Avance 3 hd 400 nmr spectrometer

UPLC/MS analysis was performed on Waters TQD spectrometer combined with UPLC Acquity H-Class with PDA eLambda detector. Waters Acquity UPLC BEH C18 1.7 μm 2.1 × 100 mm chromatographic column was used, at 40 °C, 0.300 ml/min flow rate and 1.0 μL injection volume (the samples were dissolved in LC-MS grade acetonitrile, typically at a concentration of 0.1–1 mg/ml prior to injection). All mass spectra were recorded under electrospray ionization in positive mode (ESI+) and chromatograms were recorded with UV detection in the range of 190–300 nm. The gradient conditions used were: 80% phase A (water+ 0.1% formic acid) and 20% phase B (acetonitrile + 0.1% formic acid) to 100% phase B (acetonitrile + 0.1% formic acid) at 3.0 minutes, kept till 3.5 minutes, then to initial conditions until 4.0 minutes and kept for additional 2.0 minutes. Total time of analysis – 6.0 minutes.
¹H and ¹³C NMR spectra were recorded on a Bruker Avance III HD 400 NMR spectrometer. All samples were dissolved in DMSO-d₆ with TMS as the internal standard. The spectral data of the compounds refer to their free bases.
All presented compounds were of at least 95% purity as determined by LC-MS. Syntheses and characterization details for intermediate products and final compounds as well as the spectral data for all compounds is included in the Supporting Information.

The FTIR spectra were collected from PerkinElmer Spectrum II FT-IR Spectrometer. The ¹H NMR spectra were acquired on a Bruker AVANCE III HD 400 NMR spectrometer using deuterated DMSO as the field frequency lock. The ⁶⁷Zn NMR spectra were acquired on a Bruker AV 600 NMR spectrometer using deuterated DMSO as the field frequency lock. The SEM images were collected from Hitachi SU4800. The ex situ SEM samples were obtained by disassembling the cell, extracting the electrode, washing by DI water for 3 times, and drying at vacuum (~25 °C) for 8 h.The DLS measurement was performed on DLS instrument (Zetasizer Nano ZS, Malvern Instruments Ltd) at 25 °C with scattering angle of 90° and laser wavelength of 632.8 nm. The ionic conductivities of the electrolytes were measured on a conductivity meter (DDS-11A, INESA) at ~25 °C.

An Avance III HD 400 NMR-spectrometer by Bruker (Billerica, MA, USA), which operates at 400 MHz, was used for the ¹³C-NMR measurements. Approximately 1 mL of the extraction solvent ChCl+Lev/EtOH/TriA (30:40:30) in weight was filled into Norell 507-HP-7 High-Precision-NMR sample tubes (Norell Inc., Morganton, NC, USA). The sample was measured right after preparation, one day, and three days after preparation. The sample tube was not sealed with parafilm, and the solvent was not changed to imitate the normal conditions the solvent would have to endure during cycle extraction.

Specific rotations were measured by an SGW-1 automatic polarimeter (Shanghai Jing Ke Industrial Co., Ltd., Shanghai, China). ECD spectra were measured on an Aviv Model 420SF spectropolarimeter (Aviv Biomedical Inc., Lakewood, NJ, USA). The NMR spectra were recorded on a Bruker Avance III HD-400 NMR spectrometer. HRESIMS spectra were obtained on a Waters Xevo G2 Q-TOF spectrometer fitted with an ESI source. Semi-preparative high-performance liquid chromatography (HPLC) was undertaken on a Shimadzu LC-6AD pump (Shimadzu Co., Kyoto, Japan) using a UV detector, and a YMC-Pack ODS-A HPLC column (semipreparative, 250 × 10 mm, S-5 μm, 12 nm, YMC Co., Ltd., Kyoto, Japan) was used for separation.

The ¹H-NMR, ¹³C-NMR and ¹⁹F-NMR spectra were recorded at 400 MHz, 100 MHz and 376 MHz, respectively, on a Bruker AVANCEIII HD 400 NMR spectrometer (Bruker BioSpin GmbH, Rheinstetten, Germany) in deuterated solvents (D₂O and DMSO-d₆). The chemical shift (δ) for ¹H-NMR, ¹³C-NMR and ¹⁹F-NMR are given in ppm relative to the residual signal of the solvent. Coupling constants are given in Hz. The following abbreviations are used to indicate the multiplicity: s, singlet; d, doublet; t, triplet; q, quartet; quin, quintet; m, multiplet; dd, doublet of doublets; td, triplet of doublets; dt, doublet of triplets; ddd, doublet of doublet of doublets; bs, broad signal. The reactions were monitored using TLC (thin-layer chromatography) silica gel 60 F254 (Merck KGaA, Darmstadt, Germany). Evaporation of solvents was performed under reduced pressure. Melting points were measured and recorded by the OptiMelt MPA-100 apparatus (Standford Research Systems, Sunnyvale, CA, USA) and uncorrected.

Both chemicals and anhydrous solvents of analytical grade were purchased from commercial suppliers. Six phytopathogenic fungi were provided by Institute of Pesticides, Yangtze University, and weed seeds were obtained from Jingzhou, Hubei province, China. The melting points of conjugates 4a–l were determined on an XT-4 melting point apparatus (Shanghai Jingke Industrial Co. Ltd., Shanghai, China). Thin-layer chromatography (TLC) was performed on silica gel 60 F254 (Qingdao Marine Chemical Ltd., Qingdao, China). Column chromatography purification was carried out on silica gel (200–300 mesh) (Qingdao Marine Chemical Ltd., Qingdao, China). Nuclear mass resonance (NMR) spectra were recorded in dimethyl sulfoxide (DMSO)-d₆ solution on a AVANCE III HD 400 NMR spectrometer (Bruker Corporation, Basel, Switzerland).