Term
| Physiochemical properties effected by stereochemistry |
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Definition
solubility
mp
bp
polarity
density
pka |
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Term
| Biological properties effected by stereochemistry |
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Definition
oral availability
protein binding
distribution
target activity |
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Term
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Definition
defines and describes the three dimensional spatial arrangement of atoms in a molecule
the study of isomers |
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Term
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Definition
| Compounds with the SAME molecular formula, but DIFFERENT constitutions, conformations, or configurations |
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Term
Constitutional Isomers
other name? |
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Definition
Structural isomers:
differ in connectivity of atoms |
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Term
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Definition
isomers at potential energy minima, identical in constitution/configuration. differ only in torsion angles
different functional groups rotate around C-C or C-heteroatom bonds |
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Term
Configurational Isomers
other name? |
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Definition
Stereoisomers
isomers with same connectivity, differ in position of atoms in space
(has both internal reference and aspect of comparing 2 molecules) |
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Term
| When drawing constitutional isomers, avoid labile, reactive groups, including... |
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Definition
Enol ethers
Hemi-acetals
Carbonates
Cations and Anions |
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Term
Torsion angle
(what is it and what type of isomer are we talking about?) |
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Definition
rotation around one bond in one molecule
Conformational isomers |
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Term
Eclipsed,
Staggered:
Anti, Gauche |
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Definition
energy (high to low):
Eclipsed(large group eclipsing other large group)
Gauche
Anti |
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Term
| Do alkyl groups favor equatorial or axial? |
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Definition
| equatorial - more favored as size increases |
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Term
Atropisomers
what are they and what kind of isomer |
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Definition
Conformational
steric strain locks the isomer into one of the two steroisomers (can't rotate)
possess axial chirality |
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Term
4 kinds of
Configurational Isomers |
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Definition
Geometric isomers - cis/trans
enantiomers
diastereomers
meso compounds |
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Term
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Definition
differ in position of ligand relative to a reference plain
cis, trans
applies to: alkenes, cycloalkanes |
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Term
If an alkene has more than 2 substituents, what nomeclature do we use? |
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Definition
Not cis/trans!
E/Z!
E: high priority on opp. sides
Z: high priority on same side
E like trans, Z like cis
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Term
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Definition
Stereoisomer not superimposable on it's mirror image |
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Term
What is a racemic mixture?
(racemate) |
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Definition
a 1:1 mixture of two enantiomers |
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Term
What atoms can a stereocenter occur around? |
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
Non super imposable
NON mirror image
ex. E/Z olefins; more than 1 stereocenter |
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Term
If all centers are flipped (all that were R become S, all that were S become R) what type of stereoisomer do you have? |
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Definition
Enantiomer
(if one is not flipped: diastereomer) |
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