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rational drug design > revision of nitrogen > Flashcards

revision of nitrogen Flashcards

1
Q

what sign is used in the equation for keq

A
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2
Q

what is the equation for keq

A
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3
Q

at equilibrium what is generated

A
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4
Q

what pka does a strong acid have

A
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5
Q

what affects the steric hindrance of the lone pairs of nitrogen?

A
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6
Q

what affects the aqueous solubility of the compound containing nitrogen?

A
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7
Q

what reduces basicity of nitrogen containing compounds?

A
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8
Q

why is the nitrogen atom sp2 hybridised sometimes?

A
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9
Q

when can nitrogen act as an EDG

A
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10
Q

when can nitrogen act as an EWG

A
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11
Q

why is guanidine a strong base?

A
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12
Q

what does resonance do to stability?

A
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13
Q

do you know when tautomerism occurs?

A
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14
Q

why are free amine bases not water soluble?

A
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15
Q

why are salts water soluble?

A
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16
Q

what are common quaternary ammonium salts?

A

hydrobromide
hydrochloride
carboxylates (succinates,tartarates and citrates)
methanesulphonates

17
Q

which functional group is responsible for biological activity? (loss of this group negates biological activity)

A
18
Q

why cannot oxygen act basic?

A

due to oxygen having a higher electronegativity than nitrogen which reduces the ability of lone pairs of oxygen to be protonated

19
Q

why is phenol a stronger acid than alcohols?

A
20
Q

in which position of the aromatic rings do EWG stabilise the carboxylate anion?

A
21
Q

what effect does EWG have on acidity?

A
22
Q

what does EWG do to stability of carboxylate anions?

A
23
Q

what does EDG do to stability of carboxylate anions?

A
24
Q

what effect do EDG have on acidity?

A
25
Q

why are carboxylic acids and phenols acidic?

A
26
Q

explain how do EWG increase acidity of carboxylic acids?

A
27
Q

explain how do EDG decrease acidity of carboxylic acids?

A

the EDG donates electrons of oxygen of the carboxylate group which leaves no negative charged on oxygen further preventing delocalisation of negative charge on carboxylate anion/conjugate base (localises negative charge )hence destabilising the whole carboxylate compound

28
Q

why are sulphur containing compounds more acidic than oxygen containing compounds?

A
29
Q

why do thiols (sulphur containing compounds) have a larger binding affinity for heavy metals?

A
30
Q

how do thiols treat heavy metal poisoning?

A
31
Q

how does oxygen differ from sulphur even though they are in the same group?

A
32
Q

sometimes acids are soluble in water but what can make them even more soluble?

A
33
Q

what can limit the solubility of salts?

A

rational drug design (18 decks)

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