Functional Groups

-CH3

Alkane

non-polar bonds

weak van der Waal forces

low BP

lipid soluble

neutral

Stable

 

=CH2

Alkene

nonpolar

weak van der Waal forces

low BP

lipid soluble

neutral

prone to oxidation

[image]

Cycloalkane

nonpolar

weak van der Waal forces

low BP

lipid soluble

neutral

Prone to oxidation leading to peroxide

[image]

Aromatic Hydrocarbon

nonpolar

weak van der Waal forces

low BP (but higher than alkanes, alkenes and cycloalkanes)

lipid soluble

neutral

Stable

others to know: Naphthalene (two benzenes), Anthracene (three benzenes), and Phenanthrene (two benzenes with a third catty-corner to it)

[image]

Alcohol

polar

H-bond A and D

high BP

water soluble

neutral

stable

[image]

Halogenated Hydrocarbon

permanent dipole

weak van der Waal forces

low BP

highly lipid soluble

neutral

stable

[image]

Phenol

polar, permanent dipole

H Bond A and D

high BP

water soluble

Acid

easily oxidized to quinones

[image]

Ether

polar, permanent dipole

H Bond A only

low BP

lipid soluble

neutral

can oxidize in presence of air

[image]

Aldehyde

carbonyl group is polar

H Bond A and D

Higher BP

Water soluble

Neutral

Prone to oxidation

[image]

Ketone

Carbonyl group is polar

H Bond A and D

High BP

water soluble

Neutral

Stable

[image]

Amine

Polar bond, permanent dipole

 

1°, 2° H bond donor/acceptor, 3° don’t h-bond

moderate to high BP

water solubility (1; ; 2; ; 3; amines)

;

Basic (2; ; 3; ; 1; for alkylamines / aryl decrease basicity)

;

;

;

[image]

Carboxylic Acid

polar bond, permanent dipole

H Bond A and D

high BP

water soluble

Acid

[image]

Ester

weaker polar, permanent dipole

H Bond A only

low BP

low water solubility

Neutral

easily hydrolized back to carboxylic acid

[image]

Amide

polar, permanent dipole

H Bond A and D

higher BP than esters

water soluble

neutral

[image]

Carbonate

polar, permanent dipole

H Bond A only

low BP

low water solubility

neutral

[image]

Carbamate

polar, permanent dipole

H Bond A only

low BP

water soluble

neutral

[image]

Urea

polar, permanent dipole

H Bond A and D

higher BP than esters

water soluble

neutral

stable

[image]

Amidine

very basic

[image]

Guanidine

very basic

[image]

Sulfonic Acid

ion-dipole interactions

very water soluble

strong acid

stable

[image]

Sulfonamide

high BP

soluble

weak acid

stable

[image]

Thioether

lipophilic

neutral

-NO2

Nitro

is a charged species

neutral

;

[image]

Epoxide

very reactive due to ring strain

unstable and will react with acid or base in vitro

[image]

Aziridine

similar to epoxides with high ring strain

basic

[image]

;

Beta Lactam

easily hydrolized in aqueous solutions b/c of ring strain

;

[image]

Furan

Looks like ether, but properties are similar to benzene

not very water soluble

neutral

stable

[image]

Tetrahydrofuran

cyclic ether

water soluble

neutral

prone to oxidation

[image]

Pyrrole

aromatic

not water soluble

neutral

[image]

Pyrrolidine

a secondary amine

H Bond A only

water soluble

basic

[image]

Thiophene

aromatic

not very water soluble

neutral

stable

[image]

Oxazole

aromatic

N is an H Bond A

water soluble

N is basic

[image]

Isoxazole

aromatic

N is H Bond A

water soluble

N is basic

[image]

Imidazole

aromatic

H Bond A and D

water soluble

basic

[image]

Pyrazole

aromatic

H Bond A and D

water soluble

basic

[image]

Thiazole

aromatic

H Bond A only

not very water soluble

basic

stable

[image]

Thiadiazole

can also have the N’s on the 2 and 5 positions

aromatic

not very water soluble

stable

[image]

Triazole

aromatic

not very water soluble

basic

stable

[image]

Tetrazole

aromatic

not very water soluble

basic

stable

[image]

Oxazolindin (one ketone)

polar bonds, permanent dipole

H Bond A and D

water soluble

neutral

unstable to acid/base hydrolysis

[image]

Oxazolindin (two ketones)

polar bond, permanent dipole

H Bond A and D

water soluble

acid

can form salt with strong base

[image]

Hydantoin

polar bonds, permanent dipole

H Bond A and D

water soluble

acid

can form salt with strong base

[image]

Pyridine

aromatic

H Bond A only

water soluble

weak base

can form salt with strong acid

[image]

Piperidine

aromatic

H Bond A

water soluble

[image]

Barbituric Acid

can be substituted in the 5 position to make things like phenobarbitol

strong acid

[image]

Indole

 

[image]

Benzimidazole

 

[image]

Purine

multiple H Bond A and D

highly water soluble

[image]
Quinoline
[image]

Benzodiazepine

will see substituents in the 2 position (to the right of the top N)

[image]

Phenothiazine

 

[image]
Catechol
Basic Functional Groups

Amines

Amadine

Guanidine

Aziridine

Pyrrolidine

Oxazole

Isoxazole

Imidazole

Pyrazole

Thiazole

Triazole

Tetrazole

Pyridine

Piperidine

 

Acidic Functional Groups

Phenol

Carboxylic Acid

Sulfonic Acid

Sulfonamide (unless N is disubstituted)

Oxazolindin (with two ketones only)

Hydantoin

Barbituric Acid

Water Soluble Functional Groups

Alcohol

Phenol

Aldehyde

Ketone

Amine

Carboxylic Acid

Ester (low)

Amide

Carbonate (low)

Carbamate

Urea

Sulfonic Acid

Sulfonamide

Tetrahydrofuran

Pyrrolidine

Oxazole

Isoxazole

Imidazole

Pyrazole

Oxazolindin (both)

Hydantoin

Pyridine

Piperidine

Pyrimidine

Purine

Lipophilic Functional Groups

Alkane

Alkene

Cycloalkane

Aromatic Hydrocarbon

Halogenated Hydrocarbon

Ether

Thioether

Furan (not very water sol)

Pyrrole

Thiophene (not very water sol)

Thiazole (not very water sol)

Thiadiazole (not very water sol)

Triazole (not very water sol)

Tetrazole (not very water sol)

 

 

Not Stable In Vitro

Alkene (prone to oxidation to peroxide)

Cycloalkane (prone to oxidation to peroxide)

Phenol (easily oxidizes to quinone in air)

Ether (can form peroxide in air)

Aldehyde (prone to oxidation)

Ester (easily hyrdolized back to carb. acid)

Epoxide (unstable due to ring strain)

Beta Lactam (easily hydrolized b/c of ring strain)

Tetrahydrofuran (oxidation)

Oxazolindin (unstable in acid/base)

 

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