The Activation of Carboxylic Acids via Self Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation
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1 The Activation of Carboxylic Acids via Self Assembly Asymmetric Organocatalysis: A Combined Experimental and Computational Investigation Mattia Riccardo Monaco, Daniele Fazzi, Nobuya Tsuji, Markus Leutzsch, Saihu Liao, Walter Thiel, and Benjamin List Max Planck Institut für Kohlenforschung, Kaiser Wilhelm Platz 1, D Mülheim an der Ruhr, Germany list@mpi muelheim.mpg.de Supplementary Information Theoretical Data Computational methods S 2 Brønsted acidity of TRIP AcOH heterodimer S 3 Molecular orbital energies of acetic acid S 18 Studies on the catalytic cycle S 19 Analysis of the transition states S 36 1) Desymmetrization of meso epoxides S 36 2) Kinetic resolution of racemic epoxides S 49 S-1
2 Computational methods All calculations were performed with the Gaussian09 quantum chemical program [1]. The geometry of each structure reported in the manuscript was optimized using the hybrid B3LYP functional [2] in combination with the 6 31G* basis set [3] or the correlationconsistent cc pvtz basis set [4]. The optimized stationary points were characterized as local minima or transition structures by harmonic force constant analysis. Gibbs free energies (G) were in all cases computed by including zero point vibrational energies and thermal corrections (at 300 K) obtained at the B3LYP level either using the 6 31G* or the cc pvtz basis set. References: [1] Gaussian 09, Revision D.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, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. 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, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc. Wallingford CT, [2] A. D. Becke, J. Chem. Phys., 1993, 98, [3] R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys., 1971, 54, [4] T. H. Dunning, J. Chem. Phys., 1989, 90, [5] A. D. Becke, J. Chem. Phys., 1993, 98, [6] S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys., 2010, 132, [7] B. Mennucci, J. Tomasi, J. Chem. Phys., 1997, 106, S-2
3 Brønsted acidity of TRIP AcOH heterodimer This study aimed at elucidating the effect of self assembly on the acidity of the species. The stability of acid base association complexes was evaluated using pyridine as indicator. The following species were considered: 1) TRIP / AcOH / pyridine: the three molecules do not interact (i.e. they are at infinite distance). The energies of all other structures investigated presently are given relative to the reference energy of this non interacting system. 2) TRIP AcOH / pyridine: TRIP AcOH heterodimer, no interaction with pyridine. 3) TRIP AcOH pyridine: complex between TRIP AcOH and pyridine (with hydrogen bonding between neutral species). 4) (TRIP AcOH) pyridinium: complex between TRIP AcOH anion and pyridinium ion (with hydrogen bonding between ion pairs). 5) TRIP pyridine / AcOH: TRIP pyridine complex (with hydrogen bonding between neutral species), no interaction with AcOH. 6) TRIP pyridinium / AcOH: complex between TRIP anion and pyridinium ion (with hydrogen bonding between ion pairs), no interaction with AcOH. Table SI TD 1: Gibbs free energies (G) computed at the B3LYP/cc pvtz (PCM, toluene) level for each system (1 6). G (Hartree) 1) TRIP / AcOH / pyridine ) TRIP AcOH / pyridine ) TRIP AcOH pyridine ) (TRIP AcOH) pyridinium ) TRIP pyridine / AcOH ) TRIP pyridinium / AcOH S-3
4 Figure SI TD 1: Free energy scheme of the different acid base complexes investigated. The computational results highlight the increase of the overall acidity of the species upon heterodimeric association, in line with the expected heteroconjugation effect. They reveal not only that the trimeric species 4 is more stable than complex 5 (ΔG = kcal mol 1 ), but also indicate that in this assembly the proton transfer is favored, yielding a stabilization compared with complex 3 (ΔG = 6.49 kcal mol 1 ). On the other hand, proton transfer is not favored for free TRIP and the ion pair complex 6 is found less stable than complex 5 with a standard hydrogen bonding interaction (ΔG = kcal mol 1 ) Optimized structures (Cartesian coordinates, Å). Case 2) TRIP AcOH / pyridine C C C C C C C C C S-4
5 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C O P O O C C C C C C C C C O C C C O C C O H H H H H H H H S-5
6 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 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 N C C C C S-6
7 C H H H H H Energy = Hartree Case 3) TRIP AcOH pyridine C C C C C C C C C C C C C C C C O P O C C C C C C C C C C C C C C C C C C C C C C C C C C S-7
8 C C O O C C C C C C N C C C C C O C C O 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 H H H H H H H H H H H S-8
9 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 H Energy = Hartree Case 4) (TRIP AcOH) pyridinium C N C C C C O C O C O P O O C C C C C C C C C S-9
10 C C C C C C C C C C C C C C C C C C C C C C C O 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 S-10
11 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 H H H H H H H H H H H H H H H H H H H H H H H Energy = Hartree Case 5) TRIP pyridine / AcOH S-11
12 C C C C C C C C C C C C C C C C O P O C C C C C C C C C C C C C C C C C C C C C C C C C C C C O O C C C C C C N C S-12
13 C C C C O C C O 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 H H H H H H H H H H H H H H H H H H H H H H H S-13
14 H H H H H H H H H H H H H H H H Energy = Hartree Case 6) TRIP pyridinium / AcOH C N C C C C O P O O C C C C C C C C C C C C C C C C C C C C C C S-14
15 C C C C C C C C C C O C C C C C C C C C C C C C C C C C C O C C O 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 S-15
16 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 H H H H H H H H H H H H H H Energy = Hartree S-16
17 Molecular orbitals energies of acetic acid Here we document the effect of the heterodimerizing self assembly on the energies of the frontier molecular orbitals of acetic acid (AcOH). The geometries of acetic acid monomer and of the heterodimer TRIP AcOH were optimized at the B3LYP/cc pvtz level. The energies of the molecular orbitals were obtained from single point calculations of the AcOH monomer, both in its optimum geometry and in the geometry adopted in the heterodimer complex. Optimized (B3LYP/cc pvtz) geometry of acid acetic monomer. C O O H C H H H HOMO energy = Hartree ( 7.81 ev) LUMO energy = Hartree ( 0.02 ev) B3LYP/cc pvtz geometry of acetic acid as extracted from the heterodimer. C C O O H H H H HOMO energy = Hartree ( 7.56 ev) LUMO energy = Hartree (+0.06 ev) S-17
18 Studies on the catalytic cycle The objective of this study was to examine the sequence of events in the catalytic cycle for the reaction between epoxide 3c and AcOH catalyzed by TRIP towards product 4c. The following species were considered: 1) TRIP / AcOH / 3c: the three molecules do not interact (i.e. they are at infinite distance). The energies of all other structures investigated presently are given relative to the reference energy of this non interacting system. 2) TRIP AcOH / 3c: TRIP AcOH heterodimer, no interaction with the epoxide. 3) TRIP AcOH 3c: TRIP, AcOH and epoxide in a trimolecular complex. 4) Transition state (TS). 5) TRIP 4c: complex between TRIP and product. 6) TRIP / 4c: no interaction between TRIP and product. Table SI TD 2: Gibbs free energies (G) computed at the B3LYP/cc pvtz level for each complex (1 6). S-18
19 G (Hartree) 1) TRIP / AcOH / 3c ) TRIP AcOH / 3c ) TRIP AcOH 3c ) TS ) TRIP 4c ) TRIP / 4c Optimized structures (Cartesian coordinates, Å) Case 1) TRIP / AcOH / 3c C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C S-19
20 O P O O C C C C C C C C C O C C C O C C C C O C C O 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 H H H H H S-20
21 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 H H H H H H H H H H Energy = Hartree Case 2) TRIP AcOH / 3c C C C C C C C C C C C S-21
22 C C C C C C C C C C C C C C C O P O C C C C C C C C C C C C O C C C C C C C C C O C C C O C O C H H H H H H H H H H S-22
23 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 H H H H H H H H H H H H H H H H H H H H H H H H O C C C C H H S-23
24 H H H H H H Energy = Hartree Case 3) TRIP AcOH 3c C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C O P O O C C C S-24
25 C C C C C C O C C C O C C C C O C C O 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 H H H H H H H H H H H H S-25
26 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 H H H Energy = Hartree Case 4) Transition State (TS) C C C C C C C C C C C C C C C C C C C C C S-26
27 C C C C C O P O C C C C C C C C C C C C C C C C C C O O C C C C C C O C O C C C C C O H H H H H H H H H H H H H H H S-27
28 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 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 Energy = Hartree Nimag = 1 (293i) S-28
29 Case 5) TRIP 4c C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C O P O C C C C C C C C C O O C S-29
30 C C O C C O C H C O 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 H H H H H H H H H H H H H H H H H H H H S-30
31 H H H H H H H H H H H H H H H H H H C H H H Energy = Hartree Case 6) TRIP/4c C C C C C C C C C C C C C C C C C C C C C C C C C C S-31
32 C C C C C C C C C C C C O P O C C C C C C C C C O O C C C O C C O C H C O C H H H H H H H H H H H H H H H H H H H H S-32
33 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 H H H H H H H H H H H H H H H H H H C H H H Energy = Hartree S-33
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