Identification of a Novel Heterocyclic Compound in Seabird eggs….

PDF FILE: 1,1999 vol.33,no1,p26-33

Identification of a Novel C10H6N2Br4Cl2 Heterocyclic Compound in Seabird Eggs. A Bioaccumulating Marine Natural Product?

from

Environ. Sci. Technol. 1999, 33, 26-33

S H E RYL A. T I T T LEM I E R , † M ARY S IM O N , ‡WALT E R M . JARM AN , §J O H N E . E L L I O T T , ⊥ AN DRO S S J . N O R S T RO M *, † , ‡

Department of Chemistry, Carleton University, Ottawa,

Ontario, Canada, K1S 5B6, Environment Canada, Canadian

Wildlife Service, Hull, Quebec, Canada, K1A OH3, Energy and

Geoscience Institute, University of Utah, Salt Lake City, Utah,

84108, and Environment Canada, Canadian Wildlife Service,

Delta, British Columbia, Canada, V4K 3N2

A novel brominated and chlorinated compound, C10H6N2–

Br4Cl2, bioaccumulating in seabird eggs was identified and

characterized by low- and high-resolution electron

impact ionization (EI), electron capture negative ionization

(ECNI), and ammonia positive chemical ionization (PCI)

mass spectrometry. This compound is the major congener

of a series of four hexahalogenated species. The major

congener was determined in egg samples from Leach’s storm petrel, rhinoceros auklet, glaucous-winged gull, and blackfooted albatross from the Pacific coast area; Leach’sstormpetrel, Atlantic puffin, and herring gull from the Atlantic coast; and herring gull from the Great Lakes using GCECNI-MS. Theconcentrations of C10H6N2Br4Cl2 in the Pacific Ocean samples ranged from 1.8 to 140 ng/g (wet weight), and were significantly higher than the Atlantic Ocean

samples (p ) 0.037). The Pacific Ocean samples contained

levels of C10H6N2Br4Cl2 approximately 1.5-2.5 times

higher than in the Atlantic Ocean samples of the same or

ecologically similar species. The compound was not

detected in any of the samples from the Great Lakes. The

Pacific Ocean offshore surface feeders had the highest

concentrations (34-140 ng/g) when compared to the other

samples (0.61-5.6 ng/g). Its strictly marine occurrence

and relatively high nitrogen content indicate that C10H6N2–

Br4Cl2 probably is a marine natural product, found at

highest concentrations in the Pacific Ocean surface feeding

birds. A possible structure of C10H6N2Br4Cl2 is 1,1ʹ′-dimethyltetrabromodichloro-2,2ʹ′-bipyrrole.

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PDF FILE: 1,1999 vol.33,no1,p26-33