Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: Competing routes to C C bond formation
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1 Supporting Information Theoretical studies on the bifunctionality of chiral thiourea-based organocatalysts: Competing routes to C C bond formation Andrea Hamza, a Gábor Schubert, a Tibor Soós b and Imre Pápai a, * a Institute of Structural Chemistry, Chemical Research Center of HAS, Pusztaszeri út 59-67, H Budapest, Hungary b Institute of Biomolecular Chemistry, Chemical Research Center of HAS, Pusztaszeri út 59-67, H-1025 Budapest, Hungary Contents: I. Conformational analysis for catalyst 1 (Figures S1-S3) II. Structure and relative stability of identified binary complexes (Figure S4) III. Test calculations for selected H-bonded systems (Figures S5-S6) IV. Energy diagram obtained with the solvated model (Figure S7) V. Stationary points leading to the (S) product (Figures S8-S9) VI. Cartesian coordinates of located stationary points VII. Full author list for reference 18 S1
2 I. Conformational analysis for catalyst 1 (Figures S1-S3) The results of constrained geometry optimizations carried out at B3LYP/6-31G* level for catalyst 1a are presented in Figures S1-S3. Dihedral angles describing the relative orientation of N-H bonds of thiourea and the rotation of the cyclohexyl moiety of 1a have been varied systematically by φ =10 o allowing five optimization steps for each constrained dihedral angle. The structures corresponding to the local maxima on the potential energy curves have been used to estimate the rotational energy barriers between the stable conformation by carrying out subsequent B3LYP/ G** single-point calculations for each structure. Figure S1. Energy variation along constrained geometry optimization with respect to dihedral angle SCNH (φ, shown in red). Local minima 1a 1 and 1a 2 correspond to φ = o and -9.7 o, E refers to the calculated energy gap as obtained at B3LYP/6-31G* (B3LYP/ G**) level. S2
3 Figure S2. Energy variation along constrained geometry optimization with respect to dihedral angle CNCC (φ, shown in red). Local minima 1a 3, 1a 4 and 1a 5 correspond to φ = 97.6 o, o and o, E refers to the calculated energy gap as obtained at B3LYP/6-31G* (B3LYP/ G**) level. S3
4 Figure S3. Energy variation along constrained geometry optimization with respect to dihedral angle SCNH (φ, shown in red). Local minima 1a 1 and 1a 3 correspond to φ = o and -1.1 o, E refers to the calculated energy gap as obtained at B3LYP/6-31G* (B3LYP/ G**) level. S4
5 II. Structure and relative stability of identified binary complexes (Figures S4) Structures of stationary points located for binary catalyst-substrate complexes are shown in Figure S4. Complex 2 is derived from 2 by 180 o rotation of the substrate El around the N-C bond; 2b and 3b correspond to monodentate coordination to 1a (7.5) 2 (7.1) 2b (5.7) (7.3) 3b (7.2) Figure S4. Optimized structures of catalyst-substrate adducts. Bond distances characteristic for H-bonds are given in Å, and binding energies of the substrates (in kcal/mol, with respect to dissociation limits) are shown in parentheses. S5
6 In order to estimate the effect of basis set superposition error (BSSE) on the catalyst-substrate binding energies, we computed the counterpoise corrections for complexes 2 and 3, and we obtained very similar corrections for the two binary complexes (1.1 and 1.2 kcal/mol, respectively) indicating that the inclusion of BSSE corrections does not alter the relative stability of catalyst-substrate complexes. S6
7 III. Test calculations for selected H-bonded systems Using the same methodology as described in Computational Details, we carried out test calculations for selected H bonded systems with available experimental thermochemical data and compared the calculated association energies ( E calc ) with measured free enthalpies of association ( G o exp). a) Dimerization of 2-pyridone O N H 1.75 H N E calc = kcal/mol O G o exp = -2.7 kcal/mol Figure S5. Optimized structure and thermochemical data for 2-pyridone dimer. Experimental data are taken from: Ducharme, Y.; Wuest, J. D. J. Org. Chem. 1988, 53, b) Association between a diaryl-thiourea and a diketo compound CF 3 CF 3 S N H O N H O E calc = kcal/mol G o exp = -3.4 kcal/mol O N Figure S6. Optimized structure of the H bonded adduct. Experimental data are taken from: Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217. S7
8 IV. Energy diagram obtained with the solvated model TS 4 5 (11.6) 10.0 TS 6 7 (9.7) E (kcal/mol) a + El + NuH 3 ( 1.7) TS 3 3' (4.1) 3' ( 1.0) 4 (1.8) 6 (-0.4) 5 ( 2.3) 7 ( 0.1) Figure S7. Energy profile of the C C bond formation pathways corresponding to the formation of (R) configuration of products as obtained from the solvated model. S8
9 V. Stationary points leading to the (S) product TS' 4 5 5' Figure S8. Optimized structures and selected geometric parameters of the stationary points located on route A towards the (S) product ' TS' 6 7 7' Figure S9. Optimized structures and selected geometric parameters of the stationary points located on route B towards the (S) product. S9
10 VI. Cartesian coordinates and absolute electronic energies of located stationary points The Cartesian coordinates of all located stationary points are given below. The notation corresponds to that used in the paper. For each structure, total electronic energies obtained at B3LYP/6-31G* and B3LYP/ G**//B3LYP/6-31G* levels are given in parentheses. For the located transition state structures, the number of negative eigenvalues of the Hessian at the converged structures are also indicated (n imag = 1). 1a 1 ( , ) H F H H C F H C C H H F C H C C C H S N C H C H N H C H C H C H C C H N H F C H C H F C H H F H a 2 ( , ) C C C C C C N C S N S10
11 C N C C C C C C C F C F F F F F C H H H H H H H H H H H H H H H H H H H H H a 3 ( , ) C C C C C C C F N C N C C C C C C N C C F F F S C F F H H H H H H H H H H H H H H H H H H H H H a 4 ( , ) S11
12 C C C C C C C F N C N C C C C C C N C C F F F S C F F H H H H H H H H H H H H H H H H H H H H H a 5 ( , ) C C C C C C N C S C C N C C C C C C N C C H H H H H H H H H H H H H H H H H H H H H S12
13 F F F F F F ( , ) C C C C C C C C N O O N C S C C C C C C N C N C C C C C C C F C F C F F F F H H H H H H H H H H H H H H H H H H H H H H H H H H H H b ( , ) C C C C C C N C S C F C F N S13
14 C C C C C C N C C F F F F H H H H H H H H H H H H H H H H H H H H H O N O C C H C H C C C C C H H H H H ' ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F O N O C C H H H H H H S14
15 H H H H H H H H H H H H H H H C H C C C C C H H H H H H ( , ) C C C C C C N C N C N C S C O C C C 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 C C C C C H C H C H F F F F F S15
16 F b ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F 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 H H H H C O C H H H H TS 3-3' ( , ), n imag = 1 C C C C C C N C S C F C F N C C C C C C N C S16
17 C F F F F O C C C 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 ' ( , ) C C C C C C N C S N C N C C C C C C C F C F F F F F C O C C C C O C H H H H H H H H H H H H H H H S17
18 H H H H H H H H H H H H H H " ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F O C C C 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 ( , ) C C C C C C N C S S18
19 N C N C C C C C C C F C F F F F F C O C C C O C C O N C H 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 C H C C C C C H H H H H ' ( , ) C C C C C C N C S C F C F N C C C C S19
20 C C N C C F F F F O C C C C C O O N O 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 H H H H C C C C C H H H H H TS 4-5 ( , ), n imag = 1 C C C C C C C C N O O C C C C C O O N C C C C C C C N S20
21 C S N C C C C C C C F C F F F F F 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 TS' 4-5 ( , ), n imag = 1 C C C C C C C C N O O C C C C C O O N C C C C C C C N C N C S C H H H H S21
22 H H H H H 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 C C C H C H C H F F F F F F ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F O C C C C O C C C N O C C C C C C O S22
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 ' ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F O C C C C O C C C N O C C C C C C O H H H H H H H H H S23
24 H H H 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 C C C C N C S C F C F N C C C C C C N C C F F F F O N O C C C C O C C C C C C C C O C H H H H H H H H H H H H H H H H H H S24
25 H H H H H H H H H H H H H H H H H H ' ( , ) C C C C C C N C S C F C F N C C C C C C N C C F F F F O N O C C C C C C C C C C O C 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 S25
26 H H H H H H H H H TS 6-7 ( , ), n imag = 1 C C C C C C N C S C C N C C C C C C N C C O N O C C C C C C C C C C O C 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 F F F F F F S26
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