Ćwiczenie
Ustalanie bezwzględnej konfiguracji R, S na podstawie wzorów przestrzennych


Narysuj jedną z wybranych struktur1 lub pobierz strukturę w postaci pliku xyz która jest umieszczona na koncu dokumnetu. Zoptymalizuj układ metodą półempiryczną PM3. Posługując się modelem trójwymiarowym określ konfigurację R, S chiralnych atomów węgla, poprzez obracanie cząsteczki w odpowiednich kierunkach.

 Strychnina kortyzon cholesterol



Opis określania konfiguracji R, S - zgodnej z konwencją Cahna-Ingolda-Preloga znajdziemy między innymi w książce R. T. Morrison, R. N. Boyd, Chemia Organiczna, PWN, W-wa, 1985, t. 1, str. 170-173.

Użytkownicy programu HyperChem mogą sprawdzić swoją odpowiedź wybierając z menu Display opcję Labels, a następnie w nowym oknie zaznaczając opcję Chirality.

Cholesterol


6 12.127000000 -9.188000000 2.015000000
6 12.222000000 -10.488000000 1.238000000
6 9.738000000 -10.570000000 1.811000000
6 10.977000000 -11.387000000 1.386000000
6 8.469000000 -11.401000000 1.491000000
6 13.514000000 -8.621000000 1.722000000
6 10.984000000 -8.339000000 1.430000000
6 9.732000000 -9.191000000 1.105000000
6 13.562000000 -11.082000000 1.699000000
6 14.452000000 -9.828000000 1.908000000
6 11.171000000 -12.516000000 2.411000000
6 8.715000000 -12.913000000 1.798000000
6 9.814000000 -13.111000000 2.860000000
6 13.914000000 -7.438000000 2.638000000
6 11.883000000 -9.397000000 3.525000000
6 8.118000000 -11.267000000 0.000000000
6 7.302000000 -10.876000000 2.354000000
6 16.449000000 -7.552000000 2.339000000
6 15.169000000 -6.751000000 2.081000000
6 7.434000000 -13.655000000 2.244000000
6 12.806000000 -6.374000000 2.646000000
6 17.631000000 -6.774000000 1.752000000
6 5.979000000 -11.609000000 2.032000000
6 6.211000000 -13.050000000 1.544000000
1 12.298000000 -10.213000000 0.173000000
1 10.769000000 -11.831000000 0.395000000
1 9.765000000 -10.393000000 2.901000000
1 13.553000000 -8.285000000 0.666000000
6 18.959000000 -7.449000000 2.109000000
6 19.054000000 -8.840000000 1.471000000
6 20.111000000 -6.588000000 1.592000000
8 5.051000000 -13.832000000 1.780000000
1 11.306000000 -7.902000000 0.591000000
1 10.734000000 -7.637000000 2.097000000
1 8.919000000 -8.687000000 1.397000000
1 9.695000000 -9.339000000 0.117000000
1 13.944000000 -11.683000000 0.998000000
1 13.450000000 -11.592000000 2.552000000
1 14.844000000 -9.824000000 2.829000000
1 15.189000000 -9.802000000 1.232000000
1 11.647000000 -12.148000000 3.210000000
1 11.724000000 -13.238000000 1.996000000
1 9.021000000 -13.323000000 0.939000000
1 9.526000000 -12.662000000 3.706000000
1 9.928000000 -14.091000000 3.024000000
1 14.072000000 -7.796000000 3.558000000
1 12.531000000 -8.842000000 4.047000000
1 12.012000000 -10.362000000 3.753000000
1 10.949000000 -9.120000000 3.753000000
1 7.187000000 -10.912000000 -0.092000000
1 8.177000000 -12.163000000 -0.438000000
1 8.759000000 -10.636000000 -0.438000000
1 7.182000000 -9.899000000 2.177000000
1 7.524000000 -11.016000000 3.319000000
1 16.382000000 -8.447000000 1.899000000
1 16.579000000 -7.672000000 3.323000000
1 15.262000000 -5.855000000 2.514000000
1 15.060000000 -6.636000000 1.094000000
1 7.324000000 -13.566000000 3.234000000
1 7.507000000 -14.622000000 2.001000000
1 12.570000000 -6.147000000 3.591000000
1 11.998000000 -6.731000000 2.177000000
1 13.131000000 -5.553000000 2.177000000
1 17.627000000 -5.844000000 2.121000000
1 17.539000000 -6.739000000 0.757000000
1 5.496000000 -11.104000000 1.317000000
1 5.417000000 -11.638000000 2.858000000
1 6.330000000 -13.089000000 0.552000000
1 19.013000000 -7.545000000 3.103000000
1 19.101000000 -9.533000000 2.189000000
1 19.876000000 -8.890000000 0.904000000
1 18.246000000 -9.001000000 0.904000000
1 20.617000000 -6.209000000 2.367000000
1 19.745000000 -5.841000000 1.036000000
1 20.723000000 -7.150000000 1.036000000
1 4.572000000 -14.260000000 1.013000000

Kortyzon

6 10.500000000 -11.438000000 1.641000000
6 10.588000000 -12.956000000 1.425000000
6 9.206000000 -11.061000000 2.391000000
6 9.490000000 -13.736000000 1.457000000
6 7.971000000 -11.663000000 1.714000000
6 8.152000000 -13.160000000 1.694000000
6 13.041000000 -11.676000000 2.258000000
6 13.006000000 -12.516000000 0.974000000
6 11.690000000 -10.907000000 2.503000000
6 11.935000000 -13.601000000 1.163000000
6 14.058000000 -9.491000000 1.416000000
6 14.255000000 -10.725000000 2.262000000
6 13.049000000 -8.608000000 2.135000000
6 11.748000000 -9.383000000 2.265000000
6 15.468000000 -8.904000000 1.254000000
6 16.430000000 -10.072000000 1.539000000
6 15.546000000 -11.322000000 1.718000000
8 7.200000000 -13.882000000 1.886000000
6 10.483000000 -10.790000000 0.239000000
8 10.704000000 -8.776000000 2.171000000
1 11.432000000 -11.087000000 3.565000000
1 14.408000000 -10.390000000 3.304000000
1 15.593000000 -8.572000000 0.207000000
1 13.166000000 -12.387000000 3.094000000
6 13.547000000 -9.802000000 0.000000000
6 15.763000000 -7.731000000 2.169000000
8 15.181000000 -7.623000000 3.223000000
6 16.769000000 -6.686000000 1.748000000
8 17.922000000 -6.790000000 2.570000000
1 9.113000000 -10.066000000 2.403000000
1 9.259000000 -11.403000000 3.329000000
1 9.661000000 -14.710000000 1.310000000
1 7.887000000 -11.321000000 0.778000000
1 7.146000000 -11.431000000 2.230000000
1 13.898000000 -12.940000000 0.819000000
1 12.772000000 -11.937000000 0.193000000
1 11.875000000 -14.160000000 0.336000000
1 12.178000000 -14.180000000 1.941000000
1 12.894000000 -7.773000000 1.608000000
1 13.393000000 -8.371000000 3.044000000
1 16.953000000 -9.894000000 2.373000000
1 17.059000000 -10.199000000 0.771000000
1 15.387000000 -11.786000000 0.847000000
1 15.948000000 -11.965000000 2.371000000
1 10.458000000 -9.795000000 0.332000000
1 9.674000000 -11.099000000 -0.261000000
1 11.307000000 -11.057000000 -0.261000000
1 12.693000000 -10.319000000 0.060000000
1 14.231000000 -10.342000000 -0.490000000
1 13.384000000 -8.945000000 -0.490000000
1 16.390000000 -5.766000000 1.855000000
1 17.047000000 -6.824000000 0.798000000
1 18.815000000 -6.973000000 2.158000000

Strychnina

C -3.93272093 1.49162791 -1.41904651
C -4.39672093 0.18562791 -1.26604651
C -2.70772093 1.87862791 -0.88804651
C -3.64272093 -0.76337209 -0.58204651
C -1.97172093 0.92462791 -0.20904651
C -2.42572093 -0.36737209 -0.05604651
C -0.65272093 2.07962791 1.62895349
C -0.63772093 1.08762791 0.46895349
N -1.50272093 -1.16137209 0.67095349
C -0.26372093 -0.37737209 0.76795349
C 0.58927907 1.51462791 -0.23704651
C 0.83127907 1.12962791 -1.64604651
C 0.58627907 -1.02137209 -0.36604651
C 1.62727907 -0.09237209 -1.08404651
C 0.78827907 2.66062791 1.66095349
N 1.35527907 2.61062791 0.29495349
C -1.31872093 -2.63237209 0.84195349
C 1.17327907 -2.22237209 0.26895349
C 0.00227907 -3.23037209 0.19795349
C 2.70427907 0.37662791 -0.07004651
C 3.56327907 -0.51637209 0.45195349
O 2.33927907 -2.58137209 -0.46304651
C 3.55427907 -2.01637209 0.06795349
C 2.69427907 1.91062791 0.35395349
H 1.24927907 0.75262791 0.21195349
H 0.20327907 -0.46237209 1.76495349
H 1.46027907 -2.02637209 1.31895349
H 2.10427907 -0.64337209 -1.91604651
H -0.10272093 -1.35637209 -1.16504651
H -4.48572093 2.16062791 -1.91604651
H -5.28172093 -0.07437209 -1.65204651
H -2.36772093 2.81362791 -0.99004651
H -3.96672093 -1.70237209 -0.47104651
H -0.87072093 1.61162791 2.48495349
H -1.32672093 2.79962791 1.46195349
H 1.37227907 1.79262791 -2.16404651
H 0.00227907 0.90462791 -2.15604651
H 1.37127907 2.12162791 2.26895349
H 0.77727907 3.61262791 1.96695349
H -2.11672093 -3.06937209 0.42895349
H -1.31572093 -2.80637209 1.82695349
H -0.16572093 -3.45237209 -0.76304651
H 0.26827907 -4.05937209 0.68995349
H 4.18727907 -0.08137209 1.10095349
H 3.76627907 -2.56037209 0.87995349
H 4.24927907 -2.17737209 -0.63204651
H 3.01527907 1.98862791 1.29795349
H 3.30827907 2.41862791 -0.25104651
 

[1] W 1965 roku Robert Burns Woodward (USA) otrzymał Nagrodę Nobla za wybitne osiągnięcia w sztuce syntezy organicznej -for his outstanding achievements in the art of organic synthesis? za opracowanie między innymi syntezy cholesterolu, kortyzolu, strychniny, chlorofilu.