Bonds Functional Groups Flashcards
Van der Waals important for
Hydrocarbons, lipophiic/hydrophobic molecule
Common metabolism of alkene
Epoxidation catalyzed by P450
Common metabolism of Alkane
Mostly non-reactive, but w-hydroxylation by cytochrome P450 (CYP) could occur
Common metabolism of aromatic hydrocarbon
Aromatic Hydroxylation
There is a permanent dipole between C-X, but dipole-dipole interaction is weak except for
C-F
In general, van der waals is more important for
halogneated hydrocarbons and increases with larger halogen
Periodic size trend
Bottom left is biggest size
Aliphatic alcohol
Neutral under physiological conditions: non-ionizable
Phenol
Much more acidic OH group, but still neutral at pH = 7.4…. Hydrogen bonding acceptor and donor
Hydrogen bond donor and acceptor
Keto-enol tautomerism
Hemiacetal hemiketal
Amines
Why are aryl amines not very basic?
Aryl amines are not very basic due to aromatic delocalization of lone-pair electrons
Quarternary Ammonium Salts
Permanently postively charged
Not an acid or base
Does not participate in acid or base reactions
Carboxylic Acids
Easily ionizable at pH = 7.4
Multiple sites of Hydrogen bonding (increased water solub)
ion-dipole interaction for the ionized form (Increased water solub)
Ester
H-bond acceptor
Hydrolyzed easily
Esters are often prodrugs
Amide
Does not hydrolyze easily
h-Bond donor
High water solub
Amide is neutral as N is not basic (resonance spreads lone-pair electrons)
Carbonates, Carbamates, Urea
Amidines and guanidines
Sulfonic acids and sulfonamides
Nitrate Nitrite
