a stability study of hypervalent tellurium compounds in

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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

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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.

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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

.

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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.

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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.

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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

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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.

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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-


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S9

Figure S5:

125Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (E)-1-(1-chloro-2-(4-


Figure S6:

1H NMR spectrum (200 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-

metoxyphenyl)tellanyl8c.

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S10

Figure S6: 13

C NMR spectrum (50 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-


Figure S7: 125

Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (Z)-(2-chloro-2-phenylvinyl) (4-


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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-


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S12

Figure S10: 125

Te NMR spectrum (63 MHz, DMSO-d6) of dichloro (E)-3-chloro-4-(4-


Figure S11: 1H NMR spectrum (200 MHz, DMSO-d6) of ammonium tetrachloro(4-

methoxybenzene)tellurate7.

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S13

Figure S12: 13

C NMR spectrum (50 MHz, DMSO-d6) of ammonium tetrachloro(4-


Figure S13: 125

Te NMR spectrum (63 MHz, DMSO-d6) of ammonium tetrachloro(4-


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S14

Figure S14: 1H NMR spectrum (200 MHz, DMSO-d6) of AS101.

Figure S15: 13

C NMR spectrum (50 MHz, DMSO-d6) of AS101.

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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.

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S16

Figure S18: 13

C NMR spectrum (50 MHz, DMSO-d6 and D2O) of dichloro (E)-1-(1-chloro-2-(4-


Figure S19: 125

Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (E)-1-(1-chloro-2-(4-


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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-


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S18

Figure S22: 125

Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (Z)-(2-chloro-2-


Figure S23: 1H NMR spectrum (200 MHz, DMSO-d6 and D2O) dichloro (E)-3-chloro-4-(4-


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S19

Figure S24: 13

C NMR spectrum (50 MHz, DMSO-d6 and D2O) of dichloro (E)-3-chloro-4-(4-


Figure S25: 125

Te NMR spectrum (63 MHz, DMSO-d6 and D2O) of dichloro (E)-3-chloro-4-(4-


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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.

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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.

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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.

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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.


water.

Figure S43:HRMS-MS-ESI-(-) spectrum of AS101 compound after treatment with two equivalents

of water.

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S29

Figure S44:HRMS-ESI-(-) spectrum of AS101 compound after treatment with 5 equivalents of

ethanol followed by addition of 10 equivalents of water.


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



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

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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



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

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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



O 0.000000 0.000000 0.119041

H 0.000000 0.757837 -0.476165

H 0.000000 -0.757837 -0.476165

HCl



Cl 0.000000 0.000000 0.071483

H 0.000000 0.000000 -1.215209

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S35

Ethylene glycol



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]-



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



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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S36

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



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

of38

S37

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

of38

S38

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.

a stability study of hypervalent tellurium compounds in

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