Common Abbreviations in Organic Chemistry
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Abbreviations: Solvents, Reagents, Protecting Groups, and Reaction Conditions
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- Δ heat is applied; or a pericyclic rearrangement in the absence of light
- ↑↓ reflux: heating at constant boiling temperature of solvent using a condenser
- α– alpha: the carbon bearing the functional group in question; or the optical rotation (±)
- δ chemical shift in parts per million (NMR); or—a partial charge in a covalent bond
- Φ quantum yield
- ω– omega: the (carbon) position farthest away from the functional group in question
- hν light; or photochemical rearrangement (h=Plank’s constant, ν is the frequency of a photon)
- Ac- acetyl (-COCH3)
- AcO- acetoxy (-OCOCH3), acyloxy
- AD Sharpless asymmetric dihydroxylation (“AD-mix-α™ or AD-mix-ß™” means pre-made catalyst)
- AE Sharpless asymmetric epoxidation
- AIBN N, N‘-azobisisobutyronitrile (radical initiator)
- Aldrithiol™ 2,2′-dipyridyldisulfide
- Allyl- allylic; at the position adjacent to a C=C double bond
- Alloc- allyloxycarbonyl protecting group
- Ar- aryl (any aromatic substituent, not otherwise specified)
- B2H6 diborane; the dimerized form of BH3 and functionally the same thing as BH3
- 9-BBN 9-borabicyclononane (functionally equivalent to BH3 with greater selectivity)
- BMS BH3-dimethyl sulfide complex, easier to handle than BH3
- BINAP 2,2′-bis(diphenylphosphino)-1,1 ‘- binaphthyl
- Boc- tert-butoxycarbonyl protecting group
- BOM- benzyloxymethyl protecting group
- BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphinic chloride
- Bn- benzyl (PhCR2-); any carbon directly attached to a benzene ring
- brsm % yield based on recovered starting material; (a euphemism for poor yield)
- BTAF benzyltrimethyl ammonium fluoride
- Bz- benzoyl (PhCO-); often confused with benzyl (Bn- or PhCH2)
- BHT tert-butylated hydroxytoluene (di-t-butylhydroxytoluene); a radical scavenger
- cat. catalytic or catalyst added; (sub-stoichiometric amount)
- CAN ceric ammonium nitrate
- CBS Corey-Bakshi-Shibata catalytic asymmetric ketone reducing agent
- Cbz- benzyloxycarbonyl protecting group
- CH2N2 diazomethane
- COD 1,5-cyclooctadiene
- Cp- cyclopentadienyl (a common organomettalic ligand)
- m-CPBA meta-chloroperoxybenzoic acid (or peroxyacid or peracid)
- CSA camphorsulfonic acid (a chiral and organic-soluble Bronsted acid)
- d– dextrorotatory, (+)(clockwise optical activity)
- d days of reaction time
- DAST diethylaminosulfur trifluoride
- dba- dibenzylideneacetone (a common organometallic ligand)
- DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
- DCC 1,3-dicyclohexylcarbodiimide
- DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
- DEAD diethyl azodicarboxylate (coupling agent)
- dean-stark a method of separating water out of distillate by density
- (±)-DET diethyl tartrate (chiral ligand)
- DIPA diisopropylamine
- DIPEA diisopropylethylamine (Hünig’s Base)
- DHP dihydropyran
- DHQD dihydroquinidine
- DIBAL diisobutyl aluminum hydride; or DIBAL-H
- DIBALH diisobutyl aluminum hydride; or DIBAL
- DIC diisopropylcarbodiimide
- DMAP 4-N,N-dimethylaminopyridine
- DME dimethoxyethane (solvent)
- DMF dimethylformamide (polar aprotic solvent)
- DMP Dess-Martin periodinane
- DMPM 3,4-dimethoxybenzyl
- DMS dimethyl sulfide
- DMSO dimethyl sulfoxide (polar aprotic solvent)
- DPPA diphenylphosphoryl azide
- DPS 2.2′-dipyridyldisulfide or Aldrithiol™
- dr diastereomeric ratio; (epimer A : epimer B) (can be used for E/Z alkenes)
- EDI or EDCI; ethyl N,N-dimethaminopropyl carbodiimide (water-soluble coupling agent)
- EE- 1-ethoxyethyl protecting group
- %ee percent enantiomeric excess
- eq. or equiv. the number of molar equivalents of reagent added
- Et- ethyl (-CH2CH3)
- EtOH ethanol (IUPAC); ethyl alcohol; “grain” alcohol
- ethylene oxide the simplest epoxide; oxacyclopropane
- FDPP pentafluorophenyl diphenylphosphinate
- Fmoc- 9-fluorenylmethoxycarbonyl
- gem. geminal; two of the same substituents on a carbon (or 1,1-)
- hr hours of reaction time
- [H] reduction (reagents/conditions otherwise unspecified)
- HMPA hexamethylphosphoramide (aggregate-breaking aprotic solvent)
- HMPT hexamethylphosphorus triamide (same as HMPA)
- HWE Horner-Wadsworth-Emmons Olefination
- i– see iso-
- imid. imidazole
- INV inversion of stereochemistry
- iso– any chain terminating with gem (1,1) dimethyl groups
- (±)-Ipc iso-pinylcampheyl (chiral ligand)
- KDA potassium diisopropylamide
- KHMDS potassium bis-trimethylsilylamide
- KOt-Bu potassium tert-butoxide (sterically bulky base)
- K-Selectride™ potassium tri-sec-butylborohydride
- l– levorotatory (counter-clockwise optical activity)
- LA lewis acid
- LAH lithium aluminum hydride (LiAlH4)
- LDA lithium diisopropylamide
- LDEA lithium diethylamide
- LiHMDS lithium hexamethyltrisilazide
- lindlar Lindlar’s catalyst (quinoline, Pd, Pb(OAc)2, Ca(CO3))
- lit. literature value
- LTMP lithium 2,2,6,6-tetramethyl piperidide
- m– meta (or 3-phenyl); (a 1,3-disubstituted benzene)
- M+ molecular ion peak (in mass spectrometry)
- MEM- 2-methoxyethoxyethyl protecting group
- Me- methyl (CH3-)
- MeOH methanol (IUPAC); methyl alcohol; “wood” alcohol
- MMPP magnesium monoperoxyphthalate (epoxidizing agent)
- mol molar equivalent; same as equivalent (eq. or equiv.)
- MOM- methoxymethyl protecting group
- MPM- p-methoxybenzyl protecting group
- MS molecular sieves (usu. preceded by pore size in angstroms, e.g. 4Å MS)
- Ms- methanesulfonyl-
- MTBE methyl tert-butyl ether (a solvent)
- MTM- methylthiomethyl protecting group
- MW microwave (not molecular weight in this context)
- n– normal (unbranched chain of hydrocarbons)
- N- a substituent attached to nitrogen, not the carbon chain
- N, N- two substituent groups attached to nitrogen
- NaHMDS sodium hexamethyl trisilazide
- NaOEt sodium ethoxide
- NaOMe sodium methoxide
- NaOPr sodium isoproxide
- NBS N-bromosuccinimide
- NCS N-chlorosuccinimide
- neo- neopentyl; any carbon attached to a quaternary (4º) carbon
- NIS N-iodosuccinimide
- NMM N-methylmorpholine
- NMO N-methylmorpholine-N-oxide
- N-PSP N-phenylselenophthalimide
- nosyl p-nitrophenylsulfonyl
- Ns- nosyl or 4-nitrophenylsulfonyl-
- o- ortho or (2-phenyl) on benzene, a 1,2-disubstituted benzene
- [O] oxidation (reagent/conditions not otherwise specified)
- -OBr brosylate (4-bromophenylsulfonyl- [not bromine attached to oxygen])
- -OMs mesylate (methylsulfonyl-)
- -ONs nosylate (4-nitrophenylsulfonyl-)
- -OR alkyloxy (the IUPAC prefix for an ether attachment)
- -OTf triflate )4-trifluromethylsulfonyl)-
- -OTs tosylate (4-methylphenylsulfonyl)-
- p– para or (1,4-) substitution on benzene
- PCC pyridinium chlorochromate
- PDC pyridinium dichromate (explosive version of PCC)
- peroxides a generic peroxide; radical initiator
- Ph- phenyl (benzene substituent)
- PhH benzene
- Pr- n-propyl (-CH2CH2CH3)
- Piv- pivaloyl
- PMB- p-methoxybenzyl
- PMP- p-methoxyphenyl
- PPA polyphosphoric acid
- PPL porcine pancreatic lipase
- PPTS pyridinium p-toluenesulfonate
- PTSA p-toluenesulfonic acid
- Pv- pivaloyl protecting group
- pyr. pyridine (C5H5N); a common basic solvent
- quant. a product yield that is as close to 100% as possible (most chemists don’t say 100% yield)
- R- the “Universal Descriptor” can be any atom or group; esp. alkyl groups; “rest of the molecule”
- Red-Al® sodium bis(2-methoxyethoxy-)aluminum hydride
- reflux reaction is heated at constant refluxing temperature (boiling point of) solvent
- RET retention of stereochemistry
- Rose Bengal photoexcitor of molecular oxygen (O2) to its triplet state
- sec- secondary or 2º
- SEM- [2-(trimethylsilyl)methyl]- protecting group
- SEMCl [2-(trimethylsilyl)ethoxy)methyl chloride
- sodamide sodium amide (NaNH2) a strong base
- Swern Swern oxidation (oxalyl chloride, DMSO, then Et3N)
- t– tert– (tertiary)
- TBAF tetrabutyl ammonium fluoride (same as BTAF)
- TBDMS- tert-butyldimethylsilyl protecting group
- TBDPS- tert-butyldiphenylsilyl protecting group
- TBS tert-butyldimethylsilyl (same as TBDMS-)
- TCDI thiocarbonyl di-imidazole
- tert– attached to a tertiary carbon or 3º
- Tf- trifluoromethanesulfonyl
- TFA trifluoroacetic acid
- TFAA trifluoroacetic anhydride
- THF tetrahydrofuran (solvent)
- THP- tetrahydropyran protecting group
- TIPS- triisopropylsilyl protecting group
- TMG tetramethylguanidine
- TMS- trimethylsilyl- protecting group
- TMS tetramethylsilane (the standard chemical used to reference zero ppm in NMR spectroscopy)
- TMSCl trimethylsilyl chloride
- TMSOTf trimethylsilyl triflate
- tol. toluene (solvent)
- o-tolyl ortho-toluyl
- TPAP tetra n-propyl ammonium perruthenate
- Tr- trityl = triphenylmethyl-
- Troc- 2,2,2-trichloroethoxycarbonyl
- TsCl tosyl chloride
- TsO- p-toluenesulfonate
- p-TsOH p-Toluenesulfonic acid
- vic- vicinal or related as groups on adjacent carbons or (1,2-)
- Vitride® sodium bis(2-methoxyethoxy)aluminium hydride
- w/u work-up or quench (neutralization conditions specific to the product formed and extraction)
- X- any of the Group VII atoms or halogens, unless specified otherwise
- xs excess (a molar quantity sufficient to reach full conversion of the reaction in question)
- Z- benzyloxycarbonyl (Cbz) (e.g -OZ = -OCbz) protecting group
If not found here, refer to the Database Glossary.
Abbreviations In Organic Chemistry
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