Dr.

Quanbo Xiong Texas Southern University

Functional Groups List

PHCH431, Fall 2007

Regarding this list in Exam I, you are responsible to 1. Match any of the structure of functional groups to its common name or official name, and identify its presence or absence in a given molecule. 2. List the physical and chemical properties of each functional group (except heterocycles). 3. Predict the structure of metabolites related to each functional group (except heterocycles).

Exam I Hydrocarbons Alkane

Alkene

Alkyne Aromatic Hydrocarbon Benzene (Phenyl)

Naphthalene

Anthracene

Phenanthrene

Halogenated Hydrocarbon
R X

Dr. Quanbo Xiong Texas Southern University

Oxygen containing groups Alcohols (1, 2, 3)

R OH

Glucuronic acid
COOH OH HO OH OH

Glucuronide
COOH OH HO OH O R

Phenol
OH

Ether Peroxide

Aldehyde

Ketone

Enol
R1 R2 OH R3

Acyl halide

Acetal

Dr. Quanbo Xiong Texas Southern University

R2 R1 O H O R3

Hemiacetal
R2 R1 O H
R2 R1 O R3 O R4

Ketal

Hemiketal
R2 R1 O R3 O H

Nitrogen containing groups Amines 1 2

4
R1 R N+ R R2 3

Amide

Imine

Amidine
NH R NH2

Guanidine

Dr. Quanbo Xiong Texas Southern University

NH H2 N NH2

Azo
R N N R1

Nitro

Carboxylic acids and derivatives Carboxylic acid

O R C OH

Ester
R1 O C O R2

Amide
O R1 N R3 R2

Lactone
O O

(CH2)n

Coumarin
O O

Lactam
O NH

(CH2)n

Carbonate
O R1 O O R2

Dr. Quanbo Xiong Texas Southern University

Carbamate
O R1 O N R2 R3
O R1 N R2 N R3 R4

Urea

Imide
O R1 N R2 O R3

Sulfur containing groups

Thiol
R S H

Sulfide (thioether)
R S R1
R1

Disulfide
R S S

Sulfoxide
R1 S R2 O

Sulfone
R1 S R2 O O

Sulfonic acid
O R S OH O

Sulfuric acid
O HO S OH O

Sulfate
O R O S OH O

Dr. Quanbo Xiong Texas Southern University

Sulfonamide
O R S NH2 O

Phosphor containing groups Phosphoric acid

OH HO P OH O

Phosphate
R O P OH O OH

Heterocycles Monocycles Oxygen containing Oxirane

O

Furan
O

Tetrahydrofuran
O

Nitrogen containing Aziridine

H N

Pyrrole
H N

Pyrrolidine
H N

Dr. Quanbo Xiong Texas Southern University

Pyridine
N

Piperidine
H N

Hexahydroazepine
H N

Octahydroazocine
NH

Imidazole
HN N

Pyrazole
HN N

Triazole
NH N N

Tetrazole
NH N N N

Piperazine
HN NH

Pyrimidines Uracil
NH O N H O

Thymine
NH O N H O

Cytosine

Dr. Quanbo Xiong Texas Southern University

N H2N N H O

Sulfur containing Thiophene (Thiole)

S

Thiolane
S

Heteroatom species >1 Oxazole

O N

Isoxazole
O N

Morpholine
O HN

Thiazole
S N

Thiadiazole
S N N

Bicycles Indole
H N

Isoindole
NH

Quinoline
N

Quinazoline 8

Dr. Quanbo Xiong Texas Southern University

N N

Benzodiazepine
H N N

Benzimidazole
H N N

Benzoxazole
O N

Benzothiazole
S N

Purines Adenine
H N N NH2 N N

Guanine
H N N O NH N
O N N N NH O

NH2

Xanthine

Tricycles Phenothiazine
H N S

Acridine
N

Dr. Quanbo Xiong Texas Southern University

Exam II Alkaloids Phenolics Glycosides Terpenoids Steroids Exam III Amino acids Proteins Nucleic acids Carbohydrates Lipids

10