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66 protocols using avance drx 400

1

NMR Spectroscopic Analysis of Compounds

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Solution 1D and 2D NMR experiments (1H, 13C, DEPT-135, HSQC, and HMBC) spectra were performed by using a Bruker Avance DRX 400 spectrometer in DMSO-d6 (deutered dimethyl sulfoxide, up to 99.9%) solution at 300 K, which was used as an internal standard (1H: δ = 2.50 ppm; 13C: δ = 39.50 ppm).
Solid-state 13C-NMR (ssNMR) spectra were collected by using a Bruker Avance DRX 400 (9.4T) running at rotation of 10 kHz with cross polarization and using glycine (C=O: δ = 176.03 ppm) as an internal standard.
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2

NMR Spectroscopic Analysis of Organic Compounds

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NMR spectra were recorded using Avance DRX-400 and DPX-200 spectrometers (Bruker, Milan, Italy) operating at frequencies of 400 MHz (1H) and 100 MHz (13C) and 200 MHz (1H) and 50 MHz (13C), respectively The spectra were measured in CDCl3. The 1H- and 13C-NMR chemical shifts (δ) are expressed in ppm with reference to the solvent signals (CDCl3, δH 7.26 and δC 77.1). Coupling constants are given in Hz. NOESY (2D- NOE) experiments were executed on the Bruker Avance DRX-400 instrument. Preparative TLC was performed using pre-coated silica gel 60 F-254 plates (10 × 20 cm, Merck, Sigma-Aldrich, Milan, Italy) using n-hexane-acetone 8.5:1.5 as the eluent. Spots were visualized under UV light. Compounds were recovered from the stationary phase by washing five times with CH2Cl2 (DCM). Column chromatography was performed using MN Kiesegel 60 (70–230 mesh, Macherey-Nagel, Fisher Scientific, Milan, Italy). Fractions were monitored by TLC (Silica gel 60 F254; Merck), and spots on TLC were visualised under UV light and after staining with p-anisaldehyde-H2SO4-EtOH (1:1:98) followed by heating at 110 °C. All solvents used were of analytical grade and were purchased from VWR (VWR, Milan, Italy). Anhydrous Na2SO4 was purchased from Scharlau S.L. (Milan, Italy).
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3

Comprehensive Spectroscopic Characterization

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Optical rotations were measured on a Perkin-Elmer model 343 polarimeter. UV spectra were recorded on a Hitachi U2910 UV spectrophotometer. ECD measurements were performed on a JASCO J-810 spectropolarimeter. IR spectra were recorded on a Nicolet 6700 FT-IR spectrometer. 1H and 13C, DEPT, HSQC, HMBC, NOESY, and COSY NMR spectra were recorded on a Bruker Avance DRX-400, DRX-700, or a DRX-800 MHz NMR spectrometer. ESIMS, HRESIMS, and MS2 spectra were measured on a Bruker Maxis 4G Q-TOF mass spectrometer. All mass spectrometric data were obtained in the positive-ion mode using an ESI ion source, with scan ranges (m/z) from 100 to 1000. For MS2 measurements, a dilute sample (around 1 µM in MeOH) was introduced via a syringe pump at a flow rate of 3 µL/min. Column chromatography was conducted using silica gel (65 × 250 or 230 × 400 mesh, Sorbent Technologies). Analytical thin-layer chromatography (TLC) was performed on precoated silica gel 60 F254 plates (Sorbent Technologies). Sephadex LH-20 was purchased from Amersham Biosciences. For visualization of TLC plates, sulfuric acid reagent was used. Fluorescence was tested using a Spectroline (model ENF-260C) UV light source at 386 nm wavelength. All procedures were carried at room temperature using solvents purchased from commercial sources and employed without further purification.
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4

Analytical Characterization of Organic Compounds

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All solvents and chemical reagents were purchased from commercial sources and used as provided. 1H spectra were obtained on either a Bruker Avance DRX 400 or 500 MHz NMR spectrometer as specified, and all 13C NMR were obtained on a Bruker Avance DRX 500 NMR spectrometer. NMR chemical shifts are reported in δ (ppm) relative to internal solvent peaks and coupling constants were measured in Hz. 1H splitting patterns are reported as s (singlet), d (dublet), dd (dublet of dublets), t (triplet), q (quartet), and m (multiplet). NMR spectra were processed and analyzed using MNova NMR software. Low resolution LC/MS analysis of purified compounds was performed on a Waters Acquity UPLC/ESI-TQD instrument with a 2.1 × 50 mm Acquity UPLC BEH C18 column (Product #: 186002350). Silica chromatography was performed on a Teledyne CombiFlash Rf+ instrument. All reverse phase high performance liquid chromatography (RP-HPLC) was performed on a Waters 2545 binary gradient module equipped with an XBridge prep C18 column using H2O + 0.1% formic acid and CH3CN + 0.1% formic acid (5–95% gradient) while monitoring peak collection at 254 nm.
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5

Characterization of Amphiphilic Ionic Liquids

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The structures of the prepared ILs were investigated
with 1H and 13C NMR (Bruker AVANCE DRX-400)
using DMSO-d6 as a solvent. FT-IR spectra
were recorded
using a Nicolet FT-IR spectrophotometer in the wavenumber range of
4000–400 cm–1. Thermal degradation stability
of IPy-IL and AIPy-IL was evaluated from thermogravimetric analysis
(TGA; TGA-50 SHIMADZU) using N2 at a heating rate of 10
°C.min–1. Thermal analysis was determined by
DSC (Shimadzu DTG-60 M) with the heating rate of 10 °C min–1. The surface activities of the prepared ILs were
studied using a drop shape analyzer (DSA-100) by preparing different
concentrations of ILs in aqueous solution. Also, the IFT between Arabian
heavy crude oil and sea water was determined. The micelle size and
charge of the prepared amphiphilic ILs in aqueous solutions was studied
using dynamic light scattering (DLS; Zetasizer Nano ZS, Malvern Instrument
Ltd., Malvern, UK) at ambient temperature. The size of the prepared
emulsion with time after the addition of demulsifiers was noticed
using a Fluorescent Optical microscope (Olympus BX-51 microscope attached
with a 100 W mercury lamp). To determine the relative solubility number
(RSN), 1 g of IL was dissolved in toluene/dioxane solution and titrated
against deionized water. The number of DW mills required to reach
a cloud point of a clear solution is considered as the RSN value.
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6

N3• Generation from Pt(IV) Monitoring

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The N3 generation from Pt(IV) was detected by using 1H-NMR spectroscopy (Bruker AVANCE DRX 400, Germany). Briefly, Pt(IV) dissolved in D2O (10 mM) was added to the DMPO solution (20 mM) with or without Trp (2 mM). Thereafter, the reaction solutions were treated with two ways: the one without irradiation and the one irradiated by UV light for 1 min. At last, all these solutions were investigated by 1H-NMR spectroscopy.
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7

Synthesis and Characterization of Platinum Complexes

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Synthetic procedures were performed under a dinitrogen atmosphere. All solvents used were dried over molecular sieves and stored under a dinitrogen atmosphere [44 ]. CDCl3 solutions, if not otherwise stated, were used to register 1H-, 13C{H}- and 195Pt{H}-NMR spectra with a Bruker “Avance DRX400” spectrometer. TMS was used to reference 1H and 13C chemical shifts (δ ppm), while aqueous (D2O) H2PtCl6 was used for 195Pt. When samples were dissolved in non-deuterated solvents, the instrumental lock to the deuterium signal was achieved by inserting a sealed capillary containing C6D6 into the NMR tube. FTIR spectra in attenuated total reflectance (ATR) were registered with a Perkin–Elmer “Spectrum One” spectrometer. Band intensities are described as follows: w (weak), m (medium) and s (strong). Elemental analyses (C, H, N) were performed using an Elementar “vario MICRO cube” instrument, at Dipartimento di Chimica e Chimica Industriale, Università di Pisa.
Benzylbutylamine (BzBuNH) was synthesized from benzaldehyde and butylamine [18 (link)] and distilled before use. Diethanolamine (™Fluka) was passed over dry alumina before use.
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8

Spectroscopic and Chromatographic Analysis

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All commercially available chemicals and solvents were used as received without any further purification. Melting points were determined on a Büchi apparatus and are uncorrected. 1H NMR spectra and 2D spectra were recorded on a Bruker Avance DRX 400 instrument (Bruker BioSpin GmbH, Rheinstetten, Germany), whereas 13C NMR spectra were recorded on a Bruker AC 200 spectrometer (Bruker BioSpin GmbH, Rheinstetten, Germany) in deuterated solvents and were referenced to TMS (δ scale). The signals of 1H and 13C spectra were unambiguously assigned by using 2D NMR techniques: 1H-1H COSY, NOESY, HMQC, and HMBC. Mass spectra were recorded with a LTQ Orbitrap Discovery instrument (Thermo Scientific, Brehmen, Germany), possessing an Ionmax ionization source. Flash chromatography was performed on Merck silica gel 60 (0.040–0.063 mm) (Merck KGa, Darmstadt, Germany). Analytical thin layer chromatography (TLC) was carried out on precoated (0.25 mm) Merck silica gel F-254 plates. Stock solutions of compounds for biological experiments were prepared in DMSO (St. Louis, MO, USA) and stored at 20 °C. Working dilutions contained up to 0.1% v/v DMSO.
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9

Synthesis and Characterization of CHS-CS Conjugates

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CS was coupled with CHS via an amide bond as reported with slight modification [24 (link)]. Briefly, CS (15 mg), EDC (4 mg), and NHS (2 mg) were dissolved in 0.4 mL of distilled water (DW), followed by adding dropwise into 4 mL of DMF/DW mixture (9:1, v/v) under stirring at 500 rpm at room temperature. Then, an aliquot of DMF solution containing CHS (1.0 mg/mL) was added dropwise to the mixture for 4 h. The reaction was conducted for 48 h, then the reaction mixture was poured into 200 mL methanol/ammonia solution (7/3, v/v). The precipitates were filtered, washed thoroughly with methanol and DW, and then dialyzed against DW for 48 h to remove water-soluble by-products. The resultant CHS-CS was freeze-dried. The DS (the number of CHS groups per 100 glucosamine units of CS) was controlled by varying the amount of CHS, determined by the TNBS method [23 (link)]. The formation of the CHS-CS conjugate was confirmed by proton nuclear magnetic resonance (1H-NMR) (Avance DRX-400, Bruker, Bremen, Germany) analysis.
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10

Comprehensive Organic Synthesis Protocols

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Reagents and solvents were purchased from
common commercial suppliers and were used as such unless otherwise
indicated. Organic solutions were dried over anhydrous Na2SO4 and concentrated with a rotary evaporator at low pressure.
All reactions were routinely checked by thin-layer chromatography
(TLC) on silica gel 60 F254 (Merck) and visualized by using UV or
iodine. Column chromatography separations were carried out with Merck
silica gel 60 (mesh 70–230). Flash chromatography separations
were carried out with Merck silica gel 60 (mesh 230–400). Melting
points were determined in capillary tubes (Büchi Electrotermal
model 9100) and are uncorrected. Yields were of purified products
and were not optimized. 1H NMR spectra were recorded at
200 or 400 MHz (Bruker Avance DRX-200 or -400, respectively), while 13C NMR spectra were recorded at 100 MHz (Bruker Avance DRX-400).
Chemical shifts (δ) are given in ppm relative to TMS and calibrated
using residual undeuterated solvent as internal reference. Spectra
were acquired at 298 K. Data processing was performed with standard
Bruker software XwinNMR, and the spectral data are consistent with
the assigned structures. The purity of the tested compounds was evaluated
by combustion analysis using a Fisons elemental analyzer, model EA1108CHN,
and data for C, H, and N are within 0.4% of the theoretical values
(≥95% sample purity).
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