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PAC, 1994, 66, 1077. Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994), doi:10.1351/pac199466051077


α-addition (alpha-addition)
α-effect
α-elimination
'A' value
abstraction
acceptor number (AN)
acid
acidity
acidity function
activated complex
activation energy (Arrhenius activation energy)
addend
addition
addition reaction
additivity principle
adduct
agostic
allylic substitution reaction
alternant
ambident
amphiphilic
amphiprotic (solvent)
amphoteric
anionotropic rearrangement (or anionotropy)
annelation
annulation
annulenes
antarafacial
anti
anti-Hammond effect
aprotic (solvent)
aquation
arenium ions
aromatic
Arrhenius equation
aryne
association
asymmetric induction
atomic orbital, ψ, φ, χ
attachment
autocatalytic reaction
automerization
autoprotolysis
autoprotolysis constant
azacarbenes
azenes
azylenes
Baldwin's rules
base
basicity
bathochromic shift (effect)
Bell–Evans–Polanyi principle
benzynes
bifunctional catalysis
binding site
biradical
Bodenstein approximation
bond
bond dissociation
bond energy (mean bond energy)
bond number
bond order p r s
bond-dissociation energy, D
borderline mechanism
Bredt's rule
bridged carbocation
bridging ligand
Brønsted acid
Brønsted base
Brønsted relation
Bunnett–Olsen equations
cage
cage compound
captodative effect
carbanion
carbenes
carbenium centre
carbenium ion
carbenoids
carbocation
carbonium ion
carbynes
catalysis
catalyst
catalytic coefficient
cationotropic rearrangement
cationotropy
chain reaction
chain transfer
chain-termination reaction
charge population
charge-transfer complex
chelate
chelation
cheletropic reaction
chelotropic reaction
chemical decomposition
chemical equilibrium
chemical flux, φ
chemical reaction
chemical relaxation
chemical species
chemiflux
chemoselectivity (chemoselective)
chemospecificity
chromophore
CIDNP (Chemically Induced Dynamic Nuclear Polarization)
cine-substitution
class (a) metal ion
class (b) metal ion
clathrates
colligation
common-ion effect (on rates)
compensation effect
complementary binding sites
complex
composite reaction
comproportionation
concerted process
condensation reaction
configuration (electronic)
configuration (stereochemical)
conformation
conjugate acid–base pair
conjugated system (conjugation)
conjugative mechanism
connectivity
constitution
contributing structure
coordinate covalence
coordinate link
coordination
coordination number
coordinatively saturated complex
coordinatively unsaturated complex
coronands (coronates)
correlation analysis
coupling constant (spin-spin), J
covalent bond
Cox–Yates equation
critical micelle concentration
cross-conjugation
crown
cryptand
Curtin–Hammett principle
cybotactic region
cyclization
cycloaddition
cycloelimination
de-electronation
degenerate rearrangement
delocalization
detachment
detailed balancing (principle of)
diamagnetic
diastereoisomerism
dielectric constant
dienophile
dimerization
Dimroth–Reichardt E T parameter
dipolar aprotic solvent
dipolar bond
dipole-induced dipole forces
dipole–dipole interaction
disproportionation
dissociation
distonic radical cation
donor number (DN)
downfield
driving force (affinity) of a reaction, A
dual substituent-parameter equation
dyotropic rearrangement
η (eta or hapto) in inorganic nomenclature
educt
effective charge
effective molarity (effective concentration)
eighteen-electron rule
electrocyclic reaction
electrofuge
electromeric effect
electron acceptor
electron affinity, E ea
electron attachment
electron density
electron detachment
electron donor
electron transfer
electron-deficient bond
electron-donor-acceptor complex
electron-pair acceptor
electron-pair donor
electron-transfer catalysis
electronation
electronegativity
electroneutrality principle
electronic effect of substituents: symbols and signs
electrophile (electrophilic)
electrophilicity
element effect
elementary reaction
elimination
enantiomer
enantioselectivity
encounter complex
encounter pair
encounter-controlled rate
ene reaction
energy of activation
energy profile
enforced concerted mechanism
entering group
enthalpy of activation, Δ ‡ H °
entropy of activation, Δ ‡ S °
epimerization
epimers
E T-value
excess acidity
excimer
exciplex
excited state
extended Hammett equation
external ion return
external return
extrusion transformation
fast-atom bombardment (FAB) mass spectroscopy
field effect
flash vacuum pyrolysis (FVP)
fluxional
fragmentation
free radical
frontier orbitals
functional group
gas-phase acidity
gas-phase basicity
geminate pair
geminate recombination
general acid catalysis
general base catalysis
Gibbs energy diagram
Gibbs energy of activation (standard free energy of activation), Δ ‡ G o
Gibbs energy profile
ground state
group
group electronegativity
Grunwald–Winstein equation
guest
half life, t 1 / 2
halochromism
Hammett equation (Hammett relation)
Hammond principle (Hammond postulate)
Hansch constant
hard acid
hard base
heat capacity of activation, Δ ‡ C p o
heavy atom isotope effect
hemileptic
Henderson–Hasselbalch equation
heterobimetallic complex
heteroconjugation
heteroleptic
heterolysis (heterolytic)
heterolytic bond-dissociation energy
Hildebrand parameter
Hofmann rule
homo
homoaromatic
homoconjugation
homoleptic
homolysis (homolytic)
host
Hückel (4n + 2) rule
hybridization
hydration
hydrogen bond
hydrolysis
hydron
hydrophilic
hydrophobic interaction
hyperconjugation
hypsochromic shift
identity reaction
imbalance
imenes
imin
imine radical
inclusion compound (inclusion complex)
induction period
inductive effect
inductomeric effect
inert
inhibition
initiation
inner-sphere electron transfer
insertion
intermediate
intermolecular
intramolecular
intramolecular catalysis
intramolecular isotope effect
intrinsic barrier
inverse isotope effect
inverse kinetic isotope effect
inverted micelle
ion pair
ion pair return
ionization
ionization energy, E i
ionizing power
ipso-attack
isodesmic reaction
isoelectronic
isoentropic
isoequilibrium relationship
isokinetic relationship
isolobal
isomer
isomerization
isoselective relationship
isotope effect
isotope exchange
isotopic fractionation factor
isotopic scrambling
isotopologue
isotopomer
Kamlet–Taft solvent parameters
Kekulé structure (for aromatic compounds)
kinetic ambiguity
kinetic control of product composition
kinetic electrolyte effect (kinetic ionic-strength effect)
kinetic equivalence
kinetic isotope effect
Koppel–Palm solvent parameters
Kosower Z-value
labile
leaving group
left-to-right convention
levelling effect
Lewis acid
Lewis acidity
Lewis adduct
Lewis base
Lewis basicity
Lewis formula (electron dot or Lewis structure)
ligands
line formula
line-shape analysis
linear free-energy relation
linear solvation energy relationships
lipophilic
lipophilicity
London forces
lone (electron) pair
lyate ion
lyonium ion
magnetic equivalence
magnetization transfer
Markownikoff rule
mass-law effect
matrix isolation
mean life, τ
mechanism of a reaction
mechanism-based inhibition
medium
Meisenheimer adduct
melting point (corrected/uncorrected)
mesolytic cleavage
mesomeric effect
mesomerism
metastable
metathesis
method of isotopic perturbation
methylene
methylidyne
micellar catalysis
micelle
Michaelis–Menten kinetics
microscopic chemical event
microscopic diffusion control (encounter control)
migration
migratory aptitude
migratory insertion
mixing control
Möbius aromaticity
moiety
molecular entity
molecular mechanics calculation
molecular metal
molecular orbital
molecular rearrangement
molecularity
molecule
More O'Ferrall–Jencks diagram
multi-centre bond
multi-centre reaction
n-σ* delocalization (or n-σ* no bond resonance)
narcissistic reaction
neighbouring group participation
NIH shift
nitrenes
nitrenium ions
no-bond resonance
nonclassical carbocation
normal kinetic isotope effect
nucleofuge
nucleophile (nucleophilic)
nucleophilic catalysis
nucleophilicity
onium compounds
opposing reactions
optical yield
orbital steering
orbital symmetry
order of reaction, n
outer-sphere electron transfer
oxidation
oxidative addition
oxidative coupling
π-adduct
π-bond
π-complex
π-electron acceptor/donor group
parallel reactions
paramagnetic
partial rate factor
pericyclic reaction
periselectivity
perpendicular effect
persistent
pH-rate profile
phase-transfer catalysis
photolysis
polar aprotic solvent
polar effect
polar solvent
polarity
polarizability
potential-energy profile
potential-energy (reaction) surface
pre-association
pre-equilibrium (prior equilibrium)
primary isotope effect
primary kinetic isotope effect
primitive change
principle of least nuclear motion
principle of microscopic reversibility
product development control
product-determining step
promotion
propagation
protic
protolysis
proton affinity
proton transfer reaction
protophilic (solvent)
prototropic rearrangement (or prototropy)
pseudo-catalysis
pseudo-first-order reaction
pseudo-unimolecular
pseudo-zero-order reaction
pseudomolecular rearrangement
pseudopericyclic
quantitative structure–activity relationships (QSAR)
ρ-value (rho-value)
ρσ-equation (rho-sigma equation)
radical centre(s)
radical combination
radical (free radical)
radical ion
radical pair (geminate pair)
radiolysis
rate coefficient
rate law (empirical differential rate equation)
rate of disappearance
rate of reaction, v
rate-controlling step
rate-determining step (rate-limiting step)
reacting bond rules
reaction
reaction coordinate
reaction intermediate
reaction path
reaction stage
reaction step
reactive (reactivity)
reactivity index
reactivity–selectivity principle (RSP)
rearrangement
rearrangement stage
reduction
reductive elimination
regioselectivity (regioselective)
relaxation
relaxation kinetics
resonance
resonance energy
retroaddition
retrocycloaddition
Ritchie equation
σ, π (sigma, pi)
σ-adduct
σ-bond
σ-constant
σ-orbital
salt effect
saturation transfer
Saytzeff rule
scavenger
scrambling
secondary isotope effect
secondary kinetic isotope effect
selectivity
selectivity factor, S f
selectivity of a reagent
shielding
sigmatropic rearrangement
silylene
single-electron transfer mechanism (SET)
single-step reaction
Slater-type orbital
solvation
solvatochromic relationship
solvatochromism
solvent isotope effect
solvent parameter
solvolysis
solvophobicity parameter, Sp
SOMO
sonication
special salt effect
specific catalysis
spectator mechanism
spin density
spin label
spin trapping
stable
stationary state
steady state (stationary state)
stepwise reaction
stereoelectronic
stereoelectronic control
stereoselectivity
stereospecificity (stereospecific)
steric effect
steric hindrance
steric isotope effect
steric strain
steric-approach control
stopped flow
strain
subjacent orbital
substituent atom (group)
substituent electronegativity
substitution reaction
substrate
successor complex
superacid
supramolecule
Swain–Lupton equation
Swain–Scott equation
symbiosis
symproportionation
synchronization (principle of nonperfect synchronization)
synchronous
Taft equation
tautomeric effect
tautomerism
tautomerization
tele-substitution
telomerization
termination
tetrahedral intermediate
thermodynamic control of product composition
thermodynamic isotope effect
thermolysis
torquoselectivity
total chemiflux
transferability
transformation
transient (chemical) species
transition state
transition state analogue
transition structure
transmission coefficient
transport control
trapping
tunnelling
umpolung
unreactive
unstable
upfield
valence
valence isomer
valence tautomerization
van der Waals forces
volume of activation, Δ ‡ V
Wheland intermediate
Woodward–Hoffmann rules
ylides
Yukawa–Tsuno equation
Z-value
Zucker–Hammett hypothesis
zwitterionic compounds/zwitterions