Nmr system 500 mhz spectrometer

¹H DOSY NMR spectra were recorded in perdeuterated solvents on a Varian (Palo Alto, CA, USA) NMR System 500 MHz spectrometer operating at 499.87. Chemical shifts are reported relative to the residual solvent signal. The measurements were carried out at room temperature. Each ¹H DOSY NMR measurement consisted of a series of 32 spectra: the number of scans 16, acquisition time 4s, relaxation pause d₁ = 2s—gradient power and delta time were selected in such a way as to record the decay of each of the tested signals as fully as possible.

¹H and ³¹P NMR spectra were recorded in perdeuterated solvents on a Varian (Palo Alto, CA, USA) NMR System 500 MHz spectrometer operating at 499.87 and 202.35 MHz, respectively. Chemical shifts are reported relative to the residual solvent signal (¹H) and 85% H₃PO_4(aq) (³¹P). The measurements were carried out at room temperature.
Figures S2–S6 in SM contain ¹H and ³¹P NMR spectra recorded for the solutions of the investigated ZnDOPs in perdeuterated solvents (DMSO-d₆ or CDCl₃).

Commercially available reagents were used as purchased without additional pretreatment and/or purification. Melting points were determined with an MPA100 Optimelt SRS apparatus (Stanford Research Systems, Sunnyvale, CA, USA) and are uncorrected. Nuclear magnetic resonance (NMR) spectra were recorded using a Varian NMR System 500 MHz spectrometer (Varian Inc., Palo Alto, CA, USA). Chemical shifts (δ) are reported in parts per million (ppm) related to residual deuterated dimethyl sulfoxide (DMSO-d₆, δH 2.48 ppm and δC 39.51 ppm) as internal standard; signal multiplicities (splitting patterns) are reported using the following abbreviations: s = singlet, d = doublet, t = triplet, quin = quintet, sxt = sextet, m = multiplet. Thin-layer chromatography (TLC) was carried out on aluminum plates with silica gel containing a fluorescent F₂₅₄ indicator (Kieselgel 60 F₂₅₄, Merck, Darmstadt, Germany) (0.2 mm thickness film) and the detection of compounds was performed with short-wave UV light at 254 nm. Silica gel with grain size 40 to 63 μm was used for preparative column chromatography. Fourier transform mass spectrometry (FTMS) was carried out on Q Exactive Hybrid Quadrupole-Orbitrap Mass Spectrometer, ESI (electrospray) with spray voltage 4.00 kV at IBB PAS Warsaw (Waters Corporation, Milford, MA, USA).