Supporting Information. Computational Exploration of Concerted and Zwitterionic. Mechanisms of Diels Alder Reactions between 1,2,3-Triazines and
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1 Supporting Information Computational Exploration of Concerted and Zwitterionic Mechanisms of Diels Alder Reactions between 1,2,3-Triazines and Enamines and Acceleration by Hydrogen-Bonding Solvents Yun-Fang Yang, Peiyuan Yu, and K. N. Houk* Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States S1
2 Figure S1. Gibbs free energy profiles for the endo and exo pathways of the reaction of 1,2,3- triazine 1c-HFIP with enamine 2 in solvent HFIP. The geometries were optimized in solvent. Energies are in kcal/mol. Figure S2. Gibbs free energy profiles for amine elimination step. Energies are in kcal/mol. S2
3 Energies, enthalpies, and free energies of calculated structures. The raw computational data obtained from the density functional theory calculations are given in Table S1 and Table S2. The free energies are obtained from Gaussian without Truhlar s quasiharmonic treatment. Included in the table are the electronic energies, enthalpies, and free energies of calculated structures. This is followed by the Cartesian coordinates of the structures. Table S1. Electronic energies, enthalpies, and free energies of the structures calculated at the M06-2X/6-311+G(d,p) (CPCM Chloroform )//M06-2X/ 6-31G(d). Structures ZPVE TCE TCH TCG Esol Hsol(Esol+TCH) Gsol(Esol+TCG) Imaginary Frequency (cm -1 ) 1a c N Gsol (kcal/mol) 3a amine endo endo endo endo endo endo-ts endo-ts endo-ts endo-ts endo-ts exo exo exo exo-ts exo-ts exo-ts exo-ts exo-ts TS ZPVE = zero-point vibrational energy; TCE = thermal correction to energy; TCH = thermal correction to enthalpy; TCG = thermal correction to Gibbs free energy. Table S2. Electronic energies, enthalpies, and free energies of the structures calculated at the M06-2X/6-311+G(d,p) (CPCM HFIP )//M06-2X/ 6-31G(d). Structures ZPVE TCE TCH TCG Esol Hsol(Esol+TCH) Gsol(Esol+TCG) Imaginary Frequency (cm -1 ) Gsol (kcal/mol) S3
4 1a-HFIP c-HFIP N a amine-hfip endo endo endo endo endo endo endo-ts endo-ts endo-ts endo-ts endo-ts9b endo-ts9c endo-ts9d endo-ts9d endo-ts endo-ts10b endo-ts10c endo-ts10d endo-ts10e endo-ts exo exo exo exo exo-ts exo-ts exo-ts exo-ts exo-ts exo-ts endo TS ZPVE = zero-point vibrational energy; TCE = thermal correction to energy; TCH = thermal correction to enthalpy; TCG = thermal correction to Gibbs free energy. S4
5 Cartesian coordinates of the structures. 1a N C N N C C H H H a-HFIP N C N N C C H H H C C H C O H F F F F F F c C N N N C C H C O O S5
6 C O O C H H H C H H H c-HFIP C N N N C C H C O O C O O C H H H C H H H C C H C O H F F F F F F S6
7 2 C C H C C C H H C H H H H H H N C C H H H H C C C C C C H H H H N 2 N N a C N C C H C C C S7
8 C H H H H C C C C C C H H H H H H amine C C C C H H H H H H H H N H amine-hfip C C C H H C H H H H H H S8
9 N H H C C H C O F F F F F F endo-1 C N N N C C H C C H C C C H H C H H H H H H N C C H H H H C C S9
10 C C C C H H H H H H endo-2 C N C C H C C H C C C H H C H H H H H H N C C H H H H C C C C C C H H S10
11 H H H H endo-3 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H H H H N C C H H S11
12 H H C C C C C C H H H H endo-4 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H S12
13 H H H N C C H H H H C C C C C C H H H H endo-5 C N C C H C C H C O O C O O C H H H C H H H C C C S13
14 H H C H H H H H H N C C H H H H C C C C C C H H H H endo-6 C N N N C C H C C H C C C H H C H H H S14
15 H H H N C C H H H H C C C C C C H H H H H H C C H C O H F F F F F F endo-7 C N N N C C H C C H C S15
16 C C H H C H H H H H H N C C H H H H C C C C C C H H H H H H C C H C O H F F F F F F endo-8 C N C S16
17 C H C C H C C C H H C H H H H H H N C C H H H H C C C C C C H H H H H H C C H C O H F F F F F S17
18 F endo-9 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H H H H N C C H H H H C S18
19 C C C C C H H H H C C H C O H F F F F F F endo-10 C N N N C C H C C H C O O C O O C H H H C H H H S19
20 C C C H H C H H H H H H N C C H H H H C C C C C C H H H H C C H C O H F F F F F F endo-11 C N C C S20
21 H C C H C O O C O O C H H H C H H H C C C H H C H H H H H H N C C H H H H C C C C C C H H H H S21
22 C C H C O H F F F F F F endo-ts1 C N N N C C H C C H C C C H H C H H H H H H N C C H H H H C C C C S22
23 C C H H H H H H endo-ts2 C N N N C C H C C H C C C H H C H H H H H H N C C H H H H C C C C C C H H S23
24 H H H H endo-ts3 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H H H H N C C H H S24
25 H H C C C C C C H H H H endo-ts4 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H S25
26 H H H N C C H H H H C C C C C C H H H H endo-ts5 C N N N C C H C C H C O O C O O C H H H C H H H C S26
27 C C H H C H H H H H H N C C H H H H C C C C C C H H H H endo-ts6 C N N N C C H C C H C C C H H C H S27
28 H H H H H N C C H H H H C C C C C C H H H H H H C C H C O H F F F F F F endo-ts7 C N N N C C H C C S28
29 H C C C H H C H H H H H H N C C H H H H C C C C C C H H H H H H C C H C O H F F F F F F endo-ts8 C S29
30 N N N C C H C C H C C C H H C H H H H H H N C C H H H H C C C C C C H H H H H H C C H C O H F S30
31 F F F F F endo-ts9 C N N N C C H C C H C O O C O O C H H H C H H H C C C H H C H H H H H H N C C H S31
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