Wang Med Chem

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Last updated 9:00 PM on 9/20/26
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40 Terms

1
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Sulfonic acid

pKa = -2 to 1

fully deprotonated anion at pH = 7.4

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Phosphonic acid

pKa (1) = 1-3

pKa (2) = 5-8

usually more mono or dianionic

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Carboxylic acid

pKa = 3-5

mostly deprotonated, common in NSAIDs and acidic metabolites

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Tetrazole

pKa = 4.5-5.5

carboxylate bioisostere

mostly anionic at pH = 7.4

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Sulfonamide

pKa = 7-10

ionization is highly substituent dependent

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Imide

pKa = 6-9

often partially ionized

acidic N-H between two carbonyls

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Phenol

pKa = 9-11

mostly neutral at pH = 7.4

phenolate increases polarity

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Thiol

pKa = 8-10.5

mostly neutral to partially thiolate, depending on substituents

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Alcohol

pKa = 15-18

neutral under physiological conditions

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Guanidine

pKa = 12-13.5

almost fully protonated, strong cation

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Amidine

pKa = 11-13

mostly protonated, strong cationic center

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Aliphatic amines

RNH2, R2NH, R3N

pKa = 8-11

usually protonated, key driver of salt formation

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Piperidine

pKa = 10-11.5

mostly protonated, common saturated basic heterocycle

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Morpholine

pKa = 7-8.5

partially protonated, oxygen lowers basicity

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Imidazole

pKa = 6-7.5

both neutral and protonated forms may matter

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Pyridine

pKa = 5-6.5

mostly neutral at physiological pH

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Aniline

pKa = 4-6

mostly neutral, resonance lowers N basicity

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Amide (NHR)

~1 - 1

essentially non-basic

N lone pair delocalized into carbonyl

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Quaternary ammonium

R4N+

no pKa

permanently charged

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Arginine

positively charged, polar AA

<p>positively charged, polar AA</p>
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Histidine

positively charged, polar AA

<p>positively charged, polar AA</p>
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Lysine

positively charged, polar AA

<p>positively charged, polar AA</p>
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Aspartic Acid

negatively charged, polar AA

<p>negatively charged, polar AA</p>
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Glutamic Acid

negatively charged, polar AA

<p>negatively charged, polar AA</p>
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Serine

no charge, polar AA

<p>no charge, polar AA</p>
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Threonine

no charge, polar AA

<p>no charge, polar AA</p>
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Asparagine

no charge, polar AA

<p>no charge, polar AA</p>
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Glutamine

no charge, polar AA

<p>no charge, polar AA</p>
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Cysteine

special case

forms disulfide bonds

<p>special case</p><p>forms disulfide bonds</p>
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Selenocysteine

special case

forms diselenium bonds (not as strong as disulfide bonds)

<p>special case</p><p>forms diselenium bonds (not as strong as disulfide bonds)</p>
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Glyceine

special case, no side chain

<p>special case, no side chain</p>
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Proline

special case

<p>special case</p>
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Alanine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Valine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Isoleucine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Leucine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Methionine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Phenylalanine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Tyrosine

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>
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Tryptophan

non-polar/hydrophobic

<p>non-polar/hydrophobic</p>