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1 Supporting Information Z-Selective Ethenolysis With a Ruthenium Metathesis Catalyst: Experiment and Theory Hiroshi Miyazaki,, Myles B. Herbert,, Peng Liu, Xiaofei Dong, Xiufang Xu,,# Benjamin K. Keitz, Thay Ung, ξ Garik Mkrtumyan, ξ K. N. Houk,*, and Robert H. Grubbs*, Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States Department of Chemistry and Biochemistry, University of California, Los Angeles, , United States. # Department of Chemistry, Nankai University, Tianjin , P. R. China ξ Materia Inc., 60 N. San Gabriel Blvd., Pasadena, CA, 91107, United States S1
2 Computational Details The geometries of all intermediates and transition states were optimized with B3LYP in gas phase. A mixed basis set of LANL2DZ for Ru and 6-31G(d) for other atoms were used in geometry optimizations. Single point energy calculations were performed with the M06 functional and a mixed basis set of SDD for Ru and G(d,p) for other atoms. The SMD solvation model was used in M06 single point energy calculations. THF was used as solvent. The reported free energies and enthalpies include zero-point energies and thermal corrections calculated at 298K by B3LYP. All calculations were performed with Gaussian 09. The 3D structures of molecules were generated using CYLView ( The Gibbs free energies in Gaussian were calculated under p = 1 atm. The standard free energies in solution were calculated under the standard state in solution, i.e. M = 1 mol/l. The correction was made by adding RT ln(c 0s /c 0g ) (i.e., about 1.84 kcal/mol) to energies of all structures, where c 0s is the standard molar concentration in aqueous solution (1 mol/l), c 0g the standard molar concentration in gas phase ( mol/l), and R the gas constant. Complete Reference of Gaussian 09 (Ref. 23) Gaussian 09, Revision B.01, 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, T. Keith, 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, S2
3 Figure S1. Free energies and enthalpies (in parenthesis) of the reaction of propene with ruthenium ethylidene complexes from (a) catalyst 2; (b) catalyst 3; and (c) catalyst 5 All energies are with respect to the most stable isomer of ruthenium alkylidene complexes (37, 41, and 47, respectively) and are given in kcal/mol. For clarity, the chelating adamantyl group is not shown in the 3D structures of TS22 and TS25. S3
4 Figure S2. Free energies and enthalpies (in parenthesis) of the transition states and ruthenacyclobutane intermediates in the non-productive metathesis pathways of the reaction of propene and ruthenium ethylidene complexes from (a) catalyst 2; (b) catalyst 3; and (c) catalyst 5. All energies are with respect to the most stable isomer of ruthenium alkylidene complexes (37, 41, and 47, respectively) and are given in kcal/mol. For clarity, the chelating adamantyl group is not shown in the 3D structures of TS71 and TS74. S4
5 Direct productive cleavage of ruthenacyclobutane 23 In the ethenolysis of Z-2-butene with catalyst 5 (Figure 2 in the manuscript), the first metathesis transition state TS22 leads to a ruthenacyclobutane intermediate 23, in which the nitrate is syn to the -H atom on the chelating adamantyl group. Direct productive cleavage of 23 via metathesis transition state TS25 would lead to a propene-ruthenium ethylidene complex, an isomer of 26. This direct cleavage pathway is highly unfavorable due to the high activation energy of TS25 ( G = 20.9 kcal/mol). Thus, 23 undergoes isomerization (see next page for more details) to form another ruthenacyclobutane intermediate 24, in which the nitrate is anti to the -H atom on the adamantyl. Subsequent productive cleavage of 24 (via TS23, G = 8.6 kcal/mol) is much more favorable than the direct cleavage of 23 via TS25. The 3D structure of TS25 is shown below. In TS25, the forming alkylidene is trans to the chelating adamantyl group. Both alkylidene and adamantyl are strongly electron-donating ligands and thus prefer to not be trans to each other due to trans influences. TS25 G = 20.9 kcal/mol S5
6 Interconversion of Ruthenacyclopropane Intermediates 23 and 24 The interconversion of the ruthenacyclopropane intermediates 23 and 24 occurs via monodentate nitrato complexes 23 and 24, which are five-coordinated trigonal bipyramidal geometry. Both 23 and 24 are lower in energy than corresponding bidentate nitrato complexes. The interconversion between 23 and 24 involves rotation of the Ru O dative single bond. This rotation step is expected to have low barrier. Thus, the interconversion between 23 and 24 should be facile ' 24' 24 The interconversion between the metallacycle intermediates 34 and 35 from the ethenolysis of E- 2-butene proceeds via a similar mechanism involving mono-dentate nitrato complexes 34 and 35. S6
7 34 34' 35' 35 Similarly, the interconversion between the mono-substituted ruthenacyclopentane intermediates 31 and 30 also readily occurs via stable monodentate intermediates 31 and 30. S7
8 Monodentate Transition State Structures In the ethenolysis reaction of Z-2-butene with catalyst 5, the nitrate binds to the ruthenium in a bidentate fashion in all four metathesis transition states in the catalytic cycle (Figure 2 in the manuscript). The monodentate TS structures are 1~4 kcal/mol less stable than corresponding bidentate TSs. The 3D structures of the rate-determining transition state TS22 and the monodentate nitrato isomer (TS22-mono) are shown below. The chelating adamantyl groups are not shown for clarity. TS22-mono G = 9.4 kcal/mol H = -2.9 kcal/mol TS22 G = 8.8 kcal/mol H = -5.8 kcal/mol S8
9 The (Å), SCF energies, enthalpies at 298K, and Gibbs free energies at 298K for the optimized structures a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H O N H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C S9
10 C H H H C H H H C H H H C C C H H H H C H H H C H H H N O a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H S10 C H C H H C C C H C C H C C H H H C H H H C H H H C C H C H H C H H H C H H H H N O a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H
11 C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H C H C H C H H H H C H H H O N a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N S11 C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H O N C H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru
12 O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H C H C H O N H C H H H H S a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C C C H H H C H
13 H H H N O H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H S13 H H C C C H H H H C H H H N O H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C
14 C H H H C H H H C H H H C C C H H H C H H H N O H C H H H ' a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C H H C H S14 C H C H H C C C H C C H C C H H H C H H H C H H H C C C H H H C H H H N O C H H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H
15 C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C C C H H C H H H H N O C H H H H ' a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N S15 C C H H C H H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C C C H H H C H H H O N H C H H H a.u.
16 a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. N C H C N H C C C C C C C C C H H C C C C C C C C H H C H H H H H H H H H H H H H H C Ru Cl Cl C H H H H H H C C H H C H H H H C H H S16 H C H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. O O C C H C C H H C H H H Ru C C N N C H H C C C C C H H C H H C C C H C C C C C C C H H H H C H H H H H H H H
17 H H H C H H H C H H H C H H H C H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. O O C C H C C H H C H H H Ru C C N N C H H C C C C C H H C H H C C C H C C C C C C S17 C H H H H C H H H H H H H H H H H C H H H C H H H C H H H C H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H H C C H H C H C H H C H C H H C
18 H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H C H C H C H H H C H H H O N C H H H a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C H H C H S18 H C C H H C H C H H C H C H H C H H C H C H C H H C C C H C C H C C H H H C H H H C H H H C H C H C H C H H H C H H H O N C H H H a.u a.u a.u. M06 SCF energy in solution: a.u.
19 M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. N C H C N H C C C C C C C C C H H C C C C C C C C H H C H H H H H H H H H H H H H H C Ru Cl Cl C H H H H H H C C H H C H H H H C H H H H S a.u a.u a.u. M06 SCF energy in solution: a.u. M06 enthalpy in solution: a.u. M06 free energy in solution: a.u. Ru O O N N C C C C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H C C H H C H
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