PHA 6575 Lecture 14 (Stereochemistry)

Isomers

molecules which have the same molecular formula but differ in their molecular connectivity or spatial arrangement

Constitutional Isomer

same formula with different connectivity

Positional Isomer

same formula with different position of functional groups or substituents and different spatial orientation

Functional Isomers

same molecular formulas with different connectivity and different groupings of atoms and different shapes

Stereoisomers

molecules that have the same structural formulas and bonding patterns but different arrangements of atoms in space

Conformational Isomers (Conformers)

different spatial arrangements of the atoms that result from rotation about a single bond

Geometric Isomers

isomers in which the order of atom bonding is the same but the arrangement of atoms in space is different

Optical Isomers

same formula with same connectivity but different shape (due to 3D arrangement of atoms)

Chirality

the asymmetry or "handedness" of a molecule such that it cannot be superimposed on its mirror image

Diastereomer

stereoisomers that are not mirror images of one another

Enantiomers

non-superimposable isomers that are mirror images

Higher

the Cahn-Ingold-Prelog (C-I-P) rules states that atoms with a __________ atomic number get a higher priority

Racemate

a mixture of more than one type of stereoisomer

Chiral/Racemic Switch

the replacement of a racemic product with a single stereoisomer product

Eutomer

the more potent stereoisomer

Distomer

the less potent stereoisomer

Eudismic Ratio

the ratio of the activities of the eutomer and the distomer

Dextro

right or clockwise

Levo

left or counterclockwise

Bioactive Conformer

conformer of a molecule that binds to a receptor/target

Sulfoxides

can show chirality because of their lone pair

D/L Isomerism

used based on conformation of glyceraldehydes