Glossary of Organic Chemistry Jargon and Acronyms
This is an alphabetical listing of some common jargon words, slang, and acronyms used in organic chemistry. Have a suggestion for this list? Please send us a note on the Contact page.
A |
B |
C |
D |
E |
F |
G |
H |
I |
J |
K |
L |
M |
N |
O |
P
Q |
R |
S |
T |
U |
V |
W |
X |
Y |
Z |
Numbers, Greek Letters, Symbols
A
- Ac
- Acetyl
- Acryloyl
- 2-propenoyl; the CH2CHCO group
- Ad
- Adamantyl
- Allene
- An olefin connected directly to another olefin so that the carbon in the middle is double bonded to both of the carbons next to it (that is, as C=C=C).
- Allyl/Allylic
- On the α-carbon of an olefin.
- Anh.
- Anhydrous
- Anti
- On opposite sides
- Analytical
- In chromatography, the scale at which only enough oif a mixture is separated so that each compound can be analyzed spectroscopically. Compare with Preparatory
- aq
- Aqueous
- Ar
- Any generic aromatic group (e.g. Phenyl, Benzyl, Napthyl, etc.)
- ATP
- Adenosine triphosphate
B
- BINAP
- 2,2'-(bisphenylphosphino)-1,1'-binaphthyl
- Bn
- Benzyl
- Boc
- tert-butoxycarbonyl
- BOM
- Benzyloxymethyl
- Bu
- Butyl
C
- C2
- 180° rotational symmetry about some axis (usually of a molecule)
- Carbon tet
- Carbo tetrachloride
- CBS
- Corey-Bakshi-Shibata oxazaborolidine
- Cbz
- Benzyloxycarbonyl
- cHex
- See Cy
- Cinnamic
- The PhCH=CHCO- group
- Cis
- For doubly substituted double bonds, the two substituents are on different carbons and on the same side
- Cp
- Cyclopentadienyl
- CSA
- Camphorsulfonic acid
- Cy
- Cyclohexyl
- Cyhex
- See Cy
- Cyp
- See Cp
D
- DABCO
- 1,4-diazabicyclo[2.2.2]octane
- DBU
- 1,8-diazabicyclo[5.4.0]undec-7-ene
- DCC
- Dicyclohexylcarbodiimide
- DCM
- Dichloromethane
- DDQ
- 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
- de
- Diastereomeric excess
- DEAD
- Diethyl azodicarboxylate
- DIBAL/DIBAL-H
- Diisobutylaluminum Hydride
- DIEA
- Diisopropylethyl amine (Hunig's Base)
- DIPEA
- See DIEA
- DMAP
- N,N-dimethylaminopyridine
- DMF
- N,N-dimethyl formamide
- DMP
- Dess-Martin periodinane
- DMPU
- N,N'-dimethylpropyleneurea
- DMS
- Dimethyl sulfide
- DMSO
- Dimethyl sulfoxide
E
- ee
- Enantiomeric excess
- El
- Electrophile
- Endo
- Opposite of exo, the orientation of reactants in a pericyclic reaction such that the substituents on the two reacting fragments overlap the most.
- Et
- Ethyl
- Exo
- Opposite of endo, the orientation of reactants in a pericyclic reaction such that the substituents on the two reacting fragments overlap the least.
F
- FID
- Free induction decay; the raw data from FTNMR spectroscopy, which gives chemical shift data after a Fourier-transform
- Flash
- Flash chromatography
- Fmoc
- 9-flourenylmethoxycarbonyl
- FTIR
- Fourier-transform infrared spectroscopy
- FTNMR
- Fourier-transform nuclear magnetic resonance spectroscopy
G
H
- Hetero-
- (Prefix) (1) Involving a heteroatom at a key reactive position in place of a usual carbon atom, e.g. Hetero-Diels Alder; (2) involving different components (e.g. heterodimer); (3) Not the same all throughout (e.g. heterogeneous).
- Heteroatom
- Any non-carbon atom substitutent, usually non-metal, non-halogen species (but not always).
- Heterocycle
- A cyclic, often aromatic compound with a heteroatom as a key ring atom.
- Heterodimer
- A compound composed of two different subunits; technically, a misnomer, as dimer refers to what is sometimes called the homodimer
- HMPA
- See HMPT
- HMPT
- Hexamethylphosphorotriamide, hexamethylphosphoric triamide; sometimes, hexamethyl phosphine triamide
- Homo-
- (Prefix) (1) Different from the root word by an extra methylene group, usually in the middle of a hydrocarbon chain; (2)involving the same components (e.g. homodimer); (3) The same throughout (e.g. homogeneous).
- HOMO
- Highest occupied molecular orbital
- Homodimer
- A compound composed of two identical subunits; technically, a misnomer, as dimer refers to the same thing
- Homology
- A process in which a methylene group is added to the molecule
- HPLC
- High pressure liquid chromatography or high performance liquid chromatography
- Hygroscopic
- Water absorbing. Very hygroscopic compounds can absorb humidity out of the air
I
- Im
- See Imid
- Imid
- Imidazole
- IPA
- Isopropyl alcohol
- iPr
- Isopropyl
- IR
- Infrared spectroscopy
J
K
- KAPA
- Potassium 3-aminopropyl amide
L
- LAH
- Lithium aluminum hydride
- LCAO
- Linear combination of atomic orbitals
- LDA
- Lithium diisopropylamide (lithium diisopropylamine)
- L-Selectride
- Lithium tri-sec-butylborohydride
- LTEAH
- Lithium triethoxyaluminohydride
- LUMO
- Lowest unoccupied molecular orbital
- Lut
- 2,6-lutidine
M
- MALDI
- Matrix-Assisted Laser Desorption/Ionization (Mass spectrometry); a way to ionize large molecules for mass spectroscopy using a laser-active chemical
- MassSpec
- Mass spectrometry
- MC
- Methylene chloride (See DCM)
- MCPBA
- Meta-chloroperbenzoic acid (3-chloro peroxybenzoic acid)
- Me
- Methyl
- Mes
- Mesityl (3,4,5-trimethylphenyl)
- Methylene
- A -CH2- group
- MO
- Molecular orbital, or Molecular orbital theory
- mol%
- Molar %; a reactant used at 10 mol% is used with 0.1 equivalents compared to the reference reactant or substrate
- MOM
- Methoxymethyl
- MPLC
- Medium pressure liquid chromatography
- MRI
- Magnetic resonance imagining; the use of NMR to image biological materials
- Ms
- See Mes
- MS
- Mass spectrometry
- MTM
- Methylthiomethyl
- MVK
- Methyl vinyl ketone
N
- NAD
- Nicotineamide Adenine Dinucleotide (Oxidized form of NADH)
- NADH
- Nicotineamide Adenine Dinucleotide Hydride (Reduced form of NAD)
- NADP
- Nicotineamide Adenine Dinucleotide Phosphate (Oxidized form of NADPH)
- NADP
- Nicotineamide Adenine Dinucleotide Phosphate Hydride (Reduced form of NADP)
- NBS
- N-bromosuccinimide
- nBu
- n-Butyl
- NCS
- N-chlorosuccinimide
- NIS
- N-iodosuccinimide
- NMM
- N-methylmorpholine
- NMR
- Nuclear magnetic resonance spectroscopy
- Np
- Naphthyl
- nPr
- n-Propyl
- Nu
- Nucleophile
O
- OAc
- Acetate
- Olefin
- A carbon-carbon double bond
- OTf
- Triflate (See Triflyl)
P
- PCC
- Pyridinium chlorochromate
- PG
- Any protecting group (e.g. TMS, TBS, Bn)
- Ph
- Phenyl
- Phase
- Can refer to either solid, liquid, and gas phases, or phases with regards to the separation of oils and aqueous liquids (e.g. aqueous phase)
- Pr
- Propyl
- Prep or Preperatory
- In chromatography, the scale needed to isolate compounds for further experiments. A larger scale than for analytical chromatography.
- Pyrophoric
- Ignitable when exposed to air
Q
R
- R
- (1) In a chemical diagram, any arbitrary functional group; (2) For a tetrahedral stereocenter, the configuration of bonds such that with the lowest priority group in the back, the priority order for the remaining three substituents from highest to lowest proceeds in a clockwise fashion (the same direction as "right" on a steering wheel).
- rbf
- Round-bottom flask
- Rf
- Retention factor; in TLC, the ratio of the distance the spot has moved from the baseline to the distance the solvent/eluent has gone
S
- S
- For a tetrahedral sterocenter, the configuration of bonds such that with the lowest priority group in the back, the priority order for the remaining three substituents from highest to lowest proceeds in a counter-clockwise fashion.
- sBu
- sec-Butyl
- Sep Funnel
- Separatory funnel
- SOMO
- Singly-occupied molecular orbital
- Syn
- On the same side
T
- TADA
- Transannular Diels-Alder reaction
- TBAF
- Tetrabutyl ammonium flouride
- TBDPS
- t-Butyl diphenyl silyl
- TBS
- t-Butyl dimethyl silyl
- t-Bu
- tert-Butyl
- TEA
- Triethylamine
- TES
- Triethyl silyl
- TFA
- Trifluoroacetic acid
- Tf
- See Triflyl
- THF
- Tetrahydrofuran
- THP
- Tetrahydropyran
- TIPS
- Triisopropylsilyl
- TLC
- Thin-layer chromatography
- TMS
- Trimethylsilyl
- Tos
- See Tosyl
- Tosyl
- Toluene-sulfonyl
- Tr
- See Trityl
- Trans
- For doubly substituted double bonds, the two substituents are on opposite sides and on different carbons
- Transannular
- An intramolecular reaction that occurs across a (usually large) ring
- Triflyl
- Triflouromethyl sulfonyl
- Trityl
- Triphenyl methyl
- Ts
- See Tosyl
- TS
- Transition state
U
V
- Vinyl
- Bonding directly to a double bond
W
X
Y
Z
- Z
- See Cbz
Numbers, Greek Letters, Symbols
- 9-BBN
- 9-borabicyclo[3.3.1]nonane
- α or Alpha
- Referring to the first atom or group away from some reference point (e.g. α-carbon refers to the carbon right next to the atom one is discussing). The subsequent substituents are named ascending the Greek letter scale (β, γ, &delta, and so on).
- α-helix (Alpha-helix)
- A helical coil of amino acids that have hydrogen bonds between every fourth amino acid residue
- β-sheet (Beta-sheet)
- An arrangement of amino acid chains such that each chain is H-bonded to the two chains next to it
- χ (Chi)
- A chiral auxiliary group, often (but not limited to) the Evans chiral oxazolidinone group
- χn
- A chiral auxiliary derived from R-valine (Note: n is almost a mirror image of v, which is the source of the notation; see the entry for χv
- χp
- A chiral auxiliary derived from L-phenylalanine; see the entry for χ
- χq
- A chiral auxiliary derived from R-phenylalanine (Note: q is nearly a mirror image of p, which is the source of the notation; see χp)/dd>
- χv
- A chiral auxiliary derived from L-valine; see the entry for χ
- Φ (Phi)
- (1) In a chemical diagram or formula, usually a phenyl group (the same as Ph) or a substituted phenyl group; (2) In physical chemistry or quantum mechanics, usually refers to a wavefunction or orbital that represents the behavior of the electrons in a system. ψ (psi) is also used.
- ψ (Psi)
- In physical chemistry or quantum mechanics, usually refers to the wavefunction or orbital that represent the behavior of the electrons in a system. Sometimes also φ (phi).
- [H]
- Reduction
- [O]
- Oxidation
- ‡
- Of or relating to a transition state