Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

REFERENCES

• Schnoor , J. L. 2010 . The Gulf Oil Spill . Environ. Sci. Technol. , 44 ( 13 ) : 4833
   PubMed Web of Science ®Google Scholar
• Incardona , J. P. , Collier , T. K. and Scholz , N. L. 2011 . Oil Spills and Fish Health: Exposing the Heart of the Matter . J. Expos. Sci. Environ. Epidemiol. , 21 : 3 – 4 .
   PubMed Web of Science ®Google Scholar
• Mascarelli , A. 2010 . Deepwater Horizon: After the Oil . Nature , 467 : 22 – 24 .
   PubMed Web of Science ®Google Scholar
• Meador , J. P. , Stein , J. E. , Reichert , W. L. and Varanasi , U. 1995 . Bioaccumulation of Polycyclic Aromatic Hydrocarbons by Marine Organisms . Rev. Environ. Contamin. Toxicol , 143 : 79 – 165 .
   PubMed Web of Science ®Google Scholar
• Paraíba , L. C. , Queiroz , S. C. N. , D. , A. , Maia , H. N. and Ferracini , V. L. 2010 . Bioconcentration Factor Estimates of Polycyclic Aromatic Hydrocarbons in Grains of Corn Plants Cultivated in Soils Treated with Sewage Sludge . Sci. Total Environ. , 408 ( 16 ) : 3270 – 6 . 2010
   PubMed Web of Science ®Google Scholar
• Patri , M. 2009 . Polycyclic Aromatic Hydrocarbons in air and their Neurotoxic Potency in Association with Oxidative Stress: A Brief Perspective . Ann. Neurosci. , 16 ( 1 ) : 22 – 30 .
   Google Scholar
• Moorthy , B. 2008 . The CYP1a Subfamily . Issues Toxicol. , 3 ( Cytochromes P450 ) : 97 – 135 .
   Google Scholar
• Mahadevan , B. , Courter , L. A. and Baird , W. M. 2007 . “ Mutations induced by Polycyclic Aromatic Hydrocarbons ” . In New Developments in Mutation Research , Edited by: Valon , C. L. 19 – 40 . Hauppauge, NY : Nova Science Publishers .
   Google Scholar
• Irigaray , P. and Belpomme , D. 2010 . Basic Properties and Molecular Mechanisms of Exogenous Chemical Carcinogens . Carcinogenesis , 31 ( 2 ) : 135 – 48 .
   PubMed Web of Science ®Google Scholar
• Jacob , J. 2008 . The Significance of Polycyclic Aromatic Hydrocarbons as Environmental Carcinogens. 35 Years Research on PAH-a Retrospective . Polycyc. Aromatic Comp. , 28 ( 4–5 ) : 242 – 72 .
   Web of Science ®Google Scholar
• Puga , A. , Ma , C. and Marlowe , J. L. 2009 . The aryl Hydrocarbon Receptor Cross-talks with Multiple Signal Transduction Pathways . Biochem. Pharmacol. , 77 ( 4 ) : 713 – 22 .
   PubMed Web of Science ®Google Scholar
• Belitsky , G. and Yakubovskaya , M. 2008 . Genetic Polymorphism and Variability of Chemical Carcinogenesis . Biochemistry (Moscow) , 73 ( 5 ) : 543 – 54 .
   PubMed Web of Science ®Google Scholar
• Brody , J. G. , Moysich , K. B. , Humblet , O. , Attfield , K. R. , Beehler , G. P. and Rudel , R. A. 2007 . Environmental Pollutants and Breast Cancer . Cancer , 109 ( S12 ) : 2667 – 2711 .
   PubMed Web of Science ®Google Scholar
• Luch , A. 2005 . The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons , London : Imperial College Press .
   Google Scholar
• Swartz , C. D. , King , L. C. , Nesnow , S. , Umbach , D. M. , Kumar , S. and DeMarini , D. M. 2009 . Mutagenicity, Stable DNA Adducts, and Abasic Sites induced in Salmonella by Phenanthro[3,4-b]- and Phenanthro[4,3-b]thiophenes, Sulfur Analogs of Benzo[c]phenanthrene . Mutat. Res./Fund. Molec. Mechan. Mutagen , 661 ( 1–2 ) : 47 – 56 .
   PubMed Web of Science ®Google Scholar
• Pelroy , R. A. , Stewart , D. L. , Tominaga , Y. , Iwao , M. , Castle , R. N. and Lee , M. L. 1983 . Microbial Mutagenicity of 3- and 4-Ring Polycyclic Aromatic Sulfur Heterocycles . Mutat. Res./Genet. Toxicol , 117 ( 1–2 ) : 31 – 40 .
   PubMed Web of Science ®Google Scholar
• Croisy , A. , Mispelter , J. , Lhoste , J. M. , Zajdela , F. and Jacquignon , P. 1984 . Thiophene Analogues of Carcinogenic Polycyclic Hydrocarbons. Elbs Pyrolysis of Various Aroylmethylbenzo[b]thiophenes . J. Heterocyclic Chem. , 21 ( 2 ) : 353 – 9 .
   Web of Science ®Google Scholar
• Warshawsky , D. 1992 . Environmental Sources, Carcinogenicity, Mutagenicity, Metabolism and DNA Binding of Nitrogen and Sulfur Heterocyclic Aromatics . J. Environ. Sci. Health, Part C: Environ. Carcinogen. Ecotox. Rev. , 10 ( 1 ) : 1 – 71 .
   Web of Science ®Google Scholar
• Kropp , K. G. and Fedorak , P. M. 1998 . A Review of the Occurrence, Toxicity, and Biodegradation of Condensed Thiophenes Found in Petroleum . Can. J. Microbiol. , 44 ( 7 ) : 605 – 22 .
   PubMed Web of Science ®Google Scholar
• Andersson , J. , Hegazi , A. and Roberz , B. 2006 . Polycyclic aromatic sulfur heterocycles as information carriers in environmental studies . Analyt. Bioanalyt. Chem. , 386 ( 4 ) : 891 – 905 .
   PubMed Web of Science ®Google Scholar
• Andersson , J. T. 1993 . Polycyclic Aromatic Sulfur Heterocycles III. Photochemical Stability of the Potential Oil Pollution Markers Phenanthrenes and Dibenzothiophenes . Chemosphere , 27 ( 11 ) : 2097 – 2102 .
   Web of Science ®Google Scholar
• Wang , Z. , Fingas , M. and Sergy , G. 1995 . Chemical Characterization of Crude Oil Residues from an Arctic Beach by GC/MS and GC/FID . Environ. Sci. Technol. , 29 ( 10 ) : 2622 – 31 .
   PubMed Web of Science ®Google Scholar
• Wang , Z. and Fingas , M. 2003 . Development of Oil Hydrocarbon Fingerprinting and Identification Techniques . Marine Pollut. Bull. , 47 : 423 – 52 .
   PubMed Web of Science ®Google Scholar
• McCarry , B. E. , Allan , L. M. , Legzdins , A. E. , Lundrigan , J. A. , Marvin , C. H. and Bryant , D. W. 1996 . Thia-arenes as Pollution Source Tracers in Urban Air Particulate . Polycycl. Arom. Comp. , 11 ( 1 ) : 75 – 82 .
   Web of Science ®Google Scholar
• Marvin , C. H. , McCarry , B. E. , Villella , J. , Allan , L. M. and Bryant , D. W. 2000 . Chemical and Biological Profiles of Sediments as Indicators of Sources of Genotoxic Contamination in Hamilton Harbour. Part I: Analysis of polycyclic aromatic hydrocarbons and thia-arene Ccompounds . Chemosphere , 41 ( 7 ) : 979 – 88 .
   PubMed Web of Science ®Google Scholar
• Hegazi , A. H. , Andersson , J. T. , Abu-Elgheit , M. A. and El-Gayar , M. S . 1994 . Source Diagnostic and Weathering Indicators of Tar Balls Utilizing acyclic, Polycyclic and S-Heterocyclic Components . Chemosphere , 55 ( 7 ) : 1053 – 65 .
   Google Scholar
• Wang , Z. and Fingas , M. 1995 . Use of Methyldibenzothiophenes as Markers for Differentiation and Source Identification of Crude and Weathered Oils . Environ. Sci. Technol. , 29 ( 11 ) : 2842 – 9 .
   PubMed Web of Science ®Google Scholar
• Mössner , S. G. , Lopez de Alda , M. J. , Sander , L. C. , Lee , M. L. and Wise , S. A. 1999 . Gas Chromatographic Retention Behavior of polycyclic Aromatic Sulfur Heterocyclic Compounds, (dibenzothiophene, Naphtho[B]Thiophenes, Benzo[b]naphthothiophenes and Alkyl-Substituted Derivatives) on Stationary Phases of Different Selectivity . J. Chromatograph. A. , 841 ( 2 ) : 207 – 28 .
   Web of Science ®Google Scholar
• Rosell , A. , Grimalt , J. O. , Rosell , M. G. , Guardino , X. and Albaigés , J. 1991 . The Composition of Volatile and Particulate Hydrocarbons in urban Air . Fresenius’ J. Analyt. Chem. , 339 ( 10 ) : 689 – 98 .
   Google Scholar
• de Geus , H.-J. , de Boer , J. and Brinkman , U. A. T. 1996 . Multidimensionality in Gas Chromatography . TrAC Trends Analyt. Chem. , 15 ( 5 ) : 168 – 78 .
   Web of Science ®Google Scholar
• Zeigler , C. , MacNamara , K. , Wang , Z. and Robbat , A. Jr. 2008 . Total Alkylated Polycyclic Aromatic Hydrocarbon Characterization and Quantitative Comparison of Selected Ion Monitoring versus Full Scan Gas Chromatography/Mass Spectrometry Based on Spectral Deconvolution . J. Chromatograph. A. , 1205 ( 1–2 ) : 109 – 16 .
   PubMed Web of Science ®Google Scholar
• Schade , T. and Andersson , J. T. 2006 . Speciation of Alkylated Dibenzothiophenes through Correlation of Structure and Gas Chromatographic Retention Indexes . J. Chromatograph. A. , 1117 ( 2 ) : 206 – 13 .
   PubMed Web of Science ®Google Scholar
• Baldwin , L. J. , Tedjamulia , M. L. , Stuart , J. G. M. L. , Castle , R. N. and Lee , M. L. 1984 . The Synthesis of Polycyclic Thiophenes Derived from Phenanthrene Intermediates . Journal of Heterocyclic Chemistry , 21 : 1775 – 9 .
   Web of Science ®Google Scholar
• Nishioka , M. , Lee , M. L. and Castle , R. N. 1986 . Sulphur Heterocycles in Coal-derived Products: Relation between Structure and Abundance . Fuel , 65 ( 3 ) : 390 – 6 .
   Web of Science ®Google Scholar
• Sander , L. C. and Wise , S. A. 1997 . “ NIST Special Publication 922: Polycyclic Aromatic Structure Index.” ed. U.S. Department of Commerce ” . 1 – 10 . Gaithersburg , MD : U.S. Government Printing Office .
   Google Scholar
• Panico , R. , Powell , W. H. and IUPAC . 1994 . A Guide to IUPAC Nomenclature of Organic Compounds Recommendations 1993. 2nd ed , London: Blackwell Science .
   Google Scholar
• IUPAC . 1996 . Nomenclature of Organic Chemistry. 2nd ed , Vol. 1 , London : Butterworths .
   Google Scholar
• Kudo , H. , Tedjamulia , M. L. , Castle , R. N. and Lee , M. L. 1984 . The Synthesis of Phenanthrodibenzothiophenes . J. Heterocyclic Chem. , 21 : 1833 – 9 .
   Web of Science ®Google Scholar
• Klemm , L. H. 1990 . Interrelationships among Peri-condensed Thiophenes and Some Polycyclic Aromatic Hydrocarbons . Heterocycles , 30 ( 2 ) : 1219 – 29 .
   Web of Science ®Google Scholar
• Domínguez , A. , Alvarez , R. , Blanco , C. G. and Díez , M. A. 1996 . Chromatographic evaluation of Some Selected Polycyclic Aromatic Hydrocarbons of Coal Tars Produced under Different Cooking Conditions and Pitches Derived from Them . J. Chromatograph. A. , 719 ( 1 ) : 181 – 94 .
   Web of Science ®Google Scholar
• Wang , Z. , Fingas , M. and Li. , K. 1994 . Fractionation of a light Crude Oil and Identification and Quantitation of Aliphatic, Aromatic, and Biomarker Compounds by GC-FID and GC-MS, Part I . J. Chromatograph. Sci. , 32 ( 9 ) : 361 – 6 .
   Web of Science ®Google Scholar
• Lee , M. L. , Vassilaros , D. L. and White , C. M. 1979 . Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons . Analyt. Chem. , 51 ( 6 ) : 768 – 73 .
   Web of Science ®Google Scholar
• Andersson , J. T. 1986 . Gas Chromatographic Retention Indices for all C1- and C2-alkylated Benzothiophenes and their Dioxides on Three Different Stationary Phases . J. Chromatograph. A. , 354 : 83 – 98 .
   Web of Science ®Google Scholar
• Rostad , C. E. and Pereira , W. E. 1986 . Kovats and Lee Retention Indices Determined by Gas Chromatography/Mass Spectrometry for Organic Compounds of Environmental Interest . J. High Resolut. Chromatograph. , 9 ( 6 ) : 328 – 34 .
   Google Scholar
• de Hoffman , E. and Stroobant , V. 2007 . Mass Spectrometry: Principles and Applications. , 3rd ed , West Sussex , , UK : Wiley .
   Google Scholar
• Smith , R. M. 2004 . Understanding Mass Spectra: A Basic Approach , Hoboken , NJ : John Wiley and Sons .
   Google Scholar
• Herrera , L. C. , Ramaley , L. and Grossert , J. S. 2009 . “ Fragmentation Pathways of Some Benzothiophene Radical Cations Formed by Atmospheric Pressure Chemical Ionisation ” . In Rapid Commun. Mass Spectrom Vol. 23, 5 , 571 – 9 .
   Google Scholar
• Kukula , P. , Gramlich , V. and Prins , R. 2006 . Preparation of Partially Hydrogenated 4,6-Dimethyldibenzothiophenes . Helvetica Chimica Acta. , 89 ( 8 ) : 1623 – 40 .
   Web of Science ®Google Scholar
• Boberg , F. , Bruns , W. and Musshoff , D. 1994 . Sulfur Compounds in Crude Oil. Part XIX. Mass Spectra of Alkyldibenzothiophenes . Erdöl & Kohle, Erdgas, Petrochemie , 47 ( 2 ) : 56 – 9 .
   Google Scholar
• Vassilaros , D. L. , Kong , R. C. , Later , D. W. and Lee , M. L. 1982 . Linear Retention Index System for Polycyclic Aromatic Compounds: Critical Evaluation and Additional Indices . J. Chromatograph. , 252 : 1 – 20 .
   Web of Science ®Google Scholar
• Schmid , B. and Andersson , J. T. 1997 . Critical Examination of the Quantification of Aromatic Compounds in Three Standard Reference Materials . Analyt. Chem. , 69 ( 17 ) : 3476 – 81 .
   PubMed Web of Science ®Google Scholar