Sulfonic acids and their derivatives

Question 1

Characteristics ?

Answer 1

Sulfonyl group
Stronger than Carboxylic acids
Very soluble in Water 
Aromatic / Aliphatic form 
Aromatics are Intermediates for other groups

Question 2

Reaction with Amines ?

Answer 2

Sulfonamides

Question 3

Sulfonamides Characteristics ?

Answer 3

High acidity of Hydrogen atoms attached to nitrogen (bc of strong EN of sulfonylgroup)

Form stable salts with strong alkalies
Soluble in dilute NaOH Solutions

.Sie alle sind schwache organische Säuren und meist schlecht löslich in Wasser (die Natriumsalze der Sulfonamide sind meist gut wasserlöslich)

Question 4

Reaction of Sulfonamides with HClO?

Answer 4

N-halo derivatives (e.g Chloramine T)

Question 5

How is Chloramine T made?

Answer 5

P Toluensufonamide with HClO

Question 6

Chloramine T

Answer 6

N-Halo derivative of Sulfonamides

Sodium Salt

Question 7

Chloramine B

Answer 7

Analog to Chloramine T from Benzenesulfonamide

Question 8

What happens if the chlorination from Chloramine B is taken further?

Answer 8

Dichloroderivative is formed

–> Dichloramine B

Question 9

Dichloramine B

Answer 9

Soluble in oils and salves (Salben)

Question 10

Saccarin

Answer 10

Sweetener
Cyclic amide of o (Ortho) sulfobenzoic acid
non nutritive
lightly bitter and metallic aftertaste

Question 11

How is Saccharin made?

Answer 11

Made by the oxidation of o-toluenesulfonamide,

as well as from phthalic anhydride

Question 12

Sulfonamide Drugs

Answer 12

first effective chemotherapeutic agents for the cure of bacterial infections
–> Prontosil (Steptococci) –> Red azodye

Gerhard Domagk

All the sulfonamides are capable of causing drug intoxication (poisoning), and some patients are hypersensitive to them

Question 13

N Chlorosulfonamides: Antiseptic properties of Hypochlorite solutions OF??

Answer 13

Reaction N-Halo derivatives and Sulfonamides with HclO is reversible in aqueous solution (stable when dry)

Question 14

Non generic name Sulfonamide ?

Answer 14

Derivatives of p-amino benzene sulfonamide

Question 15

Sulfanilamide

Answer 15

Drug
Essential is the direct linkage of sulfur to the benzene ring
Amino and Sulfonamid group
Antibiotic

Question 16

Die Wirkung der Sulfonamide als antimikrobielle Agenzien zur Behandlung von Infektionskrankheiten

Answer 16

Die Wirkung der Sulfonamide als antimikrobielle Agenzien zur Behandlung von Infektionskrankheiten beruht darauf, dass sie als Antimetabolite der p-Aminobenzoesäure (PABA) wirken. Sie hemmen kompetitiv dasjenige Enzym des Stoffwechselweges der Folsäure-Synthese, welches die Dihydropteroinsäure-Bildung katalysiert. Eukaryotische (und damit auch menschliche) Zellen werden hiervon nicht beeinträchtigt, da diese Folsäure nicht selbst erzeugen

Question 17

Sulfonyl gruppe

Answer 17

SO2

Question 18

Chemical name fro p-amino benzene sulfonamide?

Answer 18

Sulfanilamide

Question 19

What increased the use of sulfonamides for treatment of specific microbial infections?

Answer 19

The combination of trimethoprim and Sulfamethoxazole