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The isomer-specific analysis of di-iso-propylnaphthalenes

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Di-iso-propylnaphthalenes (DIPN), frequently observed low-level contaminants of the aquatic environment, were analysed as the sum of isomers by GC/MS in Rhine and Lippe river sediments. For future isomer-specific trace analysis, linear retention indices of the components of a technical DIPN formulation were determined on six different GC-columns. Gas-phase infrared spectra aquired by GC/FT-IR analysis on GC capillaries coated with apolar and polar stationary phases showed characteristic patterns of C-Har out of plane deformation vibrations which allowed all DIPN isomers to be distinguished. Theoretical IR spectra of all DIPN were calculated with the B3LYP functional using 6-311G(d,p) and 6-311G+(d,p) standard triple zeta basis sets. The resulting frequencies were scaled by a factor derived emprically. Theoretical and experimental IR spectra allowed the structures of seven major DIPN isomers and two minor components to be assigned to the corresponding GC-peaks. All DIPN isomers of a technical formulation were resolved on polar GC capillaries, and the composition of the technical DIPN mixture was determined.
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Keywords: Di-iso-propylnaphthalenes; GC/FT-IR; GC/MS; Isomer-specific analysis; Retention index; Sediment

Document Type: Research Article

Affiliations: 1: Institute of Organic Chemistry, D-20146 Hamburg, Germany 2: Institute of Organic Chemistry, D-38106 Braunschweig, Germany 3: Institute for Geology and Geochemistry of Petroleum and Coal, D-52056 Aachen, Germany

Publication date: May 1, 2007

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