Molecular Chirality
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Molecular Chirality

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AACIMP 2009 Summer School lecture by Victor Kuzmin. "Environmental Chemoinfornatics" course.

AACIMP 2009 Summer School lecture by Victor Kuzmin. "Environmental Chemoinfornatics" course.

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Molecular Chirality Molecular Chirality Presentation Transcript

  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 1 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c « , » . . , .
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 2 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c The term chiral (pronounced /ka l/) is used to describe an object that is non-superposable on its mirror image. The term chirality is derived from the Greek word for hand, (cheir). It is a mathematical approach to the concept of "handedness"
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 3 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c “I call any geometrical figure, or group of points, chiral, and say it has chirality, if its image in a plane mirror, ideally realized, cannot be brought to coincide with itself." William Thomson, 1st Baron Kelvin (1824–1907)
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 4 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 5 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c . « »
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 6 re re he he k k lic lic C C w om w om w w w. A B B Y Y.c Sn w. A B B Y Y.c – Cn, Dn, T, O
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 7 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c R H C N H O
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 8 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 9 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c H H CH 3 R S CH 3 H 2C CH 2 CH 3 CH 3 CH3 (+)- (-)- H C NH(CH3) R S H C OH S > (3 ) R O O H H ) CH 3 R S CH 3 CH 2 H 2C O CH 3 CH 3 H9C4 S P O NO2 CH3 (-)- (+)- ) S > R (50 ) )
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 10 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c X V Y z
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 11 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 12 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 13 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 14 re re he he k k lic lic C C w om w om w w w. A B B Y Y.c » w. A B B Y Y.c CH3 CH3 H HO COOH
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 15 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c S R T3 T2 T1 = T1’ T2’ T3’ - 1= 0 2 < 3
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 16 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 17 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 18 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 19 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c . F N! {HCFCl} + {HCClBr} + {HCFBr} + N 4 !4! Cl C Br + {CClFBr} + {HFClBr} H F C H Cl Br schF = 1.8 .1 .2 .3 .4 .5 F F F F schCl = 1.9 C H C H C H C H schC = -0.5 Cl Cl Br Br Cl Br Cl S Br schBr = 2.2 R R R R schH = -1.7 . 1) = 31.8; . 2) = 52.1; . 3) = 37.4; . 4) = 155.4; . 5) = 144.0; « » - sch i k j FDij / FDij j j
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 20 re re he he k k lic lic C C w om . w om w w w. w. A B B Y Y.c A B B Y Y.c (0.0) H (-19.2) H (9.7) (-17.4) H' ' (17.4) Cl Cl F Cl H' H' » sch H H H H H H (-19.2) (-19.2) (-22.6) (-26.8) (19.4) Cl Br Cl (-19.4) ( ---- ---- ) C1 Cl Cs Cl C2v Cl « » - SDM C Br C Br C Cl H F H H H H SDM 0, SDM=335 SDM=45 SDM=0 C1, Sn, Cnh Cs, Ci. Cs D3 Cl Br Cn, Dn, T, O SDM=0 SDM=0 »
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 21 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c 8H H7 (SRRSR) (SRRSR) 4 F C C F3 3F F4 F3 F4 6 5 6 6 2 Cl Cl 1 5 8H 8H 5 (SC) - Cl H7 Cl H7 – S1 – S5) 1 Cl 1 Cl 2 2 S1 = 1,2,3,4 i1 S2 = 2,3,4,5 i2 S3 = 3,4,5,6 i3 S4 = 4,5,6,7 i4 S5 = 5,6,7,8 i5 4F F3 F3 8H Cl SC = (i1 i2 i3 i4 i5) 6 2 6 ik (R S 0), k = 1- 5, R–« » » 5 5 H7 S–« » 8H Cl Cl H7 0– Cl 1 1 F 2 4 (RSSRS) (0S0R0)
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 22 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 23 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 24 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 25 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 26 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 27 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 28 re re he he k k lic lic C C w om 1D – 3D w om w w w. w. A B B Y Y.c A B B Y Y.c Zn Be N N Be Zn 1D Be Zn N N Zn Be A B F F (R 'R '/S 'S ') Cl Cl 2D F Cl Cl F B (R 'S'/S 'R ') A C Br F F Br (R S/SR ) F Cl Cl F 3D Br F F Br B (R R/S S) F Cl Cl F D A C - - -
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 29 re re he he k k [4] lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c X2 OH X1 OH HO X3 OH X4
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 30 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c (EDF) 2D 3D [4]
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 31 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c X X HO X OH X OH OH HO OH X X HO X OH X X X OR OR RO OR X X
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 32 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 33 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c Z1 Z1 Z1 Z1 Z1 X X X X Z2 X + H OH OH * * Y Y Y Y Y Z1 Z1 Z1 Z1 X X X X OH -Z1 Z2 Y Y Y Y X X X X X X X X OH -Z2 OH Z2 Z2 Y Y Y Y Y Y Y Y X = Cl, Br Y = OR Z1 , Z2 - Ex. Z1 = NO2 Z2 = SCH 2COOR
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 34 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c [4]
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 35 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c –« » (SCi) : SCi = (1/4)FD, FD - . » H: -0.08; F: -0.33; C:+0.26; Cl: +0.24; Br: -0.09. » »/ « » . .
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 36 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c - . R S l - . R R l
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 37 re re he he k k – lic lic C C w om w om w w w. w. A B B Y Y.c 76 A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 38 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 39 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 40 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 41 re re he he k k lic lic « » 1D - 3D C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c 1D 2D 3D B A (A) A A A A A B Ar As Ar B (A) Ar As C As D A A B A C A B C B (A) A B C A B B A D A C A E A C
  • F T ra n sf o F T ra n sf o PD rm PD rm Y Y Y Y er er ABB ABB y y bu bu 2.0 2.0 to to 42 re re he he k k lic lic C C w om w om w w w. w. A B B Y Y.c A B B Y Y.c . 1D . As Ar Bs Br Bs Br As Ar Ar As 2D B . C Ar As As Ar As Ar B . C C B As As Ar Ar . As C . Ar Ar B 3D As B B B . . As Ar Ar D C Ar Ar As As D C As As C Ar . B B B B B B B As Ar D . . Ar As Ar As C D C D As Ar As Ar