Justin Young, Leonardo Alvarez-Valtierra and David W. Pratt.

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Presentation transcript:

STUDYING THE STEREOCHEMISTRY OF NAPROXEN USING ROTATIONALLY RESOLVED ELECTRONIC SPECTROSCOPY Justin Young, Leonardo Alvarez-Valtierra and David W. Pratt. University of Pittsburgh Science(2006), vol. 323, pg. 237(4) http://www.novelcs.com/Chirality.html http://www.mcescher.com/

An Example R-naproxen S-naproxen

Diastereomers? S-naproxen R-naproxen Alvarez-Valtierra, L. (2008) University of Pittsburgh. School of Arts and Science

Low Resolution Spectrum IB IR Wavenumbers Chem. Phys. Lett. (2003), 375, pg634

Experimental Setup To Beam Machine (BM)

Red Conformer of S-Naproxen 30584.35 cm-1 30586.06 cm-1 0.08 cm-1 S-Naproxen

Red Conformer of R-Naproxen 30584.35 cm-1 30585.98 cm-1 0.08 cm-1 R-Naproxen

Right Vs. Left S-Naproxen R-Naproxen 0.08 cm-1 0.08 cm-1

Red Conformer Inertial Parameters S-Naproxen (Red) R-Naproxen S0 A” (MHz) 1241.59 (6) 1241.56 (5) B” (MHz) 214.70 (3) 214.73 (3) C” (MHz) 202.15 (3) 202.16 (3) ∆I” (amu Ǻ2) -260.8 (4) -260.7 (4) S1 A’ (MHz) 1217.62 (5) 1217.59 (5) B’ (MHz) 215.49 (3) 215.50 (3) C’ (MHz) 202.44 (2) 202.46 (2) -263.8 (4) -263.9 (4) a/b/c-character 8.3/87.6/4.2 7.8/88.7/3.5 Band origin (cm-1) 30585.2 OMC (MHz) 2.91 2.88 Temp (K) 3.0

R-Naproxen Blue Conformer 30686.50 cm-1 30687.96 cm-1 0.08 cm-1 R-Naproxen

S-Naproxen Blue Conformer 30686.50 cm-1 30687.96 cm-1 0.08 cm-1 S-Naproxen

Right Vs. Left R-Naproxen S-Naproxen 0.08 cm-1 0.08 cm-1

Blue Conformer Inertial Parameters S-Naproxen (Blue) R-Naproxen S0 A” (MHz) 1315.80 (6) 1315.71 (7) B” (MHz) 205.36 (3) 205.30 (3) C” (MHz) 196.10 (3) 196.07 (3) ∆I” (amu A2) -267.9 (5) -267.9(5) S1 A’ (MHz) 1304.20 (5) 1304.10 (7) B’ (MHz) 204.90 (3) 204.87 (4) C’ (MHz) 195.46 (3) 195.45 (3) ∆I” (amu Ǻ2) -268.4 (5) -268.9 (6) a/b/c-character 5.6/84.7/0.7 Band origin (cm-1) 30687.2 OMC (MHz) 3.32 3.91 Temp (K) 3.0

Possible R-Conformations R-Naproxen I R-Naproxen II R-Naproxen III R-Naproxen IV R-Naproxen V R-Naproxen VI MP2 / 6-31G**

Conformation Determination Experimental Theory Red Blue I II III IV V VI A” 1241.5 1315.7 1314.9 1240.6 1447.6 1254.8 1274.0 1226.7 B” 214.7 205.3 205.7 215.7 198.1 214.1 214.2 213.6 C” 202.2 196.07 195.7 202.1 191.4 200.6 197.2 199.7 MP2 / 6-31G** R-naproxen II R-naproxen I

Experimental vs. Theoretical Results (MP2 / 6-31G**) S-Naproxen (Naproxen I) R-Naproxen (Naproxen II) S0 A” (MHz) 1315.0 1314.9 1240.5 1240.6 B” (MHz) 205.7 215.7 C” (MHz) 195.7 202.1 ∆I” (amu A2) -258.8 -249.7 Experimental (Blue) (Red) A” (MHz) 1315.80 (6) 1315.71 (7) 1241.59 (6) 1241.56 (5) 205.36 (3) 205.30 (3) 214.70 (3) 214.73 (3) 196.10 (3) 196.07 (3) 202.15 (3) 202.16 (3) ∆I” (amu Ǻ2) -267.9 (5) -267.9(5) -260.8 (4) -260.7 (4) MP2 / 6-31G**

Lowest Energy Conformations S-naproxen II R-naproxen II S-naproxen I R-naproxen I Chem. Phys. Lett. (2003), 375, pg634 MP2 / 6-31G**

c c b b a a S-naproxen II R-naproxen II c c a a b b R-naproxen I S-naproxen I

Summary Rotationally resolved electronic spectra of R- and S-naproxen were obtained. For each enantiomer two conformations were assigned. As expected the conformations R and S-naproxen have matching spectra and inertial parameters

Future work Chiral axis Chiral center Diastereomers

Acknowledgments Leonardo Alvarez, Ryan Bird, Casey Clements, Adam Fleisher, Philip Morgan and Jessica Thomas Professor David W. Pratt for his encouragement and continuing support Funding by the National Science Foundation (CHE-0615755)