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SUPPLEMENTARY MATERIAL

Article: GC-MS Study of Mono- and Bishaloethylphosphonates Related to Schedule 2.B.04 of the

Chemical Weapons Convention: the Discovery of a New Intramolecular Halogen Transfer

Nerea Picazas-Márquez, 1María Sierra,1 Clara Nova,1 Juan Manuel Moreno,2 Nuria Aboitiz,1 Gema de

Rivas, 2 Miguel A. Sierra,3 Roberto Martínez-Álvarez 3* and Esther Gómez-Caballero2

1 ISDEFE, Subdirección General de Sistemas Terrestres, INTA, Campus La Marañosa, San Martín de la

Vega, E-28330, Madrid, Spain

2 Laboratorio de Verificación de Armas Químicas (LAVEMA). Área de Defensa Química, Subdirección

de Sistemas Terrestres, INTA, Campus La Marañosa, San Martín de la Vega, E-28330, Madrid, Spain.

3 Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, E-

28040 Madrid, Spain

List of Contents

EI mass spectra of trimethylsilyl monohaloalkylphosphonates 1-12 (Supplemental Figures 1-16)

CI (acetonitrile) mass spectra of compounds 1, 2 and 3 (Supplemental Figures 17-19)

EI mass spectrum of 3-iodopropyl trimethylsilyl methylphosphonate 30 (Supplemental Figure 20)

EI mass spectra of ethyl trimethylsilyl alkylphosphonates (Supplementary Figures 21-24)

EI mass spectra of bishaloalkylphosphonates 13-24 (Supplemetal Figures 25-40)

CI (acetonitrile mass spectra of compounds 13, 14 and 15 (Supplemental Figures 41-43)

EI mass spectrum of diethyl methylphosphonate (Supplemental Figure 44)

EI mass spectrum of diethyl ethylphosphonate (Supplemental Figure 45)

Cartesian coordinates and energies of optimized intermediates and transition states

GC/MS plots of investigated compounds

Retention Indexes of investigated compounds

1

Supplemental Figure 1. EI mass spectrum of 2-chloroethyl trimethylsilyl methylphosphonate 1

Supplemental Figure 2. EI mass spectrum of 2-bromoethyl trimethylsilyl methylphosphonate 2

2

PO

MeOSiMe3

O

Cl

M = 2301

PO

MeOSiMe3

O

Br

M = 274

2

Abundance

Supplemental Figure 3. EI mass spectrum of 2-iodoethyl trimethylsilyl methylphosphonate 3

3

Supplemental Figure 4. HRMS EI mass spectrum of 2-iodoethyl trimethylsilyl methylphosphonate 3

Elemental Composition Report for fragment 27 from compound 3

Multiple Mass Analysis: 2 mass(es) processed - displaying only valid results

Tolerance = 120.0 PPM / DBE: min = -1.5, max = 2.0

Element prediction: Off

Monoisotopic Mass, Odd and Even Electron Ions

64 formula(e) evaluated with 1 results within limits (all results (up to 1000) for each mass)

Elements Used:

C: 0-3 H: 0-12 O: 0-3 P: 0-1 127I: 0-1 Si: 0-1

Minimum: 80.00 -1.5

Maximum: 100.00 5.0 120.0 2.0

Mass RA Calc. Mass mDa PPM DBE Formula

278.8776 84.64 278.9103 -32.7 -117.3 0.5 C3H9O3IPSi

Supplemental Figure 5. EI mass spectrum of 2-chloroethyl trimethylsilyl ethylphosphonate 44

Supplemental Figure 6. EI mass spectrum of 2-bromoethyl trimethylsilyl ethylphosphonate 5

Supplemental Figure 7. EI mass spectrum of 2-iodoethyl trimethylsilyl ethylphosphonate 65

Abundance

m/z

Supplemental Figure 8. HRMS EI mass spectrum of 2-iodoethyl trimethylsilyl ethylphosphonate 6


Single Mass Analysis (displaying only valid results)





Elements Used:

C: 0-4 H: 0-11 O: 0-3 Si: 0-1 P: 0-1 127I: 0-1

Minimum: -1.5

Maximum: 5.0 120.0 2.0

Mass Calc. Mass mDa PPM DBE Formula

292.8932 292.9260 -32.8 -112.0 0.5 C4H11O3IPSi

6

Supplemental Figure 9. EI mass spectrum of 2-chloroethyl trimethylsilyl propylphosphonate 7

Supplemental Figure 10. EI mass spectrum of 2-bromoethyl trimethylsilyl propylphosphonate 8

7

Supplemental Figure 11. EI mass spectrum of 2-iodoethyl trimethylsilyl propylphosphonate 9

8

Supplemental Figure 12. HRMS EI mass spectrum of 2-iodoethyl trimethylsilyl propylphosphonate 9






Elements Used:

C: 0-5 H: 0-13 O: 0-3 P: 0-1 127I: 0-1 Si: 0-1

Minimum: 100.00 -1.5

Maximum: 100.00 5.0 120.0 2.0


306.9513 100.00 306.9416 9.7 31.6 0.5 C5H13O3IPSi

Supplemental Figure 13. EI mass spectrum of 2-chloroethyl trimethylsilyl isopropylphosphonate 109

Supplemental Figure 14. EI mass spectrum of 2-bromoethyl trimethylsilyl isopropylphosphonate 11

Supplemental Figure 15. EI mass spectrum of 2-iodoethyl trimethylsilyl isopropylphosphonate 12

10

Abundance

m/z

Supplemental Figure 16. HRMS EI mass spectrum of 2-iodoethyl trimethylsilyl isopropylphosphonate 12







Elements Used:

C: 0-5 H: 0-13 O: 0-3 Si: 0-1 P: 0-1 127I: 0-1

Minimum: 100.00 -1.5

Maximum: 100.00 5.0 120.0 2.0


306.9146 100.00 306.9416 -27.0 -88.0 0.5 C5H13O3IPSi

11

PO

MeO

OH

m/z 123

[M+H]+ = 231

PO

MeOSiMe3

O

Cl

M = 2301

Abundance

m/z

Supplemental Figure 17. CI (acetonitrile) mass spectrum of 2-chloroethyl trimethylsilyl

methylphosphonate 1

12

[M+H]+ = 275

PO

MeOSiMe3

O

Br

M = 274

2

Abundancem/z

m/z

Supplemental Figure 18. CI (acetonitrile) mass spectrum of 2-bromoethyl trimethylsilyl

methylphosphonate 2

13

[M+H]+ = 323

PO

MeOSiMe3

O

I

M = 322

3

Abundance

m/z

Supplemental Figure 19. CI (acetonitrile) mass spectrum of 2-iodoethyl trimethylsilyl

methylphosphonate 3

14

AbundanceAbundance

m/zm/z

Supplemetal Figure 20. EI mass spectrum of 3-iodopropyl trimethylsilyl methylphosphonate 30

Supplemental Figure 21. EI mass spectrum of ethyl trimethylsilyl methylphosphonate

15

PO

MeOSiMe3

O

M = 196

PO

EtOSiMe3

O

M = 210

Abundance

m/z

PO

OSiMe3

O

M = 224

Abundance

m/z

Supplemetal Figure 22. EI mass spectrum of ethyl trimethylsilyl ethylphosphonate

Supplemetal Figure 23. EI mass spectrum of ethyl trimethylsilyl propylphosphonate

16

PO

OSiMe3

O

M = 224

Abundance

m/z

Supplemetal Figure 24. EI mass spectrum of ethyl trimethylsilyl isopropylphosphonate

17

Supplemental Figure 25. EI mass spectrum of bis(2-chloroethyl) methylphosphonate 13

Supplemental Figure 26. EI mass spectrum of bis(2-bromoethyl) methylphosphonate 14

18

PO

MeO

O

Cl

Cl

M = 220

13

PO

MeO

O

I

I

M = 404

15

Abundance

m/z

Supplemental Figure 27. EI mass spectrum of bis(2-iodoethyl) methylphosphonate 15

19

Supplemental Figure 28. HRMS EI mass spectrum of bis(2-iodoethyl) methylphosphonate 15







Elements Used:

C: 0-3 H: 0-8 O: 0-3 Si: 0-1 P: 0-1 127I: 0-1

Minimum: 80.00 -1.5

Maximum: 100.00 5.0 120.0 1.0


249.9123 82.14 249.9076 4.7 18.8 0.0 C2 H8 O2 Si P 127I

249.9256 -13.3 -53.2 0.0 C3 H8 O3 P 127I

249.9190 100.00 249.9256 -6.6 -26.4 0.0 C3H8O3IP

249.9076 11.4 45.6 0.0 C2 H8 O2 Si P 127I

249.9256 94.56 249.9256 0.0 0.0 0.0 C3 H8 O3 P 127I

249.9076 18.0 72.0 0.0 C2 H8 O2 Si P 127I

249.9322 83.33 249.9256 6.6 26.4 0.0 C3 H8 O3 P 127I

249.9076 24.6 98.4 0.0 C2 H8 O2 Si P 127I

20

PO

EtO

O

Cl

Cl

M = 234

16

PO

EtO

O

Br

Br

M = 322

17

Supplemental Figure 29. EI mass spectrum of bis(2-chloroethyl) ethylphosphonate 16

Supplemental Figure 30. EI mass spectrum of bis(2-bromoethyl) ethylphosphonate 17

21

PO

EtO

O

I

I

M = 418

18

Abundance

m/z

Supplemental Figure 31. EI mass spectrum of bis(2-iodoethyl) ethylphosphonate 18

22

PO

OO

Cl

Cl

M = 248

19

Supplemental Figure 32. HRMS EI mass spectrum of bis(2-iodoethyl) ethylphosphonate 18

Elemental Composition Report

Single Mass Analysis (displaying only valid results)





Elements Used:

C: 0-4 H: 0-11 O: 0-3 Si: 0-1 P: 0-1 127I: 0-1

Minimum: -1.5

Maximum: 5.0 120.0 2.0

Mass Calc. Mass mDa PPM DBE Formula

263.9308 -9.3 -35.4 0.5 C4H10O3IP

Supplemental Figure 33. EI mass spectrum of bis(2-chloroethyl) propylphosphonate 19

23

PO

OO

I

I

M = 432

21

Supplemental Figure 34. EI mass spectrum of bis(2-bromoethyl) propylphosphonate 20

Supplemental Figure 35. EI mass spectrum of bis(2-iodoethyl) propylphosphonate 21

24

Abundance

m/z

Supplemental Figure 36. HRMS EI mass spectrum of bis(2-iodoethyl) propylphosphonate 21

25

PO

OO

Cl

Cl

M = 248

22

PO

OO

Br

Br

M = 336

23

Supplemental Figure 37. EI mass spectrum of bis(2-chloroethyl) isopropylphosphonate 22

Supplemental Figure 38. EI mass spectrum of bis(2-bromoethyl) isopropylphosphonate 23

26

PO

OO

I

I

M = 432

24

Abundance

m/z

Supplemental Figure 39. EI mass spectrum of bis(2-iodoethyl) isopropylphosphonate 24

Supplemental Figure 40. HRMS EI mass spectrum of bis(2-iodoethyl) isopropylphosphonate 24

27

Abundance

m/z

Supplemental Figure 41. CI (acetonitrile) mass spectrum of bis(2-chloroethyl) methylphosphonate 13

Supplemental Figure 42. CI (acetonitrile) mass spectrum of bis(2-bromoethyl) methylphosphonate 14

28

Abundance

m/z

Abundance

m/z

Supplemental Figure 43. CI (acetonitrile) mass spectrum of bis(2-iodoethyl) methylphosphonate 15

PO

MeO

O

M = 152

29

Abundance

m/z

Supplemental Figure 44. EI mass spectrum of diethyl methylphosphonate

Supplemental Figure 45. EI mass spectrum of diethyl ethylphosphonate

30

Cartesian Coordinates and Energies (in Hartree) of all optimized species

I1 X=Cl E= -488.85817

15 -0.984149000 -0.115970000 -0.898409000

6 -0.499383000 -1.047925000 -2.384459000

1 -1.341122000 -1.041773000 -3.080209000

1 0.370733000 -0.572124000 -2.838640000

1 -0.263309000 -2.072121000 -2.090860000

8 -1.395920000 1.385733000 -1.467127000

6 -1.073108000 2.579033000 -0.722276000

1 -1.143894000 2.411298000 0.354508000

1 -1.819951000 3.321414000 -1.019618000

6 0.291635000 3.107462000 -1.114974000

1 0.404144000 3.231219000 -2.190518000

1 0.551025000 4.014317000 -0.569325000

8 0.153883000 0.075581000 0.251009000

8 -2.227068000 -0.860665000 -0.235997000

14 -2.936404000 -1.034433000 1.424036000

6 -2.826248000 0.654830000 2.238650000

1 -3.365806000 1.419144000 1.670832000

1 -3.281592000 0.612447000 3.234162000

1 -1.786480000 0.968684000 2.374533000

6 -4.680358000 -1.580387000 1.020696000

1 -4.679926000 -2.505790000 0.438125000

1 -5.238976000 -1.767002000 1.943979000

1 -5.217373000 -0.816060000 0.452198000

6 -1.872538000 -2.330114000 2.259793000

31

1 -1.883866000 -3.273198000 1.705926000

1 -0.835033000 -1.994136000 2.352759000

1 -2.247013000 -2.534241000 3.268554000

17 1.626602000 1.860506000 -0.645211000

I1 X=Br = -487.08623

15 -0.974326000 -0.118886000 -0.906119000

6 -0.517041000 -1.135490000 -2.345917000

1 -1.350917000 -1.121758000 -3.050717000

1 0.378501000 -0.724091000 -2.813179000

1 -0.332519000 -2.156419000 -2.007425000

8 -1.285800000 1.371302000 -1.575767000

6 -1.092590000 2.570932000 -0.805706000

1 -1.279187000 2.407462000 0.258542000

1 -1.827415000 3.289875000 -1.184316000

6 0.280255000 3.161487000 -1.052747000

1 0.515267000 3.266522000 -2.110147000

1 0.440059000 4.086995000 -0.500333000

8 0.131859000 0.067511000 0.252700000

8 -2.299714000 -0.744283000 -0.270694000

14 -2.929622000 -1.004347000 1.401825000

6 -2.798025000 0.646844000 2.288887000

1 -3.368678000 1.428895000 1.778295000

1 -3.206684000 0.558203000 3.301337000

1 -1.755365000 0.964375000 2.387243000

6 -4.687480000 -1.544282000 1.053090000

1 -4.709540000 -2.454154000 0.446928000

1 -5.211037000 -1.754859000 1.991557000

1 -5.245845000 -0.766392000 0.524878000

32

6 -1.832128000 -2.329055000 2.146852000

1 -1.869619000 -3.254055000 1.564088000

1 -0.791304000 -1.995932000 2.205551000

1 -2.162709000 -2.566587000 3.163606000

35 1.743397000 1.897308000 -0.352073000

I1 X=I E= -485.29321

15 -0.896427000 -0.211909000 -0.935510000

6 -0.234180000 -1.422551000 -2.117764000

1 -0.698782000 -1.244263000 -3.090481000

1 0.846448000 -1.278119000 -2.187109000

1 -0.467312000 -2.427583000 -1.763731000

8 -0.518515000 1.220368000 -1.567185000

6 -0.620602000 2.500870000 -0.844987000

1 -0.524564000 2.317902000 0.227520000

1 -1.608452000 2.911082000 -1.076704000

6 0.463207000 3.414575000 -1.361899000

1 0.426087000 3.512474000 -2.445960000

1 0.363824000 4.396791000 -0.899462000

53 2.480699000 2.716878000 -0.870286000

8 -0.463861000 -0.407079000 0.640819000

8 -2.482438000 -0.422574000 -0.536817000

14 -2.143907000 -0.702582000 1.197852000

6 -2.790072000 0.640697000 2.297713000

1 -3.870069000 0.525836000 2.438252000

1 -2.318713000 0.580433000 3.284474000

1 -2.603117000 1.635492000 1.886698000

6 -2.414209000 -2.468883000 1.686443000

1 -1.969765000 -3.162571000 0.968518000

33

1 -1.973046000 -2.663347000 2.669586000

1 -3.485743000 -2.684585000 1.753589000

TS1 X=Cl E= -488.83338

15 -1.214673000 -0.038984000 -0.888245000

6 -0.482738000 -1.098767000 -2.174806000

1 -1.106165000 -1.029126000 -3.069140000

1 0.525890000 -0.742457000 -2.389709000

1 -0.455296000 -2.127662000 -1.813638000

8 -1.322181000 1.440487000 -1.598450000

6 -1.017683000 2.659905000 -0.877704000

1 -1.202375000 2.538509000 0.191790000

1 -1.694506000 3.417012000 -1.283632000

6 0.412798000 3.081998000 -1.146806000

1 0.627601000 3.154700000 -2.211705000

1 0.651807000 4.012774000 -0.632539000

8 -0.597051000 -0.020028000 0.585232000

8 -2.706816000 -0.588217000 -0.493224000

14 -2.756280000 -0.869842000 1.264803000

6 -2.948205000 0.690349000 2.316560000

1 -3.515607000 1.452487000 1.774912000

1 -3.498133000 0.444752000 3.229316000

1 -1.965029000 1.085485000 2.581304000

6 -4.609381000 -1.641827000 1.264980000

1 -4.554305000 -2.532908000 0.638177000

1 -4.891230000 -1.866213000 2.293497000

1 -5.213450000 -0.847354000 0.820277000

6 -1.755761000 -2.375663000 1.886117000

1 -1.739596000 -3.157977000 1.122777000

34

1 -0.736908000 -2.074324000 2.131504000

1 -2.259402000 -2.768980000 2.773115000

17 1.596707000 1.807011000 -0.481097000

TS1 X=Br E= -487.05460

15 -1.175595000 -0.099590000 -0.919510000

6 -0.491519000 -1.208910000 -2.190565000

1 -1.107171000 -1.121832000 -3.088522000

1 0.534519000 -0.908682000 -2.409233000

1 -0.515427000 -2.233260000 -1.816447000

8 -1.178130000 1.362757000 -1.672237000

6 -1.078642000 2.601860000 -0.931783000

1 -1.371983000 2.463889000 0.111130000

1 -1.776510000 3.292566000 -1.415618000

6 0.319349000 3.174582000 -1.046399000

1 0.658883000 3.236006000 -2.078633000

1 0.391446000 4.140782000 -0.547813000

8 -0.580224000 -0.083885000 0.553183000

8 -2.698940000 -0.567025000 -0.518695000

14 -2.678797000 -0.843812000 1.242244000

6 -2.833491000 0.695607000 2.328860000

1 -3.384768000 1.482685000 1.806413000

1 -3.382905000 0.448443000 3.241136000

1 -1.837272000 1.059569000 2.591145000

6 -4.595840000 -1.531110000 1.268009000

1 -4.583299000 -2.420136000 0.636928000

1 -4.861047000 -1.741634000 2.303573000

1 -5.160250000 -0.703613000 0.833851000

35

6 -1.783987000 -2.414402000 1.844380000

1 -1.800888000 -3.184188000 1.068057000

1 -0.751043000 -2.173268000 2.100524000

1 -2.308934000 -2.801692000 2.721285000

35 1.681110000 1.989871000 -0.112852000

TS1 X=I E = -485.275711

15 -1.313353000 -0.057863000 -0.972450000

6 -0.916953000 -0.989081000 -2.494754000

1 -1.733846000 -0.852220000 -3.206114000

1 0.017789000 -0.623693000 -2.924813000

1 -0.809862000 -2.043987000 -2.237314000

8 -1.612320000 1.517910000 -1.394332000

6 -0.530055000 2.416772000 -1.728981000

1 -1.023094000 3.293657000 -2.150666000

1 0.101940000 1.976478000 -2.514156000

6 0.369986000 2.771145000 -0.560237000

1 0.786485000 1.893905000 -0.064361000

1 1.166734000 3.444443000 -0.877845000

53 -0.662676000 3.860718000 1.051425000

8 -0.425401000 -0.247242000 0.294949000

8 -2.770972000 -0.562681000 -0.385534000

14 -2.520280000 -0.842370000 1.321090000

6 -2.489817000 0.716399000 2.388497000

1 -2.711089000 0.483128000 3.432779000

1 -1.478070000 1.137635000 2.302636000

1 -3.212720000 1.445249000 2.017743000

6 -4.565470000 -1.291556000 1.650195000

36

1 -4.667213000 -2.170077000 1.011583000

1 -4.674500000 -1.483049000 2.715614000

1 -5.078711000 -0.403149000 1.286966000

6 -1.744328000 -2.472636000 1.833297000

1 -1.957117000 -3.252811000 1.096752000

1 -0.660809000 -2.343957000 1.903750000

1 -2.137911000 -2.796987000 2.800296000

I2 X = Cl E = -449.03999

15 -0.787170000 -0.238206000 -1.041101000

6 -0.300687000 -1.495547000 -2.262050000

1 -0.842136000 -1.312222000 -3.192235000

1 0.775315000 -1.406363000 -2.431839000

1 -0.537751000 -2.483009000 -1.863959000

8 -0.375425000 1.161374000 -1.739177000

6 -0.897270000 2.485808000 -1.373930000

1 -1.745060000 2.378592000 -0.694857000

1 -1.248060000 2.906148000 -2.320421000

6 0.197226000 3.354427000 -0.808482000

1 1.097447000 3.328840000 -1.420989000

1 -0.159857000 4.379810000 -0.706596000

8 -0.237797000 -0.561396000 0.472812000

8 -2.340639000 -0.255509000 -0.500484000

14 -1.874215000 -0.653711000 1.194090000

6 -2.260652000 0.706182000 2.388556000

1 -3.343517000 0.861254000 2.446839000

1 -1.909588000 0.435141000 3.389704000

1 -1.778658000 1.643676000 2.102410000

37

6 -2.328026000 -2.395643000 1.635145000

1 -3.400205000 -2.465597000 1.846381000

1 -2.090031000 -3.097274000 0.832002000

1 -1.790668000 -2.710022000 2.536108000

17 0.697098000 2.799184000 0.884263000

I2 X=Br -447.25886

15 -0.777684000 -0.248005000 -1.020618000

6 -0.252007000 -1.495820000 -2.234775000

1 -0.774681000 -1.313674000 -3.175935000

1 0.826529000 -1.395312000 -2.380369000

1 -0.488575000 -2.487145000 -1.846103000

8 -0.360419000 1.158483000 -1.696845000

6 -0.891073000 2.477868000 -1.319395000

1 -1.665920000 2.367974000 -0.558732000

1 -1.346892000 2.858697000 -2.238079000

6 0.227654000 3.392842000 -0.893130000

1 1.062660000 3.373145000 -1.591482000

1 -0.147600000 4.410237000 -0.782370000

8 -0.264030000 -0.569766000 0.507413000

8 -2.344345000 -0.282393000 -0.517495000

14 -1.916660000 -0.675865000 1.186337000

6 -2.329062000 0.687813000 2.368894000

1 -3.410334000 0.862464000 2.385881000

1 -2.021415000 0.410258000 3.382381000

1 -1.821438000 1.618597000 2.104511000

6 -2.374718000 -2.417703000 1.621952000

1 -3.451257000 -2.490600000 1.808726000

38

1 -2.116598000 -3.119918000 0.825534000

1 -1.857008000 -2.728817000 2.535427000

35 0.992072000 2.887354000 0.905424000

I2 X = I E = -445.48211

15 -0.896427000 -0.211909000 -0.935510000

6 -0.234180000 -1.422551000 -2.117764000

1 -0.698782000 -1.244263000 -3.090481000

1 0.846448000 -1.278119000 -2.187109000

1 -0.467312000 -2.427583000 -1.763731000

8 -0.518515000 1.220368000 -1.567185000

6 -0.620602000 2.500870000 -0.844987000

1 -0.524564000 2.317902000 0.227520000

1 -1.608452000 2.911082000 -1.076704000

6 0.463207000 3.414575000 -1.361899000

1 0.426087000 3.512474000 -2.445960000

1 0.363824000 4.396791000 -0.899462000

53 2.480699000 2.716878000 -0.870286000

8 -0.463861000 -0.407079000 0.640819000

8 -2.482438000 -0.422574000 -0.536817000

14 -2.143907000 -0.702582000 1.197852000

6 -2.790072000 0.640697000 2.297713000

1 -3.870069000 0.525836000 2.438252000

1 -2.318713000 0.580433000 3.284474000

1 -2.603117000 1.635492000 1.886698000

6 -2.414209000 -2.468883000 1.686443000

1 -1.969765000 -3.162571000 0.968518000

1 -1.973046000 -2.663347000 2.669586000

39

1 -3.485743000 -2.684585000 1.753589000

TS2 X = Cl E = -448.99852

15 -0.872618000 -0.221788000 -1.336268000

6 -1.054145000 -1.386468000 -2.721091000

1 -1.896870000 -1.065768000 -3.336550000

1 -0.135310000 -1.377964000 -3.310584000

1 -1.233854000 -2.385041000 -2.319912000

8 -0.687983000 1.222604000 -2.096768000

6 -0.528677000 2.493372000 -1.423538000

1 -1.512753000 2.880602000 -1.145692000

1 -0.112708000 3.142754000 -2.200262000

6 0.435477000 2.522056000 -0.254235000

1 1.252718000 1.808711000 -0.323822000

1 0.788838000 3.534516000 -0.065437000

8 0.096769000 -0.469659000 -0.149090000

8 -2.304829000 -0.150443000 -0.447062000

14 -1.866749000 -0.251859000 1.197030000

6 -3.165707000 0.674487000 2.154327000

1 -4.044150000 0.019284000 2.232685000

1 -2.829635000 0.900128000 3.170133000

1 -3.468482000 1.598272000 1.660498000

6 -1.171283000 -1.757611000 2.034681000

1 -1.892170000 -2.136198000 2.766070000

1 -0.913849000 -2.532950000 1.311622000

1 -0.248847000 -1.488284000 2.559841000

17 -0.410674000 2.108359000 1.406610000

40

TS2 X = Br E = -447.21602

15 -0.866355000 -0.214504000 -1.321761000

6 -1.043683000 -1.392046000 -2.696695000

1 -1.882485000 -1.075848000 -3.319732000

1 -0.121779000 -1.390905000 -3.281494000

1 -1.226884000 -2.386524000 -2.287084000

8 -0.663246000 1.220388000 -2.095005000

6 -0.543912000 2.496991000 -1.424611000

1 -1.531650000 2.825875000 -1.090903000

1 -0.214120000 3.168903000 -2.223126000

6 0.493353000 2.569545000 -0.317561000

1 1.308707000 1.857967000 -0.421266000

1 0.857154000 3.587403000 -0.186307000

8 0.092267000 -0.464952000 -0.124708000

8 -2.298400000 -0.120151000 -0.439303000

14 -1.862331000 -0.246869000 1.208305000

6 -3.195887000 0.651027000 2.150782000

1 -4.078713000 -0.003215000 2.162652000

1 -2.903898000 0.831632000 3.188874000

1 -3.476887000 1.595646000 1.684088000

6 -1.198749000 -1.777763000 2.029117000

1 -1.916188000 -2.138854000 2.772268000

1 -0.984680000 -2.557284000 1.295713000

1 -0.255162000 -1.544944000 2.532690000

35 -0.263964000 2.189594000 1.568252000

TS2 X = I E = -445.435681

41

15 -0.935826000 -0.213499000 -1.306932000

6 -1.197247000 -1.409333000 -2.652991000

1 -2.050457000 -1.079926000 -3.249019000

1 -0.299292000 -1.444589000 -3.272833000

1 -1.392345000 -2.391097000 -2.219085000

8 -0.716852000 1.198169000 -2.115592000

6 -0.549563000 2.486907000 -1.476813000

1 -1.506528000 2.813828000 -1.062368000

1 -0.301782000 3.145485000 -2.314731000

6 0.592950000 2.573341000 -0.473721000

1 1.381332000 1.845882000 -0.653061000

1 0.996066000 3.584441000 -0.433794000

53 0.023419000 2.256544000 1.660204000

8 0.060010000 -0.477086000 -0.140356000

8 -2.324215000 -0.067164000 -0.370158000

14 -1.818321000 -0.220491000 1.261128000

6 -3.120279000 0.686849000 2.244898000

1 -4.020767000 0.056961000 2.240233000

1 -2.817500000 0.825958000 3.286173000

1 -3.378481000 1.653265000 1.810698000

6 -1.202541000 -1.798635000 2.032534000

1 -1.089033000 -2.581237000 1.279279000

1 -0.215199000 -1.638217000 2.475447000

1 -1.895039000 -2.125239000 2.814044000

I3 X = Cl E = -449.01251

15 -0.862007000 -0.301928000 -1.466371000

6 -1.610820000 -1.155268000 -2.891426000

42

1 -2.569398000 -0.684455000 -3.114965000

1 -0.936579000 -1.064947000 -3.745022000

1 -1.752104000 -2.207337000 -2.638535000

8 -1.023247000 1.323553000 -1.831207000

6 -0.060965000 2.309113000 -1.444421000

1 -0.551004000 3.266249000 -1.630509000

1 0.833620000 2.246804000 -2.082452000

6 0.466188000 2.220552000 -0.032317000

1 0.987473000 1.293566000 0.191599000

1 1.025965000 3.106634000 0.263664000

8 0.491984000 -0.698199000 -0.894659000

8 -2.111930000 -0.408357000 -0.289563000

14 -2.003914000 -0.147168000 1.335903000

6 -3.638737000 0.288405000 2.084571000

1 -4.253661000 -0.617232000 2.153608000

1 -3.517276000 0.692853000 3.092923000

1 -4.170380000 1.012796000 1.462943000

6 -0.655427000 -1.024337000 2.256183000

1 -0.996778000 -2.040816000 2.490322000

1 0.241006000 -1.103559000 1.636360000

1 -0.425142000 -0.520283000 3.198359000

17 -0.995267000 2.224224000 1.248776000

I3 X = Br E = -447.23126

15 -0.884475000 -0.274056000 -1.451706000

6 -1.646018000 -1.123557000 -2.873189000

1 -2.604877000 -0.649781000 -3.089129000

1 -0.977823000 -1.033218000 -3.731548000

43

1 -1.788205000 -2.175869000 -2.621933000

8 -1.040028000 1.355138000 -1.807113000

6 -0.020804000 2.309403000 -1.492972000

1 -0.465324000 3.277749000 -1.728243000

1 0.858446000 2.164908000 -2.139016000

6 0.522725000 2.269832000 -0.083244000

1 1.012405000 1.334762000 0.176300000

1 1.130750000 3.141924000 0.155343000

8 0.474153000 -0.676933000 -0.895623000

8 -2.127248000 -0.378477000 -0.270462000

14 -2.010888000 -0.140105000 1.359988000

6 -3.663083000 0.207578000 2.121274000

1 -4.240468000 -0.724598000 2.154302000

1 -3.560670000 0.577204000 3.144966000

1 -4.224559000 0.931371000 1.525878000

6 -0.648577000 -1.024916000 2.255733000

1 -0.979012000 -2.051903000 2.458699000

1 0.248802000 -1.076053000 1.634575000

1 -0.424003000 -0.546651000 3.212418000

35 -1.007766000 2.408698000 1.333188000

I3 X = I E = -445.45211

15 -0.989872000 -0.257780000 -1.434481000

6 -1.846755000 -1.079609000 -2.818414000

1 -2.802966000 -0.580539000 -2.982619000

1 -1.221931000 -1.001857000 -3.710057000

1 -2.002684000 -2.129507000 -2.565195000

8 -1.114227000 1.382375000 -1.763355000

44

6 0.001917000 2.264884000 -1.603282000

1 -0.381889000 3.247599000 -1.881554000

1 0.812279000 1.998067000 -2.297629000

6 0.640567000 2.275956000 -0.229171000

1 1.109294000 1.331380000 0.037001000

1 1.319955000 3.118302000 -0.096300000

53 -0.862363000 2.586305000 1.409840000

8 0.388506000 -0.701033000 -0.964149000

8 -2.168406000 -0.334108000 -0.195362000

14 -1.964377000 -0.106343000 1.432095000

6 -3.592636000 0.198642000 2.267067000

1 -4.152798000 -0.744358000 2.291608000

1 -3.459504000 0.537746000 3.297691000

1 -4.188465000 0.929546000 1.715564000

6 -0.590547000 -1.055717000 2.244852000

1 0.283633000 -1.101082000 1.591155000

1 -0.321171000 -0.623476000 3.211601000

1 -0.938690000 -2.082809000 2.415598000

TS3 X = Cl E = -448.97203

15 -0.927157000 -0.230939000 -1.279859000

6 -1.748764000 -0.961824000 -2.741747000

1 -2.715419000 -0.475285000 -2.879153000

1 -1.115908000 -0.819458000 -3.619177000

1 -1.886329000 -2.029473000 -2.557083000

8 -1.010318000 1.504688000 -1.554768000

6 0.216636000 2.165039000 -1.950311000

1 -0.049391000 3.043198000 -2.537913000

45

1 0.911242000 1.507888000 -2.481276000

6 0.649793000 2.447069000 -0.565957000

1 1.230151000 1.696817000 -0.036585000

1 0.460610000 3.404069000 -0.089995000

8 0.501831000 -0.597275000 -0.910651000

8 -2.078272000 -0.312227000 -0.106141000

14 -1.932452000 -0.047310000 1.574925000

6 -3.635146000 0.220365000 2.257801000

1 -4.210635000 -0.708921000 2.185501000

1 -3.589517000 0.514264000 3.309927000

1 -4.160229000 0.998490000 1.698944000

6 -0.741435000 -1.231153000 2.371104000

1 0.189324000 -1.285481000 1.800790000

1 -0.516525000 -0.924421000 3.396184000

1 -1.185837000 -2.232099000 2.403840000

17 -0.895086000 1.987280000 1.629846000

TS3 X = Br E = -447.18641

15 -0.927869000 -0.204142000 -1.249587000

6 -1.762939000 -0.918746000 -2.712611000

1 -2.717623000 -0.410047000 -2.853247000

1 -1.125122000 -0.794364000 -3.589203000

1 -1.925996000 -1.982497000 -2.525833000

8 -0.964230000 1.536204000 -1.540952000

6 0.266903000 2.144209000 -2.011641000

1 0.007708000 3.001211000 -2.632069000

1 0.929138000 1.443579000 -2.527522000

6 0.712863000 2.460189000 -0.642676000

46

1 1.255947000 1.701705000 -0.086303000

1 0.563929000 3.441385000 -0.204441000

8 0.490467000 -0.605380000 -0.878283000

8 -2.083952000 -0.244205000 -0.082717000

14 -1.955018000 -0.029766000 1.610198000

6 -3.679508000 0.138715000 2.277265000

1 -4.210634000 -0.812800000 2.164120000

1 -3.660963000 0.397283000 3.339406000

1 -4.231683000 0.911734000 1.738012000

6 -0.739202000 -1.212800000 2.375339000

1 0.198303000 -1.223390000 1.814204000

1 -0.533344000 -0.937911000 3.413300000

1 -1.159184000 -2.224969000 2.366465000

35 -0.926168000 2.194257000 1.773840000

TS3 X = I E = 445.40178

15 -0.920095000 -0.162403000 -1.204550000

6 -1.756034000 -0.880558000 -2.666246000

1 -2.705266000 -0.364189000 -2.815200000

1 -1.113772000 -0.770876000 -3.541561000

1 -1.930121000 -1.941182000 -2.471569000

8 -0.923254000 1.578709000 -1.529433000

6 0.299262000 2.131554000 -2.091274000

1 0.033415000 2.961026000 -2.745134000

1 0.923888000 1.388752000 -2.593813000

6 0.781018000 2.497002000 -0.750061000

1 1.321888000 1.753724000 -0.171435000

1 0.648712000 3.496957000 -0.352232000

47

53 -0.897278000 2.398645000 1.954529000

8 0.490375000 -0.582137000 -0.825660000

8 -2.081538000 -0.162330000 -0.047933000

14 -1.966454000 -0.001249000 1.658125000

6 -3.711352000 0.089383000 2.296053000

1 -4.210482000 -0.871046000 2.125970000

1 -3.722334000 0.297120000 3.369353000

1 -4.275581000 0.870901000 1.782330000

6 -0.760810000 -1.221318000 2.386788000

1 0.191795000 -1.195287000 1.852686000

1 -0.585040000 -1.005134000 3.444013000

1 -1.174074000 -2.233484000 2.308755000

I4 X = Cl E = -449.00682

15 -1.096525000 -0.066734000 -1.219113000

6 -2.269793000 -0.241821000 -2.614284000

1 -3.025966000 0.540193000 -2.529742000

1 -1.723694000 -0.165724000 -3.555511000

1 -2.738070000 -1.226352000 -2.538259000

8 -0.697107000 1.819610000 -1.462393000

6 0.543756000 2.387683000 -0.833136000

1 1.076922000 1.670450000 -0.217264000

1 0.334314000 3.359210000 -0.399751000

6 0.507626000 2.186030000 -2.279228000

1 0.279401000 3.006676000 -2.951000000

1 1.023762000 1.321161000 -2.687973000

8 0.249126000 -0.748142000 -1.180893000

8 -2.000408000 0.087711000 0.103117000

48

14 -1.696474000 -0.217916000 1.813421000

6 -3.318796000 0.156961000 2.633814000

1 -4.082174000 -0.555746000 2.305896000

1 -3.221233000 0.079776000 3.720424000

1 -3.655453000 1.167678000 2.391070000

6 -0.908951000 -1.891826000 2.009370000

1 -0.007351000 -1.981218000 1.398157000

1 -0.632271000 -2.053471000 3.055336000

1 -1.612611000 -2.679448000 1.719951000

17 -0.230252000 1.323510000 2.334144000

I4 X = Br E = -447.21935

15 -0.840281000 -0.170553000 -1.079141000

6 -1.742698000 -0.800820000 -2.543482000

1 -2.635548000 -0.190401000 -2.686947000

1 -1.088400000 -0.758620000 -3.415269000

1 -2.024876000 -1.837738000 -2.344762000

8 -0.750362000 1.696712000 -1.631248000

6 0.446762000 2.147568000 -2.414161000

1 0.148755000 2.796429000 -3.230851000

1 1.144180000 1.342811000 -2.631675000

6 0.304200000 2.575722000 -1.025055000

1 0.891608000 2.072350000 -0.263303000

1 -0.108890000 3.547599000 -0.779452000

8 0.586998000 -0.547455000 -0.767402000

8 -1.939738000 0.015463000 0.077198000

14 -1.869451000 0.004497000 1.845158000

6 -3.656108000 0.119166000 2.348241000

49

1 -4.199309000 -0.773133000 2.020703000

1 -3.738782000 0.193041000 3.436199000

1 -4.129428000 1.000052000 1.908213000

6 -0.843483000 -1.449740000 2.398471000

1 0.145620000 -1.441018000 1.933912000

1 -0.712548000 -1.419926000 3.484084000

1 -1.347161000 -2.388417000 2.143775000

35 -0.753002000 2.005798000 2.387369000

I4 X = I E = -445.43392

15 -0.813162000 -0.143216000 -1.054380000

6 -1.709179000 -0.814846000 -2.504943000

1 -2.598163000 -0.205073000 -2.672848000

1 -1.049188000 -0.802765000 -3.373338000

1 -1.997630000 -1.843875000 -2.276512000

8 -0.700179000 1.705233000 -1.682879000

6 0.504148000 2.100833000 -2.482665000

1 0.219258000 2.718703000 -3.327568000

1 1.188810000 1.276033000 -2.662245000

6 0.365946000 2.591856000 -1.114027000

1 0.945633000 2.113181000 -0.330421000

1 -0.029401000 3.581631000 -0.914563000

53 -0.728225000 2.203141000 2.584030000

8 0.611370000 -0.517478000 -0.726357000

8 -1.913801000 0.100036000 0.085839000

14 -1.880104000 0.049993000 1.863209000

6 -3.689707000 0.100481000 2.305663000

1 -4.193187000 -0.799670000 1.938080000

50

1 -3.811865000 0.145284000 3.391473000

1 -4.174617000 0.977182000 1.870193000

6 -0.868001000 -1.428938000 2.388342000

1 0.137288000 -1.401434000 1.961125000

1 -0.776174000 -1.444673000 3.478273000

1 -1.360925000 -2.356674000 2.077588000

TS4 X = Cl E = -448.89723

15 -0.888457000 -0.186784000 -0.793088000

6 -1.667229000 -0.001900000 -2.443500000

1 -2.375910000 0.825378000 -2.404306000

1 -0.888235000 0.185383000 -3.180467000

1 -2.182968000 -0.940994000 -2.658384000

8 -0.626537000 1.463900000 -0.226013000

6 1.300116000 2.050500000 -2.347137000

1 1.548803000 1.377099000 -3.163974000

1 1.940647000 2.006246000 -1.472071000

6 0.287291000 2.928713000 -2.435018000

1 0.078057000 3.635842000 -1.639278000

1 -0.331091000 3.001191000 -3.326153000

8 0.249533000 -1.141023000 -0.512886000

8 -2.277420000 -0.509102000 0.176622000

14 -2.264246000 -0.667722000 1.814265000

6 -3.840217000 -0.118022000 2.606797000

1 -4.596632000 -0.902968000 2.475284000

1 -3.708453000 0.045736000 3.679655000

1 -4.216040000 0.794395000 2.137444000

6 -1.022269000 -1.800865000 2.585251000

51

1 -0.125654000 -1.857534000 1.961941000

1 -0.762931000 -1.477009000 3.597340000

1 -1.459043000 -2.805928000 2.656142000

17 -0.718278000 1.551246000 1.631807000

TS4 X = Br E = -447.12799

15 -0.961889000 -0.094414000 -0.977881000

6 -1.895573000 -0.094216000 -2.555998000

1 -2.749231000 0.577154000 -2.455549000

1 -1.244143000 0.235183000 -3.364621000

1 -2.236355000 -1.115120000 -2.741420000

8 -0.772360000 1.597062000 -0.463787000

6 0.885278000 2.035482000 -2.634394000

1 0.355514000 2.823568000 -3.160853000

1 1.099995000 1.121617000 -3.181500000

6 1.315698000 2.198158000 -1.358004000

1 1.874539000 1.417788000 -0.852935000

1 1.187260000 3.140281000 -0.836455000

8 0.326601000 -0.871111000 -0.805058000

8 -2.209741000 -0.605833000 0.071703000

14 -2.273653000 -0.422843000 1.713842000

6 -3.991015000 -0.582695000 2.383473000

1 -4.248742000 -1.647710000 2.443118000

1 -4.065240000 -0.163554000 3.390612000

1 -4.716298000 -0.093205000 1.729652000

6 -0.751219000 -0.854095000 2.677526000

1 0.148688000 -0.673479000 2.083962000

1 -0.697340000 -0.294387000 3.615223000

1 -0.783877000 -1.923587000 2.922224000

52

35 -1.917951000 2.194896000 1.178193000

TS4 X = I E = -445.35709

15 -0.975615000 -0.096950000 -1.071652000

6 -1.995928000 -0.073336000 -2.593956000

1 -2.830148000 0.614307000 -2.448721000

1 -1.385976000 0.244166000 -3.439896000

1 -2.369139000 -1.085076000 -2.766267000

8 -0.694376000 1.605367000 -0.597223000

6 0.906811000 1.957826000 -2.513875000

1 0.476249000 2.805834000 -3.036628000

1 1.082369000 1.045065000 -3.075250000

6 1.245964000 2.033849000 -1.184768000

1 1.738810000 1.199234000 -0.699515000

1 1.214931000 2.980360000 -0.656251000

53 -2.046861000 2.420653000 1.142971000

8 0.310834000 -0.895627000 -1.002518000

8 -2.157037000 -0.574814000 0.043713000

14 -2.231064000 -0.301917000 1.684969000

6 -3.926509000 -0.642030000 2.353712000

1 -4.070694000 -1.728037000 2.409260000

1 -4.044498000 -0.234883000 3.361505000

1 -4.700485000 -0.227572000 1.704199000

6 -0.700079000 -0.707693000 2.653422000

1 0.203036000 -0.431155000 2.104630000

1 -0.700688000 -0.211088000 3.627358000

1 -0.670959000 -1.791544000 2.821853000

53

27 + CH2CH2 X = Cl E = -448.90528

15 -1.156601000 0.494804000 -0.454373000

6 -1.897275000 0.556769000 -2.125574000

1 -2.816859000 1.141388000 -2.079737000

1 -1.157805000 1.028560000 -2.778505000

1 -2.099379000 -0.466476000 -2.448330000

8 -1.268681000 2.130583000 -0.026346000

6 1.626355000 1.475896000 -2.999980000

1 1.783199000 0.928803000 -3.926109000

1 1.960209000 0.988017000 -2.087609000

6 1.081675000 2.694114000 -2.990277000

1 0.951672000 3.257372000 -2.069432000

1 0.773663000 3.191050000 -3.906598000

8 0.097968000 -0.271548000 -0.103102000

8 -2.499104000 -0.107702000 0.538184000

14 -2.481186000 -0.898762000 1.953737000

6 -4.175593000 -1.176313000 2.629630000

1 -4.747319000 -1.819628000 1.949246000

1 -4.138486000 -1.644292000 3.615922000

1 -4.713320000 -0.223532000 2.695389000

6 -0.900168000 -1.454575000 2.731254000

1 -0.072668000 -1.323175000 2.029358000

1 -0.706599000 -0.868358000 3.638957000

1 -0.986393000 -2.504428000 3.034821000

17 -0.667469000 2.495711000 1.618914000

27 + CH2CH2 X = Br E = -447.14498

54

15 -1.139978000 0.658591000 -0.318310000

6 -1.739361000 0.500190000 -2.040143000

1 -2.698268000 1.012744000 -2.124352000

1 -0.984677000 0.965744000 -2.680527000

1 -1.840845000 -0.560966000 -2.274595000

8 -1.407639000 2.282987000 -0.046293000

6 1.430769000 1.823819000 -3.730111000

1 1.064902000 2.448155000 -4.541049000

1 1.759629000 0.823492000 -4.000287000

6 1.511805000 2.274894000 -2.476973000

1 1.906447000 1.659070000 -1.672332000

1 1.213686000 3.286952000 -2.215065000

8 0.130077000 0.014398000 0.193191000

8 -2.518870000 -0.005667000 0.606542000

14 -2.556289000 -0.880340000 1.967365000

6 -4.275454000 -1.251149000 2.529937000

1 -4.784483000 -1.877606000 1.787086000

1 -4.276272000 -1.768054000 3.492177000

1 -4.850910000 -0.322037000 2.611463000

6 -1.008532000 -1.429831000 2.814646000

1 -0.144953000 -1.234622000 2.173731000

1 -0.890436000 -0.883668000 3.759749000

1 -1.077710000 -2.495213000 3.062747000

35 -0.761680000 3.024852000 1.600913000

27 + CH2CH2 X = I E = -445.38298

15 -1.130911000 0.398157000 -0.424464000

6 -1.572588000 0.273781000 -2.191957000

55

1 -2.585215000 0.654381000 -2.327836000

1 -0.843806000 0.870629000 -2.748005000

1 -1.507443000 -0.776490000 -2.483363000

8 -1.622017000 1.965826000 -0.042428000

6 1.495345000 1.998014000 -3.686634000

1 1.117810000 2.633035000 -4.483793000

1 1.907949000 1.038239000 -3.987223000

6 1.490488000 2.391440000 -2.411687000

1 1.894431000 1.766808000 -1.618630000

1 1.107544000 3.365642000 -2.117961000

53 -1.631779000 2.490524000 1.919659000

8 0.190646000 -0.067482000 0.149264000

8 -2.451766000 -0.425994000 0.388086000

14 -2.528266000 -0.765152000 1.983523000

6 -4.259403000 -0.865786000 2.625292000

1 -4.667556000 -1.858544000 2.391615000

1 -4.288439000 -0.738508000 3.710589000

1 -4.898332000 -0.120626000 2.145112000

6 -1.029491000 -1.393258000 2.868461000

1 -0.124616000 -1.026182000 2.377428000

1 -1.044561000 -1.114119000 3.925563000

1 -1.031947000 -2.491041000 2.812198000

GC/MS plots of investigated compounds

56

Retention indexes of investigated compounds

Compound RI2-Chloroethyl trimethylsilyl methylphosphonate (1) 1288.62-Bromoethyl trimethylsilyl methylphosphonate (2) 1363.62-Iodoethyl trimethylsilyl methylphosphonate (3) 1457.92-Chloroethyl trimethylsilyl ethylphosphonate (4) 1362.72-Bromoethyl trimethylsilyl ethylphosphonate (5) 1439.32-Iodoethyl trimethylsilyl ethylphosphonate (6) 1536.92-Chloroethyl trimethylsilyl propylphosphonate (7) 1435.12-Bromoethyl trimethylsilyl propylphosphonate (8) 1513.92-Iodoethyl trimethylsilyl propylphosphonate (9) 1608.02-Chloroethyl trimethylsilyl isopropylphosphonate (10) 1395.02-Bromoethyl trimethylsilyl isopropylphosphonate (11) 1475.82-Iodoethyl trimethylsilyl isopropylphosphonate (12) 1607.2Bis(2-chloroethyl)methylphosphonate (13) 1451.7Bis(2-bromoethyl)methylphosphonate (14) 1614.3Bis(2-iodoethyl)methylphosphonate (15) 1832.8Bis(2-chloroethyl)ethylphosphonate (16) 1421.7Bis(2-bromoethyl)ethylphosphonate (17) 1699.3Bis(2-iodoethyl)ethylphosphonate (18) 1920.4Bis(2-chloroethyl)proylphosphonate (19) 1603.7Bis(2-bromoethyl)propylphosphonate (20) 1774.7Bis(2-iodoethyl)propylphosphonate (21) 1991.7Bis(2-chloroethyl)isopropylphosphonate (22) 1561.7Bis(2-bromoethyl)isopropylphosphonate (23) 1734.1Bis(2-iodoethyl)isopropylphosphonate (24) 1948.2

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