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1 Supplementary Materials for Hydrogenation of carboxylic acids with a homogeneous cobalt catalyst Ties J. Korstanje, Jarl Ivar van der Vlugt, Cornelis J. Elsevier,* Bas de Bruin* *Corresponding author. c.j.elsevier@uva.nl (C.J.E.); b.debruin@uva.nl (B.d.B) This PDF file includes: Published 16 October 2015, Science 350, 298 (2015) DOI: /science.aaa8938 Materials and Methods Figs. S1 to S39 Tables S1 to S5 Cartesian Coordinates (XYZ Format) for All Calculated Structures
2 Materials and Methods General Methanol was distilled from CaH2 and THF from sodium/benzophenone under argon atmosphere. para-xylene was degassed and dried over 4Å molecular sieves. Liquid substrates were degassed by bubbling argon through the solution for 15 minutes. All other chemicals were obtained from Sigma-Aldrich or Alfa Aesar and were used without further purification. GC analysis for esters and for levulinic acid was performed on a Thermo Scientific Trace GC Ultra equipped with a Restek RTX-200 column (30 m x 0.25 mm x 0.5 µm). Temperature program: Initial temperature 50 C, hold for 4 min, heat to 130 C with 30 C/min, hold for 2 min, heat to 250 C with 50 C/min, hold for 9 min. Inlet temperature 200 C, split ratio of 60, 1 ml/min carrier flow, FID temperature 250 C. GC analysis for fatty acids and esters was performed on a Thermo Scientific Trace GC Ultra equipped with a Restek Stabilwax-DA column (30 m x 0.25 mm x 0.25 µm). Temperature program: initial temperature 40 C, heat to 175 C with 6 C/min, heat to 250 C with 50 C/min, hold for 18 minutes. Inlet temperature 280 C, split ratio of 40, 1.5 ml/min carrier flow, FID temperature 250 C. GC analysis for other acids except trifluoroacetic acid was performed on a Thermo Scientific Trace GC Ultra equipped with a Restek Stabilwax-DA column (30 m x 0.25 mm x 0.25 µm). Temperature program: initial temperature 40 C, heat to 175 C with 6 C/min, heat to 250 C with 50 C/min, hold for 5 minutes. Inlet temperature 280 C, split ratio of 40, 1.5 ml/min carrier flow, FID temperature 250 C. High resolution ESI-MS spectra were recorded on a JEOL AccuTOF LC-Plus JMS- T100LP spectrometer in THF or CH3CN at -30 C. 1 H, 13 C, and 19 F NMR spectra were recorded on a Bruker AMX400 or Bruker Advance II 300 MHz NMR spectrometer at 400 or 300 MHz, 125 or 100 Mhz, and 376 MHz or 282 MHz respectively. 1 H and 13 C spectra were referenced against residual solvent signal, 19 F spectra were referenced externally against CFCl3. EPR spectra were recorded on a Bruker EMXplus X-band spectrometer at 20K using liquid helium as the coolant. NMR analysis for trifluoroacetic acid was quantified via the integral of the singlet in the ppm region (TFA) and the triplet in the ppm region (TFE) compared to the integral of the internal standard, 1,4-bis(trifluoromethyl)benzene (singlet at -66 ppm, only used at higher catalyst loadings). Due to the paramagnetic nature of the cobalt catalyst, the signals can shift and therefore a second measurement with an additional amount of TFE was performed to ensure integration of the correct signal. Single Crystal X-ray Diffraction X-ray intensities were measured on a Bruker D8 Quest Eco diffractometer equipped with a Triumph monochromator ( = Å) and a CMOS Photon 50 detector at a temperature of 150(2) K. Intensity data were integrated with the Bruker APEX2 software (34). Absorption correction and scaling was performed with SADABS (35). The structures were solved with the program SHELXS-2013 (36). Least-squares refinement was performed with SHELXL-2013 (37) against F 2 of all reflections. Non-hydrogen 2
3 atoms were refined with anisotropic displacement parameters. The H atoms were placed at calculated positions using the instructions AFIX 13, AFIX 43, or AFIX 137 with isotropic displacement parameters having values 1.2 or 1.5 times Ueq of the attached C atoms. C72H64BCoO2P3, Fw = , brown block, mm, triclinic, P1 (no. 2), a = (8), b = (13), c = (14) Å, = (5), = (5), = (5), V = (4) Å 3, Z = 2, Dx = g/cm 3, = mm Reflections were measured up to a resolution of (sin / )max = 0.84 Å Reflections were unique (Rint = ), of which 6090 were observed [I>2 (I)]. 713 Parameters were refined with 0 restraints. R1/wR2 [I > 2 (I)]: / R1/wR2 [all refl.]: / S = Residual electron density between 0.64 and e/å 3. Computational details Geometry optimizations were carried out with the Turbomole program package (38) coupled to the PQS Baker optimizer (39, 40) via the BOpt package (41). We used the BP86 functional (42, 43) in combination with the def2-tzvp basis set (44, 45), and a small (m5) grid size. Grimme s dispersion corrections (version 3, disp3) were used to include Van der Waals interactions (46). All minima (no imaginary frequencies) and transition states (one imaginary frequency) were characterized by calculating the Hessian matrix. ZPE and gas-phase thermal corrections (enthalpy, 373 K) from these analyses were calculated. The nature of the transition states was confirmed by following the intrinsic reaction coordinate. General catalytic procedure Cobalt(II) tetrafluoroborate hexahydrate, triphos, and the substrate (if solid) were weighed in air in a glass insert, which was placed in a 150 ml stainless steel autoclave. The autoclave was sealed and evacuated and refilled with argon twice. Liquid substrates (3.0 mmol) were dissolved in 20 ml distilled solvent (methanol or THF) together with 74 µl p-xylene (internal standard) and transferred to the autoclave under a flow of argon. The autoclave was flushed three times with 30 bar H2, pressurized to 80 bar H2 and heated to 100 C (internal temperature) using a preheated oil bath at 140 C. Samples were taken via a sample tube at regular intervals and analyzed via gas chromatography. With trifluoroacetic acid as the substrate, 1,4-bis(trifluoromethyl)benzene was used as the internal standard (at higher catalyst loadings) and the reaction mixture was analyzed via 19 F NMR spectroscopy using CD3OD as the solvent. Under solvent-less conditions, no internal standard was used. With butyric acid under solvent-less conditions a two-layer system was obtained after catalysis and 1,4-dioxane was added after the reaction to obtain a homogeneous mixture for analysis. For isolation of substituted benzyl alcohols, the reaction mixture was evaporated to dryness. To the resulting mixture 50 ml Et2O and 50 ml saturated Na2CO3 solution were added. The layers were separated, the aqueous layer extracted twice with 50 ml Et2O, the combined organic layers were dried over MgSO4 and evaporated to dryness. Further purification was performed using column chromatography (SiO2, EtOAc/hexane 1:2; for 3-hydroxybenzyl alcohol a 2:1 ratio was used). 3
4 For isolation of the 1-butanol/butyl butyrate mixture, the same procedure was used except for the use of distillation instead of column chromatography. 1-Butanol and butyl butyrate were found to be inseparable, probably due to azeotrope formation. 4
5 Fig. S1 Quantitative poisoning results using TMTU (top) or TEMPO (bottom) as poison in the benzoic acid hydrogenation reaction. Results based on the yield of benzyl alcohol after 2 hours of reaction time relative to the unpoisoned result. A linear fitted trendline is shown and used to determine the axis intercept. 5
6 Fig. S2 ESI-MS spectra of the catalytic mixture and some independently prepared mixtures in THF. Full spectra (m/z = , left) and a zoom of the m/z = region (right). From bottom to top: catalytic mixture using 10% Co(BF4)2 6 H2O / triphos, benzoic acid, 80 bar H2, 100 C for 2 hours; a 1:1:1 mixture of Co(BF4)2 6 H2O, triphos and benzoic acid; a 1:1 mixture of Co(BF4)2 6 H2O and triphos. 6
7 Fig. S3 EPR spectra of the in situ catalytic mixture and some independently prepared mixtures in 2-methyltetrahydrofuran. Full spectra ( G, left) and a zoom of the G region (right). From bottom to top: crystalline [Co(triphos)(benzoate]BPh4; an in situ catalytic mixture using 10% Co(BF4)2 6H2O / triphos, benzoic acid, 15 bar H2, 100 C for 2 hours; a 1:1:1 mixture of Co(BF4)2 6H2O, triphos and benzoic acid; a 1:1 mixture of Co(BF4)2 6H2O and triphos; Co(BF4)2 6 H2O. 7
8 Fig. S4 Enthalpy diagram for the DFT-calculated (BP86, def2-tzvp, disp3) mechanism at 373 K. 8
9 Fig. S5 Enthalpy diagram for DFT-calculated (BP86, def2-tzvp, disp3) alternative reaction pathways at 373 K. 9
10 Table S1. Hydrogenation of methyl benzoate to benzyl alcohol and methanol catalyzed by various cobalt precursors in combination with triphos. Conditions used: 3.0 mmol methyl benzoate, mmol [Co], mmol triphos, 74 µl p-xylene (internal standard), 20 ml distilled methanol, 80 bar H2, 100 C. Conversions and yields based on GC. Entry Metal precursor Loading (mol %) Reaction time (h) Conversion (%) Yield (%) 1 Co(acac) Co(acac) Co(OAc)2 4 H2O Co(BF4)2 6 H2O Co(BF4)2 6 H2O Co(BF4)2 6 H2O Co(BF4)2 6 H2O 1 93 ND 20 8 Co(BF4)2 6 H2O 10 * Co(BF4)2 6 H2O Co(BF4)2 6 H2O Co(BF4)2 6 H2O * 3.0 mmol NEt 3 added. 3.0 mmol HBF 4 added. 20 bar H 2 used. Aerated methanol used. 30% methyl benzyl ether formed. 10
11 Table S2. Details of the substrate scope of the Co/triphos-catalyzed ester and carboxylic acid hydrogenation reaction. General conditions used: 0.15 M substrate, 1:1 Co(BF4)2 6H2O and triphos, distilled MeOH (esters) or THF (carboxylic acids), 80 bar initial H2 pressure, 100 C. Catalyst loading calculated per ester/acid group. Conversions (yields) depicted, based on GC. Entry Substrate Solvent Catalyst loading (mol %) Time (h) Conversion (%) Major product Yield (%) 1 MeOH MeOH 10 5 > MeOH MeOH > MeOH MeOH MeOH > THF >85 >
12 9 THF > MeOH 10 6 > THF > MeOH THF > THF > THF > THF % methyl stearate formed. 36% butyl butyrate formed. 31% ethyl acetate formed. 29% methyl formate formed. Based on 19 F NMR. 12
13 Table S3. Details of the functional group tolerance of the Co/triphos-catalyzed carboxylic acid hydrogenation reaction. General conditions used: 0.15 M substrate, 5 mol % 1:1 Co(BF4)2 6H2O and triphos, distilled THF, 80 bar initial H2 pressure, 100 C, 22 hours. Entry Substrate Conversion Product GC yield Isolated yield 1 > > > ND 12 ND 6 ND <1 ND 7 97 ND <1 ND 9 ND unknown - ND 10 ND unknown - ND ND: not determined. Isolated as a mixture of the two products. 13
14 Table S4. Effect of additives on the hydrogenation of benzoic acid to benzyl alcohol. General conditions used: 0.15 M benzoic acid, 5 mol % 1:1 Co(BF4)2 6H2O and triphos, 10 mol % additive, distilled THF, 80 bar initial H2 pressure, 100 C, 2 hours. Entry Metal precursor Additive Conversion (%) GC yield (%) 1 Co(BF4)2 6H2O Co(BF4)2 6H2O BF3 Et2O Co(BF4)2 6H2O Sc(OTf) Co(OAc)2 4H2O Co(OAc)2 4H2O BF3 Et2O Co(OAc)2 4H2O HBF4 (48% aq) Co(OAc)2 4H2O NaBF Co(OAc)2 4H2O NBu4BF Co(OAc)2 4H2O NaPF Co(OAc)2 4H2O NBu4PF Co(OAc)2 4H2O NaSbF Co(OAc)2 4H2O LiB(C6F5)4 2.5Et2O Co(OAc)2 4H2O FeCl3 6H2O CoCl CoCl2 BF3 Et2O CoCl2 NaSbF
15 Table S5. Selected bond distances and angles of the obtained X-ray crystal structure [Co(triphos)(κ 2 -benzoate)]bph 4. Hydrogen atoms and BPh4 anion not shown for clarity. Bond Distances (Å) Co1 O (3) Co1 O (3) Co1 P (1) Co1 P (1) Co1 P (1) C1 O (6) C1 O (5) Bond Angles (degrees) O1 Co1 O2 65.6(1) O1 Co1 P (1) O1 Co1 P (1) O1 Co1 P (1) O2 Co1 P1 96.4(1) O2 Co1 P (1) O2 Co1 P (1) P1 Co1 P (5) P1 Co1 P (5) P2 Co1 P (5) O1-C1-O (4) 15
16 Fig. S6 Gas chromatogram of methyl benzoate hydrogenation using 10 mol % Co/triphos. 16
17 Fig. S7 Gas chromatogram of methyl benzoate hydrogenation using 5 mol % Co/triphos. 17
18 Fig. S8 Gas chromatogram of tert-butyl benzoate hydrogenation using 10 mol % Co/triphos. 18
19 Fig. S9 Gas chromatogram of methyl butyrate hydrogenation using 5 mol % Co/triphos. 19
20 Fig. S10 Gas chromatogram of methyl trans-hex-3-enoate hydrogenation using 10 mol % Co/triphos. 20
21 Fig. S11 Gas chromatogram of γ-valerolactone hydrogenation using 10 mol % Co/triphos. 21
22 Fig. S12 Gas chromatogram of methyl stearate hydrogenation using 10 mol % Co/triphos. 22
23 Fig. S13 Gas chromatogram of triolein hydrogenation using 10 mol % Co/triphos. 23
24 Fig. S14 Gas chromatogram of benzoic acid hydrogenation using 2.5 mol % Co/triphos. 24
25 Fig. S15 Gas chromatogram of phthalic acid hydrogenation using 5 mol % Co/triphos. 25
26 Fig. S16 Gas chromatogram of levulinic acid hydrogenation using 10 mol % Co/triphos. 26
27 Fig. S17 Gas chromatogram of succinic acid hydrogenation using 2.5 mol % Co/triphos. 27
28 Fig. S18 Gas chromatogram of stearic acid hydrogenation using 5 mol % Co/triphos. 28
29 Fig. S19 Gas chromatogram of butyric acid hydrogenation using 5 mol % Co/triphos. 29
30 Fig. S20 Gas chromatogram of butyric acid hydrogenation using 0.1 mol % Co/triphos. 30
31 Fig. S21 Gas chromatogram of acetic acid hydrogenation using 0.25 mol % Co/triphos. 31
32 Fig. S22 Gas chromatogram of acetic acid hydrogenation using 0.1 mol % Co/triphos. 32
33 Fig. S23 Gas chromatogram of formic acid hydrogenation using 0.5 mol % Co/triphos. 33
34 Fig. S24 Gas chromatogram of formic acid hydrogenation using 0.25 mol % Co/triphos. 34
35 Fig. S25 19 F NMR spectrum of trifluoroacetic acid hydrogenation using 125 ppm Co/triphos. 35
36 Fig. S26 1 H NMR spectrum of the obtained benzyl alcohol using 2.5 mol % Co/triphos. 36
37 Fig. S27 13 C NMR spectrum of the obtained benzyl alcohol using 2.5 mol % Co/triphos. 37
38 Fig. S28 1 H NMR spectrum of the obtained 4-chlorobenzyl alcohol using 2.5 mol % Co/triphos. 38
39 Fig. S29 13 C NMR spectrum of the obtained 4-chlorobenzyl alcohol using 2.5 mol % Co/triphos. 39
40 Fig. S30 1 H NMR spectrum of the obtained 4-fluorobenzyl alcohol using 2.5 mol % Co/triphos. 40
41 Fig. S31 13 C NMR spectrum of the obtained 4-fluorobenzyl alcohol using 2.5 mol % Co/triphos. 41
42 Fig. S32 19 F NMR spectrum of the obtained 4-fluorobenzyl alcohol using 2.5 mol % Co/triphos. 42
43 Fig. S33 1 H NMR spectrum of the obtained 4-(trifluoromethyl)benzyl alcohol using 2.5 mol % Co/triphos. 43
44 Fig. S34 13 C NMR spectrum of the obtained 4-(trifluoromethyl)benzyl alcohol using 2.5 mol % Co/triphos. 44
45 Fig. S35 19 F NMR spectrum of the obtained 4-(trifluoromethyl)benzyl alcohol using 2.5 mol % Co/triphos. 45
46 Fig. S36 1 H NMR spectrum of the obtained 3-hydroxybenzyl alcohol using 2.5 mol % Co/triphos. 46
47 Fig. S37 13 C NMR spectrum of the obtained 3-hydroxybenzyl alcohol using 2.5 mol % Co/triphos. 47
48 Fig. S38 1 H NMR spectrum of the obtained mixture of 1-butanol and butyl butyrate using 0.1 mol % Co/triphos. 48
49 Fig. S39 13 C NMR spectrum of the obtained mixture of 1-butanol and butyl butyrate using 0.1 mol % Co/triphos. 49
50 XYZ data for all calculated structures ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H H H C C C C C C H H H H
51 H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H
52 H H H H Co O C O C H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H
53 H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C
54 H H H H H C C C C C C H H H H H Co O C O C H H H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C
55 H H C H H C H H P P P C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C
56 C C H H H H H C C C C C C H H H H H C C C C C C H H H H H Co O C O C H H H H H
57 ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H H H C C C C C C H H H H H C C
58 C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H
59 H Co O C O C H H H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H H
60 H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H
61 H H H H C C C C C C H H H H H Co O C O C H H H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C
62 H H C H H C H H P P P C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C
63 C C H H H H H C C C C C C H H H H H C C C C C C H H H H H Co O C O C H H H H H
64 ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H H H C C C C C C H H H H H C C C
65 C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H
66 Co C O C H H H H H O H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P P C H H H
67 C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H
68 H H H C C C C C C H H H H H Co C O C H H H H H O H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P
69 P P C H H C H H C H H C C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C
70 C C C H H H H C C C C C C H H H H H C C C C C C H H H H H H O C H C H H H
71 ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H H C C C C C C H H H H H
72 C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H
73 H H H H O C H C H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H H
74 C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H
75 H H H C C C C C C H H H H H O C C H H H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C
76 H H C H H C H H C C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C
77 H H H H H C C C C C C H H H H H C C C C C C H H H H H O C C H H H H H O C O H C H H H
78 ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H H C C C C C C H H H H H C
79 C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H
80 H H O C H C H H H O H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H
81 H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H
82 H H H H C C C C C C H H H H H O C H C H H H O H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P
83 C H H C H H C H H C C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C
84 C H H H H H C C C C C C H H H H H C C C C C C H H H H H O H H H
85 ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H H C C C C C C H H H H H
86 C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H
87 H H H O H H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = Co P P P C H H C H H C H H C C H H H C C C
88 C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H
89 C C C C C C H H H H H H O H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy = C C H H C H H C H H P P
90 P C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H C C C
91 C C C H H H H H C C C C C C H H H H H Co C O C H H H H H O H H ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 91
92 87 Energy = Co P P P C H H C H H C H H C C H H H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H
93 H C C C C C C H H H H H C C C C C C H H H H H C C C C C C H H H H H H H H
94 Acetaldehyde ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 7 Energy = H C H H C H O Acetic acid ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 8 Energy = H C H H C O O H
95 Ethanol ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 9 Energy = H C H H C H H O H Hydrogen ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 2 Energy = H H Hemiacetal ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol Energy =
96 H C H H C H O H O H Water ESCF = Hartree ZPE = Hartree ZPE + Thermal corrections (373 K) = Hartree H 373 = kcal mol -1 3 Energy = H O H
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