Stereoisomer Descriptor.

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Presentation transcript:

Stereoisomer Descriptor

Stereoisomer Enantiomer Diastereomer Erythro, threo Meso Compound Epimer Chiral Molecules With No Chiral Centers

Definitions Stereoisomers – compounds with the same connectivity, different arrangement in space Enantiomers – stereoisomers that are non-superimposible mirror images; only properties that differ are direction (+ or -) of optical rotation Diastereomers – stereoisomers that are not mirror images; different compounds with different physical properties

enantiomer

Erythro dan threo

Diastereomer: Stereoisomer yang bukan pasangan enantiomer 1 dan 2 enantiomer 3 dan 4 juga enantiomer Diastereomer: 1-3; 1-4; 2-3 dan 2-4

Epimers: distereomer yang berbeda hanya pada satu pusat kiral saja

Senyawa meso

Chiral Molecules With No Chiral Centers Allenes can be Chiral

Mycomycin, an antibiotic

Specifying Configuration (Chirality); Cahn-Ingold-Prelog Notation Specifies the "configuration" at each chiral center, equivalent to "cis-" and "trans-" etc. Abbreviated rules Assign priorities to groups attached to chiral center according to atomic # (same as Z/E rules) Compare 2nd, 3rd etc. atom from center as necessary, look for first point of difference Multiple bonds "add up" Determine direction of rotation 1 > 2 > 3 looking with #4 group pointing "away"

Prioritize Using Cahn-Ingold-Prelog Rules Look at atoms directly attached to chirality center a) higher atomic number = higher priority b) heavier isotopes = higher priority If no difference at first attached atom, move along the chain until the first point of difference. Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.