كتاب Reaction Mechanisms in Environmental Organic Chemistry
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 كتاب Reaction Mechanisms in Environmental Organic Chemistry

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Reaction Mechanisms in Environmental Organic Chemistry
Richard a. Larson , Eric J. Weber  

كتاب Reaction Mechanisms in Environmental Organic Chemistry  R_m_i_10
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Contents
Chapter
1: Organic Chemicals in the Environment 1
Environmental Fates of Organic Chemicals 1
The Carbon Cycle 2
Translocation of Organic Chemicals 7
Volatilization 7
Transport Within the Aqueous P hase 9
Partition into Solid Phases . 10
Transformation of Organic Compounds 14
Reaction Mechanisms . 14
Kinetics 15
Linear Free Energy Relationships 18
Overview of the Environment 23
The Troposphere and the Stratosphere 23
The Thermal Structure of the Atmosphere 24
Solar Energy Distribution . 26
Chemical Constituents and Their Reactions 28
Natural W aters 36
Water as Solvent and Reactant 37
Marine Waters and Estuaries . 41
Lakes and Rivers 44
The Air-Water Interface: The Surface Microlayer . 46
Groundwater 51
Organic Matter in Aquatic Environments 52
Solid Phases 60
Soil Structure 60
Aquatic Sediments . 63
Soil Organic Matter . 64
References . 83Introduction .103
Hydrolysis Kinetics 105
Specific Acid and Base Catalysis . 105
pH Dependence 106
Hydrolysis Reaction Mechanisms .107
Nucleophilic Substitution .107
SnI Mechanism 107
Sn2 Mechanism 108
Functional Group Transformation by Nucleophilic Substitution
Reactions . 109
Halogenated Aliphatics .109
Epoxides 117
Organophosphorus E sters . 122
Nucleophilic Acyl Substitution .124
Addition-Elimination Mechanism 124
Functional Group Transformation by Nucleophilic Acyl
Substitution Reactions 125
Carboxylic Acid Derivatives . 125
Carbonic Acid Derivatives . 132
Other Nucleophilic Substitution Reactions . 136
Reactions with Naturally Occurring Nucleophiles 136
Nucleophilic Reactivity .137
Reactions of Sulfur-Based Nucleophiles with Halogenated Aliphatics. 140
Neighboring Group Participation (Intramolecular Nucleophilic
Displacement) 143
Catalysis of Hydrolytic Reactions in Natural Aquatic Ecosystems . 145
General Acid and Base Catalysis . 146
Metal Ion Catalysis 147
Surface-Bound M etals 152
Clays and Clay Minerals .155
Natural Organic M atter 157
Dissolved Organic Matter .157
Soil and Sediment-Associated Organic M atter .158
References .160
3: REDUCTION . 169
Introduction .169
Reductive Transformation Pathways .171
Reductive Dehalogenation .171
Halogenated Aliphatics . 174
Halogenated Aromatics .178
X REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
2: HYDROLYSIS . 103CONTENTS XI
Nitroaromatic Reduction 181
Polynitro Aromatics 182
Regioselectivity 186
Aromatic Azo Reduction 187
N-Nitrosoamine Reduction .190
Sulfoxide Reduction 193
Quinone Reduction 194
Reductive Dealkylation 196
Reduction Kinetics 198
One-Electron Transfer Scheme .198
Structure Reactivity Relationships for Reductive Transformations . 199
Electron-Mediated Reductions .201
Natural Organic M atter .202
Mineral Systems 202
Microbial-Mediated Reductions . 205
Effects of Sorption on Reduction Kinetics 205
References 208
4: ENVIRONMENTAL OXIDATIONS .217
Molecular Oxygen . 218
Autooxidation . 221
Polymers . 225
Petroleum 226
Superoxide .227
Singlet Oxygen . 230
Ozone and Related Compounds: Photochemical Smog 234
Hydrogen Peroxide and Its Decay Products . 239
H2O2 239
Hydroxyl Radical 240
Formation . 240
Reactions with Organic Compounds . 242
Daughter Radicals: Bromide, Carbonate, etc .246
Peroxy Radicals . 247
Alkoxy and Phenoxy Radicals .250
Surface Reactions . 251
Clays .252
Silicon Oxides . 253
Aluminum Oxides 254
Iron Oxides . 254
Manganese Oxides 255
Thermal Oxidations . 257
Combustion and Incineration 257
Wet Oxidation . 259
References .261Free Aqueous Chlorine (HOCl) 275
Chlorine in Water 275
Oxidation Reactions 277
Substitution and Addition Reactions . 279
Phenols . 279
Phenolic Acids 283
Aromatic Hydrocarbons 284
Enolizable Carbonyl Compounds: the Haloform Reaction .286
Alkenes . 294
Humic Polymers and Natural W aters 296
Other Polymers 298
Combined Aqueous Chlorine (Chloramines) . 301
Formation of Chloramines 301
Formation and Reactions of Chloramines 302
Aromatic Compounds 302
Aliphatic Compounds 303
Amino Sugars 305
Amino A cids 306
Heterocyclic Nitrogen Compounds . 310
Ozone 313
Ozone in Water 314
Decomposition Mechanisms of Aqueous O zone 314
Reactions of Ozone 315
Kinetics . 315
Hydrocarbons 315
Fatty Acids 322
Phenols . 322
Nitrogen Compounds 325
Humic Materials: Natural Waters . 328
Advanced Oxidation: Wastewater Treatment 329
Chlorine Dioxide . 332
Hydrocarbons . 333
Phenols .334
Amines .336
Other Compounds 337
Surface Reactions of Disinfectants .338
References .341
x ii REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
5: REACTIONS WITH DISINFECTANTS .275Sunlight .359
Chromophores and Excited States 362
Photophysics of Light Absorption .362
Singlet and Triplet States .362
Quantum Yield 365
Chromophores . 365
Photochemical Reaction Principles .367
Direct Photolysis 367
Sensitized Photolysis 368
Radical-Producing Photochemical Reactions 368
Kinetics .369
Atmospheric Photochemistry 370
Natural Water Photochemistry 370
Inorganic Chromophores 371
Organic Chromophores 374
Interfacial Photochemistry 377
The Air-Water Interface 377
Natural Surface Films 377
Oil Spills . 378
Solid-Water and Solid-Air Interfaces . 380
Soils and Mineral Boundaries . 380
Surfaces of Organisms .383
Photoreactions of Particular Compounds . 385
Natural Organic M atter 385
Aromatic Hydrocarbons 386
Halogenated Hydrocarbons 388
Carbonyl Compounds 392
Phenols .396
Anilines .400
Nitro Compounds 401
Photochemistry in Waste Treatment .402
References .404
7: MOLECULAR REACTIONS: THE DIELS-ALDER AND
OTHER REACTIONS 415
Surface and Aqueous Catalysis of the Diels-Alder Reaction 415
Surface-Catalyzed Rearrangements .417
References .418
Index .
Index
The basic principle of this index is that hydrocarbons or compounds that have only one
functional group are indexed together under the generic name of the compound class. Therefore, chloroform and methyl iodide will both be found under Aliphatic halogen compounds.”
Also, compounds such as chloroform that are mentioned more than twice in the text are crossindexed. Pesticides and compounds with multiple functional groups are indexed under their
common names. Occasional exceptions, such as polychlorinated dibenzofurans and dioxins,
are also cross-indexed, so that their actual location should not be too difficult to find.
Absorbance, 361
Absorption. See Sorption
Acetaldehyde. SeeAldehydes
Acetone. SeeKetones
Acids. See Carboxylic acids, Sulfonic acids
Acriflavine, 328
Activated carbon
as redox catalyst, 338-339
granular, 339-341
Acyl chlorides. See Carboxylic acyl
chlorides
Acyl radicals, 243
Adsorption. See Sorption
Advanced oxidation processes, 329-331,
402-403
Advection. See Convection
Aldehydes, 31-32, 238, 306, 319-322, 329,
330
acetaldehyde, 31-32, 53, 306
acrolein, 416
citral, 394
formaldehyde, 31-33, 53, 143, 257, 329,
330-331, 376, 382
from alkoxy radicals, 250
from amines and chlorine dioxide,
336-337
from riboflavin photoreactions with
DOC, 376
glyoxal, 32, 53, 329, 376
halogenated, 296-297, 307-308
heptanal, 329
hexanal, 329
hydration of, 243
in chlorine dioxide-treated water, 334
in DOC, 53
in ozonized water, 328-329
in soils, 66
methylglyoxal, 32, 66, 329
nonanal, 296, 329
3-nonenal, 322
octanal, 296, 329
photochemical reactions of, 392-394
phthalaldehyde, 318-319
reactions with bisulfite, 243
reactions with chloramine, 303
reactions with chlorite, 336
reactions with hydrogen peroxide, 330
reactions with hydroxyl radical, 243
421422 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
reactions with super oxide, 229
taste-and-odor, 309
Aldicarb
hydrolysis, 150-151
sulfoxide, reduction, 193
Aldimines, 306
Algae
effects on photochemical reactions,
384-385
excretion products, 54
reactions with hypochlorite, 292
Aliphatic alcohols
ethanol, 31, 227, 331
ethylene glycol, 382
fatty, 383
glycerol, 159-160
methanol, 31
photochemical reaction with
hypochlorite, 276
sterols, 383
Aliphatic amines, 34
reactions with chlorine dioxide, 336-337
reactions with hypochlorite, 303-304
reactions with ozone, 325
singlet oxygen quenching by, 221
Aliphatic halogen compounds, 35
bromoform, 288, 329, 388
carbon tetrachloride, 204, 294, 388
chlorofludrocarbons (CFCs), 27, 388
dehalogenation, 253-254
chloroform, 35, 283, 294, 297, 308, 312,
331, 388
1,2-dibromo-3-chloropropane (DBCP),
112, 116, 159-160, 389
dichloromethane (methylene chloride),
35, 142
elimination reactions, 112-117, 139, 159,
174
free radical coupling, 174
haloforms (trihalomethanes), 283,
286-294, 329, 338-339
halogenated ethanes, 35, 115-116,
169-170, 177, 204, 207, 294
halogenated ethylenes, 35, 115, 174, 331
hexachlorocyclopentadiene, 389-390
hydrolysis, 104, 106, 109-112, 140, 176
methyl bromide, 140
methyl chloride, 35
methyl iodide, 35, 391
nucleophilic substitution, 139, 141-143,
159
photochemical properties of, 388
photochemical reactions of, 388-389,
391
reductive dehalogenation, 171-177, 204
vicinal dehalogenation, 174-176
vinyl chloride, 174
See also Lindane, Mirex, Toxaphene
Aliphatic hydrocarbons. SeeAlkanes
Aliphatic sulfur compounds, 35, 140, 142,
238, 381
See also Thiols
Alkaloids, 383
Alkanes. See alsoMethane
butane, 28, 237
cyclohexane, 383
ethane, 28, 320
in atmosphere, 243
in DOC, 53
long-chain, 28, 383
pentane, 322
semiconductor photooxidation of, 383
Alkenes
butadiene, 417
camphene, 294
iS-carotene, 378
chlolestene, 417
complexes with oxygen, 221
cyclohexadiene, 416
cyclohexene, 282, 333
ethylene, 29
isoprene, 29, 243
limonene, 29, 415
myrcene, 29, 243
reactions with chlorine dioxide, 333-334
reactions with hydroxyl radical, 243, 245
reactions with hypochlorite, 282-283,
294-295
reactions with nitrate radical, 238-239
reactions with ozone, 234-235, 315-318
reactions with peroxy radicals, 250
reactions with singlet oxygen, 230-232
styrene, 282, 333
Alkoxy radicals, 225, 250-251, 379
cleavage, 250
reactions with oxygen, 247
Aluminum oxide. SeeMetal oxides
Amides. SeeCarboxylic amidesINDEX 423
Amino acids
in DOC, 53
in humic materials, 78
in soils, 67
photochemical reactions, 230-231, 385
reactions with chloramines, 305
reactions with chlorine dioxide, 336-338
reactions with hypochlorite, 277, 298,
306-309, 312-313
reactions with ozone, 325
reactions with singlet oxygen, 230-234
reactions with super oxide, 229
Amino sugars
in humic materials, 78
in soils, 67
reactions with hypochlorite, 305-306
Ammonia, 147, 293, 306, 325, 327
reaction with hypochlorite, 301
reactions with ozone, 325
Amphiphiles. See Micelles
Anaerobic environments, 169, 171
Anchimeric assistance, 144
Anhydrides. SeeCarboxylic anhydrides
Anilines. SeeAromatic amines
Antioxidants, 223-224, 226
Aromatic amines
absorption spectra, 400
2-aminofluorene, 400
benzidines, 188-189, 326, 328, 401
chlorinated
photochemical reactions, 400
reductive dehalogenation, 179
coupling with humic materials, 78
formation from azo compounds,
187-189
formation from nitro compounds,
181-186, 402
jS-naphthylamine, 328
nitroanilines, 185, 188
oxidation on surfaces, 250-251, 254
photochemical reactions
direct, 400-401
in the presence of algae, 384
with acetophenone, 395
with riboflavin, 376, 403
reactions with carbonate radical, 315
reactions with hydroxyl radical, 245-246
reactions with hypochlorite, 303, 341
reactions with ozone, 325-328
Aromatic halogen compounds, 36, 259
chlorobenzenes, 178, 259, 294, 389, 400
chloronaphthalenes, 259, 285
chlorostyrenes, 259
hexachlorocyclopentadiene. SeeAliphatic
halogen compounds
photochemical reactions of, 389-390
polybrominated biphenyls, 391
polychlorinated biphenyls (PCBs), 35,
179-180
hydroxylated, 339
photochemical reactions of, 378, 383,
390-391
polychlorinated dibenzodioxins, 36, 259,
324
polychlorinated dibenzofurans, 36, 259,
324
reductive dehalogenation, 178-180
See also DDT
Aromatic hydrocarbons
alkylbenzenes, 284, 318, 386
benzene, 29, 258-259, 318, 386
benzylic, 333
biphenyl, 284
photolysis of, 372
complexes with oxygen, 221
cumene, 248
indan and indans, 29
indenes, 379
in DOC, 54
in petroleum, 378
naphthalene and naphthalenes, 29
photochemical reactions of, 378, 386
reactions with hypochlorite, 284
reactions with ozone, 317-320
reactions with singlet oxygen, 233
polycyclic (PAH), 30
as photosensitizing agents, 378
in combustion, 257-258
in wet oxidation, 259-261
photochemical reactions of, 386-387,
403-404
reactions with chlorine dioxide,
333-334
reactions with hypochlorite, 285
reactions with ozone, 232, 315, 320
reactions with singlet oxygen, 230
reactions with hypochlorite, 284-286
reactions with nitrate radical, 239424 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
reactions with ozone, 315-318
spectra of sorbed, 381
toluene, 29
Arrhenius equation, 17-18
Ascaridole, 233
Ascorbic acid, 223, 251
Astaxanthin, 49
Atmosphere
particles in, 30-31
thermal structure of, 24
Atmospheric mixing, 7-8
Atrazine, 12, 157, 190, 197, 394
Autooxidation, 221-227
Azo compounds, 172, 252-253, 256, 325,
341, 384, 395, 400, 402
dyes, 187
reduction, 187-189, 206
Benzene. SeeAromatic hydrocarbons
Benzene hexachloride. See Lindane
Benzidine. SeeAromatic amines
Benzo[a]pyrene. SeeAromatic
hydrocarbons, polycyclic
BHC. See Lindane
Bicarbonate. See Carbonates
Biomass, 6
Bisulfide (HS-), 136, 139, 143, 204-205
Bisulfite (HSO3-), 243
Borate, 147
Borohydride, as photochemical electron
donor, 391
Bromate, 329
Bromide, 329
Bromoform. SeeAliphatic halogen
compounds
Bromohydrins, 329
Bromopicrin, 329
Carbamates
dealkylation, 196, 197
hydrolysis, 104, 126, 133-135
Carbofuran, 196
Carbohydrates
in DOC, 53
in humic materials, 78
in soils, 64
in surface microlayers, 49
reactions with hypochlorite, 277
Carbon cycle, 2-7
Carbon dioxide, 3, 5-6, 310, 383, 385
hydration, 4
in soils, 63
IR absorption, 27
tropospheric, 27
Carbon monoxide, 385, 393
Carbon tetrachloride. SeeAliphatic halogen
compounds
Carbonates
inorganic, 4-5, 62, 147
reaction with hydroxyl radical, 314
organic, 126
radicals, 246-247, 314
reaction with aromatic amines, 315
Carbonyl compounds. SeeAldehydes and
Ketones
Carbonyl sulfide, 385
Carboxylic acids, 33, 297, 322, 334-335
acetic, 12, 33
benzoic, 243-244, 378
citric, 291-292, 381
reactions with hypochlorite, 291-292
cyano, 309
fatty, 33, 49, 229, 295
photochemical reactions, 377
reactions with ozone, 322
formic, 33, 319, 323-324, 381
glyoxylic, 376
halogenated, 258, 291, 296-297, 300,
310, 328-329
in DOC, 53
in humic materials, 76, 292
keto, 329
a-keto, 306
/3-keto, 291
oxalic, 319, 334
peroxy, 34, 322
phenolic, 33, 60, 65, 76, 254-256, 378,
385
reactions with hypochlorite, 281,
283-284, 291, 338-341
photochemical reaction with
hypochlorite, 276
photodecarboxylation, 381-382
phthalic, 318-320, 378
pyruvic, 33, 306, 376
tartaric, 381INDEX 425
Carboxylic
acyl chlorides
hydrolysis, 125-126
amides
from aniline oxidation on activated
carbons, 341
hydrolysis, 104, 125-126, 130-133
N-chloro, 305, 307
reactions with hypochlorite, 305
anhydrides
hydrolysis, 104, 126
esters
hydrolysis, 104, 106, 125-130,
148-149, 152
in humic materials, 77
in soils, 65
photochemical reactions, 384
phthalates, 33, 128-129
wax esters, 48-49, 383
See alsoCutin, S?ber in
i^-Carotene, 378
Catalysis
acid and base, 105-106, 146-147
buffer, 146
by clays, 155-157
metal ion, 147-152
of hydrolysis, 145-160
surface, 152-155
Catechol. See Phenols
Charge transfer. See Complexation
Chelation. See Complexation
Chloramines
dichloramine, 301
monochloramine, 301
reactions with phenols, 302
organic, 303
reactions with amino acids, 305
trichloramine, 301, 309
Chlorate, 332-333
Chlorimuron-ethyl, 136-137
Chlorinated dibenzodioxins and
dibenzofurans. See Aromatic halogen
compounds
Chlorine (Cy. See Hypochlorite
Chlorine dioxide
as oxidant, 332
decomposition, 332
photolysis, 333
reactions with alkenes, 333
reactions with amino acids, 337
reactions with aromatic hydrocarbons,
333-334
reactions with heterocyclic compounds,
337-338
reactions with hydrogen peroxide, 334
reaction with phenols, 334-336, 341
redox potential, 332
Chlorite, 332, 336
esters, 334
reactions with organic compounds,
336-337
Chlorobenzilate, 130
Chlorofluorocarbons. SeeAliphatic
halogen compounds
Chloroform. SeeAliphatic halogen
compounds
Chlorohydrins, 283, 294-295, 310, 333
Chlorohydroxybiphenyls, 339-340
Chlorophylls, 292, 312, 371, 375, 384
and derivatives, 375
Chloropicrin, 283, 389
Chlorpyrifos, 124, 149
Chromophores, 361, 365-366, 371-372,
374-376
Clay minerals, 11, 62
effects on Diels-Alder reactions,
416-417
effects on photochemical reactions,
373-374, 380
hydrolyses catalyzed by, 155-157
in oxidation reactions, 252-253
Clouds, 360
Combined chlorine. See Chloramines
Complexation
of metal ions, 147-152, 241, 252, 372,
382
of oxygen, 221, 240, 386
Convection, 9
Coordination. See Complexation
Correlation analysis, 18, 139-140
Coumarins, 60
Cresols. See Phenols
Cuticles, of plants, 383
Cutin, 72, 383
Cyano compounds. See Nitriles
Cyanogen chloride (CICN), 309
DDE, 113-114, 177, 380426 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
DDT, 12
elimination reactions, 113-114
photochemical reactions, 384
reduction, 178, 206-208
Dealkylation, reductive, 172, 196-197
Desorption, 10
Detergents. See Surfactants
Dibromochloropropane (DBCP). See
Aliphatic halogen compounds
2,4-Dichlorophenoxyacetic acid (2,4-D)
hydrolysis of esters of, 158-159
Dieldrin, 121
Diffusion
eddy, 9
molecular, 9
Dimethylglyoxal. See Ketones
Direct photolysis, 367
Dispersion. See Diffusion
Dissolved organic carbon (DOC)
as catalyst for hydrolysis, 157-158
as electron mediator in reductions, 202
effects on light transmittance, 371, 374
humic materials in, 54-60
in freshwaters, 52-53
in groundwater, 51-53
in rainwater, 52
in seawater, 52
in sediments and sediment pore waters,
64
Dissolved organic matter (DOM). See DOC
Disulfoton
hydrolysis, 145
reaction with singlet oxygen, 233
DNA, 229, 338
See also Heterocyclic nitrogen
compounds (purines, pyrimidines)
Electron mediators, 201-202
Elimination reactions, 112-117, 139, 159,
174, 227
Emulsification of petroleum, 50
Endrin, 121
Enols, 223
in haloform reaction, 286-289
in humic materials, 77
Epichlorohydrin 121-122
Epoxides, 31, 238-239, 250, 282-283, 320,
322, 333
of benzo[a]pyrene diol, 117, 120
of fatty acids, 295, 322
of phenanthrene, 285, 295
hydrolysis, 104, 106, 117-122, 155-156,
159
Esters. See Carboxylic esters. Chlorite
esters, and Phosphate esters
Estuaries. See Water
Ethanol. See Alcohols
Ethers, chlorinated diphenyl, 282-283
Ethylenediaminetetraacetic acid (EDTA),
382
Eutrophication, 45
Evaporation. See Volatilization
Excited states, 362-364, 394
Extinction, 361
coefficient, 361
Fatty acids. See Carboxylic acids
Fenpropathrin, 129, 380
Fenton reaction. See Hydroxyl radical
Flavonoids. See Phenols
Flumetralin, 383
Fluorescence, 363
Fly ash, 259
Formaldehyde. See Aldehydes
Formic acid. See Carboxylic acids
Free available chlorine. See Hypochlorite
Free radicals
coupling reactions, 174, 251, 282, 324,
326, 340
in activated carbons, 338-339
in atmospheric hydrocarbon oxidation,
235-238
in combustion, 257-259
in humic materials, 77, 193
in oxidations, 219, 222-227
in photochemical smog, 235-238
in photochemistry, 365-368, 378-379,
393-394
in reductive processes, 198
ketyl, 394
See also Alkoxy radicals. Hydroxyl
radicals. Nitrate radical, Peroxy
radicals, Phenoxy radicals,
Superoxide
Freundlich isotherm, 13
Fulvic acid. See Humic materials
Furans. See Heterocyclic compounds,
oxygenINDEX 427
Gelbstoff. See Humic materials
Global warming. SeeCarbon dioxide,
tropospheric
Glyoxal. SeeAldehydes
Groundwater. See Water
Half-life, 16
Haloform reaction. See Ketones
Haloforms. SeeAliphatic halogen
compounds
Hammett
equation, 19
substituent constants, 19-21
in ozonolysis, 322-323
in reductive processes, 200
Hard and soft acids and bases, 137-139,
150
Henry’s law, 8
Herbicides. Seenames of individual
compounds
Heterocyclic compounds
nitrogen
caffeine, 34, 326-327
carbazoles, 34, 311, 338
in humic materials, 77
indole, 311, 327, 338
isoquinoline, 34
parabanic acid, 311
purines, 311, 337
pyridine, 248, 312, 327
pyrimidines, 310
pyrroles, 232, 292, 312
quinoline, 312, 327
oxygen
benzofurans, 286
furans
in Diels-Alder reactions, 417
reactions with singlet oxygen,
230-234
oxetanes, 393
See alsoEpoxides
sulfur
thiophenes, 35, 278-279
reactions with hypochlorite, 277-278
Humic acid. SeeHumic materials
Humic materials
absorption spectra, 374-375
aquatic, 54-60
chemical degradation of, 55
effects on photochemical reactions, 375,
400-401
elemental analyses, 68
fluorescence, 58-60
fractionation, 68
free radicals in, 194
fulvic acids, 54, 68, 147
functional groups in, 69-72, 76-78
Gelbstoff, 54
humic acid, defined, 68
humin, 68
hydrated electron from, 240, 385
hydrogen peroxide from, 239-240, 385
in soils, 68-83
in surface microlayers, 50
marine, 55, 57-58
nitrogen compounds of, 56, 78
NMR spectra of, 56-58, 69-74, 293
photobleaching, 385
photochemical reactions with metal
oxides, 382-383, 385
photodecarboxylation, 385
photoionization, 240
reactions with hypochlorite, 292-293,
296-298
reactions with ozone, 328-329
singlet oxygen production from, 385
structural models for, 78-83
superoxide production from, 385
Hydrated electron, 240, 385, 387
Hydrocarbons. SeeAlkanes, Alkenes,
Aromatic hydrocarbons. Methane
Hydrogen bonding, 12
Hydrogen cyanide (HCN), 309
Hydrogen peroxide, 34, 221, 228, 230,
318-319
as oxidant, 240
disappearance, 240
formation, 239-240, 382-385, 394, 403
in advanced oxidation processes,
329-331, 404
in atmosphere, 239
in Fenton reaction, 240, 383
in rainwater, 239
in surface waters, 239-240
photo-Fenton reaction, 383
photolysis, 329-330
reactions with aldehydes, 330
reactions with chlorine dioxide, 333-334428 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
reactions with hypochlorite, 230
reactions with sulfur compounds, 240
Hydrogenolysis, 174
Hydroperoxides, 31, 34, 222, 226-227, 232,
248, 378, 382, 386
hydroxy, 317, 330
Hydroperoxyl radical. See Superoxide
Hydroquinone. See Phenols
Hydroxyl radical (HO* or *OH), 221
Fenton reaction, 229, 240-241
formation, 240-241
from hydroperoxide photolysis, 379
from hypochlorite photolysis, 274
from nitrate radical, 238
from riboflavin photolysis, 376
from semiconductor photolysis, 381,
403-404
in advanced oxidation processes, 329-331
in atmosphere, 242
in combustion, 257
in ozone decomposition, 314, 325
in surface waters, 242, 372
in wet oxidation, 261
reaction with alkanes, 29, 243
reaction with bromide, 246
reaction with carbonate, 246
reactions with aromatic compounds,
244-246, 325
reactions with nitrogen oxides, 247
Hydroxylamine, 302
Hypobromite, 293, 329
Hypochlorite (hypochlorous acid)
and activated carbons, 338-341
as disinfectant and bleaching agent, 276,
299-300
as oxidant, 277
breakpoint reaction, 301-302
formation from chlorine hydrolysis,
275-276
in chlorine dioxide reactions, 333-334,
336
photolysis, 276
pKa, 276
reactions with alkenes, 294-295
reactions with amino acids, 277, 298,
306-309
reactions with amino sugars, 305-306
reactions with aromatic amines, 302-303,
341
reactions with aromatic hydrocarbons,
284-286
reactions with carboxylic acids, 283-284,
290-291, 295
reaction with hydrogen peroxide, 230
reactions with ammonia and amines, 276
reactions with enolizable ketones,
286-291
reactions with heterocyclic nitrogen
compounds, 292-293, 310-312
reactions with humic materials, 293,
296-298
reactions with inorganic anions and
cations, 276-277, 293
reactions with lignin, 297-298
reactions with phenols, 279-283, 289,
292, 334-336, 338-341
reactions with proteins, 292, 298-299
reactions with thiamin, 313
redox potential, 274
See also Chloramines
Indirect photolysis. SeeSensitized
photolysis
Infrared (IR). See Solar radiation
Inner-sphere mechanism, 198
Insecticides. See names of individual
compounds
Internal conversion, 363
Intersystem crossing, 363-364
Iron oxides. See Metal oxides
Ketones, 32
acetone, 32, 277, 286, 392
acetophenone, 395
biacetyl (dimethylglyoxal), 32
a-diketones, 336
jS-diketones, 288-289
fluorenone, 33, 286
halogenated, 294, 299, 370
in haloform reaction, 286-291
ninhydrin, 289
photochemical reactions of, 392-398
reactions with chlorite, 336
reactions with hypochlorite, 277
See alsoQuinones
Kinetics
and mechanisms, 14-15INDEX 429
of photochemical reactions, 369-370
of radical chain reactions, 224
orders of reactions and, 15-17
oxidation, 217
ozonation, 315
reduction, 198
Lactams, 126
Lactones, 31, 126, 223
See also MX
Lakes. See Water
Landfills, 52
Leaves
effects on photochemical reactions, 383
singlet oxygen production at surfaces of,
231, 383
Light
absorption, 361
solar. See Solar radiation
transmittance, in natural waters, 371
wave-particle duality, 361
Lignin, 65, 74-75
reactions with hypochlorite, 299-300
Lindane, 176
Linear free-energy relationships, 18-22
Malathion, 124
Maleic hy dr azide, 328
Metal ions
cobalt(III) in riboflavin photoreactions,
376
copper(II)
in riboflavin photoreactions, 376
reactions with peroxy radicals, 248
iron(II)
in reduction processes, 202-204
oxidation of, by molecular oxygen, 219
photooxidation catalysis by, 378
iron(III)
photolysis of complexes, 241, 372, 385,
404
thermal reactions, 259
manganese (II)
reaction with hypochlorite and alkenes,
282
Metal oxides
aluminum, 154-155, 254, 381
effects on spectra of sorbed molecules,
381
in oxidation reactions, 251-257
in soils, 62
in surface catalysis of hydrolysis,
152-155
iron, 153, 252, 254, 381, 383
photoreduction, 382-383
manganese, 252, 255-256, 381
photoreduction, 255, 383
semiconductor properties, 381, 403
silicon, 253, 381, 383
singlet oxygen production by illuminated,
231
titanium, 153, 381-383, 403
zinc, 381-382
Methane, 27-28
in atmosphere, 242-243
in groundwater, 52
reactions with HO*, 28, 235-239, 242-243
Methoxychlor
dealkylation, 197
elimination reactions, 113-114
photochemical reactions, 384, 397-398
Methylene blue, 234, 368, 403
Methylglyoxal. SeeAldehydes
Micelles, 40-41
Microorganisms
in reductive processes, 205
See also Algae
Mirex, 177
Molecularity of a reaction, 15
Molinate, 382
Monochloramine. See Chloramines
Monosaccharides. SeeCarbohydrates
Monoterpenes. SeeAlkenes
Mustard gas, 145
MX, 296, 298
Naphthalene. SeeAromatic hydrocarbons
Natural organic matter (NOM). See DOC
Neighboring-group participation, 143-145
Nitrate anion, 241, 323-324, 311-312, 389
Nitrate radical, 238-239
Nitriles, 34-35, 306
halogenated, 297, 307-309
reactions with hypochlorite, 307
Nitrilotriacetic acid (NTA), 304, 382
Nitrite, 241, 302, 371-372430 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
Nitro compounds, 325, 372-373
absorption spectra, 401
photochemical reactions
direct, 401-402
with hypochlorite, 276
reaction with hydroxyl radical, 244
reaction with superoxide, 229-230
reduction, 172, 181-186, 202-206
See alsoParathion, TNT, Trifluralin
Nitrogen mustards, 145
Nitrogen oxides, 27, 30, 236-238, 247, 302
Nitrosamines, 34, 172
reduction, 190-192
n -? 7T* transition, 365-366, 393, 401
NTA. See Nitrilotriacetic acid
Nucleophilic displacement, 103, 141
by sulfur nucleophiles, 136, 140-142
hard-soft acid-base model, 138-139
intramolecular, 143-145
naturally occurring nucleophiles, 141
SnI mechanism, 107-108, 118-120
Sn2 mechanism, 108-109, 118-120, 121
Swain-Scott relationship, 140
Oceans. See Water
Olefins. SeeAlkenes
Oligosaccharides. See Carbohydrates
Optical density, 361
Outer-sphere mechanism, 198
Oxetanes. See Heterocyclic compounds,
oxygen
Oxidation state, 169-170
Oxygen
as oxidant, 218-221
atoms, 219
ground-state molecular, 219
in combustion, 257
in soils, 62-63
in surface microlayers, 219
in water, 219
in wet oxidation, 259-261
photolysis, 24, 218
reduction, 221-222
singlet, 226, 230-234, 368, 376, 378-379
UV absorption, 26
Ozone
as disinfectant, 313
decomposition in water, 314
formation in photochemical smog
episodes, 235-238
formation in stratosphere, 24, 234
in advanced oxidation processes, 329-331
in surface microlayer destruction, 378
layer, 24, 218, 234
photolysis, 329
reaction with bromide, 329
reaction with carbonates, 314-315
reaction with iodide, 314-315
reactions in cloud droplets, 235
reactions with aliphatic amines, 325
reactions with alkenes, 234-235, 316
reactions with amino acids, 325-326
reactions with aromatic amines, 325-326
reactions with aromatic hydrocarbons,
235, 315-321
reactions with fatty acids, 322
reactions with heterocyclic compounds,
326-328
reactions with humic materials, 328-329
reactions with phenols, 322-325
reaction with superoxide, 241
redox potential, 313
UV absorption, 26
PAHs. SeeAromatic hydrocarbons,
polycyclic
PAN. See Peroxyacetyl nitrate
Parathion
hydrolysis, 124, 149-150, 156-157
oxidation to paraoxon, 253
photochemical reactions of, 380, 401
rearrangement, 418
reduction, 182
Partition coefficients, 12, 207
PCBs. See Aromatic halogen compounds
PCDDs. SeeAromatic halogen compounds
PCDFs. SeeAromatic halogen compounds
Peptides. See Proteins
Pernitrate esters. See Peroxyacetyl nitrate
Peroxides, 330-331, 378
cyclic, 232, 319, 387
See also Hydrogen peroxide.
Hydroperoxides, Tetroxides
Peroxy acids. SeeCarboxylic acids, peroxy
Peroxy radicals, 222-223, 230, 238-239,
247-250, 335, 381, 394
bimolecular decay, 249-251INDEX 431
elimination reactions, 221, 248-249,
394-395
in atmosphere, 247
in surface waters, 248
reactions with Cu(II), 248
reactions with NO and NO2, 242, 247,
250
reactions with organic compounds, 248,
250, 322
“Peroxyacetyl nitrate,” 237-238, 247-248
Pesticides. Seenames of individual
compounds
Petroleum
autooxidation, 226-227
in surface microlayers, 50
photochemistry of, 50, 226-221, 378-380,
387
singlet oxygen in, 368
spills, 378
See alsoAliphatic hydrocarbons.
Aromatic hydrocarbons
Phenols, 30-31, 223
BHT, 223, 233
catechol, 253-254, 323-325, 397
chlorophenols, 178, 279, 300, 323-324,
396-397
reductive dechlorination, 178-180
flavonoids, 290
from petroleum photolysis, 378
guaiacol, 335
hydroquinone, 254-256, 323, 334, 397
in Diels-Alder reactions, 416
in humic materials, 76-77
in surface microlayers, 50
naphthols, 285, 373, 378, 398
nitrophenols, 31, 185, 237, 283, 323-324,
335
oxidative polymerization, 253-256
phenol and alkylphenols (cresols), 31, 33,
279-283, 302, 324, 378
photochemical reactions of, 373, 378,
396-398
with riboflavin, 376, 403
pyrogallol, 253
reactions with chloramine, 302
reactions with chlorine dioxide, 334-337
reactions with chlorite, 336
reactions with hydroxyl radical, 244-245,
325
reactions with hypochlorite, 279-283,
289-293, 298, 335, 338-341
reactions with nitrate radical, 238-239
reactions with ozone, 322-325
reactions with peroxy radicals, 248
reactions with singlet oxygen, 233-234
resorcinol, 290, 335, 340
vitamin E, 223
See also Carboxylic acids, phenolic;
Lignin
Phenoxy radicals, 251, 282, 340
Phorate, 193
Phosmet, 124
Phosphate, 147
Phosphorescence, 364
Phosphorus esters
hydrolysis, 104, 122-124, 138-139, 145,
147-149, 156-157
in soils, 64
Photochemical oxidants, 236
Photons, 361
Photophysical processes, 359, 362
Photosensitizers. See Sensitized photolysis
Photosynthesis, 5
Phthalate esters. SeeCarboxylic esters
Phthalic acid. See Carboxylic acids
Phytic acid. See Phosphorus esters
7T -? 7T* transition, 365-366, 401
Pigments, plant, 383
See also Chlorophylls
Pimaricin, 376
Polychlorinated dibenzodioxins and
dibenzofurans. SeeAromatic halogen
compounds
Polycyclic aromatic hydrocarbons. See
Aromatic hydrocarbons, polycyclic
Polyethylene, 226
Polynuclear aromatic hydrocarbons. See
Aromatic hydrocarbons, polycyclic
Polysaccharides. SeeCarbohydrates
Polystyrene, 225-226
Polyvinyl chloride, 258-259
Polyvinylidene chloride, 258-259
Precipitation. See Water
Primary production. See Photosynthesis
Proflavine, 328
Pronamide, 132
Proteins
in DOC, 53432 REACTION MECHANISMS IN ENVIRONMENTAL ORGANIC CHEMISTRY
in surface microlayers, 49
reactions with chlorine dioxide, 337
reactions with hypochlorite, 292, 299
Pteridines, 372
Pyridine. SeeHeterocyclic compounds,
nitrogen
Pyruvic acid. See Carboxylic acids
Quantum yields, 365, 369
Quenching of excited states, 364
Quinalphos, 157
Quinones, 30, 32, 254, 320, 334-335, 373,
387, 397-398
dyes, 195
halogenated, 283, 285, 287, 300
in humic materials, 77, 202
in soils, 66
reactions with ozone, 235
reactions with phenoxy radicals, 251
reactions with superoxide, 230
reduction, 172, 194-195, 199, 251
Radicals. SeeFree radicals
Rain. SeeWater
Rate constants
and mechanisms, 15
Reaction kinetics. See Kinetics
Reaction mechanism, 14-15
Reaction orders. See Kinetics
Redox potential of waters, 217-218
Resorcinol. See Phenols
Respiration, 6
Riboflavin, 234
photochemistry of, 375-376, 394, 403
tetracetyl ester, 376, 403
Rose bengal, 234, 368
Rubber, 226, 415
Saponins, 48
Schiff bases, 14
Sediments, 63-64
Semiconductors, 381
Sensitized photolysis, 234, 368
sensitizing agents, 368, 383, 385, 393
See also Oxygen, singlet
Silicate, dissolved, 147
Singlet excited states, 362-364
Singlet oxygen. SeeOxygen, singlet
Soil
light penetration into, 380
organic matter, 63-83, 158-160
singlet oxygen at surfaces of, 231
structure, 60-62
Solar radiation, 26, 359-360
absorption of, 365
infrared, 27, 360
ultraviolet, 26, 360
visible, 26, 360
Solubility. See Water
Soot, 30
Sorption, 10-13
coulombic, 11
effects on photochemical and
photophysical processes, 374, 381
effects on spectra of sorbed molecules,
381
hydrogen-bonded, 12
hydrophilic, 11
hydrophobic, 12
in reductive processes, 205-208
Steady-state approximation, 17
Stratification
atmospheric, 24
in lakes, 45
in soils, 60
Stratosphere, 24
Streams. See Water
Suberin, 65, 72
Sugars. See Carbohydrates
Sulfonic acids. 111, 337
Sulfonylureas
hydrolysis, 126, 135-136
Sulfoxides, 381
reduction, 172, 193
Sulfur compounds. SeeAliphatic sulfur
compounds; Bisulfide; Heterocyclic
compounds, sulfur; Sulfonic acids;
Sulfonylureas; Sulfoxides;
Thiocarbamates; and Thiols
Sunlight. See Solar radiation
Superoxide
and hydroperoxyl radical, 227-228
dismutation, 228
from elimination reactions, 227, 248-249
from humic material photolysis, 385
from iron(II) oxidation, 219-220
from riboflavin photolysis, 376INDEX 433
from semiconductor photolysis, 381-382
in advanced oxidation processes, 329-330
in atmosphere, 228
in ozone decomposition, 314-315
in photochemistry, 368
in water, 227
lifetime, 228
reactions with nitrogen oxides, 241
reactions with organic compounds,
229-230
reaction with ozone, 234, 241
Surface films. See Surface microlayers
Surface microlayers, 41, 46-50
oxygen in, 219
photochemistry in, 377-378
singlet oxygen in, 231, 368
Surfactants, 377-378
dry, 47
wet, 47
Taft equation, 22-23
in reductive processes, 200
Terpenes. SeeAlkenes
a-Terpineol, 295
Tetroxides, 225, 249-250, 331
Thiamin, 313
Thiobencarb, 382-383
Thiocarbamates, 126
Thiols, 34-35
reactions with chloramine, 303
reactions with hypochlorite, 277, 298
Thiometen, 145
Titanium dioxide. See Metal oxides
TNT, 183-184, 401
Total organic carbon (TOC). See Dissolved
organic carbon
Toxaphene, 177, 294
Translocation, 7-13
Transmittance, 361
Transport. See Translocation
Trifluralin, 183
Trihalomethanes (THMs). SeeAliphatic
halogen compounds
Triplet excited states, 362-364
Troposphere, 23
Ultraviolet. See Solar radiation
Ureas, 104
Vitamin C. SeeAscorbic acid
Vitamin E. See Phenols
Volatilization, 7
of petroleum, 50
Water
dissolved inorganic species, 41, 44
estuaries, 43
freshwater (lakes and streams), 37, 43-47
global distribution, 36
groundwater, 36, 51-52, 403
in Diels-Alder reactions, 416
in soils, 62-63
IR absorption, 27
light transmittance in, 370
oceans and seawater, 41-43
pore, 64
precipitation (rainwater), 46
properties, 37
solutions and solubility, 38-41
structure of liquid, 37-38
surface tension, 46
vapor, photolysis, 241
wastewaters, 402-404
See also Dissolved organic matter.
Humic substances. Surface
microlayers
Wax esters. SeeCarboxylic esters
Wood, singlet oxygen production at
surfaces of, 231


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