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drug structure > stereochemistry > Flashcards

stereochemistry Flashcards

1
Q

what is stereochemistry?

A

subdiscipline of chemistry that looks at the spacial arrangement of atom

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2
Q

what is important in drug action?

A

3D structure is important in drug action

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3
Q

what are isomers?

A

compounds have the same molecular formula

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4
Q

types of isomers?

A

constitutional or structural isomers
stereoisomers

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5
Q

what are stereoisomers?

A

compounds that are the same but have a different arrangement of space

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6
Q

what are conformation isomers?

A

different conformations of the same molecule
interconvert easily through rotation around single bond

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7
Q

what are configuration stereoisomers?

A

same groups are different in how they’re arranged around central carbon atoms
don’t interconvert easily so bond needs to be broken to interconvert

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8
Q

what is strain?

A

when stable molecule have weaker bonds than acyclic c-c bond and more unstable than propane

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9
Q

what are constitutional or structural isomers?

A

compounds with same molecular formula but different arrangement of atoms

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10
Q

what are the two types of newman projections?

A

eclipsed conformer high energy
staggered conformer low energy

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11
Q

what is the bond angle in angle strain?

A

60

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12
Q

what is the structure of torsional strain?

A

‘planar molecule
can’t do bond rotation
hydrogens are eclipsed’

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13
Q

structure of cyclobutane?

A

‘90 degrees angle
high ring strain
non-planar conformer minimizing eclipsing’

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14
Q

structure of cyclopentane?

A

‘angle 180 degrees
non-planar minimizing eclipsing
little ring strain’

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15
Q

structure of cyclohexane chair conformation?

A

angle 109.5 degrees if non-planar
no ring strain
no eclipsing in chair conformation

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16
Q

what are the hydrogens in cyclohexane arranged like?

A

either axial or equitorial

17
Q

how are axial and equatorial relationship changed?

A

via ring flip of conformer
the conformers energy stays the same

18
Q

how do you assign priority groups?

A

by looking at atomic number
(higher atomic mass for isotopes)

19
Q

structure of cyclohexane boats?

A

no ring strain
eclipsed in boat conformation
in twist-boat the flagpole and eclipsed interactions reduced
both boat and twist-boat are higher energy than chair

20
Q

what is tetrahedral carbon that can always be arranged in two ways called?

A

‘spatial sequence about a stereogenic centre’

21
Q

what are enantiomers?

A

‘two molecules with opposite configurations at all centres’

22
Q

what are R and S configurations?

A

R- clockwise rotation
S- anticlockwise

23
Q

what are diasterioisomer?

A

‘stereoisomers that aren’t an enantiomer’
so don’t have opposite configurations at all centres

24
Q

what are meso compounds?

A

groups around stereogenic centres that are symmetrical

25
Q

when is a meso compound optically inactive?

A

when there’s a plane of symmetry

26
Q

conformation vs configuration?

A

changing conformation doesn’t affect configuration

27
Q

what is the (+)- or dextrorotatory enantomer?

A

plane rotates clockwise
and isomer is active

28
Q

what is (–)- or laevorotatory enantiomer?

A

plane rotates anticlockwise
and isomer is inactive

29
Q

what is the equimolar mixture?

A

racemate or racemic mixture
where the enantiomer is optically inactive (±)-

30
Q

what are the physical properties of enantiomers and racemates?

A

between enantiomers the melting points are the same
racemates have different melting points
optical rotation is different in both
Pharmacological properties are different as well

31
Q

what is the equation for specific rotation?

A

observed rotation/concentration (g/ml)* path length (dm)

32
Q

example of a stereoisomer?

A

thalidomide:
one is an antidepressant and the other causes birth defects

drug structure (9 decks)

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