Pharm Chem Exam 1

The relative acidity and basicity of the functional groups can be measured by comparing their _____ values

pK

The relative acidity and basicity of the environment they reside in can be measured by comparing their _____ values

pH

Which is more acidic?

0.1M or 0.00001M

0.1M

A strong acid has a ____ pKa

low

Is carboxylic acid acidic or basic and what is the pKa range?

Acidic

2.5-5

Are beta-dicarbonyl groups acidic or basic and what is the pKa range?

acidic

4.5-8.5

Are sulfonamides acidic or basic and what is the pKa range?

acidic

5-10

Are sulfonylureas acidic or basic and what is the pKa range?

Acidic

5-6

Are tetrazoles acidic or basic and what is the pKa range?

acidic

4.5-6

Are phenols acidic or basic and what is the pKa range?

acidic

9-10

Are sulfates acidic or basic and what is the pKa range?

acidic

1-2

Are phosphates and phosphonates acidic or basic and what is the pKa range (for 1st and 2nd phosphate)?

acidic

1.5-2.5

6.5-7.5

Are aliphatic/alicyclic amines acidic or basic and what is the pKa range?

Basic

9-11

Are aromatic amines acidic or basic and what is the pKa range?

basic

2-5

Are imines acidic or basic and what is the pKa range?

basic

3-4

Is hydrazine acidic or basic and what is the pKa range?

basic

7.5-8.5

Are amidines acid or basic and what is the pKa range?

basic

10-11

Is guanidine acidic or basic and what is the pKa range?

Basic

12-13

Are nitrogen containing aromatic heterocycles acidic or basic and what is the pKa range?

basic

1-5

What is the Henderson-Hasselbalch equation?

pH=pKa + log (base/acid)

When pH > pKa, the environment is more ____ than the functional group

basic

In a ______ environment, protons are less available and are primarily removed from their respective functional groups

basic

In a basic environment (pH>pKa) acidic functional groups primarily

ionized

In a basic environment (pH>pKa) basic functional groups are primarily

unionized

A positive value for log(base/acid) indicated that the ____ form is predominant

base (unprotonated)

When pH < pKa, the environment is more ___ than the functional group

acidic

In an acidic environment, acidic functional groups are primarily

unionized (protonated)

In an acidic environment, basic functional groups are primarily

ionized (protonated)

A base in ionized when

protonated it has accepted a proton, resulting in a charged species. A

An acid is ionized when

unprotonated

An acid is unionized when

protonated

A base in unionized when

unprotonated

A negative value when solving the HH equation the ___ form is predominant

protonated

How many violations of the rule of five can an orally active drug have?

No more than one

Rule of five: No more than 5 ______

hydrogen bond donors (total number of N-H and O-H bonds)

Rule of five: No more than 10

hydrogen bond acceptors (all nitrogen/oxygen atoms)

Rule of five: Molecular mess less than

500 daltons

Rule of five: An octanol-water partition coefficient log P not greater than

5

The electronic effect of a functional group is measured by its ability to

either donate or withdraw electrons to adjacent atoms or functional groups

The intrinsic inductive character of a functional group depends on its overall

electronegativity

The larger the electronegativity, the ___ ability to attract electrons

greater

Electron donating groups are

Nucleophiles: Negatively charged or have a lone pair of electrons

Electron withdrawing groups are

electrophiles: positively charged

Does penicillin G or V have better oral bioavailability and why?

V because if what electron withdrawing group (ether oxygen connected to ring)