Page 1200 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

by t-butoxy radical, 289, 1022 hydrolysis of, 648–649 1187
interacting state model for, 1057–1058 intramolecular catalysis of formation, 675
effect of bond energies on, 1001 mechanism of formation, 646–650 Index
intramolecular, 1040–1041 pH-rate profile for formation and hydrolysis,
photochemical, 1118–1121 647–649
intramolecular, 1122, 1123, 1126 potential energy diagram for, 648–650
reactivity-selectivity relationship for, 1002 computation of, 648–650
structure-reactivity relationships for, 1056–1062 indacene
Bell-Evans-Polyani relationship for, stability of, 754
1056–1057 1-indanones, formation by Nazarov reaction, 909
transition state, computational model for, 1058 index of aromaticity, 719
hydrogen bonding induced decomposition of peroxides, 977
in enols, 605–606 inductive effect, 12, 338
hydrolases intermediates
epoxide, 224–227 in reaction mechanisms, 253
mechanism of, 216–217 internal return
in resolution of enantiomers, 216–221 in hydrocarbon deprotonation, 581–582
hydrolysis in nucleophilic substitution, 396–398
of acetals, 641–645 intersystem crossing, 1075
of amides, 662–664 intrinsic barrier, in Marcus equation, 293
of enamines, 653
intrinsic reaction coordinate, 279
of enol ethers, 485 in computational modeling of chelation control,
of esters, 654–658 681
of imines, 647–649 iodination, see also halogenation
of vinyl ethers, 485 of aromatic compounds, 804
hydroxy group iodohydrins
directing effect in epoxidation, 194–197 formation of, 492
directing effect in hydrogenation, 174–176
ion pairs
neighboring group participation by, 420–421
in nucleophilic substitution, 395–398, 404
hydroxyl radical
IP, see ionization potential
reaction with halomethanes, 1059–1060
ionization potential, 9, 95
hyperconjugation, 22–24
(Ipc) 2 BH, see diisopinocampheylborane
of alkyl groups, 23
Ipso substitution, 778, 814–816
in amines, 315, 1054
Ireland-Claisen rearrangement, 937–938
anomeric effect, relation to, 230–231
stereoselectivity of, 937
in carbocations, 301, 305, 307, 429
effect of solvent on, 937
in disubstitute methanes, 81–85
isobenzofuran
of heteroatoms, 81–85
as Diels-Alder diene, 760, 858, 864
in natural population analysis, 62
isobutene
in radicals, 981–982
acid-catalyzed dimerization, 455
in regiochemistry of E1 reactions, 555–556 isodesmic reactions
in relation to alkene conformation, 146–7 definition, 51
in relation to rotational barriers, 78–81
for determining hydrocarbon stability, 265
role in kinetic isotope effects, 333
for evaluation of carbonyl addition
role in substitution effects, 297–8
intermediates, 329–330
for evaluation of stabilization of carbonyl
IA, see index of aromaticity compounds, 320–321
imidazole derivatives isoindole
in catalytic triad of enzymes, 675–676 stability of, 760
intramolecular catalysis by, 671–672 isopinocampheylborane
N-acyl, 324 hydroboration by, 530
reactivity of, 664 isotope effects, see kinetic isotope effects
nucleophilic catalysis by, 656 isotopic labeling
imines, 646 in detection of internal return, 396–398
[2+2] cycloaddition reactions with ketenes, in hydrolysis of aspirin, 670–671
891–892 in racemization of benzhydryl
configuration of, 121 p-nitrobenzoates, 396
equilibrium constants for formation, table, 646 in solvolysis of sulfonate esters, 395–396