Document 3exr8pqgp1JYKZVxB8om3R9bx
t
IKS journal or tub aoac (Vol. W, No. 1, 1073)
llsr of Isotopic Abundance. Ratios in Identification of Polychlorinated Hiphenyls by Mass Spectrometry
JAM!* W. HOTF. n..| WILLIAM J. MORRIS* lloplinx Marine Station, Pacific Crotr, Calif. 93960 f'iunignn Corp., Sunnyvale, Calif. 94036
I'ulyrlilorltiiilrtl hiphent In nrr Imlitslrinl mon orgnnochlorine jiestirides and fungicides
u bleb nrc hciita detected through-
mil tltr
ecosystem* llcrno*>c of llir pre*-
rin*r of other residues, combined ko* climmn-
IhhuHiIi* - out -- )UTlnvlft inl Iw iinl ft*r
Ibdr iimlirmolIon. IsIoh Uotopir idmodntirc *\c lUcitreliriti priOinliilily of the *c
curreoee of Ions of different mnmiri) in the
molerulnr rliulrr lin* hern ealrnluleO for llir
which might Ire present in samples containing PCH's (20-24). PolychlorodilieiucKjMlioxins nnd imlyclilnrodilirntnfnrrtns, toxic minor components
in some commercial PCB's and cblorophenol fungicides, can lie distinguished by MS if they arc present in samples (25). Mnsssfiectra arc also available for chlorinaled naphthalenes (C.N) (2G),
poivehiorittAtcd biphenyls, pflljrltlnrlnalrd INilychlorinnted terphenyls (PCT) (II), and
terphenyls. ami rhhirj tinletl naphthalenes. phthnlnU.1 esters (27), all of which interfere in
Mum speetm ( mono* through drrsrltlornbi* phenyl Itntr Itrrrt tnkeo with unit rrmltillniit rnmptilrr-rnntmlled GO-MS system and parml Ion rlinlrra wrrr nmirhnl with llir tlicorctlenl iMtlnpIr pattern*. This method provide* the iinomhiiliiniiii identification of |kilyclilorl* nalcd biphenyl* iit tltr premier of other substance*.
PCB nnalvsis (28-30). We describe a method which "provides unam
biguous identification of PCB's in the presence of the above interfering substances. The mass sjicctra of PCB's, PCT's, and C.Vs are charac terized by a strong parent ion cluster with an isotopic, abundance ratio determined by the num ber of chlorine atoms substituted on the rings.
Chlorinated hydrocnrtxni* other than insertitide residues were detected in environmental wim ples in the mid* 1960`s (1,2). Since polychlorinated biphenyl (1'CB) compounds mid common chlori nated itiMYliritle* havp similar retention times (3), unknown |tenk could not Ite identified by pasditpiid ohromnlngrapliv (05 LC) ntone. Jensen (I) nnd Widmnrk (5), using combined gas chro matography-mass sjtectrometry (GC-MS), pro . vulod the first analytical evitlence (or the presence of PCH's in environmental snmples. Sitire then,
Although most workers using MS are probably aware of these isotopic clusters, no one. to date has compared theoretical ion intensities to ob served s|>cctra. Gk cl of. (21) calculated the inten sities of chlorine isotojie i>cakn for up to 12 chlorinc atoms, but offered no spectra for comparison.
From the natural abundance ratios of chlorine nnd cnrlwn isofojies (31), we have calculated the theoretical probability of the occurrence of ions of different masses in the molecular cluster for all degrees of chlorination in CN's, PCB's, and
several laltorntorics have used GC-MS to confirm the presence of I'Clfa in a range of orgnmama
PCT's. Using a computer-controlled GC-MS sys tem, ive have taken the mass spectra of monothrough decnchlorobipheny) and have compared
Several workers have recently used GC-MS to chmaclerise the I'CIJ comioncnta in technical mixtures (10-15), and a method (or measuring l'CW isomers has been based on MS identification
the observed isotopic abundance ratios to the theoretical values. The matching of PCT and CM ratios is the subject of another paper in prepara tion.
of the com|Kinei<.s in commercial Aroclors (10). Safe nnd Hutiingri' have use<l MS to confirm photolysis of a licNnchlurnbiphonyl isomer (17) and to show chlorine randomization in I'CB'a prior to fragmentation (18). The same workers have obtained the most informative data on tin? mass spectra of I'Ull's to (Into (10).
Mass spectra are available for moat of the com
' /Ipparaiut
METHOD
The gas chromatograph-moss electrometer cm* ployed was a Finnigan Model 1015 C quadrupole
with a glass column and gloss jet separator. TheCCMH wn controlled by a Hysugm ImlitsirltM 1 to com puter. The details of thia entire unit have been de scribed (32).
ROTK A MW
Specific nt thin kIihIjp act proximate)? multiplier 2.> temperature'.
The follow were treed: OV-t on QP-a lure 24.V76P proximate)? grammed as d
Materimh
Technics! A Santo) sorrad* 0.5 *g/*l for Individual tew 2,2*-di- (H. W 2>4,.*,3',4,,.V-h phenyl. The < prepared in e chlorination e ehloride (33).
Cos C/irsma
Our efforts * spectrum tor PCB'a. Where le* grains of t by solid probe spectrometer.' by MS wenamr lion of A rocto#
Depending** temperature* lows: Aroclor 240*C; ArocJot jected for each of isomers a lion of Arnrhrr
In all rases, computer to chlorinated rpe digital output most intense tc
Calculation of Abundance*
The theoreti m*pl*Titiar clu* r..f.fe The pr<l;.vMirie for UC ami OP dances, the p* 'C, one rarbwe atonia being '*C led naphthalan
MQNS 08277*
1.1, 1073)
HOTi: A MOIUUA' MAM SI'KC'TIIOMKTIIV OK VCIU
JHf)
Hiugieidrs onlnmiitg
Alld Mpnncnts nrophcnol i.' if they m arc also CX) (W), II), aim! .crlerr in
tea iinam prcwncc ;'hc mn* iv charac* i wilh nn ihrmnn he ring*, probably
l date . '* to oIh heinten 12 chlompariwin.
chlorine lated the t of ions ter for nil H>, mill MS sysof monorompnred .*n (o (fir iand ON i preparA-
utter rmuMtrii|M>l(i ThrOC 160 com* ' torn do*
Npcrilic mnH *t>cctromi'lrie nmhiinuM ui*d for (l'CH). .u<l potyHdorii.nl.-d li-rph.-nvls
) T),r
thi* uludy nrr rs f*IVwx; inn mount lciM|M>ml ut* ap (IN ihiiIituIi-m huvv HI I'Mtlmii nl,r*T> imd il t< lore
proximately I; elrmou energy 70 rV, eh-rimo I be pfolmtiilil y i.f nil
U(1 > O.WH, f im 1'(!
mttlli|tlirr 2.H kV; trimmer linr `ilO'C; epiTitnr CUtll, nhd twu *'(' -- 0.(t0'. I'C.'ll tmilcciifcH Imvc 11
lrui|n*rnlmc 2.tr(5.
rnrluii, nlrnnx, ftiviiiR a j>riibfd>itily of all lxit>K
The ^billowing rum eluontnlogrAphie conditions *C 0.K74, line nC - 0.1 IS, and two '*C 0 tK)7.
were nxeil: ruliiiiiii .V X 2 mm ill parked with .'I' I'CT moIccutcH have IM i-ailmri atoms. Riving a
OV I on (ill Ml mesh Supeleoport; injector (nn|>rrn. probat>ility of all being UC 0.HI7, one nC tine 24.V2(iirC; currier giw helium, flow rule ap 0.100, ami two "C - 0.OIC.
proximately 26 nd/min; column temperature pro
The probabilities of chlorine isotope* used are
grammed a* desrrilwd below.
0.7M for *Ct And 0.24C for ,PCI (It). The occurrence
; of *11 was not considered in the calculation* Ihtausc of its small natural Abundance.
,
Terhmcnl Arorloo'*' 1212, J214, awl J2fH (Mon-
The theoretical values were computed on n
r-nuto) were dissolved in liexnno lo ronoenlrntiom; of WANG Model 3C0 electronic calculator for C'N's
0..p> jir/^1 (or OC separation ]>rior to MS nnnlysia. having fiom I lo 8 Hdoiinc atoms, for I'CH's having
ludividuul burner* analysed directly by MS include: from t to 10 chlorine ntoinn, and for l'CT's having
2,2'-<li* (It. Wrhb), 2,f>,2'>.V*lcUft- ((). Ilutzingcr), from I to M chlorine atoms per mnli-nde. A bm-.iuiid
2,41.'i,?',4','i'*Iicxa (C. Kngt-I), nml dcvnchlorobi. expansion was \ised to determine coefficient*, nml llu*
phenyl. The completely substituted biphenyl wm various eombiiintion* uf chlorine nml cnrlxni i'nlo|M's
prepnred in one of our InhorMoncu by exhaustive were worked into the probability formu/n used by
chlorination of Aroelor 1208 with Antimony pento* lJcynon (11) and Uk rt o/. (21). The theoretical
chloride (33).
Abundances are computed for M *, M * + 1, M * + 2,
Cru Chri<ninrn|irftfih,V'AfaM Spectrometry
etc., and nrc expressed as the corres))onding m/e for each chemical aperies. The values are expre^rd rela
Our efforts were directed At obtaining a good mass tive to the moat intense ion in the molecular cluster,
rpertrum for eneh degree u( ehlorinniion in (he with the parent ion alwnys being llio lowest in/e in
PCH's. Where imlividunl isomers were Available, a the group. Table t gives (he parent ion (MM and
few grAinr. n( pure crystal wen* introduced directly most intense ion for ail rhlorinntcd speeien of CN's,
by solid )*robe into the ionising chnmbcr o( the mass PCB'a, nnd I'CT's.
|>crtrnmetei\ The rem/iining s|'cHia were obtained by MS M-nnnihg of selected penk.r After GO sepnra.
Results and ItiM-usalm
j lion of Aioclor mixlurtu.
Table 2 presents (he theoretical probability of
; Depending on the Aroelor being sepnrAted, column the occurrence of ions in (he molecular duster
. teinpemtures were programmed at 4 */mm aa fol for CN's, I'CB's, nnd FCT's. As the probability
j lows: Aroelor 12.12, ISO- 2211*0; Aroelor I2M, 170- of the occurrence of a7Cl increases with increasing
240#C; Aroelor 1208, H)0-2M)*C, Total Amount in. degree of chlorination, the differences bet ween in
jccled for eneh Aroelor km (J..V 1.0 pg. Identification tensities in the dusters become less pronounced.
of isomers was iwwintcd by previous MS eliarnclcmalion of Aroelor mixtures <10--I.*)).
In nil mes, u graphical output wm plotted by the romputvr to show the entire spectrum of each
This is accompanied by n shift of the most intense ion in the cluster from the parent ion (M+) to M+-f 2, then to M* -f i, nnd finally, in the
chloriiuiled species. The computer also provided a higher chlorinated lerphcnyls, to M+ + 6. These
digilel output of cacIi moleeulAr cluster, with the patterns of intensity nrc unique for each chemical
most intense ion normalued to (00%.
species, thus providing a ready means of identifi
CofeuhtlioM <tj Theoretical Innlnpir
Ainnuiniu-ra
The theoretical relntive abundances of ions in the molecular Hunter were determined by using the natural occurri-nco of carbon And rtilorinc isotojies. The ptobAbilitien of carltou imtopea used Arc O.flHff (or C And 0.011 for `C (14). From these abun dances, the probAbility of ntl enrbon Atoms Ircing 'C, one cArlwn Atom being **0, And two enrbon Atoms being "C cah b determined fur the ehlorin. ted nAphthslone* (CN), polychlorinated biphenyls
cation. This becomes evident, when the observed m/e
intensities of mono* through dcrachlorobipbcnyl (Table 3) ore. compared to the theoretical PCH values. The observed rntioa in the molecular duster ore nearly a perfect match with that expected for each PCM. The only places where there arc noticeable deviations front the ex|*ected values are icon at m/o 25S in tri-; m/c 400 in nona-; and m/c 404, 400, and 600 in drea-. An explanation for this may Iw that these spectra
HONS 082775
1U0 70UHNAL or THE aaac (Vol. 66, No. 1, 1073)
Table I. Parent Ion and moil Intent# Ion for CN't, PCS'*. end PCT'o
Chlorinated nnHlh*ln<l (CN) CieH|oClo -a
V` No. ol Cl
Mott M4 Intense*
Polychlorinated biphenyl* (PCS) CirHt# oClo 10
No. ot Cl
Mott M f Intenao
Polychlo Inated terphenylt (PCt) CiiHit^eCle- *
No. ot Cl
Mott M4 Intense
0 178 1 162 2 196 ) 7 4 264 (766) 5 798 (W) 6 337 (334) ; 366 (368) a 400 <<04)
0 164 1 188 2 222
3 256 4 790 (292) S 374 (376) 6 351 (360) 7 392 (394) 426 (430) 9 460 (464) 10 494 (498)
0 2)0 1 764 2 298
3 3)2 4 366 (368) 5 400 (407) 6 434 (436) 7 468 (470) 8 50? (506)
9 536 (540) 10 570 (M4) 11 604 (Wl) 12 638 (644) 13 672 (678) 14 706 (717)
f'n.Mil ion l mvil nlento union oMtervmo indicated In parentltesea.
wrrc t.'ikt n while the eonccntrnliona of the com* JiOlllldh ^ ere elmugiiiR in the ion source, thus afTerling ion intensities. Kvpn will these devialions, n chi-square test shows the matching of observed to expected intensities to 3C significant at the (Ml /a level for nil PCH's.
Toblo t. Theeretlea probability of the oecurranca of Ion* In the meletular cl<i*ter In
CN'*. PCB'i, and PCT'a*
------------_
1M 163 164 166
18) 169 190 191
196 191 191 199 700 201
??? 273 774 27S 226 277
7 JO 2)1 237 ?)) 734
CN
PCD
PCT
------------------- __________ _______ ____________
/nofio
ICO.00
11.71
33.17
3.61
mono
100.00
13.53
3J.44 - 4.41
iff
100.00
11.28
6S.77
7.35
11.00
1.20
df
100.00
13.53
66.04
8.8?
11.17
1.44
Ut
109.00
11.27
98.37
11.03
12.44
(Continued)
m/e
236 237.
257 258
?f0 26] 262
264 2GS 266 267 268 269 270 271 272
290 291 292 293 794 295 296 297 298 299 300 301 302 303 304 305 306 307 308
Table . {Continued) CN rco
3.65 0.39
fa fra 76.35 8.61 >00.00 11 23 49.25 5.49 10.86
1.19 0.92
pen fa 61.14
6.89 100.00
11.24 65.54
7.33 21.66 2.39
3.57 0.39 0.24
fri 13.53 98.64 1? 7fl 4.31
3 73
totie **76.20
10.31 100.00
13.44 49.47
6.67 10.97
1.4) 0 96
PCT
mono 100.00 20. 34.55
6,6? 0.C3
df 100.00 20 30 67.15
13 23 11.90 2.16
(Continued)
arm;
32
M 3* JJ JJ n n r v n v 34 34
35 r *. *
mmvw t >r
HONS 062776
N<*. 1,107,'I)
nt nyU(CCt)
(**> (402) <4) <>0> (SM) (MO) OM) Wt (614) <6>9) (Ml)
PCT
m.M M.U MM 6.6? A)
Im I 100.00
10 AMO IMJ 11.10 MO
(Omltovetf)
ROTi: A MOHJUK- MASK UPFCTIlOMrTRV OK I'CHi
m/
in m m sv 329 329 330 331 iil 333 334 335 330 337 330 339 340 341 342
350 359 300 301 302 363 364 365 366 367 360 369 370 371 372 373 174 375 376 377 370
392 393 394 395 396 397 391 399 400 401 402 401 404 405 406 407 400 409 410 411 412 411
TikU X. (Confinuad)
CN PCI)
Mit 50.96
0.75 100.00 11.24 01.03
0.10 35.79
3.90 0.04 0.97 1.17
hcpli* 43.71
4.93 100.00
11.25 98.12 11.00 53.56
3.90 17.50
3.95 3.48 0.38 0.39
oc<* 33.44
3.77 07.40
9.03 100.00
117? 65.44
7.31 26.01
2.90 7.03 070 1.16 0.13
pen (a 61 04 0.26 100 00 13.46 65.70 0.70 21.69 2.86 1.62 0.47 0.25
hex* 50.91
6.69 100.00
13.47 61.91 10.90 15.95 4.77 6.9?
1.17 1.20 0.15
hopt.x 43.66
5.9) 100.00
13 <9 96.20 13.11 53.76
7.16 17.70 2.34 3.52 0.4C 0.40
PCT
Ui 100.00 20.29 99.74
19.85 33.79 6.47 4.09 0.70
tefra 75.56 15.34 100 00 19.99 50.10
9.76 11.41 2.11 1.06 0.17
pent* 60.61 12.30 100.00 20.06 66.35 13.00 22.26
4.26 3.63 0.69 0.20
(Oent/nuerf)
101
Table X. (Conf/nwatf)
m/e
PCD
PCT
426 33.36
427 4.51
426 07.71
479 11.77 430 J00.00
431 13.41
437 65.56
433 1.76
434 26 92 60.62
415 1.57 10.26
436
7.10
100 00
437
0.93
20.10
439
1.19
82 62
439
0.15
16.36
440
o.n
36.65
441 7.12
442 9.26
443 1.74
444 1 79
445 0.73
446 nona
0.01
460 25 97
461 3.51
462 76.12
463 10.31
464 100.00
4(5 13.44
466 76.41
467
10.23
hepi*
469 37.59 43.45
469 5.00 6 12
470
12.36
100 00
471 1.63 20.12
472
2.72
90.90
473
0.36
19 60
474
0.39
54.57
475 10.69
476 10.20
477 3.49
479 3.69
479 0.61
490 doe*
0.41
494 20.79
495 2.91
490 67.96
497 9.17
499 100.00
499 11.45
500 07.27
501 11.70 ocr*
502 50.04 33.04
503 6.67 6.7)
501 19.71 96.92
505 2.61 17.49
50G
9.40
100.00
507
0.71
19.96
508 1.02 66.02
509
0.13
13.01
M0 27.37
611 5.30
512 7.32
1.30 1.24
515 0.22
610 0.17
(Cant/nuetf)
HONS 082777
IV
rot.-nvai, or- tim; aoac (Vol. W, No. |f7.i)
Thl/. (ConMnunrt)
m/
rCT
AOM $K ?5.75 5)7 S.2I 5)8 76.06 5)9 1S.S4 540 too 00 541 20 00 54? 76.87 543 15 21 544 MU
545 7.44
546 12.66 547 ?. 4? 548 ?.8) 549 0.53 550 0.41
570 20.64 571 4)9 57? 67.68 57) 1) 66 574 100 00 575 ?0,03 576 87.72 577 17.41 578 50.62 579 9.93 580 ?0.10 581 3.89 58? 5.58 58) 1.06 584 1.07 585 0.?0 586 0.14
604 U 16*91
695 ).4J 606 60.96 607 12.30 608 100.00 609 20.06 610 98.57 611 19.61 61? 64.89 61) 12.79 614 29.99 6 IS 5.84 616 9.93 617 1.90 618 2.36 619 0.44 6?0 0 40
6)8 12.89 6)9 2.61
640 50.67 641 10.2)
tablal. (Conimuatf)
m/
PCT
64? 9) 39 643 19.35 644 100.00 645 19 94 646 73.97 647 1462 648 38 99 649 7.63 650 ISO? 651 ? 90 65? 4.27 653 0.81 654 0.89 655 0.16 656 0.14
67? 9.9)
(7) 201 674 42.?8 675 8.64 676 83.14 677 16.71 678 100 00 679 19.97 680 8211 681 16.28 68? 48.6? 68) 9 55 614 21 37 685 4.15 686 7.06 687 1.35 661 1.76 689 0.3) 690 0.3)
706 7.81 707 1.58 708 35.81 709 7.24 710 76.25 711 15.34 712 100 00 713 20 00 714 9025 715 17.93 716 59.31 717 11 69 718 29.78 719 5.72 7?0 11.04 721 ?.l) 722 3.20 723 0.61 724 0.71 725 0 1)
------------------ Probabilities used: '*C - 0.989. l,C - 0.011; MCl (ConfMWtf) 0.754, "CI - 0.24G.
The isotopic patterns are lx*ttcr own in the plotted sperira (Iurs. 1-10). To save apace, only the area of the molecular cluster and the major
ax-. anr sivan. TNr wtrn show the molwular duster always to be the moat in-
tense with the loss of even numlers of chlorine atoms favored ujM*n fragmentation,
M.*5 rdmiaficaljm of IVB's a:U nvt l* by t'r,iir>;f;5)fine ir.-weticni** n they h.i parent ions, relative to the PCll's, ami can tie
Hf>
Si-Ml'tWIW
MONS 082778
No. 1, 1073)
8,811; "Cl .*r* of cWormc ioI I* nfTeided try have wrnk r, aimI crii
1(01 li AMOMUA; MAW orKCTUOMKTUY OF VCJla
10.1
TftbU I. 0kirV(4 m/ InlinillUn In the mlcultf tluilir el
m/t Jnlenuty
***/ lnn**M
III 199 190 191
m 77) 774 m 770 w
766 257 751 759 700 761 7(7 761
790 791 797 791 794 795 796 797 798
)?4 175 176 17/ 978 179 l.W 111 137 111 114
168 159 XiO 1C1 16? 161 164 165 866 167 168 169
397 191 194
mono 100.00
11.51 11.16
4.14 d( ion no
70 *4 M
*.!*9 40.54 in tn 100.00 11.49
97.61
1711 79.11
JO 1.16 0.76
llM 71.14 10.44 100.00 11.6/ 41.84
6.87 10.14
l.W 0.96
pent* 61.84
7.15 100.00
17.96 66.11 8.77 71.94
7.99 1.86 0.17 0.74
/>* 51.17 6.11 100.00 11.37 80.95 10. 15.61
6.65 8.71
1.71 1.17
9 15
hipl< 61.70
6. 100.00
tie/it*
195 1102 196 9G.09 197 11.08
51.07 >77 * if 400 16 M 401 7 U 40? 1.14 40J 0 4A 404 O.JO
orf* 476 14..K 477 4.56 478 88.10 479 11.51 410 100.0B 431 13.41 43? 65.11
433 0.7) 4J4 76.11 415 1.78 416 6.99 437 0.17
418 1.16 499 0.11 440 0.11
460 461 467 463 464 465 466 467 468 469 470 471 472 471 474
494 <95 496 497 498 499 500 501 507 503 504 505 506 507 508 509
75.19 148 75.55 10.01
100.00 13.77 77.07 9.69 35.91
4 95 11.59
M2 2.61 0.75 0.11
dec* 75.59
3.34 71.55
9.84 100.00
14.28 97.4? 11.64 SI.69 6.86 20.28
2.71 5.42 0.75 104 0.14
IrlcHeif lv their clinnii`(rri(ir Nn'V peaks (-0
!'!). I 'hli*i<>lii*wiis nml c)tl>tii>-i rim
U*
illM llilJilHtril 1>\ lli.'M
.(.>. u., Im.iIi i .(.111)
l'r*in|!>nni | C| hnnim-iit U\>**h l"nl-:ill.*tu '
I'hllmlnle r*1n. him' vlminrlni^1 i< spmini will*
A Iiasr prilk u.hmaIIv nl in/r I 1!) nml have im iwUi|iir duster (27).
A mtnr UAunniinivn Inni In (Jf'-\JS jmnlvi-
of riivll'tinil'llllll | >11 | *41 -. Ill" HCI. |,|
itlhiii'liiinr lull*in will linmiii' |m ,i
y m>>n
Vllluillde im im nM hi til iiti(lfii(|.l|i
Aekimu l*'il||mii'i11
W<* wish to thimk Kmrst .1. Iti.mlti mill .In.... . I). for nmtiMimicr in tnkinit lltr inn** *pt-ttrn mid Philip (1. Murphy for assisimmn in ppnring the mnnuRcripl.
ItEJ'KIlKNrKB
(1) Jhilmm, J. (H)0') Ann/i^l 90, 407-17/*
(2) Robinson, J., Richardson, A., Crnltlrcc, A.,
Coillson, J., A Full*, G. (1067) Nature 214,
1307-13!I ,
.
(3) Reynolds, 1>. (1000) /full. Environ, Coti/oni.
Toxicol. 4, 12ft-143
(4) Jensen, 8. (I0GG) A'ru* AVt. J2, 612
(5) Widmerk, G. (1007) JAOAC 50, IUG0
(6) Koeninti, J., ten Noever tie Draw, M., & dr
Vos, R. (1000) Nature 221, H20-112R
(7) MitNicrn, H., Hdehcl, W., 1-orke, h., Lainonl,
T., Relink1, A., Ctomnrlie. K., Unglcv, G., A
Frouty, H. (1070) /Vsfir. ,1/onit. J. 4, 1 11- Ml
(8) Rnglcv, G., Reiihcl, W., A Crummtip, K. (1070)
JAOAC S3, 2.!>)-26l
(0) Hiros, F., Walker, A., A Mcdlvcry, A. (107U)
Hull. Environ. Contain. Toxicol. 5, 317-323
(10) HutMURpr, O., Jamieson, W., A Zitko, V.
<lf>70) Nature 226, 004
(11) SullmR, 1)., A llnckina, J. (1071) JAOAC 54,
801-807
s
(12) Sissons, I)., A Welti, 17. (1971) J. ChromtUoqr.
60, 15-32
(13) Tits, A., A do Vos, R. (1071) Environ. Sri
Trrhnol. 5, 1210-1218
(14) Wchl, H,, A MrCalJi A. (1072) .MOAC 55,
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(15) Willis, 17., A Addison, R. (1072) J. Fish. Hr*.
Hoard Can. 29, .'*02-50.**
(1C) Hole. J., A Murphy, J*. (1071) Hull. Environ.
Contam. Toxicol. 6, 377-384
7-mono; 7.7'dl; ?,4,4'-u(; 2,5,1',5'teOs; l.4,5.2'.5'penis; 2,4,.2',4'.5'-hoe; /.M.e.l'.l'.SMtepie; 7.J.4.8.?'. 1',5',6'ocU; 2.1,4,5,6.?',r,4',8'noni; decsehlorobl-
phenyl.
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(10) Hale, S., A llelMtigrr, O, (1(172) J. Chem. Soc,
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(24) Htitxiirger, 0.f Jamieson, W., A Safe, S. (1971)
JAOAC 54, 178-180
(20) l')rr*tonc, 0-, Hom, J., Brown, N., Barron, R.,
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(20) GncrlUx, ))., A haw, L. (1072) Hull. Environ. Contain. Torirol. 7, 243-2M
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P. (1072) (/((. Ktmron. ContQin. Toxieol. 7, 200-201
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(31) Beytmn, J. (I960) Matt Spectrometry and lit A)if>tiention to Organic Chemitlry, d*cvirr, Amsterdam, p. 298
(32) Bom-Mi, 1?. (KcU. 1071) Amrr. fxib. 27- 37 (33) Htilringer, O., Safe. S., A 7JLko, V. (1071) Hull.
Environ. Contain- 7'ojicol. 6, 209-219 (34) MrLnfTcrty, F. (1907) Interpretation of Afoot
Spectra, Hcmjainin, New York, p. 210
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MONS 08785