1.42 1.41 2.07 CP 2 2 TS 2 2 Figure S5. Structures of π-complex and oxidative addition TS for the reaction of [ 2 Li] 2 2 2 + allyl acetate. Bond lengths are in Å. The activation energy (ZPE corrected, kcal/mol) is shown above an arrow. S5

3. Reaction Pathways, Energetics and Representative Structures of Heterocuprate Reactions. 3-1. [X] + Allyl Acetate (X = CN, Cl, S, N 2 ) Scheme S3. Reaction of X and Allyl Acetate X + Ac " RT! X "! X "! Ac Ac " X X "!! Ac Ac Ac " CP MX ' TS MX ' PD MX Ac X! X "! X "! TS RE-X X "! X + "! X + "! CP XM ' TS XM ' PD XM TS RE-X E rel (kcal/mol) +30 X = CN TS XM ' 24.9 TS RE-X + Ac +20 +10 0 RT 0.0 CP MX ' 9.7 9.1 CP XM ' 21.7 TS MX ' 17.9 22.4 PD MX (= PD XM ) + Ac CN + butene + Ac 2.2 Reaction coordinate Figure S6. Energy diagram (ZPE corrected) for the reaction of CN and allyl acetate. E rel (kcal/mol) TS XM ' +30 TS X = Cl RE-X 25.4 + Ac +20 17.6 21.5 22.4 CP MX ' TS MX ' PD 9.0 MX +10 (= PD XM ) RT 8.6 + Ac 0 CP XM ' 0.0 Cl + butene + Ac 1.7 Reaction coordinate Figure S7. Energy diagram (ZPE corrected) for the reaction of Cl and allyl acetate. S6

+20 +10 0 E rel (kcal/mol) X = S RT 0.0 CP MX ' 8.0 7.2 CP XM ' TS XM ' 20.2 TS RE-X + Ac 17.9 10.3 17.2 TS MX ' PD MX (= PD XM ) + Ac S + butene + Ac 10 6.9 Reaction coordinate Figure S8. Energy diagram (ZPE corrected) for the reaction of S acetate. and allyl +20 +10 0 10 E rel (kcal/mol) X = N 2 RT 0.0 TS XM ' 20.7 CP MX ' 10.8 17.5 TS MX ' 10.5 CP XM ' 2.4 PD MX (= PD XM ) + Ac TS RE-X + Ac 15.3 N 2 + butene + Ac 9.2 Reaction coordinate Figure S9. Energy diagram (ZPE corrected) for the reaction of N 2 acetate. and allyl 2.05 2.14 1.39 1.50 N 1.48 1.97 2.16 2.68 N 1.43 1.40 2.19 CP MX ' TS MX ' N N 2.13 2.07 1.39 1.48 1.50 2.16 2.36 2.09 1.39 1.42 2.13 CP XM ' TS XM ' Figure S10. Structures of π-complexes and oxidative addition TSs in the reaction of CN and allyl acetate. S7

3-2. [(CN)Li][ 2 Li] + Allyl Acetate Scheme S4. Reaction of [(CN)Li][ 2 Li] and Allyl Acetate Li Li C N +! " Ac Li 1 N C Li 2! " CP MC Li 1 N C "! Li 2 " C Li 1! N TS MC N C Li 1 " Li 2 Li 2! Li 2 Li 1 N C PD MC-Li (= PD CM-Li ) CP CM TS CM 2 Li LiAc CN CN CN + PD MC (= PD CM ) TS RE-CN +10 E rel (kcal/mol) TS CM 13.0 TS RE-CN + 2 Li LiAc 9.1 0 10 RT 0.0 4.6 CP CM 3.9 CP MC 5.2 TS MC 2.6 PD CM (= PD MC ) + 2 Li LiAc 13.6 PD MC-LI (= PD CM-Li ) CN + butene + 2 Li LiAc 8.7 Reaction coordinate Figure S11. Energy diagram (ZPE corrected) for the reaction of [(CN)Li][ 2 Li] and allyl acetate. S8

1.91 Li1 1 N 2.09 2.19 1.38 1.51 2.14 Li 2 1.88 1.47 1 N 1.88 1.99 2.63 " 2.10 1.42! 1.40 2.04 159 Li 1 Li 2 1.74 CP MC TS MC Li 1 1.86 N Li 2 2.05 2.12 1.50 1.80 1.40 1.50 2 N 1.88 140 Li 1 2.17 2.34 " 2.09! 1.39 1.43 2.09 Li 2 1.75 CP CM TS CM Figure S12. Structures of π-complexes and oxidative addition TSs in the reaction of [(CN)Li][ 2 Li] and allyl acetate. S9

3-3. [(CN)Li][ 2 Li] 2 2 + Allyl Acetate 2.08 2.17 N 1.98 1.38 1.50 1.47 2.22 CP MC 2 2 (0.0) Li 1 Li 2 1.96 +11.0 1.98 2.15 2.47 1.43 1.39 2.37 N 1.96 Li 1 154 TS MC 2 2 (+11.0) Li 2 1.79 N 2.12 Li 1 1.94 Li 2 2.04 1.90 1.39 1.50 1.49 +10.4 Li 1 126 1.96 N 2.16 2.09 2.30 1.39 1.42 Li 2 1.79 2.14 CP CM 2 2 (+6.7) TS CM 2 2 (+17.1) Figure S13. Structures of π-complexes and oxidative addition TSs for the reaction of [(CN)Li][ 2 Li] 2 2 and allyl acetate. Energies relative to CP MC 2 2 and energy changes (ZPE corrected, kcal/mol) are shown in parentheses and above arrows, respectively. S10

4. Energies and Cartesian Coordinates of Stationary Points. Table S1. Energies of Stationary Points in the Reaction of 2 and Allyl Acetate E E + ZPE H G 2-277.2788056-277.211157-277.204889-277.23879 Allyl acetate -345.8069514-345.684403-345.675185-345.718571 CP' -623.0692584-622.878092-622.861593-622.924547 TS' -623.0600555-622.869896-622.853688-622.915404 PD Ac -623.088521964-622.897400-622.880094-622.946873 PD -394.4532915-394.311619-394.30095-394.346331 Ac -228.6362049-228.587703-228.583227-228.613577 TS RE -394.43116-394.289781-394.279376-394.324641-237.255025-237.220323-237.216073-237.243918 butene -157.2303165-157.122125-157.115906-157.149639 Table S2. Energies of Stationary Points in the Reaction of [ 2 Li] 2 ( 2 2 ) and Allyl Acetate E E + ZPE H G [ 2 Li] 2-569.5200648-569.374956-569.35868-569.417231 Allyl acetate -345.798836-345.675714-345.666495-345.709789 CP Li -915.335766-915.066603-915.03996-915.127472 CP -915.3112763-915.041664-915.016137-915.09691 TS -915.3020137-915.033904-915.008375-915.089613 CP syn -915.3203142-915.050372-915.025758-915.104619 TS syn -915.294167-915.026492-915.000867-915.082036 PD Li -915.3493137-915.081436-915.054453-915.141023 PD -394.4497882-394.307448-394.296765-394.342635 2 Li LiAc -520.8955666-520.770322-520.756234-520.810428 TS RE -394.4258421-394.283684-394.273383-394.318286-237.248811356-237.213780-237.209549-237.237366 butene -157.2284519-157.119802-157.113593-157.147309 CP 2 2-1225.391337-1224.9567-1224.920162-1225.02777 TS 2 2-1225.378382-1224.944747-1224.907638-1225.01719 S11

Table S3. Energies of Stationary Points in the Reaction of X and Allyl acetate E E + ZPE H G CN -330.2789647-330.237159-330.230283-330.26599 CP MX ' (X = CN) -676.071638-675.906097-675.889704-675.952144 TS MX ' (X = CN) -676.0504514-675.88697-675.870636-675.933168 CP XM ' (X = CN) -676.0726032-675.906999-675.890689-675.951987 TS XM ' (X = CN) -676.0452072-675.881925-675.865532-675.927745 PD MX (= PD XM, X = CN) -447.4195548-447.30542-447.294511-447.341208 TS RE-X (X = CN) -447.412531-447.298184-447.287728-447.333591 CN -290.2218916-290.215187-290.210691-290.234098 Cl -697.669089-697.633663-697.62756-697.661999 CP MX ' (X = Cl) -1043.462673-1043.303785-1043.288894-1043.34792 TS MX ' (X = Cl) -1043.440514-1043.283781-1043.268141-1043.32948 CP XM ' (X = Cl) -1043.463169-1043.304445-1043.288591-1043.35074 TS XM ' (X = Cl) -1043.433982-1043.277619-1043.262705-1043.32125 PD MX (= PD XM, X = Cl) -814.8096041-814.702285-814.691959-814.737756 TS RE-X (X = Cl) -814.8023011-814.694709-814.684923-814.730132 Cl -657.6087041-657.607904-657.604239-657.631314 S -675.5340497-675.461122-675.452523-675.494804 CP MX ' (X = S) -1021.329469-1021.132768-1021.115747-1021.17913 TS MX ' (X = S) -1021.311999-1021.117085-1021.099401-1021.16497 CP XM ' (X = S) -1021.330635-1021.134006-1021.116044-1021.18254 TS XM ' (X = S) -1021.308046-1021.113405-1021.095605-1021.16138 PD MX (= PD XM, X = S) -792.6869043-792.541377-792.529176-792.578601 TS RE-X (X = S) -792.6759733-792.530359-792.518389-792.568265 S -635.4877351-635.449027-635.443377-635.477813 N 2-371.948463-371.834475-371.825163-371.867708 CP MX ' (X = N 2 ) -717.7397103-717.501725-717.483417-717.548262 TS MX ' (X = N 2 ) -717.727679-717.491015-717.472743-717.538555 CP XM ' (X = N 2 ) -717.7399202-717.502095-717.483695-717.549146 TS XM ' (X = N 2 ) -717.7223359-717.485857-717.467532-717.533072 PD MX (= PD XM, X = N 2 ) -489.1141983-488.927545-488.913761-488.968363 TS RE-X (X = N 2 ) -489.093802-488.906734-488.893617-488.946352 N 2-331.9067081-331.826004-331.819525-331.855155 S12

Table S4. Energies of Stationary Points in the Reaction of [(CN)Li][ 2 Li] ( 2 2 ) and Allyl Acetate E E + ZPE H G [(CN)Li][ 2 Li] -622.502212785-622.384173-622.368636-622.425304 CP MC -968.3083625-968.066157-968.040018-968.125995 TS MC -968.2925262-968.051626-968.025682-968.110058 CP CM -968.2951625-968.052566-968.026462-968.111512 TS CM -968.2797967-968.039195-968.013197-968.096778 PD MC-Li (= PD CM-Li ) -968.3223804-968.081504-968.054658-968.143783 PD MC (= PD CM ) -447.4002159-447.285438-447.274585-447.321001 TS RE-CN -447.3900981-447.275094-447.264651-447.310517 CN -290.1904586-290.183662-290.179159-290.201683 CP MC 2 2-1278.390054-1277.982882-1277.945761-1278.05717 TS MC 2 2-1278.370694-1277.96536-1277.927401-1278.04304 CP CM 2 2-1278.380065-1277.97219-1277.934537-1278.04724 TS CM 2 2-1278.360905-1277.955645-1277.917741-1278.03249 S13

Cartesian Coordinates of All Stationary Points 2 + allyl acetate (B3LYP/SDD for and 6-31+G(d) for the rest, CPCM (solvent = THF)) 2 SCF Done: E(RB+HF-LYP) = -277.278805583 A.U. 1 29 0-0.000000 0.000316 0.000000 2 6 0-1.963106 0.001749 0.000000 3 6 0 1.963099-0.002599 0.000000 4 1 0-2.384713 0.512941 0.885114 5 1 0-2.384713 0.512941-0.885114 6 1 0-2.384953-1.020263 0.000000 7 1 0 2.386226 1.018896 0.000000 8 1 0 2.384097-0.514291 0.885112 9 1 0 2.384097-0.514291-0.885112 Allyl acetate SCF Done: E(RB+HF-LYP) = -345.806951428 A.U. -------------------------------------------------------------------------------------------------------- ------------------------------------------------------------------------------------------------------ 1 6 0-3.186282-0.186574 0.401664 2 6 0-2.115756-0.269125-0.394443 3 6 0-0.866468 0.527527-0.182199 4 1 0-3.196801 0.454619 1.282619 5 1 0-4.092945-0.751066 0.194838 6 1 0-2.127861-0.918752-1.272610 7 1 0-0.912319 1.128650 0.731634 8 1 0-0.659644 1.191164-1.029933 9 8 0 0.245491-0.412202-0.070984 10 6 0 1.481191 0.114459 0.026286 11 8 0 1.697900 1.315470 0.025957 12 6 0 2.534047-0.959006 0.139524 13 1 0 2.364428-1.553159 1.044728 14 1 0 3.524035-0.501746 0.180837 15 1 0 2.473588-1.639538-0.716893 CP' SCF Done: E(RB+HF-LYP) = -623.069258378 A.U. --------------------------------------------------------------------------------------------------------------- --------------------------------------------------------------------------------------------------------------- 1 6 0-3.634846-0.618275 0.823619 2 29 0-1.938116 0.008476-0.059555 3 6 0-2.133526 1.964926-0.496372 4 6 0-0.762490-1.649099-0.078705 5 6 0-0.084156-0.581516-0.711796 6 6 0 0.975083 0.212238-0.035262 7 8 0 2.315932-0.405268-0.312251 8 6 0 3.386859 0.190205 0.215017 9 8 0 3.338016 1.189177 0.924610 10 6 0 4.672502-0.504271-0.175763 11 1 0 0.861744 0.224367 1.052459 12 1 0 1.036504 1.240048-0.400388 13 1 0-0.082940-0.525875-1.802780 14 1 0-1.231861-2.435042-0.668969 15 1 0-0.512581-1.930100 0.945221 16 1 0 5.507481-0.086189 0.389990 17 1 0 4.854884-0.361995-1.247781 S14

18 1 0 4.598191-1.581588 0.005040 19 1 0-3.458139-0.991854 1.847672 20 1 0-4.112389-1.444092 0.267290 21 1 0-4.368108 0.202564 0.892970 22 1 0-3.042754 2.109293-1.106549 23 1 0-2.294362 2.528315 0.440102 24 1 0-1.298448 2.449824-1.030470 TS' SCF Done: E(RB+HF-LYP) = -623.060055486 A.U. 1 6 0-3.340605-1.103708 0.751794 2 29 0-1.883959-0.015353-0.043673 3 6 0-0.060752-0.274025-1.055556 4 6 0 0.721545 0.673299-0.344695 5 6 0-2.552377 1.860031 0.100219 6 6 0-0.575213-1.472122-0.474939 7 8 0 2.555869 0.362846-0.703510 8 6 0 3.334601 0.104910 0.300724 9 6 0 4.741193-0.342211-0.095835 10 8 0 3.016570 0.170684 1.504130 11 1 0 0.810665 0.583019 0.732277 12 1 0 0.778837 1.685725-0.729497 13 1 0-0.224293-0.091609-2.119202 14 1 0-0.972955-2.252061-1.122072 15 1 0-0.166515-1.829354 0.471236 16 1 0 5.443929-0.164935 0.723091 17 1 0 5.080747 0.169287-1.001498 18 1 0 4.722090-1.419145-0.308056 19 1 0-3.024883-2.068779 1.169441 20 1 0-4.079014-1.293753-0.042216 21 1 0-3.826133-0.508459 1.537234 22 1 0-3.652395 1.860419 0.053791 23 1 0-2.267496 2.280242 1.079491 24 1 0-2.177640 2.549353-0.672728 PD Ac SCF Done: E(RB+HF-LYP) = -623.088521964 A.U. 1 29 0 0.784072-0.202502 0.001506 2 6 0 0.816855-1.538087-1.428257 3 6 0 1.129919-1.450390 1.471786 4 6 0 0.213905 1.482995-1.176002 5 6 0 0.872730 1.917322-0.012435 6 6 0 0.455539 1.496627 1.260875 7 1 0-0.026002-2.215000-1.248545 8 1 0 0.742719-1.107579-2.430631 9 1 0 1.754818-2.095258-1.326352 10 1 0 1.070832-2.475427 1.095457 11 1 0 0.402616-1.301137 2.276492 12 1 0 2.138335-1.251341 1.855023 13 1 0 0.647273 1.670963-2.154076 14 1 0-0.853511 1.266010-1.154973 15 1 0 1.887030 2.311988-0.119663 16 1 0 1.089651 1.685835 2.123030 17 1 0-0.598597 1.290381 1.460274 18 8 0-2.985620 1.272718 1.586968 19 6 0-3.947026 0.803759 0.908365 20 8 0-5.153471 1.194000 0.961524 21 6 0-3.624462-0.315614-0.097321 22 1 0-3.548314 0.118461-1.103594 23 1 0-2.673761-0.803682 0.136707 24 1 0-4.428987-1.058713-0.124372 ------ S15

PD SCF Done: E(RB+HF-LYP) = -394.453291504 A.U. ---- ---- 1 6 0-1.534333 1.471201-0.019371 2 29 0-0.253311-0.009673-0.021264 3 6 0-1.592425-1.434453-0.013327 4 6 0 1.481008 1.218784 0.222645 5 6 0 1.842290-0.004882-0.365496 6 6 0 1.485642-1.234747 0.211935 7 1 0 1.392538 1.309355 1.305914 8 1 0 1.605800 2.147493-0.326675 9 1 0 2.114038 0.000061-1.424836 10 1 0 1.614714-2.157931-0.345577 11 1 0 1.394778-1.336060 1.294237 12 1 0-2.551559 1.071577-0.010781 13 1 0-1.368370 2.097402 0.864305 14 1 0-1.373400 2.072429-0.921680 15 1 0-1.156552-2.436410-0.043388 16 1 0-2.189421-1.308911 0.896564 17 1 0-2.229631-1.273906-0.889741 TS RE SCF Done: E(RB+HF-LYP) = -394.431159973 A.U. --------------------------------------------------------------------------------------------------------------- 1 6 0 2.233483-0.683483 0.026725 2 29 0 0.368665-0.126550-0.058476 3 6 0-1.507425 0.884268 0.228910 4 6 0-1.689770-0.433813-0.360883 5 6 0-1.300725-1.608237 0.246016 6 6 0 0.286371 2.015327 0.016304 7 1 0 2.836875-0.062768-0.653946 8 1 0 2.621370-0.523627 1.045138 9 1 0 2.404829-1.736967-0.232933 10 1 0 1.251250 1.963088 0.525617 11 1 0-0.317099 2.785525 0.493271 12 1 0 0.414009 2.241181-1.045466 13 1 0-1.133518-1.670860 1.321079 14 1 0-1.349458-2.550934-0.292656 15 1 0-1.949237-0.466090-1.422170 16 1 0-1.591813 0.957705 1.313124 17 1 0-2.010097 1.689315-0.297692 ------------------------------------------------------------------------------------------------------------- SCF Done: E(RB+HF-LYP) = -237.255025013 A.U. -------------------------------------------------------------------------------------------------------------- ------------------------------------------------------------------------------------------------------------ 1 29 0 0.000000 0.000000 0.478093 2 6 0 0.000000 0.000000-1.418649 3 1 0 0.000000 1.033944-1.784269 4 1 0 0.895422-0.516972-1.784269 5 1 0-0.895422-0.516972-1.784269 -------------------------------------------------------------------------------------------------------------- butene SCF Done: E(RB+HF-LYP) = -157.230316491 A.U. ------------------------------------------------------------------------------------------------------------ ------------------------------------------------------------------------------------------------------------ 1 6 0 1.867828 0.023073-0.277452 S16

2 6 0 0.722344-0.303645 0.333298 3 6 0-0.540399 0.516536 0.313261 4 6 0-1.733559-0.241336-0.296622 5 1 0 1.967772 0.946240-0.848551 6 1 0 2.746112-0.617846-0.227472 7 1 0 0.670136-1.242967 0.893079 8 1 0-0.366861 1.448637-0.241186 9 1 0-0.798512 0.803815 1.344400 10 1 0-1.539699-0.502102-1.344153 11 1 0-1.932140-1.172486 0.249364 12 1 0-2.644095 0.368942-0.260388 [ 2 Li] 2 + allyl acetate (B3LYP / SDD for and 6-31+G(d) for the rest) [ 2 Li] 2 SCF Done: E(RB+HF-LYP) = -569.520064783 A.U. -- 1 6 0-1.969465-2.048690-0.000000 2 29 0-0.000116-1.915259-0.000000 3 3 0 1.627147 0.001396-0.000000 4 29 0 0.000116 1.915261 0.000000 5 6 0-1.969465 2.045317 0.000000 6 6 0 1.969465-2.045319-0.000000 7 3 0-1.627147-0.001398 0.000000 8 6 0 1.969465 2.048689 0.000000 9 1 0-2.078158-3.142761-0.000000 10 1 0 2.080162-3.139183-0.000000 11 1 0-2.539943-1.721753 0.891085 12 1 0 2.539477-1.717546 0.891132 13 1 0 2.539477-1.717546-0.891132 14 1 0-2.539943-1.721753-0.891085 15 1 0-2.080168 3.139180 0.000000 16 1 0 2.078162 3.142759 0.000000 17 1 0-2.539476 1.717540 0.891132 18 1 0 2.539941 1.721750 0.891085 19 1 0 2.539941 1.721750-0.891085 20 1 0-2.539476 1.717540-0.891132 -------------------------------------------------------------------------------------------------------------- Allyl acetate SCF Done: E(RB+HF-LYP) = -345.798836011 A.U. -------------------------------------------------------------------------------------------------------------- 1 6 0-3.198476-0.168226 0.386352 2 6 0-2.111471-0.283450-0.380877 3 6 0-0.859540 0.510827-0.175777 4 1 0-3.225489 0.501403 1.244162 5 1 0-4.103078-0.734530 0.181282 6 1 0-2.108769-0.965900-1.230611 7 1 0-0.905458 1.121456 0.731414 8 1 0-0.656735 1.176228-1.023025 9 8 0 0.246830-0.424105-0.064114 10 6 0 1.483067 0.121477 0.023948 11 8 0 1.687039 1.318458 0.011564 12 6 0 2.542584-0.947491 0.144273 13 1 0 2.384092-1.529059 1.059144 14 1 0 3.528414-0.480969 0.170394 15 1 0 2.479078-1.642270-0.699873 - CP Li SCF Done: E(RB+HF-LYP) = -915.335766015 A.U. -- S17

1 6 0-2.806389 2.315539 1.023528 2 29 0-1.528944 1.894939-0.432432 3 6 0-0.279242 1.714316-1.933491 4 3 0-2.944392 0.255131 0.774619 5 29 0-2.001339-1.835684-0.143218 6 6 0-0.789354-2.189799-1.645296 7 3 0-0.087680-0.244248-0.949297 8 6 0-3.296627-1.708876 1.351215 9 8 0 1.549336-0.381154 0.054414 10 6 0 2.168644 0.053705 1.017184 11 6 0 1.592812 0.978840 2.053077 12 8 0 3.437212-0.281266 1.277151 13 6 0 4.107545-1.202335 0.381702 14 6 0 4.970512-0.500117-0.627263 15 6 0 5.167457 0.815480-0.724171 16 1 0-1.177325-3.157573-1.999456 17 1 0 0.276674-2.378808-1.429230 18 1 0-0.840756-1.534408-2.533589 19 1 0-3.444614-2.778853 1.557314 20 1 0-2.976995-1.282218 2.321796 21 1 0-4.322885-1.334710 1.160362 22 1 0 5.812706 1.228888-1.493697 23 1 0 4.695664 1.521886-0.046851 24 1 0-2.682434 3.407185 1.070203 25 1 0-3.892369 2.178329 0.848413 26 1 0-2.605311 1.973498 2.057610 27 1 0-0.412771 2.690178-2.426495 28 1 0 0.804586 1.649442-1.735138 29 1 0-0.517877 0.977578-2.721603 30 1 0 5.465656-1.179221-1.322154 31 1 0 4.714222-1.832592 1.040712 32 1 0 3.359215-1.829647-0.111445 33 1 0 0.819955 1.602729 1.597496 34 1 0 1.124615 0.373139 2.839084 35 1 0 2.369949 1.592967 2.513097 CP SCF Done: E(RB+HF-LYP) = -915.311276261 A.U. - 1 6 0 0.258621 3.485479 0.919021 2 29 0 1.461436 2.322170-0.144036 3 3 0-1.075377 2.240603 0.002962 4 6 0 2.872092 1.462052-1.206789 5 8 0-2.753398 1.542791-0.230902 6 6 0-3.474783 0.533034-0.233371 7 6 0-4.947548 0.605048-0.529418 8 8 0-3.031761-0.677203 0.024052 9 6 0-1.565191-0.806140 0.347019 10 6 0-1.133704-2.225303 0.401096 11 6 0-0.668581-2.898663-0.742811 12 29 0 0.900829-2.043954 0.235626 13 6 0 2.489727-2.337655-0.982667 14 3 0 2.360913-0.257602-0.056035 15 6 0 1.480255-0.949567 1.865040 16 1 0 1.034848 4.123664 1.364519 17 1 0-0.286644 3.075769 1.791976 18 1 0-0.423282 4.203474 0.420562 19 1 0 3.197732 2.327046-1.804079 20 1 0 3.797831 1.135802-0.692572 21 1 0 2.624253 0.690299-1.956008 22 1 0-0.589938-3.983375-0.743394 23 1 0-0.722323-2.439376-1.728306 24 1 0 1.421260-1.733944 2.635659 25 1 0 2.521226-0.574760 1.953876 26 1 0 0.835153-0.129402 2.213370 S18

27 1 0 2.667847-3.418868-0.892599 28 1 0 2.319196-2.142407-2.051390 29 1 0 3.468696-1.882573-0.727384 30 1 0-1.404169-2.784723 1.294792 31 1 0-1.044381-0.265474-0.448010 32 1 0-1.432769-0.290048 1.300534 33 1 0-5.394243-0.388925-0.576847 34 1 0-5.437532 1.191753 0.255846 35 1 0-5.099115 1.134398-1.475372 ------------------------------------------------------------------------------------------------------------- TS SCF Done: E(RB+HF-LYP) = -915.302013669 A.U. 1 6 0 0.214686 3.530739 0.940219 2 29 0 1.423497 2.390595-0.126233 3 6 0 2.839259 1.542752-1.202276 4 3 0-1.166586 2.321172-0.006388 5 8 0-2.642064 1.396805-0.230451 6 6 0-3.511983 0.475208-0.193340 7 8 0-3.290317-0.719613 0.178077 8 6 0-4.928854 0.812329-0.625652 9 6 0-1.422293-1.156707 0.640007 10 29 0 0.913106-2.030318 0.219283 11 6 0 2.459278-2.262132-1.021836 12 6 0-1.138430-2.495416 0.282419 13 6 0-0.523138-2.836377-0.949607 14 6 0 1.633121-1.058209 1.839845 15 3 0 2.319701-0.106043-0.022077 16 1 0 0.976237 4.166989 1.413806 17 1 0-0.347936 3.101478 1.791006 18 1 0-0.458444 4.251969 0.435890 19 1 0 3.133703 2.421209-1.795392 20 1 0 3.783768 1.228613-0.714644 21 1 0 2.591702 0.775042-1.956785 22 1 0-0.384768-3.882959-1.208232 23 1 0-0.592792-2.158767-1.798938 24 1 0 1.466534-1.808756 2.624761 25 1 0 2.724974-0.875811 1.860865 26 1 0 1.137217-0.139432 2.182624 27 1 0 2.649146-3.342432-1.012329 28 1 0 2.265954-1.971755-2.061588 29 1 0 3.406690-1.795174-0.698036 30 1 0-1.376283-3.278704 0.999434 31 1 0-1.061474-0.353915 0.011503 32 1 0-1.591749-0.905192 1.679173 33 1 0-5.581129-0.060286-0.560115 34 1 0-5.319564 1.615550 0.009078 35 1 0-4.913459 1.188255-1.654805 --------------------------------------------------------------------------------------------------------------- CP syn SCF Done: E(RB+HF-LYP) = -915.320314240 A.U. -- 1 6 0-1.571001-2.384137-1.258496 2 29 0-2.713383-1.117049-0.283942 3 3 0-0.209270-1.217723-0.014040 4 3 0-2.022885 1.031681 0.690205 5 29 0 0.292029 1.596792 0.231543 6 6 0-1.302858 2.852911-0.111663 7 6 0-3.946334 0.098999 0.661566 8 6 0 1.628033 2.521275-0.973189 9 6 0 2.344815 1.512787-0.326853 10 6 0 2.880534 0.327639-1.090029 11 8 0 3.445975-0.687444-0.202189 12 6 0 2.703597-1.718961 0.181159 S19

13 6 0 3.437941-2.657920 1.099677 14 6 0-0.079953 0.286566 1.786799 15 8 0 1.538449-1.888374-0.165105 16 1 0-2.348286-2.897126-1.846794 17 1 0-1.056872-3.190527-0.706587 18 1 0-0.856741-2.007731-2.013093 19 1 0-4.875888-0.489680 0.647967 20 1 0-3.779370 0.310604 1.736227 21 1 0-4.214409 1.057065 0.180467 22 1 0 1.663571 3.545467-0.610710 23 1 0 1.302811 2.408289-2.007254 24 1 0 0.501550 0.909263 2.487937 25 1 0-1.068749 0.189657 2.273011 26 1 0 0.372938-0.713127 1.904572 27 1 0-0.860583 3.834093-0.314838 28 1 0-1.918451 2.618254-0.996340 29 1 0-2.007123 3.048854 0.724146 30 1 0 2.920596 1.768452 0.563061 31 1 0 3.748817 0.615409-1.692624 32 1 0 2.138334-0.137357-1.743810 33 1 0 4.518465-2.595400 0.956697 34 1 0 3.208570-2.379333 2.135819 35 1 0 3.082527-3.677964 0.937736 -- TS syn SCF Done: E(RB+HF-LYP) = -915.294167005 A.U. -- -- 1 6 0 3.083082 1.013356-1.868713 2 29 0 2.946009 0.016382-0.168127 3 3 0 1.009952-1.177569 1.052997 4 29 0-1.302107-1.299879 0.212900 5 6 0-2.436440-1.524416-1.368276 6 6 0-3.256721-0.636451-0.589923 7 6 0-3.342292 0.740221-0.833674 8 6 0 3.057962-0.997734 1.514587 9 3 0 1.166289 1.449456-1.211382 10 8 0-0.459713 1.871341-0.705601 11 6 0-1.180964 2.369322 0.216751 12 8 0-2.381501 2.053850 0.441870 13 6 0-0.566157 3.436836 1.114455 14 6 0-0.787297-0.686396 2.071708 15 6 0 0.026667-2.621686-0.491517 16 1 0 4.108961 0.742903-2.157120 17 1 0 3.089365 2.120885-1.853836 18 1 0 2.469172 0.704515-2.737247 19 1 0 4.134296-0.895893 1.718498 20 1 0 2.570563-0.605126 2.425690 21 1 0 2.890644-2.091907 1.495783 22 1 0-2.750652-2.562273-1.457556 23 1 0-1.936915-1.130082-2.253077 24 1 0-1.760598-0.485409 2.534803 25 1 0-0.305579-1.433548 2.731056 26 1 0-0.226652 0.257571 2.185572 27 1 0-0.453409-3.379608-1.113984 28 1 0 0.802707-2.137144-1.100796 29 1 0 0.499802-3.156796 0.348370 30 1 0-3.966187-1.066742 0.115308 31 1 0-4.204737 1.290727-0.480623 32 1 0-2.813904 1.164657-1.679946 33 1 0-1.256028 3.730657 1.907708 34 1 0 0.364270 3.062810 1.556694 35 1 0-0.314324 4.315708 0.508892 - PD Li SCF Done: E(RB+HF-LYP) = -915.349313719 A.U. S20

1 6 0 3.899635 0.190512 1.411553 2 29 0 2.975720-0.812760-0.016078 3 3 0 2.375340 1.474910 0.689492 4 3 0 0.536160-0.535244-0.611389 5 6 0 2.115063-1.823936-1.467906 6 8 0 0.343466 1.248614-0.262329 7 6 0 0.534443 2.517690-0.336576 8 6 0-0.497332 3.366840-1.054732 9 8 0 1.535790 3.068967 0.189016 10 6 0-0.846812-1.841883 1.175299 11 29 0-2.129582-0.805488 0.109299 12 6 0-2.846474 0.338639 1.764820 13 6 0-3.843470 0.255020 0.780559 14 6 0-3.587092 0.600451-0.556563 15 6 0-1.715391-1.472584-1.690445 16 1 0 4.654626-0.541907 1.732763 17 1 0 3.349347 0.435975 2.341316 18 1 0 4.486521 1.088853 1.139789 19 1 0 3.006662-2.250954-1.953939 20 1 0 1.495836-2.695089-1.195609 21 1 0 1.596131-1.303010-2.296518 22 1 0-4.304580 0.354499-1.332691 23 1 0-2.867572 1.380217-0.798484 24 1 0-1.468730-2.522680 1.767472 25 1 0-0.173603-2.448424 0.562423 26 1 0-0.269694-1.213629 1.861659 27 1 0-2.610700-2.014546-2.014345 28 1 0-1.535250-0.653061-2.395131 29 1 0-0.875351-2.173294-1.698081 30 1 0-4.708860-0.376290 0.985984 31 1 0-2.060514 1.089108 1.697508 32 1 0-3.003561-0.103537 2.743242 33 1 0-1.342001 3.552946-0.378847 34 1 0-0.069545 4.331073-1.337143 35 1 0-0.881147 2.848795-1.938634 --------------------------------------------------------------------------------------------------------------- PD SCF Done: E(RB+HF-LYP) = -394.449788223 A.U. - - 1 6 0-1.540350 1.462576-0.018701 2 29 0-0.254960-0.009587-0.021746 3 6 0-1.596463-1.427154-0.011941 4 6 0 1.486615 1.221461 0.221020 5 6 0 1.845540-0.004321-0.361782 6 6 0 1.491066-1.236486 0.209760 7 1 0 1.401094 1.316270 1.302849 8 1 0 1.617401 2.148694-0.327160 9 1 0 2.116420 0.000780-1.418600 10 1 0 1.626021-2.157565-0.347649 11 1 0 1.403043-1.343053 1.290450 12 1 0-2.555563 1.060890-0.011144 13 1 0-1.374875 2.086470 0.865928 14 1 0-1.377728 2.062127-0.921029 15 1 0-1.157348-2.426938-0.041905 16 1 0-2.191989-1.300426 0.897658 17 1 0-2.231072-1.265695-0.888892 ------ 2 Li LiAc SCF Done: E(RB+HF-LYP) = -520.895566557 A.U. ----- ----- 1 6 0-1.842892 1.969506-0.001116 2 29 0-1.744803-0.001755 0.000287 S21

3 3 0 0.209698-1.602213-0.002489 4 6 0-1.838908-1.973166 0.001296 5 3 0 0.206140 1.602595 0.002502 6 8 0 1.924790 1.132153 0.000202 7 6 0 2.516962 0.010208-0.001833 8 6 0 4.034896-0.008178 0.001124 9 8 0 1.919033-1.110428-0.002725 10 1 0-1.498473 2.530082-0.892291 11 1 0-2.933118 2.110993-0.002419 12 1 0-1.500551 2.531718 0.889860 13 1 0-2.928786-2.117314 0.003933 14 1 0-1.496285-2.533926-0.890466 15 1 0-1.492125-2.533511 0.891722 16 1 0 4.396282-0.590879-0.853315 17 1 0 4.389515-0.514337 0.906314 18 1 0 4.444375 1.002914-0.038336 ---- TS RE SCF Done: E(RB+HF-LYP) = -394.425842122 A.U. ------ ------ 1 6 0 2.244276-0.619762 0.038447 2 29 0 0.370039-0.130199-0.067428 3 6 0-1.533809 0.860583 0.234416 4 6 0-1.684471-0.462555-0.347554 5 6 0-1.236931-1.625821 0.247000 6 6 0 0.235629 2.020206 0.016192 7 1 0 2.830455 0.029190-0.629005 8 1 0 2.611005-0.460615 1.063530 9 1 0 2.445329-1.663322-0.233074 10 1 0 1.186943 1.985379 0.550373 11 1 0-0.387218 2.791946 0.465316 12 1 0 0.390584 2.235462-1.044044 13 1 0-1.069057-1.694238 1.320310 14 1 0-1.257915-2.565918-0.295448 15 1 0-1.950959-0.503565-1.404280 16 1 0-1.611980 0.936664 1.317912 17 1 0-2.066483 1.648884-0.287181 - SCF Done: E(RB+HF-LYP) = -237.248811356 A.U. - 1 29 0 0.000000 0.000000 0.476286 2 6 0 0.000000 0.000000-1.419582 3 1 0 0.000000 1.038540-1.764931 4 1 0 0.899402-0.519270-1.764931 5 1 0-0.899402-0.519270-1.764931 butene SCF Done: E(RB+HF-LYP) = -157.228451872 A.U. - 1 6 0 1.866481 0.020012-0.278250 2 6 0 0.722846-0.299284 0.336514 3 6 0-0.540681 0.518682 0.309964 4 6 0-1.732841-0.244121-0.295104 5 1 0 1.966836 0.936582-0.857904 6 1 0 2.743965-0.619670-0.223457 7 1 0 0.672456-1.231588 0.904019 8 1 0-0.366743 1.445754-0.251856 9 1 0-0.798229 0.817198 1.337622 10 1 0-1.535441-0.516521-1.338498 S22

11 1 0-1.934136-1.169657 0.259116 12 1 0-2.643534 0.366169-0.267784 [ 2 Li] 2 2 2 + allyl acetate (B3LYP / SDD for and 6-31G(d) for the rest) CP 2 2 SCF Done: E(RB+HF-LYP) = -1225.39133702 A.U. 1 6 0-1.046716-1.824337-1.845443 2 29 0-0.000701-1.741751-0.164858 3 6 0 1.014278-1.795497 1.511448 4 3 0-2.453154-1.000153-0.469240 5 8 0-3.349190 0.669371-0.505169 6 6 0-3.377322 1.906238-0.488123 7 8 0-2.317219 2.676056-0.439736 8 6 0-0.969552 2.007947-0.433411 9 6 0 0.098102 2.997558-0.140111 10 29 0 1.751039 1.859537 0.263604 11 6 0 2.097382 0.939603-1.518587 12 6 0-4.676635 2.671945-0.524152 13 6 0 0.552111 3.234831 1.167529 14 6 0 3.040069 1.380636 1.750048 15 3 0 2.429292-0.425669 0.350464 16 1 0-0.281100-2.259742-2.505294 17 1 0-1.329383-0.881638-2.349476 18 1 0-1.909253-2.511477-1.941513 19 1 0 0.382455-2.434050 2.150035 20 1 0 2.001324-2.288895 1.529914 21 1 0 1.114311-0.853129 2.075553 22 1 0 1.126204 4.128915 1.399236 23 1 0 0.079811 2.752215 2.021159 24 1 0 2.604357 1.759728-2.054937 25 1 0 2.774433 0.075757-1.641291 26 1 0 1.198948 0.694339-2.100656 27 1 0 3.798332 2.178665 1.707389 28 1 0 2.567517 1.447996 2.739337 29 1 0 3.626507 0.442410 1.772881 30 1 0 0.336749 3.701453-0.936009 31 1 0-1.017890 1.224090 0.325905 32 1 0-0.867555 1.548025-1.417549 33 1 0-4.507952 3.747063-0.456123 34 1 0-5.201008 2.438623-1.456879 35 1 0-5.313281 2.341194 0.302534 36 8 0 4.054512-1.529565-0.084828 37 6 0 3.916382-2.755590-0.798057 38 6 0 5.278284-0.859344-0.380227 39 1 0 3.934354-2.579578-1.882516 40 1 0 4.724856-3.448992-0.529217 41 1 0 2.953908-3.184365-0.513418 42 1 0 5.288874 0.061764 0.204024 43 1 0 6.134147-1.486872-0.097648 44 1 0 5.339729-0.616392-1.449643 45 8 0-3.617369-2.210753 0.502102 46 6 0-3.218974-3.532253 0.868579 47 6 0-4.926273-1.877613 0.955019 48 1 0-3.223475-3.643784 1.960720 49 1 0-3.895667-4.273378 0.422629 50 1 0-2.205704-3.674567 0.489565 51 1 0-5.123357-0.856557 0.626419 52 1 0-5.670448-2.559048 0.520944 53 1 0-4.981654-1.933711 2.050585 TS 2 2 SCF Done: E(RB+HF-LYP) = -1225.37838196 A.U. S23

1 6 0 1.261091 0.902161 2.138150 2 29 0-0.025489 1.540549 0.788914 3 6 0-1.281933 2.458663-0.414067 4 3 0 2.503408 0.843051 0.360482 5 8 0 3.284500-0.599809-0.383852 6 6 0 3.563290-1.822689-0.577686 7 6 0 5.028883-2.232296-0.454598 8 8 0 2.741659-2.734807-0.870244 9 8 0 3.443758 2.458876-0.174017 10 6 0 4.573300 2.364762-1.038929 11 6 0 3.065306 3.800204 0.116191 12 6 0 0.735664-2.233426-0.849978 13 6 0 0.076258-3.096265 0.043100 14 6 0-0.255652-2.716696 1.365526 15 29 0-1.512796-1.697810 0.148194 16 6 0-2.659747-1.057586 1.656097 17 3 0-2.443584 0.599771-0.214974 18 6 0-2.164593-1.116876-1.674025 19 8 0-4.385112 1.176667-0.504683 20 6 0-5.460122 0.258333-0.307065 21 6 0-4.743368 2.228529-1.400502 22 1 0 0.614877 0.890534 3.029352 23 1 0 2.092971 1.578744 2.410787 24 1 0 1.683894-0.116622 2.091885 25 1 0-0.692873 3.358791-0.649314 26 1 0-1.543173 2.052845-1.409191 27 1 0-2.206009 2.846279 0.048634 28 1 0-0.732364-3.434751 2.027239 29 1 0 0.296244-1.920768 1.859107 30 1 0-3.178863-0.695197-1.741575 31 1 0-1.491261-0.463151-2.246986 32 1 0-2.211724-2.065306-2.225420 33 1 0-3.418098-1.842720 1.784696 34 1 0-2.088774-0.978643 2.585394 35 1 0-3.208022-0.107961 1.549363 36 1 0-0.258148-4.061682-0.332693 37 1 0-5.593732 2.796898-1.001180 38 1 0-5.010095 1.822552-2.386040 39 1 0-3.876490 2.883094-1.493600 40 1 0-5.753103-0.205773-1.258637 41 1 0-6.326450 0.775098 0.126490 42 1 0-5.109894-0.510539 0.381516 43 1 0 2.816875 4.340163-0.807686 44 1 0 3.877436 4.327102 0.635785 45 1 0 2.183749 3.751255 0.757674 46 1 0 5.452286 2.835330-0.577363 47 1 0 4.364003 2.854511-1.999823 48 1 0 4.754115 1.300578-1.193750 49 1 0 0.994963-1.225946-0.555719 50 1 0 0.709300-2.434211-1.912653 51 1 0 5.392713-1.981684 0.548166 52 1 0 5.156672-3.300906-0.635610 53 1 0 5.631076-1.664129-1.172429 ---------- X + allyl acetate (B3LYP / SDD for and 6-31+G(d) for the rest, CPCM (solvent = THF) CN SCF Done: E(RB+HF-LYP) = -330.278964680 A.U. S24

1 29 0-0.000000 0.280131 0.000000 2 6 0-0.003092 2.214142 0.000000 3 6 0 0.002320-1.620560 0.000000 4 1 0 0.507266 2.629839 0.885026 5 1 0 0.507266 2.629839-0.885026 6 1 0-1.025709 2.627417 0.000000 7 7 0 0.002259-2.796057 0.000000 CP MX ' (X = CN) SCF Done: E(RB+HF-LYP) = -676.071638035 A.U. 1 6 0 3.055610-1.749051-0.374586 2 29 0 1.773225-0.286084 0.089367 3 6 0 2.449800 1.544945-0.152860 4 7 0 2.899427 2.620957-0.308022 5 6 0 0.104250-1.314489 0.682410 6 6 0-0.210009 0.033670 0.828052 7 6 0-1.012738 0.802215-0.175984 8 8 0-2.438756 0.868845 0.227525 9 6 0-3.299210-0.022030-0.287302 10 6 0-4.678057 0.131760 0.310339 11 8 0-3.003049-0.863000-1.123625 12 1 0-0.239634-1.877178-0.183956 13 1 0 0.413909-1.911312 1.538189 14 1 0-0.091529 0.508857 1.803519 15 1 0-0.723015 1.853460-0.219641 16 1 0-0.966601 0.360380-1.173161 17 1 0-4.688009-0.328517 1.306427 18 1 0-5.413299-0.373731-0.319108 19 1 0-4.940174 1.187126 0.429398 20 1 0 3.976442-1.643558 0.223228 21 1 0 2.675055-2.770077-0.218973 22 1 0 3.353913-1.664610-1.433027 -------------------------------------------------------------------------------------------------------------- TS MX ' (X = CN) SCF Done: E(RB+HF-LYP) = -676.050451380 A.U. 1 6 0-3.032579-1.522913 0.809786 2 29 0-1.794638-0.225090-0.027712 3 6 0-0.446049-1.614349-0.410321 4 6 0 0.034426-0.484858-1.142184 5 6 0 0.708114 0.576344-0.538232 6 6 0-2.605469 1.540842 0.066284 7 7 0-3.136628 2.584136 0.134605 8 8 0 2.859032 0.286691-0.814542 9 6 0 3.535675 0.196866 0.270407 10 6 0 5.033668-0.093539 0.104300 11 8 0 3.084209 0.350500 1.432684 12 1 0-0.001868-1.849849 0.557500 13 1 0-0.843384-2.469033-0.952336 14 1 0-0.178058-0.425268-2.211046 15 1 0 0.850341 1.507224-1.073632 16 1 0 0.895732 0.592253 0.529743 17 1 0 5.255164-0.533439-0.872249 18 1 0 5.382522-0.757145 0.902301 19 1 0 5.588302 0.849928 0.191264 20 1 0-3.911053-1.553695 0.153696 21 1 0-2.641152-2.532283 0.957939 22 1 0-3.308296-1.077934 1.772871 CP XM ' (X = CN) S25

SCF Done: E(RB+HF-LYP) = -676.072603213 A.U. 1 6 0-1.606596 2.140409-0.470000 2 29 0-1.755931 0.165468-0.170664 3 6 0-3.464213-0.494968 0.533156 4 7 0-4.506028-0.843825 0.954199 5 6 0-0.614925-1.630692-0.298924 6 6 0 0.100880-0.533771-0.760624 7 6 0 1.150594 0.156279 0.056545 8 8 0 2.459463-0.416160-0.315780 9 6 0 3.540304 0.075086 0.306456 10 6 0 4.812320-0.572309-0.186880 11 8 0 3.491733 0.944670 1.165058 12 1 0-0.481853-2.001958 0.716414 13 1 0-1.144294-2.287447-0.985294 14 1 0 0.140462-0.334813-1.833673 15 1 0 1.195505 1.228713-0.143742 16 1 0 1.011717-0.002569 1.130021 17 1 0-0.912761 2.424392-1.277776 18 1 0-1.244203 2.631656 0.449741 19 1 0-2.586813 2.585543-0.703381 20 1 0 4.962519-0.334162-1.246359 21 1 0 4.742099-1.662008-0.101572 22 1 0 5.662063-0.207411 0.392893 TS XM ' (X = CN) SCF Done: E(RB+HF-LYP) = -676.045207213 A.U. --------------------------------------------------------------------------------------------------------------- 1 6 0-1.870356 2.128862 0.209313 2 29 0-1.639206 0.176718-0.116686 3 6 0 0.670302 0.626299-0.346793 4 6 0 0.076736-0.350845-1.190469 5 6 0-0.465374-1.535962-0.697381 6 6 0-3.236350-0.746871 0.472103 7 7 0-4.229737-1.253936 0.836204 8 8 0 2.762338 0.380520-0.672053 9 6 0 3.426295-0.023825 0.351027 10 8 0 2.977938-0.131958 1.517315 11 6 0 4.878179-0.429232 0.073564 12 1 0-0.206907-1.898947 0.296765 13 1 0-0.936984-2.248685-1.367940 14 1 0-0.046039-0.105640-2.247266 15 1 0 0.807848 1.637972-0.699672 16 1 0 0.832259 0.435712 0.707828 17 1 0-1.500219 2.744542-0.620028 18 1 0-1.351126 2.432562 1.127959 19 1 0-2.944908 2.304496 0.337280 20 1 0 5.305792 0.155158-0.746719 21 1 0 4.897528-1.486516-0.222176 22 1 0 5.489066-0.316972 0.974151 PD MX (= PD XM, X = CN) SCF Done: E(RB+HF-LYP) = -447.419554847 A.U. 1 6 0 0.354844 2.135945 0.026690 2 29 0 0.060635 0.187942-0.016476 3 6 0 1.850096-0.508278-0.031978 4 7 0 2.950130-0.906930-0.039369 5 6 0-1.107592-1.806772 0.276121 6 6 0-1.798254-0.816808-0.388797 7 6 0-1.901596 0.508637 0.152951 S26

8 1 0-0.855670-2.742110-0.216461 9 1 0-0.917377-1.748119 1.348558 10 1 0-2.030793-0.961008-1.446953 11 1 0-1.990463 0.638594 1.233359 12 1 0-2.367028 1.284944-0.446935 13 1 0 1.070951 2.261205 0.842641 14 1 0-0.527675 2.756905 0.171488 15 1 0 0.823738 2.331429-0.942228 TS RE-X (X = CN) SCF Done: E(RB+HF-LYP) = -447.412531013 A.U. 1 6 0 0.433373 2.096069-0.058708 2 29 0-0.180405 0.118815 0.022261 3 6 0-2.057363-0.233954 0.020954 4 7 0-3.208772-0.448821 0.020653 5 6 0 1.165606-1.957089-0.291533 6 6 0 1.662668-0.909924 0.421391 7 6 0 1.833364 0.448394-0.127039 8 1 0 1.005678-1.896997-1.368181 9 1 0 0.985836-2.920080 0.180167 10 1 0 1.834588-1.036963 1.493025 11 1 0 2.467566 1.088683 0.477576 12 1 0 2.055864 0.506077-1.193081 13 1 0 0.335495 2.391144 0.988166 14 1 0-0.482338 2.293375-0.624480 15 1 0 1.264566 2.609897-0.533719 CN SCF Done: E(RB+HF-LYP) = -290.221891582 A.U. --------------------------------------------------------------------------------------------------------------- --------------------------------------------------------------------------------------------------------------- 1 29 0 0.000000 0.765346 0.000000 2 6 0 0.000234-1.076745 0.000000 3 7 0-0.000200-2.247797 0.000000 Cl SCF Done: E(RB+HF-LYP) = -697.669088978 A.U. 1 29 0-0.000000 0.352799 0.000000 2 6 0 0.003408 2.269018 0.000000 3 1 0-0.508022 2.675780 0.887167 4 1 0 1.028660 2.672718 0.000000 5 1 0-0.508022 2.675780-0.887167 6 17 0-0.001945-1.874680 0.000000 CP MX ' (X = Cl) SCF Done: E(RB+HF-LYP) = -1043.46267325 A.U. -- -- 1 6 0 3.189198-1.623983-0.383854 2 29 0 1.713934-0.388872 0.090340 3 6 0-0.286213-0.073161 0.799676 4 6 0-1.072696 0.672854-0.233112 5 8 0-2.483865 0.820829 0.187640 6 6 0-3.391064-0.055679-0.270023 7 8 0-3.143429-0.954250-1.060799 S27

8 17 0 2.326102 1.920368-0.166462 9 6 0 0.043200-1.415886 0.684363 10 6 0-4.753530 0.196852 0.330890 11 1 0-1.058528 0.174382-1.204356 12 1 0-0.733263 1.704523-0.337451 13 1 0-0.161559 0.430458 1.760127 14 1 0 0.370447-1.989474 1.549705 15 1 0-0.282517-2.000953-0.174563 16 1 0-4.966725 1.268546 0.384559 17 1 0-4.771142-0.197615 1.354656 18 1 0-5.518516-0.313291-0.257929 19 1 0 2.912713-2.689826-0.362384 20 1 0 4.036547-1.492035 0.310205 21 1 0 3.569696-1.402272-1.394960 --------------------------------------------------------------------------------------------------------------- TS MX ' (X = Cl) SCF Done: E(RB+HF-LYP) = -1043.44051436 A.U. 1 6 0 2.908148 1.702828 0.693671 2 29 0 1.750440 0.284459-0.018422 3 17 0 2.797405-1.726151 0.141783 4 6 0 0.317686 1.530852-0.492488 5 6 0-0.141443 0.335266-1.136599 6 6 0-0.846482-0.656137-0.464278 7 8 0-2.990301-0.349305-0.791287 8 6 0-3.685127-0.171370 0.270823 9 8 0-3.264416-0.270620 1.450565 10 6 0-5.167816 0.160347 0.052502 11 1 0-0.143247 1.831142 0.449228 12 1 0 0.688837 2.353515-1.099970 13 1 0 0.083260 0.193824-2.195047 14 1 0-0.998782-1.625494-0.923680 15 1 0-1.039213-0.586649 0.600687 16 1 0-5.348827 0.565533-0.947174 17 1 0-5.515058 0.867748 0.812631 18 1 0-5.755793-0.760325 0.162114 19 1 0 3.564790 2.018508-0.126007 20 1 0 2.375836 2.569174 1.095604 21 1 0 3.497470 1.216957 1.479541 -------------------------------------------------------------------------------------------------------------- CP XM ' (X = Cl) SCF Done: E(RB+HF-LYP) = -1043.46316919 A.U. 1 6 0-1.725853 2.203500-0.410642 2 29 0-1.609435 0.235040-0.197947 3 17 0-3.660129-0.712288 0.626258 4 6 0 0.234890-0.519989-0.760350 5 6 0-0.518866-1.585354-0.298523 6 6 0 1.286779 0.160779 0.065540 7 8 0 2.586756-0.419909-0.313704 8 6 0 3.677481 0.082331 0.284997 9 6 0 4.940414-0.581119-0.209032 10 8 0 3.639993 0.970272 1.124303 11 1 0 1.144344-0.005408 1.137319 12 1 0 1.336853 1.234644-0.127131 13 1 0 0.289011-0.324939-1.833731 14 1 0-1.075220-2.221228-0.983237 15 1 0-0.422725-1.942101 0.726138 16 1 0 5.800911-0.191166 0.337516 17 1 0 5.067296-0.387905-1.280509 18 1 0 4.875137-1.666491-0.076094 19 1 0-1.705990 2.699975 0.574723 20 1 0-0.916622 2.649474-1.011261 21 1 0-2.680257 2.484084-0.886376 S28

TS XM ' (X = Cl) SCF Done: E(RB+HF-LYP) = -1043.43398165 A.U. 1 29 0-1.523723 0.225037-0.126861 2 6 0-0.378566-1.630923-0.516553 3 6 0 0.172227-0.520177-1.126343 4 6 0 0.761032 0.550317-0.381881 5 8 0 2.830099 0.243795-0.727432 6 6 0 3.521694-0.017802 0.324920 7 8 0 3.093388-0.005308 1.502421 8 6 0 4.998198-0.338649 0.067500 9 1 0-0.871325-2.401408-1.102169 10 1 0-0.180723-1.858218 0.530394 11 1 0 0.071718-0.392869-2.206000 12 1 0 0.934506 0.463896 0.684020 13 1 0 0.898822 1.519337-0.838116 14 1 0 5.442192-0.838111 0.933199 15 1 0 5.113788-0.961532-0.825305 16 1 0 5.542177 0.597985-0.110387 17 6 0-1.713182 2.184042 0.055703 18 1 0-1.142108 2.572940 0.909022 19 1 0-1.400167 2.726835-0.845596 20 1 0-2.781263 2.364251 0.231980 21 17 0-3.470351-0.799289 0.563408 PD MX (= PD XM, X = Cl) SCF Done: E(RB+HF-LYP) = -814.809604118 A.U. 1 6 0-0.416003 2.158341-0.050718 2 29 0-0.074522 0.230739-0.000925 3 6 0 1.825410 0.691725-0.103286 4 6 0 1.918325-0.658513 0.423540 5 6 0 1.534343-1.747577-0.303128 6 17 0-2.032732-0.817794 0.043738 7 1 0 1.464377-2.732637 0.151045 8 1 0 1.338181-1.680962-1.373368 9 1 0 2.123991-0.778978 1.489789 10 1 0 1.992493 0.837471-1.172429 11 1 0 2.170208 1.509695 0.523349 12 1 0-1.450366 2.163838-0.402143 13 1 0 0.241281 2.721117-0.713016 14 1 0-0.335017 2.507673 0.981608 TS RE-X (X = Cl) SCF Done: E(RB+HF-LYP) = -814.802301145 A.U. -- 1 6 0 0.434253 2.116076-0.062432 2 29 0-0.145246 0.152630 0.002466 3 17 0-2.273614-0.409660 0.025674 4 6 0 1.736727-0.847609 0.451305 5 6 0 1.845398 0.530441-0.091667 6 6 0 1.434983-1.936936-0.297167 7 1 0 1.329060-1.879202-1.380202 8 1 0 1.334018-2.919376 0.157675 9 1 0 1.854241-0.962350 1.531545 10 1 0 2.447852 1.184953 0.531424 11 1 0 2.117657 0.587602-1.146369 12 1 0 0.377558 2.436766 0.979191 13 1 0-0.519215 2.266137-0.583800 S29

14 1 0 1.214220 2.651587-0.597662 Cl SCF Done: E(RB+HF-LYP) = -657.608704139 A.U. 1 29 0 0.000000 0.000000 0.788055 2 17 0 0.000000 0.000000-1.344330 S SCF Done: E(RB+HF-LYP) = -675.534049725 -- 1 29 0-0.000000 0.715455 0.000000 2 6 0-0.633931 2.542748 0.000000 3 1 0-1.250580 2.766557 0.886792 4 1 0 0.201241 3.263629 0.000000 5 1 0-1.250580 2.766557-0.886792 6 16 0 0.813082-1.361303 0.000000 7 6 0-0.667802-2.478332 0.000000 8 1 0-0.327976-3.519460 0.000000 9 1 0-1.285505-2.315565 0.888595 10 1 0-1.285505-2.315565-0.888595 --------------------------------------------------------------------------------------------------------------- CP MX ' (X = S) SCF Done: E(RB+HF-LYP) = -1021.32946884 A.U. --------------------------------------------------------------------------------------------------------------- 1 6 0 2.655353 2.008027 0.364873 2 29 0 1.348680 0.593841-0.147801 3 16 0 2.212202-1.546571-0.059487 4 6 0 3.982056-1.323662 0.428482 5 6 0-0.404682 1.532363-0.606573 6 6 0-0.606055 0.167259-0.822822 7 6 0-1.323807-0.717309 0.146648 8 8 0-2.741721-0.905603-0.261512 9 6 0-3.694048-0.173249 0.331283 10 6 0-5.050145-0.426750-0.285380 11 8 0-3.493589 0.611659 1.247937 12 1 0-1.318025-0.315774 1.161396 13 1 0-0.935881-1.737352 0.146646 14 1 0-0.490302-0.235675-1.830875 15 1 0-0.182558 2.202376-1.435147 16 1 0-0.770142 2.012908 0.300059 17 1 0-5.207741-1.495561-0.458728 18 1 0-5.101545 0.078356-1.258038 19 1 0-5.833142-0.028910 0.363252 20 1 0 2.284970 3.038578 0.247479 21 1 0 3.575404 1.915940-0.236313 22 1 0 2.953977 1.884237 1.419775 23 1 0 4.472957-2.301258 0.492937 24 1 0 4.516204-0.713418-0.306745 25 1 0 4.059306-0.829205 1.401860 ------------------------------------------------------------------------------------------------------------ TS MX ' (X = S) SCF Done: E(RB+HF-LYP) = -1021.31199910 A.U. ------------------------------------------------------------------------------------------------------------- ------------------------------------------------------------------------------------------------------------ 1 6 0 2.553357 1.815949 0.779588 2 29 0 1.364243 0.511691-0.096206 S30

3 16 0 2.378132-1.508711-0.212577 4 6 0 4.071759-1.247343 0.476064 5 6 0-0.150321 1.762916-0.385274 6 6 0-0.526469 0.591027-1.106733 7 6 0-1.090461-0.534418-0.491414 8 8 0-3.166373-0.461149-0.747529 9 6 0-3.867718-0.384124 0.327919 10 8 0-3.430809-0.490326 1.497579 11 6 0-5.359795-0.106528 0.111611 12 1 0-0.574098 1.943819 0.602961 13 1 0 0.140308 2.657159-0.931817 14 1 0-0.351682 0.558165-2.183298 15 1 0-1.110525-1.482038-1.016061 16 1 0-1.217229-0.573111 0.584446 17 1 0-5.723236-0.580265-0.805503 18 1 0-5.505854 0.976744 0.007812 19 1 0-5.944946-0.450199 0.969591 20 1 0 3.475174 1.857616 0.185449 21 1 0 2.139658 2.823612 0.884736 22 1 0 2.784711 1.408938 1.772269 23 1 0 4.617100-2.196093 0.436138 24 1 0 4.624719-0.502400-0.104180 25 1 0 4.028087-0.914699 1.517709 -------------------------------------------------------------------------------------------------------------- CP XM ' (X = S) SCF Done: E(RB+HF-LYP) = -1021.33063502 A.U. --------------------------------------------------------------------------------------------------------------- 1 6 0 1.393596 1.984140 0.718016 2 29 0 1.291335 0.038697 0.287622 3 16 0 3.263839-0.824963-0.537732 4 6 0 4.428239 0.611491-0.552004 5 6 0 0.115127-1.696955 0.216283 6 6 0-0.602885-0.626379 0.748172 7 6 0-1.600147 0.158916-0.045090 8 8 0-2.943065-0.403197 0.223814 9 6 0-3.990144 0.218439-0.334051 10 6 0-5.297611-0.435016 0.047805 11 8 0-3.891432 1.197896-1.060471 12 1 0 0.584921-2.433859 0.864157 13 1 0 0.002461-1.980409-0.829581 14 1 0-0.687909-0.524923 1.832240 15 1 0-1.424086 0.085615-1.122357 16 1 0-1.628232 1.212211 0.241837 17 1 0-5.452942-0.349975 1.129620 18 1 0-5.274765-1.502198-0.197977 19 1 0-6.121651 0.050162-0.478501 20 1 0 0.490005 2.404497 1.188813 21 1 0 2.238567 2.180922 1.399106 22 1 0 1.585822 2.569474-0.197376 23 1 0 4.553225 1.022448 0.454749 24 1 0 4.055465 1.409723-1.201638 25 1 0 5.407881 0.288113-0.921934 -------------------------------------------------------------------------------------------------------------- TS XM ' (X = S) SCF Done: E(RB+HF-LYP) = -1021.30804554 A.U. --------------------------------------------------------------------------------------------------------------- 1 6 0-1.589758 2.071753-0.286337 2 29 0-1.233874 0.123085-0.309143 3 16 0-3.048435-0.989573 0.450300 4 6 0-4.284232 0.311973 0.878724 5 6 0-0.045995-1.609446-0.552543 6 6 0 0.555991-0.514281-1.184929 7 6 0 1.175743 0.541066-0.467749 8 8 0 3.227627 0.211426-0.660323 S31

9 6 0 3.880963 0.093803 0.441973 10 6 0 5.345749-0.329063 0.288444 11 8 0 3.414118 0.269008 1.591232 12 1 0-0.490435-2.406514-1.142270 13 1 0 0.184647-1.845983 0.485413 14 1 0 0.486490-0.420144-2.270277 15 1 0 1.262041 0.508683 0.611785 16 1 0 1.333533 1.497742-0.945958 17 1 0 5.937946 0.019734 1.139586 18 1 0 5.395007-1.425682 0.264855 19 1 0 5.773547 0.045092-0.646519 20 1 0-1.493087 2.450401 0.741490 21 1 0-0.929763 2.663193-0.933357 22 1 0-2.627220 2.227816-0.610236 23 1 0-5.164826-0.176464 1.309984 24 1 0-3.879490 1.015983 1.611443 25 1 0-4.595803 0.871534-0.008357 PD MX (= PD XM, X = S) SCF Done: E(RB+HF-LYP) = -792.686904282 A.U. -- 1 6 0 0.318356 2.045655 0.013929 2 29 0-0.299166 0.188707-0.012918 3 6 0-2.243728 0.770627 0.156395 4 6 0-2.267186-0.549402-0.384958 5 6 0-1.669246-1.604856 0.281330 6 16 0 1.570015-1.020190-0.044224 7 1 0-1.508570-2.558239-0.214333 8 1 0-1.509462-1.577602 1.359211 9 1 0-2.501867-0.668345-1.445813 10 1 0-2.300126 0.914174 1.236587 11 1 0-2.603630 1.598900-0.446648 12 1 0 0.972112 2.113836 0.888033 13 1 0-0.472495 2.794012 0.064275 14 1 0 0.895875 2.157171-0.908780 15 6 0 2.982692 0.158970 0.013013 16 1 0 3.902309-0.433032-0.034077 17 1 0 2.967718 0.847496-0.836551 18 1 0 2.988367 0.736195 0.942053 TS RE-X (X = S) SCF Done: E(RB+HF-LYP) = -792.675973333 A.U. - 1 6 0-0.287894 2.071430 0.037882 2 29 0-0.200211-0.005656-0.032760 3 16 0 1.795884-0.939863-0.046247 4 6 0-2.234902-0.479239-0.394932 5 6 0-2.067446 0.879794 0.141579 6 6 0-1.954393-1.612127 0.313918 7 1 0-1.784900-1.590171 1.390277 8 1 0-2.002254-2.591016-0.156416 9 1 0-2.453844-0.568953-1.461679 10 1 0-2.529425 1.654159-0.462725 11 1 0-2.251064 1.000375 1.209450 12 1 0-0.119261 2.326713-1.010681 13 1 0 0.651996 2.025841 0.596849 14 1 0-0.937085 2.803993 0.511416 15 6 0 2.998344 0.461187 0.047257 16 1 0 4.010650 0.046360 0.016694 17 1 0 2.879395 1.145895-0.797812 18 1 0 2.885523 1.022354 0.980424 S S32

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