Stereochemistry is the Spatial Orientation of Atoms in a Molecule Tetrahedral Carbon is responsible for stereochemistry
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1 Stereochemistry is the Spatial Orientation of Atoms in a Molecule Tetrahedral Carbon is responsible for stereochemistry History: : Biot optical activity 1848: Pasteur - optical activity of tartaric acid crystals in wine mirror images 1874: LeBel and Van t Hoff tetrahedral carbon 1894: Fisher ID 16 stereoisomers of aldohexoses, including D-glucose 1915: John Steinbeck - sugar analysis in Spreckels Sugar Company
2 Stereoisomers May Have Different Properties Yeast one isomer undergoes fermentation; the other does not. Amino acids one isomer is predominant in nature one isomer gives lemons their flavor; the other isomer gives oranges their flavor Aspartame S isomer is sweet; R isomer is bitter
3 One Stereoisomer of Aspartame fits into the Sweetness Receptor Site; the others do not. three-point attachment theory (AH-B-X)
4 The Nose is capable is distinguishing between stereoisomers thedailyblarg.com piperbasenji.blogspot.com Receptor sites for sense of smell are chiral In general, stereoisomers do not interact identically with other chiral molecules.
5 Why Do Roses Smell So Sweet? ( Rose oxide has 4 stereoisomers " 4 different smells
6 Stereoisomers Are Used in Drugs Ibuprofen S isomer works; R isomer does not. Thalidomide one isomer is a sedative; the other causes birth defects Stereochemistry
7 cis/trans (E/Z) isomers are geometric isomers Unsaturated fats are cis or trans Cis-platin cancer drug What is the structure of transplatin?
8 Introduction to Stereochemistry (Klein, Ch. 5) Stereoisomers are different from structural (constitutional) isomers. Structural Isomers have different connectivty Stereoisomers Isomers have different orientation in space Which compounds are structural isomers? Which compounds are stereoisomers?
9 Stereoisomers are classified as enantiomers and diastereomers. Enantiomers are stereoisomers that are mirror images of each other and are not superimposable on each other. Diastereomers are stereoisomers that are not mirror images of each other. Example: cis and trans isomers Enantiomers have a chirality center. A chirality center has four different atoms or groups bonded to it. If a molecule has a plane of symmetry or center of symmetry, then it is achiral. Optically active compounds are enantiomers that rotate a plane of polarized light
10 Isomers Constitutional (structural) Enantiomers Mirror images, not superimposable Stereoisomers Diastereomers Non-mirror images Conformational isomers D and L Optically active Determine by experiment Chirality center R and S By priority rules Geometric Cis and trans E and Z Meso More than 1 chirality center but achiral
11 1. Are your two hands enantiomers or diastereomers or the same? 2. Determine whether each object is chiral. Hint: check for a plane of symmetry or center of symmetry.
12 A B C D E F G H I
13 Objective: Identify the chirality center. Determine the configuration (R or S) at each chirality center.
14 Enantiomers have a chirality center. A chirality center has four different atoms or groups bonded to it. The configuration at a chirality center is R or S. Priority rules to rank atoms/groups are based on atomic weight. Point lowest priority group away from you. 1 --> 2 --> 3: CW = R CCW = S R S
15 Objective: Identify the chirality center. Determine the configuration (R or S) at each chirality center.
16 Objective: For each compound, identify the chirality center. Determine the configuration (R or S) at each chirality center.
17 Ibuprofen is an OTC analgesic. It has one chirality center. Mark the chirality center with a *.
18 Ibuprofen is an OTC analgesic. It has one chirality center. Mark the chirality center with a *. Determine the configuration (R or S). Hint: Which direction is the H pointing?
19 Ibuprofen is an OTC analgesic. Draw the Fischer projection of Ibuprofen.
20 Fischer Projection Horizontal lines: wedges (point toward you) Vertical lines: dashes (point away from you) Fischer projection is a shortcut to using wedges and dashes.
21 Aspartame (NutraSweet) is an artificial sweetener (180x sweeter than sucrose) ID the chirality center(s).
22 Aspartame (NutraSweet) is an artificial sweetener (180x sweeter than sucrose) Determine the configuration at each chirality center. Draw the Fischer projection.
23 D-Limonene has an orange smell and is the R enantiomer. ID the chirality center. Draw the R isomer. Draw the Fischer projection.
24 Which compounds are chiral? If chiral, identify the chirality center(s). Determine the configuration (R/S) at each chirality center. CEN, 9/21/98, Counting on Chiral Drugs. Celgene develops single-isomer Ritalin.
25 Some Compounds Have More Than 1 Chirality Center 2 n rule - compound with n chiral C can have a max of 2 n stereoisomers. Chiral: no plane of symmetry. 0 chirality centers: usually achiral. (Find a plane of symmetry.) 1 chirality center: chiral ==> enantiomers 2 chirality centers: depends. If mirror images are superimposable ==> same. If mirror images are not superimposable ==> enantiomers and determine R/S at each chirality center. Non-mirror images ==> Diastereomers Meso compounds - achiral compound that contains chiral C. Why achiral? Contains a plane of symmetry.
26 Practice Makes Perfect! a. CH 2 Cl 2 and CH 2 ClBr. Find the plane of symmetry. b. Is BrClC=C=CBrCl chiral?
27 C=C bond involves a bond and bond C1-C2 bond involves sp 2 hybrid orbitals (s + p x + p z ) C1-C2 bond involves p y orbitals C2-C3 bond involves sp 2 hybrid orbitals (s + p + p ) C2-C3 bond involves p orbitals
28 Practice Makes Perfect! Tartaric acid has more than 1 chirality center. ID the chirality centers. Determine the number of stereoisomers. Which isomers are enantiomers? Which are diastereomers? Is there a meso compound? Draw the Fisher projection of each isomer.
29 5942/enlarge Polarized light micrograph of tartaric acid crytals Wine crystals ( wine diamonds ) are indicative of good quality.
30 Tartaric acid has stereoisomers. (Apply 2 n rule) R, R S, R S, S R, S Naturally occurring Which isomers are Enantiomers? Which isomers are Diastereomers? Is there a Meso compound?
31 Tartaric acid has 4 stereoisomers. (Apply 2 n rule) R, R S, R S, S R, S Naturally occurring Enantiomers = A and C Meso compound = B and D which means B and D are.
32 Tartaric acid has 3 stereoisomers. (B and D are the same - Meso) R, R S, R S, S R, S Naturally occurring Change an acid group on B and D to a methyl group. Do you still have a meso compound? If not, what type of isomer?
33 Optical Activity is the ability of a substance to rotate the plane of polarized light. Specific Rotation = [α] Std C = 1 g/ml and l = 1 dm Non std conditions: [α] = α c x l What type of substance is optically active? CW rotation = (+) or D CCW rotation = (-) or L
34 Tartaric Acid is optically active. It has 3 stereoisomers. Naturally occurring (R, R)-tartaric acid [α] = o. R, R S, R S, S R, S Naturally occurring What is [α] of (S, S)-tartaric acid? What is [α] of (2R, 3S)-tartaric acid? What is [α] of a 50% (R, R):50% (S, S) mixture of tartaric acid? What is this type of mixture called?
35 Glucose and Galactose are 2 examples of Aldohexoses How many aldohexose stereoisomers are there? Draw an enantiomer of D-gluose. Draw a diastereomer of D-galactose.
36 In each of the following pairs of compounds, one is chiral and the other is achiral. Identify each compound is chiral or achiral, as appropriate.
37 Identify the relationship in each of the following pairs. Do the drawings represent constitutional isomers or stereoisomers, or they just different ways of drawing the same compound? If they are stereoisomers, are they enantiomers or diastereomers? a. b.
38 Ritalin has 2 chirality centers. How many stereoisomers does Ritalin have? Draw each stereoisomer. Which isomers are enantiomers? Which are diastereomers?
39 Which ring(s) is/are planar? What is the hybridization at? For the non-planar ring(s), what is the conformation? Are groups in axial or equatorial position? How many chirality centers? What is the configuration at each chirality center? CEN, 9/1/14, p. 56 PAINS (pan assay interference) compounds
40 Which ring(s) are planar? For the non-planar rings, what is the conformation? Are the groups in the axial or equatorial position? How many chirality centers? What is the configuration at each chirality center? CEN, 9/1/14, p. 20 HIV drug binds to coreceptor CCR5 on T cells and blocks HIV gp120 protein from coreceptor.
41 Do Human Pheromones Exist? ( ) How many stereoisomers?
42 A B C D E F
43 G H I J K L
44 Stereochemistry has its own Vocabulary Optical purity - chiral compound in which only one enantiomer is present. Enantiomeric excess (ee) - difference between % of major enantiomer present in a mixture and % of minor enantiomer. Optically pure = 100% ee, Racemic mixture = 0% ee. Resolution - separation of racemic mixture into its enantiomers. Erytho and threo - Molecule with 2 or more chirality centers: Erythro: like substituents are on the same side of a Fischer projection. Threo: like substituents are on opposite sides of a Fischer projection. Stereospecific reaction - reaction in which stereoisomeric reactants give stereoisomeric products. E.g., S N 2 Stereoselective reaction - single reactant can form two or more stereoisomers, with one major product (syn, anti, inversion of configuration)
45
46 How is Stereochemistry Involved?
Isomers Have same molecular formula, but different structures
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