Chemistry and Toxicological Implications

A. NOMENCLATURE AND SELECTED PHYSICAL AND SPECTROSCOPIC PROPERTIES OF POLYCYCLIC AROMATIC HYDROCARBONS (PAHs) AND POLYCYCLIC AROMATIC COMPOUNDS (PACs) 440

1. Combustion-Generated PAHs and PACs 440

2. Structures and IUPAC Rules for Nomenclature 440

a. PAHs 440

b. PACs 444

3. Solubilities and Vapor Pressures 451

4- Gas - Particle Partitioning, Sampling Techniques, and Ambient Levels of Selected PAHs and PACs 453

a. PAHs 454

b. PACs 461

5. Absorption and Emission Spectra of Selected PAHs and PACs 461

B. BIOLOGICAL PROPERTIES OF PAHs AND PACs. I: CARCINOGENICITY 466

1. Historical Perspective: Benzo[a]pyrene, the "Classic Chemical Carcinogen" 466

2. Carcinogenicity of PAHs, Cancer Potencies, and Potency Equivalence Factors 467

3. Carcinogenicity of Nitroarenes and Other Nitro-PACs 473

C. BIOLOGICAL PROPERTIES OF PAHs AND PACs. II: MUTAGENICITY 475

1. Short-Term Tests for Genetic and Related Effects 475

2. The Ames Salmonella typhimurium Reversion Assay 475

a. Principle of Method: Direct vs Activatable Bacterial Mutagens 475

b. Assay Procedure 478

c. The "Microsuspension Modification" 478

d. The Salmonella typhimurium Reversion Assay for Gas-Phase Mutagens 479

e. Accuracy and Precision 480

f. Some Mutagenic Potencies in the Salmonella typhimurium Assay 480

g. Microbiology and Analytical Chemistry: Bioassay-Directed Fractionation and Chemical Analysis of Complex Mixtures of POM 482

3. The Salmonella TM677 "Forward Mutation" Assay 483

4- Human Cell Mutagenicities of PAHs and PACs 484

D. BACTERIAL AND HUMAN CELL MUTAGENICITIES OF POLLUTED AMBIENT AIR 486

1. Bacterial Mutagenicity of Urban Air: A Worldwide Phenomenon 486

a. Background 486

b. Particle Size Distribution of PAHs and Mutagenicity 487

c. Variables Influencing Mutagenicity Levels 488

2. Sources, Ambient Levels, Transport, and Transformation: Some Case Studies 491

a. Bacterial Mutagenicity 491

b. Human Cell Mutagenicity 497

3. Bioassay-Directed Chemical Analysis for PAHs and PACs in Fine Ambient Aerosols Using a Human Cell Assay 497

4. Bioassay-Directed Chemical Analysis for Vapor-Phase and Particle-Phase PAHs and PACs in Ambient Air Using Bacterial Assays 502

E. ATMOSPHERIC FATES OF PARTICLE-ASSOCIATED PAHs: HETEROGENEOUS REACTIONS 504

1. Background 504

2. Theoretical and Experimental Structure - Reactivity Relationships 505

3. Field Studies of Atmospheric Reactions: Transport and Transformation 507

a. Decay of Particle-Associated PAHs in Ambient Air 507

b. Time - Concentration Profiles of Particle-Phase PAHs during Transport across an Air Basin 508

4- Photochemical Reactions of Particle-Associated PAHs 510

a. Photooxidadon in Solution and "Liquid-like" Surfaces of Organic Aerosols 510

b. Photooxidadons on Inorganic Solid-Air Surfaces 512

5. Gas - Particle Reactions 513

a. Qzonolysis 513

b. Nitration 515

6. Atmospheric Fates of Particle-Associated Nitroarenes 518

a. Gas - Particle Reactions 518

b. Photochemical Reactions 518

F. REACTIONS OF GAS-PHASE PAHs: ATMOSPHERIC FORMATION OF MUTAGENIC NITROARENES 519

1. Combustion-Generated Primary Emissions of Nitroarenes 519

2. Atmospheric Formation of Nitro-PAHs and Nitro-PACs 520

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