Arx300 spectrometer

The nuclear magnetic resonance (¹H-NMR) spectra were recorded using a Bruker ARX300 spectrometer (300 MHz) with a QNP probe. The acrolein solution was prepared by dissolving acrolein (5 uL) in DMSO-d₆ (1 mL) and the NMR spectrum for acrolein was recorded. Then, a solution of dimercaprol (50 mg) in DMSO-d₆ (1 mL) was added. The mixture was thoroughly shaken and allowed to incubate for 1 hr in the dark and then the NMR spectrum for the reaction products was recorded.

Solvents and reagents were purchased from commercial vendors and were used without any further purification. Melting points were determined using capillary tubes with a Mel-Temp apparatus and are uncorrected. Infrared spectra were obtained using KBr pellets. IR spectra were recorded using a Perkin-Elmer 1600 series or Spectrum One FTIR spectrometer. ¹H NMR spectra were recorded at 300 MHz using a Bruker ARX300 spectrometer with a QNP probe. ESIMS analyses were performed at the Purdue Campus-Wide Mass Spectrometry Center on a Finnegan-MATT LCQ Classic mass spectrometer. Analytical thin layer chromatography was done on Baker-flex silica gel IB2-F plates, and compounds were visualized with short wavelength UV light and ninhydrin staining. Silica gel flash chromatography was accomplished using 230–400 mesh silica gel. HPLC analyses were completed on a Waters 1525 binary HPLC pump/Waters 2487 dual λ absorbance detector system using a 5 μM C₁₈ reverse phase column. Compound purities were estimated by reversed phase C₁₈ HPLC, with UV detector at 254 nm, and the major peak area of each tested compound was ≥95% of the combined total peak area. All yields refer to isolated compounds. The rat plasma stability analysis of 16 was performed at Cyprotex US, LLC 313 Pleasant St. Watertown, MA 02472.