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Nomenclature of stereoisomers

Presentation on Nomenclature of stereo isomers.

Nomenclature of stereoisomers

  1. 1. NOMENCLATURE OF STEREOISOMERS Presented by, Anbu Dinesh Jayakumar, M.Pharmacy (Semester-II) Sri Ramakrishna Institute Of Paramedical Sciences Coimbatore 1
  2. 2. CONTENTS What is Stereochemistry? Classification Conformational vs Configurational Isomers Absolute configuration Relative configuration Problems to solve Conclusion Reference 2
  3. 3. 3 WHAT IS STEREOCHEMISTRY ?  Stereochemistry is the study of the relative arrangement of atoms or groups in a molecule in three dimensional space.Stereo-isomers are molecules, which have the same chemical formula and bond connectivity but different relative arrangement in three-dimensional space
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  5. 5. 5  Enantiomers are chiral molecules that are mirror images of one another.  These molecules are non-superimposable on one another.  Chiral molecules with one or more stereocenters can be enantiomers. ENANTIOMER S
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  7. 7. 7 The arrangement of atoms that characterizes a particular stereoisomer is called its Configuration. A. Absolute configuration B. Relative configuration
  8. 8. R/S NOMENCLATURE SYSTEM (Cahn–Ingold–Prelog convention) 8 Absolute configuration
  9. 9. The Cahn-Ingold-Prelog system provides sets of rules which allows us to define the stereochemical configuration of any stereocenter using the designations • (Rectus meaning Right Handed)-(R) • (Sinister meaning Left Handed)-(S)LATIN The ‘R’ and ‘S’ nomenclature is used to name the enantiomers of a chiral compound. 9
  10. 10.  A curved arrow is drawn from the highest priority (1) to the lowest priority (4) substituent.  If the arrow points towards counter-clockwise direction the stereocenter is labelled as S ("Sinister" → Latin= "left").  If the arrow points towards clockwise the stereocenter is labelled as R ("Rectus" → Latin= "right").  The R or S is then added as a prefix to the name of the enantiomer . NAMING R & S CONFIGURATION 10
  11. 11. 11  Atomic Number: The number of the protons present in the nucleus of an atom is called atomic number.  Mass Number: The number of the neutrons and protons present in the nucleus is called mass number.  Isotopes: Isotopes are the different element having same atomic number but different mass number.
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  13. 13. RULE-1 A substituent with a higher atomic number takes priority over a substituent with a lower atomic number.  Hydrogen is the lowest priority substituent, because it has the lowest atomic number. A)Isotopes (Same Atomic number but Different Mass number) Atoms with highest ATOMIC MASS NUMBER is given first priority 13
  14. 14. ii) The lowest priority substituent should always point away from the viewer (a dashed line indicates this).  Imagine a clock and a pole.  Attach the pole to the back of the clock, so that when when looking at the face of the clock the pole points away from the viewer in the same way the lowest priority substituent should point away 14
  15. 15. iii) Draw an arrow from highest priority atom to the 2nd highest priority atom to the 3rd highest priority atom.  The 4th highest priority atom is placed in the back, the arrow should appear like it is going across the face of a clock.  If it is going Clockwise, then it is an R-enantiomer.  If it is going Counter-clockwise, it is an S-enantiomer. 15
  16. 16.  If the two substituents are of equal rank, proceed along the two substituent chains until there is a point of difference. Determine the chain which has the first connection to an atom with the highest priority (the highest atomic number). That chain has the higher priority. If the chains are similar, proceed down the chain, until a point of difference. RULE-2 16
  17. 17. Example: An ethyl substituent takes priority over a methyl substituent.  At the connectivity of the stereocenter, both have a carbon atom, which are equal in rank.  Methyl has only has hydrogen atoms attached to it, whereas the ethyl has another carbon atom.  The carbon atom on the ethyl is the first point of difference and has a higher atomic number than hydrogen  Therefore the ethyl takes priority over the methyl. 17
  18. 18. RULE-3 If the chain is connected to the same kind of atom twice or three times, check the atom connected to has a greater atomic number than any of the atoms that competing chain is connected to.  If competing chain has none of the atoms at the same point which has a greater atomic number: the chain bonded to the same atom multiple times has the greater priority  However, one of the atoms connected to the competing chain has a higher atomic number: that chain has the higher priority. 18
  19. 19.  1-methylethyl substituent takes precedence over an ethyl substituent.  Connected to the first carbon atom, ethyl only has one other carbon  Whereas the 1-methylethyl has two carbon atoms attached to the first; this is the first point of difference.  Therefore, 1-methylethyl ranks higher in priority than ethyl. 19
  20. 20.  The compound containing double or triple bonded to an atom means that the atom is connected to the same atom twice.  In such a case, follow the same method as above 20
  21. 21. Determining R/S when the #4 Substituent is in front (“Wedge”) Priorities assigned based on atomic number. F>O>C>H. So F is #1 and H is #4. #4 priority is pointing out of the page ( “wedge”). #4 priority is on a dash:  Clockwise = R  Counter-clockwise = S #4 priority is on a wedge:  Clockwise = S  Counterclockwise = R (R)-1-fluoroethanol 21
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  24. 24. Fischer Projections 24
  25. 25. Step:1 : Assign priority numbers to the four ligands (groups) bonded to the chiral center using the CIP priority system. Step 2 – VERTICAL OPTION: The lowest priority ligand is on a Vertical bond and it is pointing away from the viewer. Trace the three highest-priority ligands starting at the highest-priority ligand (① → ② → ③) in the direction . 25
  26. 26. In the compound below, the movement is clockwise indicating an R-configuration. The complete IUPAC name for this compound is (R)-butan-2-ol. 26
  27. 27. STEP 2 - HORIZONTAL OPTION If the lowest-priority ligand is on a Horizontal bond, then it is pointing toward the viewer. Trace the three highest-priority ligands starting at the highest-priority ligand (① → ② → ③) in the direction that will give wrong answer. Note in the table below that the configurations are reversed from the first example 27
  28. 28. The movement is clockwise (R) which is wrong, so the actual configuration is S. The complete IUPAC name for this compound is (S)-butan-2-ol. LIMITATION.  A Fischer projection restricts a three-dimensional molecule into two dimensions.  Consequently, there are limitations as to the operations that can be performed on a Fischer projection without changing the absolute configuration at chiral centers. 28
  29. 29. 29 E–Z configuration E–Z configuration/ E–Z convention, is used for describing the absolute stereochemistry of double bonds in organic chemistry. Following CIP rules , Each substituent on a double bond is assigned a priority. Two groups of higher priority (opposite sides of the double bond), the bond is assigned the configuration E (German word "opposite"). Two groups of higher priority (same side of the double bond), the bond is assigned the configuration Z (German word "together").
  30. 30. 30 RELATIVE CONFIGURATION  The relationship between different atoms in a molecule is called relative configuration.  Relative configuration refers to the configuration of a molecule in relation to other atoms on the same molecule or in relation to another form of the same molecule.  There are several different types of relative configurations possible, these include: i) Cis and trans ii) Syn & Anti iii) D&L iv) d,l
  31. 31. 31 i) CIS & TRANS  When the substituent groups are oriented in the same direction, the diastereomer is referred to as cis,  When the substituents are oriented in opposing directions, the diastereomer is referred to as trans.  cis–trans isomerism of 1,2-dichloroethene.
  32. 32. 32  Alicyclic compounds can also display cis–trans isomerism.  Example of a geometric isomer due to a ring structure, consider 1,2-dichlorocyclohexane:
  33. 33. 33 ii) SYN & ANTI  Syn and anti are identical to Z (usammen) and E(ntgegen) is used to describe the geometry about carbon-nitrogen double bonds.  The lone pair of electrons is given the lowest priority and the sequence rule is applied .  For example, N-methyl imines, the imine on the left has the highest priority group attached to the carbon in the double bond (ethyl) on the same side as the highest priority group attached to the nitrogen in the double bond (the methyl has higher priority than the lone pair).  Therefore the molecule is the syn isomer (but would now be called the Z isomer).By the same reasoning, the molecule on the right is the anti of E isomer. Again, the key point is that the lone pair has a lower priority than any atom. Z E
  34. 34. 34 iii) D & L NOMENCLATURE (Fischer–Rosanoff convention)  When the –OH group on this carbon is on the right, then sugar is the D-isomer,  When it is on the left, then it is the L-isomer L D
  35. 35. 35 D & L NOMENCLATURE (More than one stereo center)  D & L convention is used to distinguish between enantiomers of chiral monosaccharides and chiral alpha-amino acids, based on the molecule drawn as a Fischer projections in a specific orientation.  The Land D forms of the sugar depends on the orientation of the –H and –OH groups around the carbon atom adjacent to the terminal primary alcohol carbon(carbon 5 in glucose) determines whether the sugar belongs to the D or L series.  The D-and L-notation is based on glyceraldehyde.  When the –OH group on this carbon is on the right, then sugar is the D-isomer,
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  37. 37. 37 iv) D (+) & L (-) configuration (+) enantiomers rotate plane-polarized light clockwise (dextrorotary or d )  (-) enantiomers rotate it counter-clockwise (levorotary, or l).  It is measured by using polarimeter
  38. 38. Determine R/S Configuration GLYCERALDEHYDE LACTIC ACID 38
  39. 39. (R)-glyceraldehyde  Hydrogen(1) (#4) priority, and hydroxyl oxygen(8) priority (#1).  Two carbon groups (6) has priority #2(aldehyde or methanol)  On moving one more bond away from chiral center the aldehyde has an double bond to oxygen, while methanol group has a single bond to an oxygen.  If the atom is the same, double bonds have a higher priority than single bonds.  Aldehyde group is assigned #2 priority and the methanol group the #3 priority.  #4 priority group ( H) and it is pointed back away from us, Trace a circle defined by the priority groups, circle is clockwise, this molecule is (R)-glyceraldehyde. 39
  40. 40. (S)-Lactic Acid.  H is the #4 substituent and OH is #1.  Owing to its three bonds to oxygen, the carbon on the acid group takes priority #2, and the methyl group takes #3.  The #4 group, hydrogen, happens to be drawn pointing toward us (out of the plane of the page) in this figure.  The circle traced from #1 to #2 to #3 is clockwise,  The chiral center has the S configuration. 40
  41. 41. 41 Cis / Trans A B C
  42. 42. 42 C) cis (the two ethyl groups are on the same side) A) trans (the two hydrogen atoms are on opposite sides) B) cis (the two hydrogen atoms are on the same side, as are the two ethyl groups)
  43. 43. PROBLEMS 43
  44. 44. 44 (S) I > Br > F > H. The lowest priority substituent, H, is already going towards the back. It turns left going from I to Br to F, so it's a S. (R) Br > Cl > CH3 > H. You have to switch the H and Br in order to place the H, the lowest priority, in the back. Then, going from Br to Cl, CH3 is turning to the right, giving you a R. (R) OH > CN > CH2NH2 > H. The H, the lowest priority, has to be switched to the back. Then, going from OH to CN to CH2NH2, you are turning right, giving you a R.
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  46. 46. REFERENCE: Schore and Vollhardt. Organic Chemistry Structure and FunctionPg no(554- 620) McMurry, John and Simanek, Eric. Fundamentals of Organic Chemistry. 6thedition Pg no(335-420) Organic Chemistry, Volume 2: Stereochemistry And The Chemistry Natural Products, 5/E by I.L FINAR Volume 2 Pg no(561-670) 46
  47. 47. 47
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Presentation on Nomenclature of stereo isomers.

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