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Abstract

Structures of six cyclic polysulfides, previously unkown as organic environmental pollutants, were analyzed from a sediment sample from the Eastern Gulf of Finland. The determinations were done by gas chromatography (GC) coupled to mass spectrometry. High-resolution mass spectrometry measurements of the isotopic composition of four compounds could be done to confirm their molecular formulae. Total low-resolution mass spectrometry spectra were used to elucidate structures of all six compounds by a thermochemical approach, application of fragmentation rules and by ICLU simulation of the spectra. The compounds were found to be (in the order of GC retention) 1,2,4-trithiacycloheptane, tetrathiacyclopentane, 1,2,4,5-tetrathiacyclohexane, 1,2,3,4-tetrathiacycloheptane, 1,2,3,4-tetrathiacyclohexane and 1,2,4,6-tetrathiacyclooctane.

Keywords

electron impact mass spectra high-resolution mass measurement novel sediment contaminants simulation of mass spectra

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References

Tolstikov

G.A.

Schultz

E.E.

and Tolstikov

A.G.

, “Natural polysulfides”, Russian Chem. Rev. 66(9), 901 (1997).

Ponomarev

D.A.

Takhistov

V.V.

and Vainiotalo

, in New Advances in Analytical Chemistry, Volume 3, Ed by Atta-Ur-Rahman

Taylor and Francis, London, UK, pp. 211–275. (2000).

Viktorovskii

I.V.

Khoroshko

L.O.

Russkikh

Y.V.

Takhistov

V.V.

and Paasivirta

, “Alkylated and chlorinated polysulfides detected in sediments of the Eastern Gulf of Finland”, Eur. J. Mass Spectrom. 5, 295 (1999).

Paasivirta

, ICLU, GWBASIC program for isotope clusters calculations. Department of Chemistry. University of Jyväskylä, Finland (1988, update 1999).

Takhistov

V.V.

, Organic Mass Spectrometry (Russ.). Nauka: Leningrad, Russia (1990).

Ponomarev

D.A.

Golovin

A.V.

and Takhistov

V.V.

, “Free radicals in mass spectrometry. Part 1. General fragmentation rules for organic and organometallic compounds under electron impact”, Eur. J. Mass Spectrom. 8, 409 (2002).

Block

Bentley

M.D.

Davis

F.A.

Douglass

I.B.

and Lacadie

J.A.

“Electron impact induced processes and photochemically labile organic sulfur compounds. A mass spectral study of dialkyl thiolsulfonates, disulfides, trisulfides, and α-disulfones”, J. Org. Chem. 40(19), 2770 (1975).

Alonso

M.E.

Aragona

Chitty

A.W.

Compagnone

and Martin

, “Mass spectral studies on unsymmetrical dialkyl disulfones. Intramolecular 1,2-, 1,3-, and 1.4-hydrogen migration processes,” J. Org. Chem. 43(23), 4491 (1978).

Gupta

Knight

A.R.

and Smith

P.J.

, “Mass spectral studies of symmetrical and unsymmetrical dialkyl disulfides”, Can. J. Chem. 59, 543 (1981).

10.

Heller

S.R.

and Milne

G.W.A.

EPA/NIH Mass Spectral Data Base (1978).

11.

Mottram

D.S.

and Whitfield

F.B.

, “Volatile Compounds from the Reation of Cysteine, Ribase, and Phospholipid in Low-Moisture System”, J. Agr. Food Chem. 43(8), 984 (1995).

12.

Field

and Foster

C.H.

, “Biologically Oriented Organic Sulfur Chemistry. IV. Synthesis and Properties of 1,2,5-Triephane, a Model for Study of Sulfide and Disulfide moieties in Promiximity”, J. Org. Chem. 35, 749 (1970).

13.

Ponomarev

D.A.

and Takhistov

V.V.

, in Recent Advances in Analytical Techniques, Ed by Atta-Ur-Rahman

Harwood Academic Publishers, Reading, UK, pp 369–432 (2000).

14.

Holzmann

Susilo

and Gmelin

, “Collisional activation study of cyclic polysulfides,” Org. Mass Spectrom. 17, 165 (1982).

15.

Kuo

M.-C.

Chien

and Ho

C.-T.

, “Novel polysulfides identified in the volatile components from Welsh Onions (Allium fistulosum L var. maichuon) and Scallions (Allium fistulosum L var. caespitosum)”, J. Agric. Food Chem. 38, 1378 (1990).

16.

Kuo

M.-C.

and Ho

C.-T.

, “Volatile constituents of the distilled oils of Welsh onions (Allium fistulosum L Variety Maichuon) and Scallions (Allium fistulosum L Variety Caespitosum)”, J. Agric. Food Chem. 45, 111 (1992).

Mass Spectrometric Identification of Cyclic Polysulfides in Sediment of the Eastern Gulf of Finland. I

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