Acidic/ Basic Functional Groups

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This only includes the functional groups mentioned in the notes from Dr. Doerksen.

What is the approximate pKa of a sulfonic acid?

1

What is the approximate pKa of a carboxylic acid?

4-5

What is the approximate pKa of a sulfonylurea?

5.5-8

What is the approximate pKa of an aromatic sulfonamide?

7-9

What is the approximate pKa of an imide?

8-10

What is the approximate pKa of a phenol?

10

What is the approximate pKa of a catechol?

10

What is the approximate pKa of a resorcinol?

10

What is the approximate pKa of a hydroquinone?

10

What is the approximate pKa of a primary amine?

9-10

What is the approximate pKa of a secondary amine?

9-10

What is the approximate pKa of a tertiary amine?

9-10

What is the approximate pKa of a pyrrolidine?

9-10

What is the approximate pKa of a piperidine?

9-10

What is the approximate pKa of a piperazine?

9-10

What is the approximate pKa of a morpholine?

9-10

What is the approximate pKa of a tetrahydroisoquinoline?

9-10

What is the approximate pKa of an aniline?

4-5

What is the approximate pKa of a pyridine?

4-5

What is the approximate pKa of a quinoline?

4-5

What is the approximate pKa of a benzimidazole?

4-5

What is the approximate pKa of an isoquinoline?

4-5

What is the approximate pKa of a pyrazole?

2-3

What is the approximate pKa of a thiazole?

2-3

What is the approximate pKa of a pyridazine?

2-3

What is the approximate pKa of a imidazole?

6-7

Are alcohols acidic, basic, or neutral?

neutral

Are phenols acidic, basic, or neutral?

acidic

Are ethers acidic, basic, or neutral?

neutral

Are primary amines acidic, basic, or neutral?

basic

Are secondary amines acidic, basic, or neutral?

basic

Are tertiary amines acidic, basic, or neutral?

basic

Are aromatic amines acidic, basic, or neutral?

basic, but significantly less so than non-aromatic amines

Are carboxylic acids acidic, basic, or neutral?

acidic

Are esters acidic, basic, or neutral?

reactive, but neither acidic nor basic

Are amides acidic, basic, or neutral?

neutral

Are thioethers acidic, basic, or neutral?

neutral

Are sulfonic acids acidic, basic, or neutral?

acidic

Are sulfonamides acidic, basic, or neutral?

acidic

Are sulfonylureas acidic, basic, or neutral?

acidic

Are pyrroles acidic, basic, or neutral?

neutral

Are pyrrolidines acidic, basic, or neutral?

basic

Are thiophenes acidic, basic, or neutral?

neutral

Are tetrahydrothiophenes acidic, basic, or neutral?

neutral

Are imidazoles acidic, basic, or neutral?

basic

Are pyrazoles acidic, basic, or neutral?

basic

Are imidazolines acidic, basic, or neutral?

basic

Are imidazolidines acidic, basic, or neutral?

basic

Are oxazoles acidic, basic, or neutral?

neutral at physiological pH

Are isoxazoles acidic, basic, or neutral?

basic

Are 2-oxazolines acidic, basic, or neutral?

basic but unstable to acids

Are oxazolidines acidic, basic, or neutral?

basic but unstable to acids

Are thiazoles acidic, basic, or neutral?

basic

Are triazoles acidic, basic, or neutral?

basic

Are tetrazoles acidic, basic, or neutral?

basic, but with 1 acidic nitrogen

Are pyridines acidic, basic, or neutral?

basic

Are piperidines acidic, basic, or neutral?

basic

Are pyrazines acidic, basic, or neutral?

neutral at physiological pH

Are pyrimidines acidic, basic, or neutral?

basic

Are pyridazine acidic, basic, or neutral?

basic

Are piperazines acidic, basic, or neutral?

basic

Are morpholines acidic, basic, or neutral?

basic

Are uracils acidic, basic, or neutral?

basic

Are thymines acidic, basic, or neutral?

basic

Are cytosines acidic, basic, or neutral?

basic

Are indoles acidic, basic, or neutral?

neutral

Are benzimidazoles acidic, basic, or neutral?

basic

Are benzoxazoles acidic, basic, or neutral?

neutral at physiological pH

Are benzthiazoles acidic, basic, or neutral?

neutral at physiological pH

Are purines acidic, basic, or neutral?

basic

Are adenines acidic, basic, or neutral?

basic

Are guanines acidic, basic, or neutral?

basic

Are xanthines acidic, basic, or neutral?

basic

Are quinolines acidic, basic, or neutral?

basic

Are isoquinolines acidic, basic, or neutral?

basic

Are tetrahydroisoquinolines acidic, basic, or neutral?

basic

Are imides acidic, basic, or neutral?

acidic

Are catechols acidic, basic, or neutral?

acidic

Are resorcinols acidic, basic, or neutral?

acidic

Are hydroquinones acidic, basic, or neutral?

acidic

Are anilines acidic, basic, or neutral?

basic

Are bisanilines acidic, basic, or neutral?

neutral at physiological pH

Are phenothiazines acidic, basic, or neutral?

neutral at physiological pH

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