Alphabetical Index

Additional Indexes

Physical Constants Units of Measure Physical Quantities SI Prefixes Ring Index General Formulae Exact Formulae Source Documents Terms by IUPAC Division Terms by Organization

Version 5.0.0 (14588 Terms)

DOI: 10.1351/goldbook

Jan Kaiser - Content Editor
Stuart J. Chalk - Technical Editor
Joint Subcommittee
on the IUPAC Gold Book

Terms (515) sourced from: 10.1351/pac199466051077

"Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)", Muller, P., Pure and Applied Chemistry 1994, 66(5), 1077

'A' value Arrhenius equation abstraction acceptor number acid acidity acidity function activated complex activation energy addition addition reaction additivity principle adduct agostic allylic substitution reaction alternant ambident amphiphilic amphiprotic solvent amphoteric anionotropic rearrangement annelation annulation annulenes antarafacial anti aprotic solvent aquation arenium ions aromatic aryne association asymmetric induction atomic orbital (\(\psi,\varphi,\chi\))attachment autocatalytic reaction automerization autoprotolysis autoprotolysis constant α-addition α-effect α-elimination π-adduct σ-adduct

Baldwin's rules Bell–Evans–Polanyi principle Brønsted relation Bredt's rule Brønsted acid Brønsted base Bunnett–Olsen equations base basicity bathochromic shift benzynes bifunctional catalysis binding site biradical bond bond dissociation bond energy bond number bond order (\(p_{\rm{rs}}\))bond-dissociation energy (\(D\))borderline mechanism bridged carbocation bridging ligand

Cox–Yates equation Curtin–Hammett principle cage cage compound captodative effect carbanion carbenes carbenium centre carbenium ion carbenoids carbocation carbonium ion carbynes catalysis catalyst catalytic coefficient chain reaction chain transfer charge population charge-transfer complex chelation cheletropic reaction chelotropic reaction chemical decomposition chemical equilibrium chemical flux (\(\varphi\))chemical reaction chemical relaxation chemical species chemically induced dynamic nuclear polarization chemoselectivity chromophore cine-substitution class (a) metal ion class (b) metal ion clathrates colligation common-ion effect on rates compensation effect complex composite reaction comproportionation concerted process condensation reaction configuration of electrons configuration in sterochemistry conformation conjugate acid–base pair conjugated system connectivity constitution contributing structure coordination coordination number coordinatively saturated complex coordinatively unsaturated complex correlation analysis coupling constant covalent bond critical micelle concentration cross-conjugation crown cryptand cybotactic region cyclization cycloaddition cycloelimination σ-constant

Dimroth–Reichardt E_T parameter (\(E_{\rm{T}}\))degenerate rearrangement delocalization detachment detailed balancing diamagnetic diastereoisomerism dienophile dimerization dipolar aprotic solvent dipolar bond dipole–dipole interaction disproportionation dissociation distonic radical cation donor number driving force (\(A\)) of a reaction dual substituent-parameter equation dyotropic rearrangement

educt effective charge effective molarity eighteen-electron rule electrocyclic reaction electrofuge electromeric effect electron acceptor electron affinity electron attachment electron density electron detachment electron donor electron transfer electron-deficient bond electron-pair acceptor electron-pair donor electron-transfer catalysis electronegativity electroneutrality principle electronic effect of substituents: symbols and signs electrophile electrophilicity element effect elementary reaction elimination enantiomer encounter complex encounter-controlled rate ene reaction enforced concerted mechanism entering group enthalpy of activation entropy of activation epimerization epimers excimer exciplex excited state extended Hammett equation extrusion transformation π-electron acceptor/donor group

fast-atom bombardment mass spectrometry field effect flash vacuum pyrolysis fluxional fragmentation frontier orbitals functional group

Gibbs energy diagram Gibbs energy of activation Grunwald–Winstein equation gas-phase acidity gas-phase basicity geminate pair geminate recombination general acid catalysis general base catalysis ground state group group electronegativity guest

Hammett equation Hammond principle Hansch constant Henderson–Hasselbalch equation Hildebrand parameter Hofmann rule Hückel (4n + 2) rule half life halochromism hard acid hard base heat capacity of activation heavy atom isotope effect heterobimetallic complex heteroconjugation heteroleptic heterolysis heterolytic bond-dissociation energy homo homoaromatic homoconjugation homoleptic homolysis host in biotechnology hybridization hydration hydrogen bond hydrolysis hydron hydrophilic hydrophobic interaction hyperconjugation hypsochromic shift η in inorganic nomenclature

ipso-attack identity reaction imbalance inclusion compound 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 inverted micelle ion pair ion pair return ionization ionization energy ionizing power 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 Koppel–Palm solvent parameters kinetic control of product composition kinetic electrolyte effect kinetic equivalence kinetic isotope effect

Lewis acid Lewis acidity Lewis adduct Lewis base Lewis basicity Lewis formula London forces labile leaving group left-to-right convention levelling effect ligands line formula line-shape analysis linear free-energy relation linear solvation energy relationships lipophilic lipophilicity lone pair lyate ion lyonium ion

Markownikoff rule Meisenheimer adduct Michaelis–Menten kinetics More O'Ferrall–Jencks diagram Möbius aromaticity magnetic equivalence magnetization transfer mass-law effect matrix isolation mechanism of a reaction mechanism-based inhibition medium melting point corrected mesolytic cleavage mesomeric effect mesomerism metathesis method of isotopic perturbation micellar catalysis micelle microscopic diffusion control migration migratory aptitude migratory insertion mixing control moiety molecular entity molecular mechanics calculation molecular metal molecular orbital molecular rearrangement molecularity molecule multi-centre bond multi-centre reaction

NIH shift n-σ* delocalization narcissistic reaction neighbouring group participation nitrenes nitrenium ions nonclassical carbocation nucleofuge nucleophile 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

pH-rate profile paramagnetic partial rate factor pericyclic reaction periselectivity persistent phase-transfer catalysis photolysis polar effect polarity of a solvent polarizability potential-energy profile potential-energy surface pre-association pre-equilibrium primary isotope effect primitive change principle of least nuclear motion principle of microscopic reversibility product development control product-determining step protolysis proton affinity proton transfer reaction protophilic pseudo-catalysis pseudopericyclic

quantitative structure–activity relationships

Ritchie equation radical radical centre radical ion radical pair radiolysis rate law rate of reaction rate-controlling step rate-determining step reacting bond rules reaction coordinate reaction path reaction stage reaction step reactive reactivity index reactivity–selectivity principle rearrangement stage reduction reductive elimination regioselectivity relaxation resonance resonance energy

SOMO Saytzeff rule Slater-type orbital Swain–Lupton equation Swain–Scott equation saturation transfer scavenger secondary isotope effect selectivity selectivity factor shielding sigmatropic rearrangement silylene single-electron transfer mechanism single-step reaction solvation solvatochromic relationship solvatochromism solvent isotope effect solvent parameter solvolysis solvophobicity parameter sonication special salt effect specific catalysis spectator mechanism spin density spin label spin trapping stable stationary state steady state stepwise reaction stereoelectronic stereoelectronic control stereoselectivity stereospecificity steric effect steric hindrance steric isotope effect steric-approach control stopped flow strain subjacent orbital substituent atom substitution reaction substrate successor complex superacid supramolecule symbiosis synchronization synchronous σ, π

Taft equation tautomerism tautomerization tele-substitution telomerization termination tetrahedral intermediate thermodynamic control of product composition thermodynamic isotope effect thermolysis torquoselectivity transferability transformation transient species transition coordinate transition state transition state analogue transition structure trapping tunnelling

umpolung unreactive unstable

ρ-value valence valence isomer valence tautomerization van der Waals forces volume of activation

Yukawa–Tsuno equation ylides

Z-value Zucker–Hammett hypothesis zwitterions