Page 1of38
S1
Supporting Information for
A stability study of hypervalent tellurium compounds
in aqueous solutions.
Cleverson R. Princival,1Marcos. V. L. R. Archilha,1 Alcindo A. dos Santos,
1Maurício P.
Franco,1Ataualpa A. C. Braga,
1André F. Rodrigues-Oliveira,
1 Thiago C. Correra,
1Rodrigo L. O. R.
Cunha*,2
and João V. Comasseto*,1,3
.
1Instituto de Química, Universidade de São Paulo, São Paulo-SP, Brazil.
2 Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, Santo André-SP, Brazil.
3Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo,
Diadema-SP, Brazil.
CONTENTS
Supplemental figures S2
Chemistry S3
Stability study of hypervalent compounds of tellurium¨ S7
NMR spectra S8
HRMS-ESI-(-) spectra S27
Theoretical calculations details S31
Scheme S1 S31
Table S1 S31
Cartesian Coordinates S32
References S38
Page 2of38
S2
SUPLEMENTAL FIGURES
Figure S1: (A) 125
Te NMR spectrum and (B) HRMS-ESI-(-) spectrum of AS101 after treated with
propylene glycol.
Figure S2: HRMS-ESI-(-) spectrum of AS101 compound after treatment with 5 equivalents of
ethanol.
Page 3of38
S3
Chemistry
General Chemical methods. Chemical reagents were purchased from Sigma Aldrich. The course of
the reactions was monitored by thin layer chromatography (TLC) on 0.20 mm silica gel 60 F254
plates (Merck, Germany), then visualized with an UV lamp. Nuclear magnetic resonance spectra
(NMR) were recorded on Bruker AC 200 spectrometer (Bruker BioSpin GmbH, Rheinstetten,
Baden-Wurttemberg, Germany) operating at 200, 50 and 63 MHz for 1H,
13C and
125Te NMR,
respectively. CDCl3 and DMSO-d6 were used as solvents and as internal references,
tetramethylsilane (TMS) for 1H NMR, CDCl3 for
13C NMR and diphenylditelluride for
125Te NMR.
Data for NMR spectra are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, br s =
broad singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublets, m = multiplet), coupling
constant (Hz), integration.
Microwave reactions were performed with a CEM Discover Synthesis Unit (CEM Co., Matthews,
NC, USA), with a continuous focused microwave power delivery system in a glass vessel (10 or 35
mL) sealed with Teflon cap, under magnetic stirring.
All high resolution mass spectra were acquired in a q-ToF spectrometer Maxis 3G Bruker Daltonics.
Prior to experiments all dry solvents were previously degassed and the concentrations of working
samples in each experiment were of 1 x 10-4
and 1 x 10-5
mol/L.
Syntheses procedures
Preparation of tellurium tetrachloride
In a 50 mL round bottomed flask equipped with a Vigreux column (25 cm), a reflux condenser and a
drying tube, was placed elemental tellurium (200 mesh) previously dried overnight in an oven at 100
°C (3.82 g, 30 mmol) and SO2Cl2 (7.5 mL, 90 mmol). The system was placed into the oven of a
microwave apparatus and then it was irradiated for 4 h at 65 ºC and at 100 W. After this time all the
tellurium powder was consumed and the excess of SO2Cl2 was removed by distillation under
vacuum, leaving behind a white solid which was submitted to high vacuum and heating and then
used for further reactions without purification. Yield: 7.59 g (94%) 1,2
.
Page 4of38
S4
Preparation of p-methoxyphenyltellurium trichloride
In a glass pressure resistant tube (35 mL) equipped with a magnetic stirring bar were placed tellurium
tetrachloride prepared as described for 1 (1.02 g, 8 mmol) and neat anisole (0.87 mL, 8 mmol). The tube was
closed and placed in the oven of a microwave apparatus and then irradiated for 3 min at 50 o C and at 100 W,
after cooling to room temperature. The yellow solid obtained was recrystallized from acetic acid.Yield: 2.34 g
(86%); m.p.: 181-182 °C, literature:2-4
182 °C.
Dichloro (E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol
To a pressure resistant glass tube (10 mL) equipped with a magnetic stirring bar were added 1-
ethynylcyclohexanol (248 mg, 2 mmol) and crushedp-methoxyphenyltellurium trichloride (682 mg,
2 mmol). The tube was then placed in the microwave apparatus and irradiated for 15 minutes at 70
°C and 100 W. After that, the tube was opened and the residue was dissolved in chloroform and
precipitated with hexane.
Yield: 734 mg (79%); colorless crystalline solidm.p: 138-139 °C.
1H NMR (200 MHz, DMSO) δ (ppm) 8.18 (d, J = 8.9 Hz, 2H), 7.23 (d, J = 8.9 Hz, 2H), 6.31 (s, 1H),
3.85 (s, 3H), 2.58 – 0.95 (m, 10H). 13
C NMR (50 MHz, DMSO) δ 161.9, 160.9,137.48 (s), 122.43,
121.94, 115.79, 75.24, 55.90, 34.59, 24.79, 21.39.125
Te NMR (63 MHz, DMSO) d 1001.0; IR (ATR)
νmax/cm-1
3488, 3066, 3017, 2964, 2864, 1294, 1052, 789, 743, 489; anal. calcd. for C15H19Cl3O2Te
(465.2692): C, 38.72, H, 4.12; found: C, 39.02, H, 4.11.
Page 5of38
S5
Dichloro (Z)-(2-chloro-2-phenylvinyl) (4-metoxyphenyl)tellanyl
To a glass pressure resistant tube (10 mL) equipped with a magnetic stirring bar were added
ethynylbenzene (204 mg, 2 mmol) and crushed p-methoxyphenyltellurium trichloride (682 mg, 2
mmol). The tube was then placed in the oven of a microwave apparatus and irradiated for 15 min at
70 °C and 100 W. After that, the tube was opened and the residue was dissolved in chloroform and
precipitated with hexane. Yield: 726 mg (82%); colorless crystalline solid
1H NMR (200 MHz, DMSO) δ (ppm) 8.48 (s, 1H), 8.20 (d, J = 9.0 Hz, 2H), 7.87 (dd, J = 6.5, 3.0
Hz, 2H), 7.59 – 7.44 (m, 3H), 7.19 (d, J = 9.0 Hz, 2H), 3.86 (s, 3H).13
C NMR (50 MHz, DMSO) δ
161.8, 144.9, 136.5, 134.2, 131.5, 129.3, 128.5, 127.6, 125.9, 115.3, 55.9.125
Te NMR (63 MHz,
DMSO) 854.0 IR (ATR) νmax/cm-1
3041, 2838, 1570, 1581, 1490, 1255, 1026, 737. m.p.: 134-135 °C
CAS: 133040-43-4
Dichloro (E)-3-chloro-4-(4-metoxyphenyltellanyl)-2 methylbut-3-en-2-ol
To a glass pressure resistant tube (10 mL) equipped with a magnetic stirring bar were added 2-
methylbut-3-yn-2-ol (168 mg, 2 mmol) and crushedp-methoxyphenyltellurium trichloride (682 mg, 2
mmol). The tube was then placed in the oven of a microwave apparatus and irradiated for 15 min at
75 °C and 100 W. After that, the tube was opened and the residue was dissolved in chloroform and
precipitated with hexane. Yield: 722 mg (85%); colorless crystalline solid.
1H NMR (200 MHz, DMSO) δ (ppm) 8.19 (d, J = 8.9 Hz, 2H), 7.24 (d, J = 9.0 Hz, 2H), 6.30 (s, 1H),
3.86 (s, 3H), 1.65 (s, 6H). 13
C NMR (50 MHz, DMSO) δ 161.9, 159.4, 137.5, 122.6, 121.5, 115.8,
73.1, 55.9, 28.9.125
Te NMR (63 MHz, DMSO) δ 1000.4. IR (ATR) νmax/cm-1
3427, 3073, 2970,
1583, 1492, 1255, 1182, 823; CAS: 244214-20-8.
Page 6of38
S6
Ammoniumtrichloro(dioxoethylene-O,O′)tellurate
In a 25 mL round bottomed flask equipped with reflux condenser and a magnetic stirring bar was
placed TeCl4(1,35 g, 5 mmol) ethylene glycol (775 mg, 12,5 mmol) and dry CH3CN (10 mL) as
solvent. The mixture was heated under reflux for 4 h. The white crystalline product precipitates out
of the solution during the course of the reaction. The product was collected by filtration and
dried.Yield: 2,2 g (71%)
1H NMR (200 MHz, DMSO) δ (ppm) 10.87 (t, 4H), 6.59 (s, 4H).
13C NMR (50 MHz, DMSO) δ
67,4. 125
Te NMR (63 MHz, DMSO) δ 1678.0. CAS 106566-58-9
Ammonium tetrachloro(4-methoxybenzene)tellurate
In a 50 mL round bottomed flask was placedp-methoxyphenyltellurium trichloride (1.02 g 3 mmol)
and HCl (20 mL 6M) as solvent. The mixture was stirred for 30 minutes and then was added
ammonium chloride (160 mg 3 mmol). The mixture was stirred for an additional 1 hour. Then the
mixture was left at 4 °C for 24 hours and colorless crystals were formed. The product was collected
by filtration and dried. Yield: 1,1 g (93%)
1H NMR (200 MHz, DMSO) δ 8.35 (d, J = 9.0 Hz, 2H), 7.39 – 6.84 (m, 6H), 3.80 (s, 3H).
13C NMR
(50 MHz, DMSO) δ 160.7, 144.2, 135.7, 113.8, 55.9.125
Te NMR (63 MHz, DMSO) δ 1238.9 IR
(ATR) νmax/cm-1
3188, 1585, 1574, 1404, 1251, 1186,1013, 935, 817. HRMS [M] (376.8300)calc.
for C7H7Cl4OTe (376,8313)Anal. calcd. for C7H11Cl4NOTe C, 21.31, H, 2.81, N, 3.55; found: C,
21.44, H, 2.73, N, 3.54
Page 7of38
S7
STABILITY STUDY OF HYPERVALENT TELLURIUM COMPOUNDS.
Forced degradation or stress test is a good strategy to demonstrate the degradation routes and the
nature of the formed products of compounds which are to be appliedinin vitro and in vivo 5a
biologic
studies. Herein, we report a systematic stability study of organotellurium compounds used in
biological activities studies.
Exposure stability study in water.
In a 5 mm NMR tube, 50 mg of the compoundunder investigation was diluted in a mixture of 360 μL
of DMSO-d6 and 40 μL D2O. A capillary glass tube containing diphenylditelluride was used as a
chemical shift standard. The same sample was maintained for a period of 30 days in solution in this
mixture. The 125
Te NMR spectrum was recorded daily for 7 days and weekly for up to 30 days.
Exposure stability study in PBS
In a 5 mm NMR tube, 50 mg of the compound under investigationwas diluted in a mixture of 300 μL
of DMSO-d6 and 30 μL D2O. A capillary glass tube containing diphenylditelluride was used as a
chemical shift standard. The same sample was maintained for a period of 30 days in this solution and
then the 125
Te NMR spectrum was recorded.
Thermal stability study
In a 5 mm NMR tube, 50 mg of the compound under study was diluted in a mixture of 360 μL of
DMSO-d6 and 40 μL D2O or PBS. A capillary glass tube containing diphenylditelluride was used as
a chemical shift standard. An initial 125
Te NMR spectrum was recorded at 25 °C. The same sample
was heated (40 °C) for 24-96 hours and125
Te NMR spectrwere recorded.
Exposure stability study in a HCl/DMSO mixture.
In a 5 mm NMR tube, 50 mg of the compound under study was diluted in a mixture of 300 μL of
DMSO-d6 and 30 μL (6 mol/L) of HCl. A capillary glass tube containing diphenylditelluride was
used as a chemical shift standard. After 24 hours a 125
Te NMR spectrum was recorded at 25 °C.
Page 8of38
S8
NMR SPECTRA
Figure S3: 1H NMR spectrum (200 MHz, DMSO-d6) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S4:
13C NMR spectrum (50 MHz, DMSO-d6) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Page 9of38
S9
Figure S5:
125Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S6:
1H NMR spectrum (200 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-
metoxyphenyl)tellanyl8c.
Page 10of38
S10
Figure S6: 13
C NMR spectrum (50 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-
metoxyphenyl)tellanyl8c.
Figure S7: 125
Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-
metoxyphenyl)tellanyl8c.
Page 11of38
S11
Figure S8:
1H NMR spectrum (200 MHz, DMSO-d6) of dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
Figure S9: 13
C NMR spectrum (50 MHz, DMSO-d6) of dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
Page 12of38
S12
Figure S10: 125
Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
Figure S11: 1H NMR spectrum (200 MHz, DMSO-d6) of ammonium tetrachloro(4-
methoxybenzene)tellurate7.
Page 13of38
S13
Figure S12: 13
C NMR spectrum (50 MHz, DMSO-d6) of ammonium tetrachloro(4-
methoxybenzene)tellurate7.
Figure S13: 125
Te NMR spectrum (63 MHz, DMSO-d6) of ammonium tetrachloro(4-
methoxybenzene)tellurate7.
Page 14of38
S14
Figure S14: 1H NMR spectrum (200 MHz, DMSO-d6) of AS101.
Figure S15: 13
C NMR spectrum (50 MHz, DMSO-d6) of AS101.
Page 15of38
S15
Figure S16: 125
Te NMR spectrum (63 MHz, DMSO-d6) of AS101.
Spectra of exposure stability study of organotelluranes 8a-c in water.
Figure S17: 1H NMR spectrum (200 MHz, DMSO-d6 and D2O) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl)cyclohexanol8a.
Page 16of38
S16
Figure S18: 13
C NMR spectrum (50 MHz, DMSO-d6 and D2O) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S19: 125
Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (E)-1-(1-chloro-2-(4-
methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Page 17of38
S17
Figure S20: 1H NMR spectrum (200 MHz, DMSO-d6 and D2O) of dichloro (Z)-(2-chloro-2-
phenylvinyl) (4-metoxyphenyl)tellanyl8c.
Figure S21: 13
C NMR spectrum (50 MHz, DMSO-d6 and D2O) of dichloro (Z)-(2-chloro-2-
phenylvinyl) (4-metoxyphenyl)tellanyl8c.
Page 18of38
S18
Figure S22: 125
Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (Z)-(2-chloro-2-
phenylvinyl) (4-metoxyphenyl)tellanyl8c.
Figure S23: 1H NMR spectrum (200 MHz, DMSO-d6 and D2O) dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
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S19
Figure S24: 13
C NMR spectrum (50 MHz, DMSO-d6 and D2O) of dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
Figure S25: 125
Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (E)-3-chloro-4-(4-
metoxyphenyltellanyl)-2 methylbut-3-en-2-ol8b.
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S20
Spectra of exposure stability study in water of tellurate 7, AS101 and tellurium tetrachloride.
Figure S26: 125
Te NMR spectrum (63 MHz, DMSO-d6 and 2 equivalent of H2O) of AS101.
Figure S27: 13
C NMR spectrum (50 MHz, DMSO-d6 and 2 equivalent of H2O) of AS101.
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S21
Figure S28: 13
C NMR spectrum (50 MHz, DMSO-d6 and 10 equivalent of H2O) of AS101.
Figure S29: 125
Te NMR spectrum (63 MHz, DMSO-d6 and 1 equivalent of H2O) of TeCl4.
Page 22of38
S22
Spectra of exposure stability study in PBS of organotellurane 8a and tellurate 7.
Figure S30: 13
C NMR spectrum (50 MHz, DMSO-d6 and PBS after 96 hours at 40 °C) of dichloro
(E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S31: 125
Te NMR spectrum (63 MHz, DMSO-d6 and PBS after 96 hoursat 40 °C) of dichloro
(E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
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S23
Figure S32: 1H NMR spectrum (200 MHz, DMSO-d6 and and PBS after 96 hoursat 40 °C) of
dichloro (E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S33: 1H NMR spectrum (200 MHz, DMSO-d6 and PBS after 30 day at 25 °C) of tellurate 7.
Page 24of38
S24
Figure S34: 13
C NMR spectrum (50 MHz, DMSO-d6 and PBS after 30 days at 25 °C) of tellurate 7.
Figure S35: 125
Te NMR spectrum (63 MHz, DMSO-d6 and PBS after 30 day at 25 °C) of tellurate 7.
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S25
Spectra of exposure stability study of organotellurane 8a in HCl.
Figure S36: 1H NMR spectrum (200 MHz, DMSO-d6 and HCl 6M after 24 hours) of dichloro (E)-1-
(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Figure S37: 13
C NMR spectrum (50 MHz, DMSO-d6 and HCl 6M after 24 hours) of dichloro (E)-1-
(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
Page 26of38
S26
Figure S38: 125
Te NMR spectrum (63 MHz, DMSO-d6 and HCl 6M after 24 hours) of dichloro (E)-
1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl)cyclohexanol8a.
Figure S39: 125
Te NMR spectrum (63 MHz, DMSO-d6 and basic buffer pH = 8 after 6 days at room
temperature) of dichloro (E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
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S27
Figure S40:125
Te NMR spectrum (63 MHz, DMSO-d6 and acid buffer pH = 5.5 after 48 hours at
room temperature) of dichloro (E)-1-(1-chloro-2-(4-methoxyphenyltellanyl)vinyl) cyclohexanol8a.
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S28
HRMS-ESI-(-) SPECTRA
Figure S41: HRMS-ESI-(-) spectrum of AS101 compound after treatment with two equivalents of
water.
Figure S42: HRMS-ESI-(-) spectrum of AS101 compound after treatment with 100 equivalents of
water.
Figure S43:HRMS-MS-ESI-(-) spectrum of AS101 compound after treatment with two equivalents
of water.
Page 29of38
S29
Figure S44:HRMS-ESI-(-) spectrum of AS101 compound after treatment with 5 equivalents of
ethanol followed by addition of 10 equivalents of water.
Figure S45: HRMS-ESI-(-) spectrum of AS101 compound after treatment with 5 equivalents of
ethanol followed by addition of 100 equivalents of water.
Figure S46: HRMS-ESI-(-) spectrum of AS101 compound after treatment with two equivalents of
propylene glycol.
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S30
Figure S47: HRMS-ESI-(-) spectrum of tellurate 7 after treatmentwith PBS after 30 days at 25 °C.
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S31
THEORETICAL CALCULATIONS
Scheme S1. Hydrolysis of compounds AS101 (first line), 7 (second line) and 8b (third line) with one equivalent of water and Free Gibbs Energy is given at the right side of the reaction. Table S1. Atomic charges from NPA of Tellurium and the atoms bonded to the center atom.
Compound Atomic charges
Te Oaxial Otrans-Cl Caryl Colefin Cltrans-Cl Cltrans-O
AS101 +1.894 -0,839 -0,870 - - -0.600 and
-0.585
-0,648
7 +1.450 - - -0.436 - -0.562, 0.561, -0.558 and -
0.557
-
8b +1.565 - - -0.419 -0.397 -0.573 and
-0.558
-
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S32
CARTESIAN COORDINATES:
Compound AS101
Potential Energy = -1617.85242666 Eh
Free Gibbs Energy = -1617.824634 Eh
Te 0.005048 0.160760 -0.456530
Cl 2.633858 0.070940 -0.368062
Cl -0.044827 2.545271 0.754654
Cl -2.600479 0.089624 -0.304780
O -0.011855 -1.839534 -0.775776
O 0.021472 -0.410937 1.452161
C -0.336206 -2.544070 0.425088
H -1.427230 -2.580962 0.550528
H 0.048782 -3.563235 0.332795
C 0.320019 -1.811644 1.568583
H 1.408860 -1.951830 1.555565
H -0.078093 -2.124613 2.536760
Compound7
Potential Energy = -2195.15824132 Eh
Free Gibbs Energy = -2195.078993 Eh
Te 1.459557 -0.084796 -0.002711
C -0.652264 0.135335 0.002202
C -1.228599 1.408750 0.000323
C -1.453205 -1.003425 0.004049
C -2.607992 1.533104 -0.001318
H -0.612830 2.302937 -0.003427
C -2.838626 -0.884131 0.005863
H -1.009246 -1.994322 0.005368
C -3.418695 0.389485 0.002198
H -3.073547 2.513661 -0.005828
H -3.445209 -1.781937 0.009347
Cl 1.180733 -1.883790 -1.895418
Cl 1.600229 1.835973 -1.776792
Cl 1.200125 -1.990193 1.785133
Page 33of38
S33
Cl 1.588059 1.725680 1.884743
O -4.759512 0.610810 0.001257
C -5.607757 -0.538919 0.008836
H -5.444390 -1.139030 0.909296
H -6.627024 -0.156067 0.003770
H -5.441278 -1.153906 -0.880880
Compound 8b
Potential Energy = -2005.29845772 Eh
Free Gibbs Energy = -2005.102111 Eh
Te -0.756160 0.154733 -1.080853
Cl -1.034497 2.718300 -0.503829
Cl -0.457746 -2.377567 -1.647632
C 1.234988 0.300375 -0.373071
C 1.529415 1.045394 0.772819
C 2.245956 -0.339781 -1.082554
C 2.838970 1.134496 1.209805
H 0.741818 1.539776 1.334984
C 3.566219 -0.250458 -0.648296
H 2.022343 -0.925237 -1.969228
C 3.862634 0.486460 0.502615
H 3.087147 1.698533 2.103383
H 4.343961 -0.754532 -1.210191
O 5.114389 0.628207 1.011670
C 6.177135 -0.037140 0.327391
H 6.287131 0.343768 -0.692752
H 7.078304 0.181752 0.897977
H 6.009866 -1.118523 0.303324
C -1.751587 -0.353225 0.744526
C -1.222541 -1.121123 1.704633
H -1.829164 -1.361086 2.573362
Cl 0.318198 -1.875655 1.776940
C -3.208226 0.103942 0.912334
C -3.877428 0.477630 -0.402610
Page 34of38
S34
H -4.936242 0.674530 -0.213073
H -3.456093 1.389513 -0.838263
H -3.811828 -0.337009 -1.131262
C -3.283073 1.252234 1.911961
H -4.329418 1.535815 2.067479
H -2.853194 0.951088 2.871458
H -2.739268 2.126681 1.544460
O -3.892525 -1.045681 1.459324
H -4.785976 -0.750537 1.684271
Water
Potential Energy = -76.4342601688 Eh
Free Gibbs Energy = -76.430505 Eh
O 0.000000 0.000000 0.119041
H 0.000000 0.757837 -0.476165
H 0.000000 -0.757837 -0.476165
HCl
Potential Energy = -460.782707817 Eh
Free Gibbs Energy = -460.793995 Eh
Cl 0.000000 0.000000 0.071483
H 0.000000 0.000000 -1.215209
Page 35of38
S35
Ethylene glycol
Potential Energy = -230.250218450 Eh
Free Gibbs Energy = -230.192497 Eh
O -1.483274 -0.538694 0.205107
H -1.040372 -1.346270 -0.085665
C -0.713798 0.559558 -0.283608
H -0.682425 0.542691 -1.381932
H -1.238832 1.467494 0.022953
C 0.684357 0.580979 0.268569
H 1.191143 1.497112 -0.064982
H 0.657006 0.583845 1.365957
O 1.368277 -0.579928 -0.208197
H 2.210101 -0.639115 0.258627
Compound [TeOCl3]-
Potential Energy = -1464.01247078 Eh
Free Gibbs Energy = -1464.044042 Eh
Te 0.000211 0.345329 -0.129010
Cl -0.001134 -2.145329 0.161818
Cl 2.652274 0.338332 -0.261480
Cl -2.651768 0.339393 -0.261641
O -0.000039 0.874022 1.606332
Compound 7_OH
Potential Energy = -1810.78582219 Eh
Free Gibbs Energy = -1810.691264 Eh
Te -1.533318 0.014923 -0.223436
C 0.573897 0.157573 -0.127944
C 1.193728 1.320734 -0.593543
C 1.335758 -0.898898 0.361944
C 2.576209 1.414069 -0.580147
H 0.605257 2.153374 -0.965593
C 2.725152 -0.814250 0.373032
H 0.853100 -1.799014 0.731391
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C 3.346628 0.346457 -0.101458
H 3.074553 2.309968 -0.937218
H 3.305018 -1.650307 0.747365
Cl -1.362544 -1.038118 2.394208
Cl -1.726359 2.465188 0.744772
Cl -1.249078 -2.427385 -1.211790
O 4.694917 0.527805 -0.137005
C 5.512757 -0.540639 0.340406
H 5.356458 -1.448696 -0.250437
H 6.540730 -0.200433 0.223920
H 5.312455 -0.747321 1.396536
O -1.314992 0.816469 -2.071027
H -2.193541 0.947307 -2.459013
Compound 8b_OH
Potential Energy = -1620.92324848 Eh
Free Gibbs Energy = -1620.714221 Eh
Te 0.787143 -0.659138 -0.996803
Cl 1.112881 -2.548638 1.096632
C -1.185746 -0.446816 -0.249644
C -1.445792 -0.412922 1.122693
C -2.222618 -0.317209 -1.167513
C -2.743396 -0.230647 1.570170
H -0.637491 -0.511865 1.842100
C -3.532266 -0.139008 -0.723795
H -2.024952 -0.335095 -2.235116
C -3.791472 -0.091381 0.649176
H -2.962406 -0.186575 2.632651
H -4.329803 -0.039014 -1.451061
O -5.030555 0.087911 1.185089
C -6.118467 0.242364 0.273799
H -6.237372 -0.648555 -0.350674
H -7.005520 0.376929 0.890869
H -5.975939 1.122182 -0.361772
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C 1.740598 0.809961 0.242224
C 1.191167 1.993818 0.536235
H 1.754759 2.713479 1.123421
Cl -0.347269 2.618882 0.075496
C 3.169326 0.542456 0.733704
C 3.889958 -0.525107 -0.076489
H 4.932167 -0.574483 0.251430
H 3.451886 -1.516509 0.077611
H 3.881466 -0.286190 -1.144761
C 3.154355 0.187452 2.215424
H 4.179573 0.038129 2.571102
H 2.693175 0.992910 2.794205
H 2.590846 -0.734487 2.384302
O 3.865838 1.798795 0.554989
H 4.748091 1.678404 0.932506
O 0.366319 0.729038 -2.433686
H 0.747956 0.388045 -3.256307
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REFERENCES
(1) Petragnani, N.; Mendes, S. R.; Silveira, C.; Tetrahedron Lett. 2008, 49, 2371-2372.
(2) Princival, C.; Dos Santos A, A.; Comasseto, J. V. J.; Braz. Chem. Soc., 2015, 26, 832-836.
(3) Cunha, R. L. R. O.; Omori, A. T.; Castelani, P.; Toledo, F. T.; Comasseto, J. V.; .J.
Organomet. Chem.2004, 689, 3631-3636.
(4) Reichel, L.; Kirschbaum, E.; .Liebigs Ann. Chem. 1936, 523, 211-223.
(5) Petragnani, N.; Stefani, H. A.; Tellurium in Organic Synthesis, 2nd ed.; Elsevier: Amsterdam,
2007
(6) Stability testing of new drug substances and products. In: International conference on
harmonization, IFPMA, Geneva 2003, 1-20.