Unity spectrometers

All chemicals were reagent grade and were used as received. Moisture-sensitive reactions were performed under an inert atmosphere (dry nitrogen) with dried solvents. Reactions were monitored by TLC using Merck silica gel 60 F-254 thin-layer plates. Flash column chromatography was carried out on Merck silica gel 60 (230–400 mesh). ¹H NMR and ¹³C NMR spectra were recorded on Varian (Palo Alto, CA) Unity spectrometers at 400 and 500 MHz for ¹H and at 100 and 125 MHz for ¹³C. Coupling constants (J) are reported in hertz. High-resolution mass spectra (HRMS) were recorded in the University of Illinois Mass Spectrometry Laboratory. qNMR spectra were recorded using Varian (Palo Alto, CA) 500 MHz Unity spectrometers with 1,3,5-trimethoxybenzene (99.96% purity; Sigma-Aldrich TraceCERT^®, SKU:74599–1G) as the internal total-spin-count quantitation standard; 60° pulse excitation, 60 s recycle delay, 65,536 data points, 1.0 Hz line-broadening due to exponential multiplication, and 16 accumulations. qNMR data were processed using Mnova NMR software (Mestrelab, Escondido, CA). All NMR spectra (including qNMR spectra) are provided in the Supporting Information. All tested compounds are >95% pure by qNMR analysis.

All chemicals were reagent grade. Pentamidine and netropsin were purchased from Aldrich. ¹H NMR and ¹³C NMR spectra were obtained on Varian (Palo Alto, CA) Unity spectrometers at 400 and 500 MHz for ¹H and at 100 and 125 MHz for ¹³C. Elemental analyses were carried out in the University of Illinois Microanalysis Laboratory. HPLC/MS analyses were performed by using an Agilent LC/MSD Trap XCT Plus system (Agilent Technologies, Santa Clara, CA) with an 1100 series HPLC system including a degasser, an autosampler, a binary pump, and a multiple wavelength detector. All final compounds were ≥95% pure as determined by elemental analysis or analytical HPLC/MS analysis and were also characterized by ¹H NMR and HRMS.

All reagents were purchased from Aldrich (Milwaukee, WI). The purity of compounds investigated were confirmed by ¹H, ¹³C and ³¹P NMR spectroscopy at 400 MHz or 500 MHz performed on Varian (Palo Alto, CA) Unity spectrometers. High-resolution mass spectra were obtained at the University of Illinois Mass Spectrometry Laboratory. Cellulose thin layer chromatography (TLC) plates were visualized by using iodine or a sulphosalicylic acid-ferric chloride stain. The syntheses and characterization of 4–12 were described previously^{30 (link)}.

All chemicals were reagent grade. ¹H and ¹³C NMR spectra were obtained on Varian (Palo Alto, CA) Unity spectrometers at 400 or 500 MHz for ¹H and at 100 or 125 MHz for ¹³C. Elemental analyses were carried out in the University of Illinois Microanalysis Laboratory. HPLC-MS analyses were performed by using an Agilent LC/MSD Trap XCT Plus system (Agilent Technologies, Santa Clara, CA) with an 1100 series HPLC system including a degasser, an autosampler, a binary pump, and a multiple wavelength detector. All final compounds were ≥95% pure as determined by HPLC and structures were characterized by ¹H NMR, LC-MS and HRMS. More detailed information on the synthesis of benzoic acids can be found in the Supporting Information.