Med Chem Test #1 - pKa, func groups, and everything else

name? and pKa? acid or base? conjugate acid or base name?

phenol, 9-11, acid, phenolate

name? and pKa? acid or base? conjugate acid or base name?

sulfonamide, 9-11, acid, sulfonamidate

name? and pKa? acid or base? conjugate acid or base name?

imide, 9-11, acid, imidate

name? and pKa? acid or base? conjugate acid or base name?

alkylthiol, 9-11, acid, thiolate

name? and pKa? acid or base? conjugate acid or base name?

thiophenol, 9-11, acid, thiophenolate

name? and pKa? acid or base? conjugate acid or base name?

N-Arylsulfonamide, 4-7, acid, N-arylsulfonamidate

name? and pKa? acid or base? conjugate acid or base name?

sulfonimide, 4-7, acid, sulfonimidate

name? and pKa? acid or base? conjugate acid or base name?

alkylcarboxylic acid, 4-7, acid, alkylcarboxylate

name? and pKa? acid or base? conjugate acid or base name?

arylcarboxylic acid, 4-7, acid, arylcarboxylate

name? and pKa? acid or base? conjugate acid or base name?

sulfonic acid, 0-1, acid, sulfonate

name? and pKa? acid or base? conjugate acid or base name?

arylamine, 3-6, base, arylammonium

name? and pKa? acid or base? conjugate acid or base name?

aromatic amine, 3-6, base, aromatic ammonium

name? and pKa? acid or base? conjugate acid or base name?

imine, 3-6, base, iminium

name? and pKa? acid or base? conjugate acid or base name?

alkylamine, 10-11, base, alkylammonium

name? and pKa? acid or base? conjugate acid or base name?

amidine, 10-11, base, amidinium

name? and pKa? acid or base? conjugate acid or base name?

guanidine, 10-11, base, guanidinium

name? acid, base, or neutral?

alkyl alcohol, neutral

name? acid, base, or neutral?

amide, neutral

name? acid, base, or neutral?

amine oxide, neutral

name? acid, base, or neutral?

ether, neutral

name? acid, base, or neutral?

diarylamine, neutral

name? acid, base, or neutral?

ketone/aldehyde, neutral

name? acid, base, or neutral?

ester, neutral

name? acid, base, or neutral?

nitrile, neutral

name? acid, base, or neutral?

thioether, neutral

name? acid, base, or neutral?

sulfonic acid ester, neutral

name? acid, base, or neutral?

quaternary ammonium, neutral

name? acid, base, or neutral?

sulfoxide, neutral

name? acid, base, or neutral?

sulfone, neutral

amine without hydrogens pKa

35

H2O/ ROH pKa

16

HCl pKa

-7

H3O+ pKa

-2

EWG in order

yes

EWG or EDG? -⁺NR₃

W

EWG or EDG? -NO₂

W

EWG or EDG? -C≡N

W

EWG or EDG? -SO₃H

W

EWG or EDG? ketone

W

EWG or EDG? COOH

W

EWG or EDG? ester

W

EWG or EDG? aldehyde

W

EWG or EDG? amide without hydrogens on N

W

EWG or EDG? I

W

EWG or EDG? Br

W

EWG or EDG? Cl

W

EWG or EDG? F

W

EDG in order

yes

EWG or EDG? benzene

D

EWG or EDG? alkyl

D

EWG or EDG? amide w/ H

D

EWG or EDG? ether

D

EWG or EDG? alcohol

D

EWG or EDG? amines

D

antagonist

ligand prevents normal function

partial agonist

ligand “resumes” normal function partially

full agonist

ligand “resumes” normal function

inverse agonist

ligand does OPPOSITE of normal function

acids definition (H+ and e-)

donate H+, accept e-

bases definition (H+ and e-)

accept H+, donate e-

strong acids

HCl, H2SO4, HI, HNO3, HBr, HClO4, H3PO4

strong bases

KOH, NaOH

strongest base in the body

hydroxide (OH-)

strongest acid in the body

hydronium (H3O+) and H+

henderson-hasselback equation

pKa = pH + log (A-/HA)

stomach pH

3

small intestine pH

7

large intestine pH

8

duodenum pH

5

solubility and absorption are (inversely/directly) related

inversely

ionization and solubility are (inversely/directly) related

directly

ionization and absorptivity are (inversely/directly) related

inversely

what does Lemke’s emperical approach give you

water solubility potential

molecules with water solubility potential 3-4 C

OH, phenol

molecules with water solubility potential 3 C

amine, COOH, ester

molecules with water solubility potential 2-3 C

amides

molecules with water solubility potential 2 C

urea, carbamate, carbonate, ether, aldehyde, ketone

molecules with water solubility potential 20-30 C

ionized compounds

water solubility potential: OH

3-4

water solubility potential: phenol

3-4

water solubility potential: amine

3

water solubility potential: COOH

3

water solubility potential: ester

3

water solubility potential: amides

2-3

water solubility potential: urea

2

water solubility potential: carbamate

2

water solubility potential: carbonate

2

water solubility potential: ether

2

water solubility potential: aldehyde

2

water solubility potential: ketone

2

water solubility potential: ionized compounds

20-30

name?

urea

name?

carbamate

name?

carbonate

define IMHB

intramolecular hydrogen bonding (same molecule)

IMHB (decreases/increases) solubilizing ability of fg

decreases

will salts of SA + SB dissociate?

yes

will salts of SA + WB dissociate?

yes

will salts of WA + SB dissociate?

yes

will salts of WA + WB dissociate?

no