INDEX
689
Neutrons 19
Newman projection
butane 58
cyclohexane, boat conformation 65
chair conformation 63
definition 57
ethane 57
methylcyclohexane, conformational isomers
67
Nicotinamide adenine dinucleotide, see
NAD
+
Nicotinamide adenine dinucleotide, reduced
see NADH
Nicotinamide
in nucleotides 560
structure 413
Nicotine, structure 412
Nicotinic acetylcholine receptors 413
Nicotinic acid, structure 413
Nitration, of aromatic rings 305
using acetyl nitrate, pyrrole 422
using benzoyl nitrate, indole 444
Nitriles
bonding molecular orbitals 35
conjugated 396
hydrolysis to carboxylic acid
acid-catalysed 244
base-catalysed 244
as stabilized anions 365
useful reactions 204, 239, 366
Nitro group
charge separation 134
aliphatic, useful reactions 366
Nitrogen
electronic configuration 23
sp hybrid orbitals, stereochemistry 56
sp
2 hybrid orbitals, stereochemistry 56
sp
3 hybrid orbitals 33
stereochemistry 56
sp
3 hybridized, electronic configuration 33
Nitrogen heterocycles, basicity 143
Nitrogen inversion 74
energy barrier 74
in tropane alkaloids 118
Nitromethane
acidity 365
as stabilized anion 365
Nitronium ion, in aromatic nitration 305
Nitrophenols, acidity 134
Nizatidine, structure 436
Noble gases, electronic configuration 23
Nodes, in atomic orbitals 22
Nomenclature
acronyms 15
aromatic rings 8
bridged ring systems 116
examples 8–14
functional groups, 5
heterocycles
fused 448
fused to benzene ring 438–9
non-aromatic 403
hydrocarbons, Table 7
lactams 265
lactones 255
non-systematic, Table 15
nucleosides and nucleotides, Table 551
oligosaccharides 483
pteridine 449, 452
purine 448
pyranose and furanose rings 468
systematic 6–8
trivial 15
Non-ribosomal peptide biosynthesis 535
modular 535
Noradrenaline (norepinephrine)
biosynthesis 602
methylation to adrenaline 200
structure 447
Norepinephrine, see noradrenaline
Norfloxacin, structure 442
Nucleic acids 551–8
abbreviations 551
base sequence 551
chemical synthesis 566–9
DNA sequencing gel 565
purine bases 550
pyrimidine bases 550
sequence determination 564
sequencers, automated 566
structure 551
synthesis, solid phase 566
Nucleophiles
acetylides
aldehydes and ketones 241
S N 1 and S N 2 reactions 205
alcohols, S N 1 and S N 2 reactions 198
amines, S N 1 and S N 2 reactions 201
cyanide
aldehydes and ketones 238
S N 1 and S N 2 reactions 204
definition 171
enamines 366–9
enolate anions 357
examples 171
Grignard reagents
aldehydes and ketones 240
carboxylic acid derivatives 271
S N 1 and S N 2 reactions 204
halide, S N 1 and S N 2 reactions 198
hydride
reduction of aldehydes and ketones
235
reduction of carboxylic acid derivatives
267–9
S N 1 and S N 2 reactions 205
in S N 2 reactions 183, 185
stabilized anions 365
thiols, S N 1 and S N 2 reactions 199
water, S N 1 and S N 2 reactions 198
Nucleophilic addition
to carbonyl groups 222
to conjugated carbonyl derivatives
393–401
to iminium ions 369
to pyridinium salts 414
Nucleophilic aromatic substitution 411,
544
1,3-azoles 437
pyridine 411
isoquinoline 443
quinoline 441
Nucleophilic substitution reactions 198–206
derivatives of sulfuric and phosphoric acid
272–82
in glycoside synthesis 479
Nucleophilicity
and basicity 185, 207, Table 186
of N and O nucleophiles, Table 186
common reagents, Table 186
Nucleosides
as antiviral agents 558
definition 549
as N-glycosides 478
nomenclature, Table 551
structure 228, 550
Nucleoside triphosphates, in DNA replication
553
Nucleotides
abbreviations, Table 551
biosynthesis 563
definition 549
nomenclature, Table 551
phosphoramidite coupling 568
sequence determination 564
Numbering
azoles 432
heterocycles, fused to benzene ring 439
in systematic nomenclature 7
Nystatin, mode of action 294
Octet rule 19, 23
Ofloxacin, structure 442
Oils, see fats and oils
Oleic acid
metabolism 593
structure 259, 593
Oligonucleotide synthesis 566–9
Oligosaccharides 482–4
definition 463
systematic nomenclature 483
Opium
alkaloids 162, 186, 343
extraction of morphine 162
Optical
activity 73, 76
isomers 73
purity 76
calculation 77
rotation, glucopyranose anomers 227
Orbitals
atomic, see atomic orbitals
molecular, see molecular orbitals
Organophosphorus derivatives
as enzyme inhibitors 531
as acetylcholinesterase inhibitors 280
Ornithine, structure 503
Orotic acid, in nucleotide biosynthesis 563
Orotidylic acid, in nucleotide biosynthesis 563
Orsellinic acid, biosynthesis 385
Oxalic acid, acidity 144
Oxaloacetate
in aldol reaction, Krebs cycle 363
from carboxylation of pyruvate 610
in Krebs cycle 585, 589
Oxalosuccinate
decarboxylation 389
in Krebs cycle 586
Oxazole
basicity 433
reactivity 432
structure 432
689
Neutrons 19
Newman projection
butane 58
cyclohexane, boat conformation 65
chair conformation 63
definition 57
ethane 57
methylcyclohexane, conformational isomers
67
Nicotinamide adenine dinucleotide, see
NAD
+
Nicotinamide adenine dinucleotide, reduced
see NADH
Nicotinamide
in nucleotides 560
structure 413
Nicotine, structure 412
Nicotinic acetylcholine receptors 413
Nicotinic acid, structure 413
Nitration, of aromatic rings 305
using acetyl nitrate, pyrrole 422
using benzoyl nitrate, indole 444
Nitriles
bonding molecular orbitals 35
conjugated 396
hydrolysis to carboxylic acid
acid-catalysed 244
base-catalysed 244
as stabilized anions 365
useful reactions 204, 239, 366
Nitro group
charge separation 134
aliphatic, useful reactions 366
Nitrogen
electronic configuration 23
sp hybrid orbitals, stereochemistry 56
sp
2 hybrid orbitals, stereochemistry 56
sp
3 hybrid orbitals 33
stereochemistry 56
sp
3 hybridized, electronic configuration 33
Nitrogen heterocycles, basicity 143
Nitrogen inversion 74
energy barrier 74
in tropane alkaloids 118
Nitromethane
acidity 365
as stabilized anion 365
Nitronium ion, in aromatic nitration 305
Nitrophenols, acidity 134
Nizatidine, structure 436
Noble gases, electronic configuration 23
Nodes, in atomic orbitals 22
Nomenclature
acronyms 15
aromatic rings 8
bridged ring systems 116
examples 8–14
functional groups, 5
heterocycles
fused 448
fused to benzene ring 438–9
non-aromatic 403
hydrocarbons, Table 7
lactams 265
lactones 255
non-systematic, Table 15
nucleosides and nucleotides, Table 551
oligosaccharides 483
pteridine 449, 452
purine 448
pyranose and furanose rings 468
systematic 6–8
trivial 15
Non-ribosomal peptide biosynthesis 535
modular 535
Noradrenaline (norepinephrine)
biosynthesis 602
methylation to adrenaline 200
structure 447
Norepinephrine, see noradrenaline
Norfloxacin, structure 442
Nucleic acids 551–8
abbreviations 551
base sequence 551
chemical synthesis 566–9
DNA sequencing gel 565
purine bases 550
pyrimidine bases 550
sequence determination 564
sequencers, automated 566
structure 551
synthesis, solid phase 566
Nucleophiles
acetylides
aldehydes and ketones 241
S N 1 and S N 2 reactions 205
alcohols, S N 1 and S N 2 reactions 198
amines, S N 1 and S N 2 reactions 201
cyanide
aldehydes and ketones 238
S N 1 and S N 2 reactions 204
definition 171
enamines 366–9
enolate anions 357
examples 171
Grignard reagents
aldehydes and ketones 240
carboxylic acid derivatives 271
S N 1 and S N 2 reactions 204
halide, S N 1 and S N 2 reactions 198
hydride
reduction of aldehydes and ketones
235
reduction of carboxylic acid derivatives
267–9
S N 1 and S N 2 reactions 205
in S N 2 reactions 183, 185
stabilized anions 365
thiols, S N 1 and S N 2 reactions 199
water, S N 1 and S N 2 reactions 198
Nucleophilic addition
to carbonyl groups 222
to conjugated carbonyl derivatives
393–401
to iminium ions 369
to pyridinium salts 414
Nucleophilic aromatic substitution 411,
544
1,3-azoles 437
pyridine 411
isoquinoline 443
quinoline 441
Nucleophilic substitution reactions 198–206
derivatives of sulfuric and phosphoric acid
272–82
in glycoside synthesis 479
Nucleophilicity
and basicity 185, 207, Table 186
of N and O nucleophiles, Table 186
common reagents, Table 186
Nucleosides
as antiviral agents 558
definition 549
as N-glycosides 478
nomenclature, Table 551
structure 228, 550
Nucleoside triphosphates, in DNA replication
553
Nucleotides
abbreviations, Table 551
biosynthesis 563
definition 549
nomenclature, Table 551
phosphoramidite coupling 568
sequence determination 564
Numbering
azoles 432
heterocycles, fused to benzene ring 439
in systematic nomenclature 7
Nystatin, mode of action 294
Octet rule 19, 23
Ofloxacin, structure 442
Oils, see fats and oils
Oleic acid
metabolism 593
structure 259, 593
Oligonucleotide synthesis 566–9
Oligosaccharides 482–4
definition 463
systematic nomenclature 483
Opium
alkaloids 162, 186, 343
extraction of morphine 162
Optical
activity 73, 76
isomers 73
purity 76
calculation 77
rotation, glucopyranose anomers 227
Orbitals
atomic, see atomic orbitals
molecular, see molecular orbitals
Organophosphorus derivatives
as enzyme inhibitors 531
as acetylcholinesterase inhibitors 280
Ornithine, structure 503
Orotic acid, in nucleotide biosynthesis 563
Orotidylic acid, in nucleotide biosynthesis 563
Orsellinic acid, biosynthesis 385
Oxalic acid, acidity 144
Oxaloacetate
in aldol reaction, Krebs cycle 363
from carboxylation of pyruvate 610
in Krebs cycle 585, 589
Oxalosuccinate
decarboxylation 389
in Krebs cycle 586
Oxazole
basicity 433
reactivity 432
structure 432