Functional Groups

Benzoic acid

p-aminobenzoic acid (PABA)

Pyrrole

2-Pyrroline

1,2,3 thiadiazole

3-pyrroline

1,3,4-thiadiazole

Pyridine

Piperidine

pyridazine

Pyrimidine

pyrazine

Piperazine

1,4-thiazine

1,4-oxazine

6H-1,2,4-oxadiazine

4H-1,2,4-oxadiazine

6H-1,2,4-thiadiazine

tetrahydro-1,2,4-thiadiazine

1H-azepine

7H-azepine

oxepine

6H-1,4-Diazepine

1H-1,4-diazepine

5H-1,4-diazepine

quinoline

benzene + pyridine

Isoquinoline

benzene + pyridine

tetrahydro-isoquinoline

benzene + piperidine

Benzimidazole

benzene + imidazole

Indole

benzene+pyrrole

found in tryptophan

purine

Adenine and Guanine base

6-mercaptopurine

Phenothiazine

Hydroxyl

primary, secondary, tertiary

very polar, increase solubility of 5-6 carbons

Alcoholic hydroxyl if linked to aliphatic chain

Phenolic hydroxyl if linked to aromatic ring

Amino

primary, secondary, tertiary, quaternary(form ammonium salts, soluble due to charge)

very polar, increase solubility of 5-6 carbons

Carboxylic Acid

Weakly polar, increase solubility of 2-3 c

acidic

Cyano

Weakly polar, increase solubility of 2-3 c

Nitro

Weakly polar, inc solubility of 2-3 c

Ester

polar, Prescence of more c makes esters more lipophilic and increases absorption

Amide

Weakly polar, inc solubility by 2-3 c

Imide

Weakly Polar, inc solubility by 2-3 carbons

Sulfonamide

Weakly polar, inc solubility by 2-3 c

Ether

Very weakly polar

more lipophilic than alcohol

Alkyl Groups

Very lipophilic, more c = more lipophilicity

methyl, ethyl, n-propyl

Aromatic radicals

very lipophilic, high absorbed

benzyl, phenyl

Halogens

Contains nonmetals, 7 valence electrons in it's outermost energy level. Very reactive

F, C, B, I very lipophilic