Stereochemistry: biological significance of isomerism
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2 S Stereochemistry: biological significance of isomerism Craig Wheelock October 17 th, (copies of slides can be downloaded from my homepage)
3 Learning Objectives Understand concepts of stereochemistry and isomerism Be able to assign isomer configuration ationalize energy-dependence of cyclohexane conformations Know biological significance of isomerism and optical activity
4 Stereochemistry Types of Isomers Structural (constitutional) same molecular formula, different attachment order Geometric (cis and trans, E and Z ) molecular rigidity (alkenes and cyclic systems) Conformational (cyclohexane) molecular shape Optical (chirality) arrangement ( right- or left-handedness ) X W C Z Y
5 Importance of stereochemistry trans fat elevated risk in coronary heart disease cis trans Thalidomide (Neurosedyn) S teratogenic and causes birth defects effective against morning sickness
6 Geometric Isomers occurs in only 2 classes of compounds: 1. Alkenes 2. Cyclic systems
7 ALKENES cis and trans E and Z
8 ALKENE GEOMETY A EVIEW sp 2 C C π bond σ bond sp 2 π bond σ bond planar SIDE VIEW END VIEW
9 π OTATION BEAKS TE BOND Unlike σ bonds, π bonds do not rotate. NO! requires kcal/mole to break the π bond this does not happen at reasonable temperatures
10 CIS / TANS ISOMES Because there is no rotation about a carbon-carbon bond, isomers are possible C C C C cis substituents on the same side of main chain trans substituents on opposite sides of main chain
11 COMPAE cis / trans ISOMES IN ING COMPOUNDS C C C C cis trans In alkenes cis / trans isomers used to be called geometric isomers, a term generally not generally used for cyclic systems (rings)
12 TWO IDENTICAL SUBSTITUENTS If an alkene has 2 identical substituents on one of the double bond carbons, cis / trans (or E / Z ) isomers are not possible C 3 3 C C 2 C 3 C 2 C 3 C 2 C 3 C 3 all of these compounds are identical no cis / trans isomers
13 OTE COMPOUNDS WIT NO CIS / TANS C 3 C 3 C 3 C 3 C 2 C 3 3 C C 3 no cis / trans isomers
14 NAMING cis trans ISOMES OF ALKENES cis / trans main chain stays on same side of double bond = cis main chain crosses to other side of double bond = trans C 3 C 2 C 2 C 3 C 3 C 2 cis-3-hexene C 2 C 3 trans-3-hexene notice that these prefixes are in italics
15 E / Z SYSTEM OF NOMENCLATUE To avoid the confusion between what the main chain is doing and the relationship of two similar groups.. the IUPAC invented the E / Z system Cl I F cis? trans? This system also allows alkenes like the one above to be classified.. an impossibility with cis / trans
16 E / Z NOMENCLATUE In this system the two groups attached to each carbon are assigned a priority ( 1 or 2 ) If priority 1 groups are both on same side of double bond: Z isomer = zusammen = together (in German) same side Z E opposite sides If priority 1 groups on opposite sides of double bond: E isomer = entgegen = opposite (in German)
17 ASSIGNING PIOITIES Cahn-Ingold Ingold-Prelog System 1. Look at the atoms attached to each carbon of the double bond 2. Atom of higher atomic number has higher (1) priority example F > 1 2 F I Br 1 I > Br atomic number 9 > 1 53 > 35 2 bigger is better Since the 1 s are on the same side, this compound is Z (Z )-1-bromo-2-fluoro-1-iodoethene notice use of parentheses
18 3. If you can t decide using the first atoms attached, go to the next atoms attached. If there are non-equivalent paths, always follow the path with atoms of higher atomic number. Once you find a difference, you can stop. 1 C> 6 > 1 2 C 3 C 2 F C2C3 1 2 C C F C path goes to F not to comparison stops here path goes to C not to F>C 9 > 6 This molecule has Z configuration
19 4. The atoms in double bonds are replicated at either end of the double bond. C C 2 C C 2 C C 2 O C O>C 8 > 6 C O C O 1 Then, when comparing groups, follow the path of highest priority as before.
20 EXAMPLE USING EPLICATION 1 C C C C 2 C C C C 3 C 3 2 C C C > C 3
21 cis / trans with rings C 3 C 3 C 3 cis-1,2-dimethylcyclohexane C 3 C 3 cis-1,3-dimethylcyclohexane C 3 trans-1,2-dimethylcyclohexane C 3 C 3 trans-1,3-dimethylcyclohexane C 3 C 3 C 3 cis-1,4-dimethylcyclohexane C 3 trans-1,4-dimethylcyclohexane
22 DOUBLE BONDS IN INGS
23 INGS trans double bonds are not possible until the ring has at least eight carbon atoms if C<8 then the chain is too short to join together cis C = 5 cis C 2 C 2 C 2 C 2 trans C = 8 cis C = 6 smallest ring that can have a trans double bond trans Note that both cis and trans exist for C8
24 cis and Z are not always the same for a given ring O>C 8 > C 2 O 1 2 C> 6 > 1 bonds in the ring are cis but this compound is E
25 Applying Cahn-Ingold Ingold-Prelog Is this molecule cis or trans, E or Z??? Cl I F cis? Z? trans? E? atomic number F Cl Br I Increasing priority 2 1 Cl F 1 I Cl 1 I F 1 E Z
26 Lets Practice.... atomic number for N=7 List the following atoms/groups in order of increasing priority 1) -N 2, -, -C 3, -Cl -, -C 3, -N 2, -Cl 2) -CO 2, -CO 2 C 3, -C 2 O, -O, - -, -C 2 O, -CO 2, -CO 2 C 3, - O O C O O C O C O C O C C 2 CC 2 C 3 butyl < 3) C C 2 CC 3 C 3 isobutyl O
27 Why do we care about cis and trans?????
28 Trans-fat = Geometric isomers contains trans vs. cis bond saturated cis double bond trans double bond Oleic acid C18, cis Melting point = 13 C Elaidic acid C18, trans Melting point = 45 C
29 CYCLOEXANE Conformational isomers
30 PLANA CYCLOEXANE (doesn t exist) 120º If cyclohexane were planar all of the hydrogens would be eclipsed, resulting in torsional strain. There would also be angle strain - a hexagon has 120 o internal angles. cyclohexane is not planar...
31 CYCLOEXANE CONFOMATIONS CAI BOAT
32 CAI BOAT
33 CAI CONFOMATION
34 SELECTED DIMENSIONS FO TE CAI Van der Waal s radius of = 1.20 Å distances greater than 2.40 Å have no steric interaction 2.40 Å 2.49 Å 2.50 Å 1.09 Å 1.54 Å normal C- and C-C bond lengths 1.20 Å 2.49 Å All of the hydrogens are more than 2.40 Å apart.
35 COMPLETE STAGGEING ABOUT ALL BONDS axial equatorial
36 AXIAL AND EQUATOIAL YDOGENS Chair conformations axial equatorial
37 BOAT CONFOMATION
38 SELECTED DIMENSIONS FO TE BOAT Van der Waal s radius of = 1.20 Å distances greater than 2.40 Å have no steric interaction 2.40 Å 2.27 Å 2.27 Å 1.84 Å Bond lengths are normal. A number of pairs of hydrogens are closer than 2.40 Å Å
39 TE CAI CONFOMATION AS LOWE ENEGY TAN TE BOAT E N E G Y 29 kj/mol 0 kj/mol boat chair
40 INTECONVESIONS ING INVESION
41 ING INVESION starting ring axial red equatorial blue axial blue equatorial red axial and equatorial hydrogens are interchanged when the ring is inverted inverted ring
42 CONVESION OF CAI TO BOAT 46 kj/mol 0 kj/mol (reference) 29 kj/mol chair conformation envelope transition state boat conformation
43 CYCLOEXANE ING INVESION chair 1 envelope 1 boat chair 2 envelope 2
44 TWIST BOAT
45 TE BOAT IS A FLEXIBLE CONFOMATION IT WILL TWIST O FLEX twisting relieves the eclipsing at the bottom of the ring... and the top axial hydrogens move apart TWIST BOAT SKEW BOAT
46 TE TWIST BOAT AS LOWE ENEGY TAN TE BOAT E N E G Y 6 kj/mol 0 kj/mol boat twist boat
47 TE COMPLETE PICTUE
48 cyclohexane conformation affects the energy state
49 OTE MOLECULES TAT AVE CAI AND BOAT CONFOMATIONS
50 NITOGEN AND OXYGEN ETEOATOMS CAN EPLACE CABON O N O O O N O O All of these atoms have sp 3 hybridization
51 LAGE INGS AVE MANY CONFOMATIONS AND TEY AE MOE FLEXIBLE C7 etc C8 etc The bigger the ring, the more flexible. We study cyclobutane, cyclopentane and cyclohexane specifically because the rings are common and they have conformations that are easily defined.
52 LAGE MOLECULES AVE MANY POSSIBLE CONFOMATIONS Drawn as a regular figure One of its many possible conformations involving twisting and rotation Conformations are not easy to define.
53 LAGE INGS CAN FOM A COWN One of the more interesting conformations of large rings is the crown. If the peak carbons are replaced by oxygens you get a crown ether. Crown ethers are good at complexing (dissolving) metal cations : O : O O : O :.... : O O : KCl O O O K + O O O Cl-
54 18-crown-6 coordinating ether Nobel Prize in Chemistry 1987
55 To recapitulate... geometric isomers alkenes and cyclic systems cis / trans and E / Z use Cahn-Ingold-Prelog priority rules cyclohexane has multiple conformations affects substituent interaction & energy states stereoisomers can have significant biological effects
56 What s next??? After the break, we will discuss optical isomers omework assignment for the break What is symmetry??
57 WIC OBJECTS AE SYMMETIC? WIC OBJECTS AE SYMMETIC? (mirror image is identical) sym asym sym asym (due to pattern) asym asym
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