Abbreviations

March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 7th Edition (2013)

Common Abbreviations

Other, less common abbreviations are given in the text when the term is used.

Acetyl

acac

Acetylacetonate (ligand)

AIBN

Azobisisobutyronitrile

Aqueous

ARC

Anion relay chemistry

Axial

9-Borabicyclo[3.3.1]nonylboryl

9-BBN

9-Borabicyclo[3.3.1]nonane

BDE

Bond dissociation energy

BER

Borohydride exchange resin

BINAP

(2R,3S)-2,2′-bis-(diphenylphosphino)-1,1′-binapthyl

BINOL

1,1′-Bi-2-naphthol

BMS

Borane methyl sulfide

Benzyl

–CH₂Ph

Boc

tert-Butoxycarbonyl

Bpy (Bipy)

2,2′-Bipyridyl

BSA

N-O-Bis(trimethylsily)acetamide

n-Butyl

–CH₂CH₂CH₂CH₃

Brosylate, O-(4-Bromophenyl) sulfenate

Benzoyl

CAN

Ceric ammonium nitrate

(NH₄)₂Ce(NO₃)₆

cat

Catalytic

Cbz

N-Carbobenzyloxy

Circular dichroism

Chap

Chapter(s)

Chirald

(2S,3R)-(+)-4-dimethylamino-1,2-diphenyl-3-methylbutan-2-ol

CIDNIP

Chemically induced dynamic nuclear polarization

CIP

Cahn–Ingold–Prelog

CNDO

Complete Neglect of Differential Overlap

cod

1,5-Cyclooctadienyl (ligand)

cot

1,3,5-Cyclooctatrienyl (ligand)

Cyclopentadienyl

Cyclohexyl

°C

Temperature in degrees Celcius

Three dimensional

DABCO

1,4-Diazabicyclo[2.2.2]octane

DAST

Diethylammoniumsulfer trifluoride

Et₂NSF₃

dba

Dibenzylidene acetone

DBN

1,5-Diazabicyclo[4.3.0]non-5-ene

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCC

1,3-Dicyclohexylcarbodiimide

c-C₆H₁₁–N=C=N–c-C₆H₁₁

DDQ

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DDT

1,1,1-Trichloro-2,2′-bis(p-chlorophenyl)ethane

DEA

Diethylamine

HN(CH₂CH₃)₂

DEAD

Diethylazodicarboxylate

EtO₂C–N=NCO₂Et

DHAD

Dihydroquinidine

DHU

Dicyclohexylurea

DIAD

Diisopropylazodicarboxylate

Dibal-H

Diisobutylaluminum hydride

(Me₂CHCH₂)₂AlH

DMA

Dimethylacetamide

DMAP

4-Dimethylaminopyridine

DME

Dimethoxyethane

MeOCH₂CH₂OMe

DMEAD

Di-2-methoxyethyl azodicarboxylate

DMF

N,N′-Dimethylformamide

DMS

Dimethyl sulfide

DMSO

Dimethyl sulfoxide (ligand)

DNA

Deoxyribonucleic acid

DOSY

Diffusion-ordered NMR Spectroscopy

dppb

1,4-Bis-(Diphenylphosphino) butane

Ph₂P(CH₂)₄PPh₂

dppe

1,2-Bis-(Diphenylphosphino)ethane; see also Diphos

Ph₂PCH₂CH₂PPh₂

dppf

Bis(Diphenylphosphino)ferrocene

dpm

1,1-Bis(diphenylphosphino)methane

dppp

1,3-Bis(Diphenylphosphino)propane

Ph₂P(CH₂)₃PPh₂

e⁻

Transfer of electrons

% ee

% Enantiomeric excess

1-Ethoxyethoxy

EtO(Me)CH–

Ethyl

–CH₂CH₃

EDA

Electron donor–acceptor orbital

EDTA

Ethylenediaminetetraacetic acid

Equiv

Equivalent(s)

EPR

Electron paramagnetic resonance spectroscopy

ESR

Electron spin resonance spectroscopy

FMO

Frontier molecular orbital

FVP

Flash vacuum pyrolysis

Gas chromatography

Hour (hours)

hν

Irradiation with light

Hartree–Fock

HMO

Hückel molecular orbital

HMPA

Hexamethylphosphoramide

(Me₂N)₃P=O

HMPT

Hexamethylphosphorus triamide

(Me₂N)₃P

NMR

Proton nuclear magnetic resonance spectroscopy

HOMO

Highest occupied molecular orbital

HPLC

High-performance liquid chromatography

HSAB

Hard–Soft Acid–Base

IBX

o-Iodoxybenzoic acid

i-Pr

Isopropyl

–CH(Me)₂

Infrared spectroscopy

IUPAC

International Union of Pure and Applied Chemistry

ISC

Intersystem crossing

LCAO

Linear combination of atomic orbitals

LICA (LIPCA)

Lithium N-isopropyl-N-cyclohexylamide

LDA

Lithium diisopropylamide

LiN(i-Pr)₂

LHMDS

Lithium hexamethyl disilazide

LiN(SiMe₃)₂

LTMP

Lithium 2,2,6,6-tetramethylpiperidide

LUMO

Lowest unoccupied molecular orbital

Mcpba

m-Chloroperoxybenzoic acid

Methyl

–CH₃ or Me

MEM

β-Methoxyethoxymethyl

MeOCH₂CH₂OCH₂-

Mes

Mesityl

2,4,6-tri-Me–C₆H₂

min

minutes

MMPP

Magnesium monoperoxyphthalate

Molecular Orbital

MOM

Methoxymethyl

MeOCH₂–

Methanesulfonyl

MeSO₂–

MTO

Methyl trioxorhenium

NBS

N-Bromosuccinimide

NCS

N-Chlorosuccinimide

NHS

N-Hydroxysuccinimide

NIS

N-Iodosuccinimide

NMO

N-Methylmorpholine N-oxide

NMP

N-Methylpyrrolidinone

NMR

Nuclear magnetic resonance

NOESY

Nuclear overhauser effect spectroscopy

NOE

Nuclear overhauser effect

Nu (Nuc)

Nucleophile

OBs

O-(4-Bromophenyl)sulfinate

Oxone®

2 KHSO₅·KHSO₄·K₂SO₄

Polymeric backbone

PCC

Pyridinium chlorochromate

PDC

Pyridinium dichromate

PEG

Polyethylene glycol

PES

Photoelectron spectroscopy

Phenyl

PhH

Benzene

PhMe

Toluene

PIFA

Phenyliodine (III)-bis-(trifluoroacetate)

PPHF

Pyridinium poly(hydrogen fluoride)

PMHS

Polymethylhydrosiloxane

n-Propyl

–CH₂CH₂CH₃

Pyridine

Quant

Quantitative yield

Red-Al

[(MeOCH₂CH₂O)2AlH₂]Na

ROESY

Rotating-frame NOE spectroscopy

Room temperature

sBuLi

sec-Butyllithium

CH₃CH₂CH(Li)CH₃

seconds

salen

Bis (salicylidene) ethylenediamine

sc CO₂

supercritical CO₂

SCF

self-consistant field

SDS

Sodium dodecyl sulfate

Sec.

Section(s)

SET

Single electron transfer

Siamyl

(Sia)₂BH

Disiamylborane sec-Isoamyl

SOMO

Singly occupied molecular orbital

Tritium

TBAF

Tetrabutylammonium fluoride

n-Bu₄N⁺ F⁻

t-Bu

tert-Butyl

–CMe₃

TEAB

Tetraethylammonium bromide

TEBA

Triethylbenzylammonium

Bn(Et₃)₃N⁺

TED

Tetraethylenediamine

TEMPO

2,2,6,6-Tetramethylpiperidinyloxy free radical

TFA

Trifluoroacetic acid (solvent)

CF₃COOH

tfa

Trifluoroacetic acid (ligand)

(CF₃CO)₂O

Tf (OTf)

Triflate

–SO₂CF₃ (–OSO₂CF₃)

THF

Tetrahydrofuran (solvent)

THP

Tetrahydropyran

TMEDA

Tetramethylethylenediamine

Me₂NCH₂CH₂NMe₂

TMS

Trimethylsilyl or tetramethylsilane

–Si(CH₃)₃

Tol

Tolyl

4-(Me)C₆H₄

TOSMIC

Toluenesulfonylmethyl isocyanide

TPAP

Tetrapropylammonium perruthenate

Pr₄N⁺RuO₄⁻

TPP

Triphenylphosphine (solvent)

tpp

Triphenylphosphine (ligand)

pPh₃

Ts(Tos)

Tosyl = p-Toluenesulfonyl

4-(Me)C₆H₄SO₂

Ultraviolet spectroscopy

VCD

Vibrational circular dichroism

VDW

van der Walls

vis

Visible

XPS

X-ray photoelectron spectroscopy

Biographical Statement

Professor Michael B. Smith was born in Detroit, Michigan in 1946. In 1957, he and his family moved to Madison Heights, Virginia. After graduation from Amherst County high school, he entered Ferrum Jr. College and graduated with an A.A. Professor Smith transferred to Virginia Polytechnic Institute (Virginia Tech), where he did undergraduate research with Professor Harold Bell, and graduated with a B.S in chemistry in 1969. After working as an analytical chemist at the Newport News Shipbuilding and Dry Dock Co. (Tenneco) in Newport News, Virginia for three years, he began graduate studies at Purdue University under the mentorship of Professor Joseph Wolinsky. Professor Smith graduated with a Ph.D. in Organic chemistry in 1977. He spent one year as a faculty research associate at the Arizona State University in the Cancer Research Institute, directed by Professor George R. Pettit, and a second year doing postdoctoral work at the Massachusetts Institute of Technology under the mentorship of Professor Sidney Hecht. In 1979 he began his independent academic career, where he now holds the rank of full professor.

Professor Smith is the author of approximately 90 independent research articles, and 20 published books. The books include the 5th and 6th edition of March's Advanced Organic Chemistry (Wiley), volumes 6–12 of the Compendium of Organic Synthetic Methods (Wiley), Organic Chemistry a Two Semester Course (HarperCollins) into its 2nd edition, and Organic Synthesis (Elsevier) in its 3rd edition. A new undergraduate organic chemistry book, Organic Chemistry: An Acid-Base Approach, was published in 2011 by the CRC Press.

Professor Smith's current research involves the synthesis and structural verification of lipids obtained from the dental pathogen Porphyromonas gingivalis, which show inflammatory activity, induce bone degeneration and are involved in triggering multiple sclerosis. A main area of research is the synthesis of fluorescent dye-heterocyclic conjugates that target hypoxic cancerous tumors, allowing non-invasive fluorescence imaging in the near IR. The synthesis of anti-cancer alkaloids is also ongoing.