The Journal of Organic Chemistry
Standard Abbreviations and Acronyms
observed optical rotation in degrees cm–1 wavenumber(s) [] specific rotation [expressed without cod 1,5-cyclooctadiene units; the units, (degmL)/(gdm), compd compound are understood] concd concentrated Å angstrom(s) concn concentration Ac acetyl COSY correlation spectroscopy acac acetylacetonate cot 1,3,5,7-cyclooctatetraene ADP adenosine 5-diphosphate Cp cyclopentadienyl AIBN 2,2-azobisisobutyronitrile m-CPBA meta-chloroperoxybenzoic acid AM1 Austin model 1 CV cyclic voltammetry AMP adenosine 5-monophosphate chemical shift in parts per million Anal. combustion elemental analysis downfield from tetramethylsilane anhyd anhydrous d day(s); doublet (spectral); deci AO atomic orbital d density aq aqueous DABCO 1,4-diazabicyclo[2.2.2]octane Ar aryl dansyl 5-(dimethylamino)- atm atmosphere(s) 1-naphthalenesulfonyl DBN 1,5-diazabicyclo[4.3.0]non-5-ene ATP adenosine 5-triphosphate DBU 1,8-diazabicyclo[5.4.0]undec-7-ene ATPase adenosinetriphosphatase av average DCC N,N-dicyclohexylcarbodiimide 9-BBN 9-borabicyclo[3.3.1]nonyl DCE 1,2-dichloroethane 9-BBN–H 9-borabicyclo[3.3.1]nonane DDQ 2,3-dichloro-5,6-dicyano- Bn, Bzl benzyl 1,4-benzoquinone DEAD diethyl azodicarboxylate bpy 2,2-bipyridyl BOC, Boc tert-butoxycarbonyl DEPT distortionless enhancement by bp boiling point, base pair polarization transfer br broad (spectral) DFT density functional theory Bu, n-Bu normal (primary) butyl DIBALH diisobutylaluminum hydride s-Bu sec-butyl DMA dimethylacetamide DMAP 4-(N,N-dimethylamino)pyridine t-Bu tert-butyl DMDO dimethyldioxirane Bz benzoyl (not benzyl) DME 1,2-dimethoxyethane B3LYP 3-parameter hybrid Becke exchange/ DMF dimethylformamide Lee–Yang–Parr correlation functional DMPU 1,3-dimethyl-3,4,5,6-tetrahydro- °C degrees Celsius 2(1H)-pyrimidinone calcd calculated DMSO dimethyl sulfoxide cAMP adenosine cyclic 3,5-phosphate DMT 4,4 -dimethoxytrityl CAN ceric ammonium nitrate CASSCF complete active space self-consistent (4,4-dimethoxyltriphenylmethyl) field DNA deoxyribonucleic acid CASPT2 complete active space with second-order DPS tert-butyldiphenylsilyl perturbation theory dr diastereomeric ratio cat catalytic DTT dithiothreitol CBZ, Cbz benzyloxycarbonyl (preferred over the E1 unimolecular elimination abbreviation Z) E2 bimolecular elimination CC coupled cluster ED50 dose effective in 50% of test subjects CD circular dichroism EDTA ethylenediaminetetraacetic acid cDNA complementary deoxyribonucleic acid EI electron impact EPR electron paramagnetic resonance c-Hex, c-C6H11 cyclohexyl CI chemical ionization; configuration eq equation interaction equiv equivalent CIF crystallographic information file er enantiomeric ratio CIDNP chemically induced dynamic nuclear ESI electrospray ionization polarization Et ethyl cm centimeter(s) FAB fast atom bombardment FD field desorption Me methyl FID flame ionization detector; free induction MEM (2-methoxyethoxy)methyl decay Mes 2,4,6-trimethylphenyl (mesityl) Fmoc 9-fluorenylmethoxycarbonyl [not methylsulfonyl (mesyl)] FT Fourier transform MHz megahertz g gram(s); prefix to NMR abbreviation min minute(s); minimum denoting gradient-selected (e.g. mM millimolar (millimoles per liter) gCOSY, gHMQC) MO molecular orbital GC gas chromatography mol mole(s); molecular (as in mol wt) GTP guanosine 5-triphosphate MOM methoxymethyl h hour(s) mp melting point HF Hartree–Fock MP Møller–Plesset perturbation theory HMBC heteronuclear multiple bond correlation MRCI multi-reference configuration interaction HMPA hexamethylphosphoric triamide mRNA messenger ribonucleic acid (hexamethylphosphoramide) Ms methylsulfonyl (mesyl) HMQC heteronuclear multiple quantum MS mass spectrometry correlation MTBE methyl tert-butyl ether HOMO highest occupied molecular orbital MW, mol wt molecular weight HPLC high-performance liquid m/z mass-to-charge ratio (not m/e) chromatography N normal (equivalents per liter) HRMS high-resolution mass spectrometry NAD+ nicotinamide adenine dinucleotide HSQC heteronuclear single quantum correlation NADH reduced NAD Hz hertz NBO natural bond orbital ICR ion cyclotron resonance NBS N-bromosuccinimide INDO intermediate neglect of differential NCS N-chlorosuccinimide overlap NICS nucleus-independent chemical shift IP ionization potential nm nanometer(s) IR infrared NMO N-methylmorpholine-N-oxide J coupling constant (in NMR NMP N-methylpyrrolidone spectrometry) NMR nuclear magnetic resonance k kilo NOE nuclear Overhauser effect K kelvin(s) (absolute temperature) NOESY nuclear Overhauser effect spectroscopy L liter(s) NRT natural resonance theory LAH lithium aluminum hydride Nu nucleophile LCAO linear combination of atomic orbitals obsd observed LD50 dose that is lethal in 50% of test subjects OD optical density LDA lithium diisopropylamide; local density ORD optical rotary dispersion approximation PCC pyridinium chlorochromate LFER linear free energy relationship PDC pyridinium dichromate LHMDS lithium hexamethyldisilazane, lithium PES photoelectron spectroscopy bis(trimethylsilyl)amide Ph phenyl lit. literature value (abbreviation used with piv pivaloyl period) pm picometer(s) LTMP lithium 2,2,6,6-tetramethylpiperidide PM3 parametric method 3 LUMO lowest unoccupied molecular orbital PMB p-methoxybenzyl μ micro PPA poly(phosphoric acid) m multiplet (spectral); meter(s); milli ppm part(s) per million M molar (moles per liter); mega PPTS pyridinium para-toluenesulfonate M+ parent molecular ion Pr propyl MALDI matrix-assisted laser desorption i-Pr isopropyl ionization PT perturbation theory max maximum PTC phase-transfer catalysis MCD magnetic circular dichroism py pyridine MCR multicomponent reaction q quartet (spectral) MCSCF multi-configuration self-consistent field QSAR quantitative structure–activity MD molecular dynamics relationship RCM ring-closure metathesis vis visible redox reduction–oxidation vol volume rel relative v/v volume per unit volume Rf retention factor (in chromatography) (volume-to-volume ratio) RHF restricted Hartree–Fock wt weight ROESY rotating frame Overhauser effect w/w weight per unit weight spectroscopy (weight-to-weight ratio) ROMP ring-opening metathesis polymerization ZINDO Zerner parameterization of intermediate rRNA ribosomal ribonucleic acid neglect of differential overlap rt room temperature s singlet (spectral); second(s) SAR structure–activity relationship SCF self-consistent field SEM scanning electron microscopy SET single electron transfer SN1 unimolecular nucleophilic substitution SN2 bimolecular nucleophilic substitution SN nucleophilic substitution with allylic rearrangement SOMO single-occupied molecular orbital t triplet (spectral) t time; temperature in units of degrees Celsius (ºC) T absolute temperature in units of kelvins (K) TBAB tetrabutylammonium bromide TBAC tetrabutylammonium chloride TBAF tetrabutylammonium fluoride TBS tert-butyldimethylsilyl TBHP tert-butyl hydroperoxide TCA trichloroacetic acid TCNE tetracyanoethylene TDDFT time-dependent density functional theory TEAB tetraethylammonium bromide temp temperature Tf trifluoromethanesulfonyl (triflyl) TFA trifluoroacetic acid TFAA trifluoroacetic anhydride THF tetrahydrofuran THP tetrahydropyran-2-yl TIPS triisopropylsilyl TLC thin-layer chromatography TMAI tetramethylammonium iodide TMEDA N,N,N,N-tetramethyl- 1,2-ethylenediamine TMS trimethylsilyl; tetramethylsilane TOF time-of-flight Tr triphenylmethyl (trityl) tRNA transfer ribonucleic acid tR retention time (in chromatography) Ts para-toluenesulfonyl (tosyl) TS transition state UHF unrestricted Hartree–Fock UV ultraviolet VCD vibrational circular dichroism