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Deuterated nmr solvents

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Deuterated NMR solvents are specialized laboratory chemicals used in nuclear magnetic resonance (NMR) spectroscopy. These solvents contain deuterium (2H) instead of the more common hydrogen (1H) isotope, which provides a distinct signal in NMR analysis that does not interfere with the signals from the analyte of interest.

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Lab products found in correlation

Cell culture media and supplements, by Thermo Fisher Scientific (2 mentions) Mestrenova mnova 12, by Mestrelab Research (2 mentions) Ecz 500 nmr spectrometer, by JEOL (2 mentions) Acetylthiocholine iodide, by Merck Group (1 mentions) Temephos, by Merck Group (1 mentions) Triton x 100, by Merck Group (1 mentions) Hplc grade methanol, by Thermo Fisher Scientific (1 mentions) Ms grade water, by Avantor (1 mentions) Hexane, by Thermo Fisher Scientific (1 mentions) Acetonitrile, by Thermo Fisher Scientific (1 mentions) Ethyl acetate, by Thermo Fisher Scientific (1 mentions) Acetonitrile, by Avantor (1 mentions) Potassium periodate, by Merck Group (1 mentions) Butyrylthiocholine, by Merck Group (1 mentions) Ethopropazine hydrochloride, by Merck Group (1 mentions) Formic acid, by Thermo Fisher Scientific (1 mentions) Ammonium formate, by Thermo Fisher Scientific (1 mentions) Optima lc ms grade acetonitrile, by Thermo Fisher Scientific (1 mentions) Ay9944, by Merck Group (1 mentions) Easycyp bactosomes, by Xenotech (1 mentions)

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Deuterated solvents (94 citations) NMR solvents (33 citations) Deuterated solvents for NMR (8 citations) Deuterated solvents for NMR spectroscopy (3 citations)

17 protocols using deuterated nmr solvents

1

Characterization of Pesticide Residues

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Temephos, TDP, SODP, potassium periodate, acetylthiocholine iodide (ATCh), 5,5-dithio-2-bis-nitrobenzoic acid (DTNB), Triton X-100, butyrylthiocholine, and ethopropazine hydrochloride were purchased from Sigma-Aldrich (St. Louis, MO, USA). Ethyl-paraoxon was obtained from Supelco. T.M. FOS® 500 CE (46%) was acquired from Agromundo, S.A. de C.V. (Mexico City, Mexico). HPLC-grade methanol, ethyl acetate, hexane, and acetonitrile (ACN) were purchased from Fisher Chemical (Fair Lawn, NJ, USA). Ultrapure water was obtained from a Milli-Q system (Millipore, USA). MS-grade water and acetonitrile were purchased from J.T. Baker (Center Valley, PA, USA). Deuterated NMR solvents were acquired from Cambridge Isotope Laboratories (Tewksbury, MA, USA). Sodium hypochlorite (Cloralex®, 5% chlorine solution) was acquired from Alen del Norte, S.A. de C.V. (Monterrey, NL, Mexico). The Drabkin reagent was obtained from Hycel (Houston, TX, USA). All other chemicals were of the highest purity available.
Verdín-Betancourt F.A., Figueroa M., López-González M.D., Gómez E., Bernal-Hernández Y.Y., Rojas-García A.E, & Sierra-Santoyo A. (2019). In vitro inhibition of human red blood cell acetylcholinesterase (AChE) by temephos-oxidized products. Scientific Reports, 9, 14758.
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2

Profiling Cytochrome P450 Metabolism

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Optima LC-MS grade acetonitrile, water, formic acid, and ammonium
formate used in liquid chromatography were purchased from Fisher Scientific
(Santa Clara, CA). BACs of various alkyl chain lengths (C10-,
C12-, C14-, and C16-BAC), the DHCR7
inhibitor AY9944, and all synthetic reagents and starting materials were from
Sigma-Aldrich (St. Louis, MO). Deuterated NMR solvents were from Cambridge
Isotopes Laboratories, Inc. (Andover, MA). Human liver tissues were obtained
from the School of Pharmacy Human Liver Bank at the University of Washington
(Seattle, WA). Human recombinant CYP enzymes individually-expressed in
Escherichia coli (EasyCYP Bactosomes) co-expressing human
cytochrome P450 reductase and, where indicated as +b5, supplemented
with purified human cytochrome b5 (CYPs 1A2, 2A6+b5, 2A13,
2B6+b5, 2C8+b5, 2C9+b5, 2C19+b5,
2D6, 2E1+b5, 2J2, 3A4+b5, 3A5+b5,
4A11+b5, 4F2+b5, and 4F3B+b5) and membrane
protein from E. coli with empty expression plasmid (EasyCYP
Control Bactosomes) were from XenoTech, LLC (Lenexa, KS). Human recombinant
CYP4F12 containing human cytochrome P450 reductase and cytochrome b5in insect microsomes isolated from baculovirus-transfected insect cells (CYP4F12
Supersomes) and negative control insect cell microsomes (Control Supersomes)
were from Corning (Corning, NY). NADPH co-factor was from Oriental Yeast (Tokyo,
Japan).
Seguin R.P., Herron J.M., Lopez V., Dempsey J.L, & Xu L. (2019). Metabolism of Benzalkonium Chlorides by Human Hepatic Cytochromes P450. Chemical research in toxicology, 32(12), 2466-2478.
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3

Lanthanide Complex Synthesis and Characterization

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All air- and water sensitive procedures were carried out using standard Schlenk techniques. Deuterated NMR solvents were purchased from Cambridge Isotope Laboratories (MA) and used as received. Hexahydrates of GdCl3, YCl3, and EuCl3 were obtained from Alfa Aesar (REacton, Ward Hill, MA). Cyclen and DOTA were purchased from Strem Chemicals (Newburyport, MA). All other organic solvents and bulk inorganic reagents were purchased from EM Science (Gibbstown, NJ) and used as received, except where indicated. Distilled water was purchased from Arrowhead (Louisville, KY). Dionized water was generated from a PURELAB Ultra Mk2 water purifier (Elga). 1H T1 measurements were acquired on a Varian 400MR NMR Spectrometer at 9.4 T, or on a Bruker mq 60 NMR Analyzer at 1.4 T. 19F-NMR spectra were acquired on a Varian VNMRS 500 NMR Spectrometer at 11.7 T. Chemical shifts were referenced to residual solvent (1H) or C6F6 (19F).
Wu X., Dawsey A.C., Siriwardena-Mahanama B.N., Allen M.J, & Williams T.J. (2014). A (Fluoroalkyl)Guanidine Modulates the Relaxivity of a Phosphonate-Containing T1-Shortening Contrast Agent. Journal of fluorine chemistry, 168, 177-183.
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4

Inert Atmosphere Synthesis and Characterization

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All air- and water-sensitive procedures were carried out either in a Vacuum Atmospheres glovebox under nitrogen (0.5−10 ppm of O2 for all manipulations) or using standard Schlenk techniques under nitrogen. Deuterated NMR solvents were purchased from Cambridge Isotopes Laboratories. Benzene and dichloromethane-d2 were dried over sodium benzophenone ketyl and distilled prior to use. Formic acid (HCOOH) was purchased from Sigma-Aldrich and used under a N2 atmosphere without further purifications. Acetic acid was dried over CaH2 and distilled prior to use. The integrity of this material was checked regularly by NMR. Cyclooctadiene iridium chloride dimer (7) was purchased from Sigma-Aldrich and used as received. Sonication procedures were done in a VWR desktop sonic cleaner bath. Silver trifluoromethylsulfonate was purchased from Alfa Aesar and used as received. 1H, 13C, and 31P NMR spectra were obtained on Varian 600 or 500 MHz spectrometers with chemical shifts reported in units of ppm. All 1H chemical shifts were referenced to the residual 1H solvent (relative to TMS). NMR spectra were taken in 8-inch J-Young tubes (Wilmad) with Teflon valve plugs. All spectra were processed using MesRe Nova (v.11.0.4–11998). MALDI mass spectrometry was conducted on a Bruker Autoflex system.
Lauridsen P.J., Lu Z., Celaje J.J., Kedzie E.A, & Williams T.J. (2018). Conformational Twisting of a Formate-Bridged Diiridium Complex Enables Catalytic Formic Acid Dehydrogenation. Dalton transactions (Cambridge, England : 2003), 47(38), 13559-13564.
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5

NMR Spectroscopy of Chemical Compounds

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1H, 13C, and 19F NMR spectroscopies
were performed on
a JEOL 400 MHz NMR. Deuterated NMR solvents were purchased from Cambridge
Isotope Labs. Chemical shifts were referenced to the residual solvent
peaks in the NMR spectra. Complete NMR spectra are provided in the Supporting Information.
O’Rourke B., Lauderback C., Teodoro L.I., Grimm M., Zeller M., Mirjafari A., Guillet G.L, & Hillesheim P.C. (2021). Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids. ACS Omega, 6(47), 32285-32296.
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6

Oxidative Stress Assay Protocol

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All solvents used for chromatographic separations (ACS reagent, HPLC, and LC-MS grade) were purchased from Fisher Scientific (Fair Lawn, NJ). Bovine serum albumin (BSA), 2′,7′-dichlorodihydrofluorescin diacetate (H2DCF-DA), digitonin, DMSO, EDTA, esterase, FeSO4, flavin adenine dinucleotide phosphate (FAD), glucose-6-phosphate (G-6-P), glucose-6-phosphate dehydrogenase (G-6-P-D), H2O2, menadione, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT), nicotinamide adenine dinucleotide phosphate (NADP), quercetin, L-sulforaphane, Trizma base, and Tween 20, were purchased from Sigma-Aldrich (St. Louis, MO). Cell culture media and supplements were obtained from Life Technologies, Inc. (Grand Island, NY). Deuterated NMR solvents were purchased from Cambridge Isotope Laboratories (Andover, MA).
Li J., Yuan C., Pan L., Benatrehina P.A., Chai H., Keller W.J., Naman C.B, & Kinghorn A.D. (2017). Bioassay-guided Isolation of Antioxidant and Cytoprotective Constituents from a Maqui Berry (Aristotelia chilensis) Dietary Supplement Ingredient as Markers for Qualitative and Quantitative Analysis. Journal of agricultural and food chemistry, 65(39), 8634-8642.
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7

Synthesis and Purification of N-Alkylimidazoles

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N-Alkylimidazoles were prepared following previously reported procedures.5,6 (link) Acetone as a reaction solvent was dried over anhydrous CaSO4 and then distilled. Acetonitrile (MeCN) as a reaction solvent was dried over anhydrous K2CO3 and then distilled. Tetrahydrofuran (THF) was distilled with some benzoquinone and sodium. Deuterated NMR solvents were bought from Cambridge Isotope Laboratories and used as received. All other chemicals and solvents were used as received.
Chae H., Lee Y.H., Yang M., Yoon W.J., Yoon D.K., Jeong K.U., Song Y.H., Choi U.H, & Lee M. (2019). Interesting phase behaviors and ion-conducting properties of dicationic N-alkylimidazolium tetrafluoroborate salts. RSC Advances, 9(7), 3972-3978.
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8

Fluorescence-based Oxidative Stress Assay

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CA, CAAE,
CAPE, cinnamic aldehyde, sodium phosphate monobasic monohydrate (NaH2PO4 H2O), sodium phosphate dibasic heptahydrate
(Na2HPO4 7H2O), 1,1-diphenyl-2-picrylhydrazyl
radical (DPPH), NaIO4, KIO4, 2,4-dinitrochlorobenzene
(DNCB), and N-acetylcysteine (NAC) were purchased
from Sigma-Aldrich (Steinheim, Germany). Deuterated NMR solvents were
acquired from Cambridge Isotope Laboratories. Ethanol (EtOH) (96%)
and formic acid (FA) (99–100%) were obtained from VWR International
(Pennsylvania, US). Acetonitrile (ACN) (≥99.9%), LC-grade water,
and the 2 mL deep-well plates were acquired from Thermo Fisher Scientific
(Seelze, Germany). N-Terminal acetylated peptide Ac-PHCKRM was obtained
from Peptide 2.0 (Chantilly, US), while Ac-RFAACAA was acquired from
RS Synthesis (Louisville, United States). Monobromobimane (MBrB) was
purchased from Cayman Chemical (Michigan, United States). 96-well
black plates were purchased from PerkinElmer (Massachusetts, United
States).
Ndreu L., Hurben A.K., Nyman G.S., Tretyakova N.Y., Karlsson I, & Hagvall L. (2023). Investigation into Propolis Components Responsible for Inducing Skin Allergy: Air Oxidation of Caffeic Acid and Its Esters Contribute to Hapten Formation. Chemical Research in Toxicology, 36(6), 859-869.
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9

Synthesis and Characterization of Air-Sensitive Complexes

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Unless otherwise stated, all reactions
were performed under a dinitrogen
atmosphere using either a controlled-atmosphere glovebox or Schlenck
line techniques. 1,2-bis(diphenylphosphino)ethane (dppe) was purchased
from Strem Chemicals and used without further purification. Crystalline
bis(trifluoro-methanesulfonyl)imide was purchased from Acros Organics
and used without further purification. Research-grade gases were purchased
from Matheson and used directly. All solvents were dried and deoxygenated
by purging with dry dinitrogen gas for 15 min before passing through
packed columns of activated alumina and activated copper. After synthesis,
materials were stored under dry argon in an atmosphere-controlled
glovebox until their use in testing.
Solution-state NMR spectra
were recorded on a Varian 300 MHz instrument
with 1H shifts reported relative to the residual solvent
peak, and 31P peaks reported relative to 85% H3PO4. Deuterated NMR solvents were purchased from Cambridge
Isotopes Laboratories. Deuterated benzene was purified by vacuum distillation
from a sodium/benzophenone solution before use. Deuterated bromobenzene
was dried over CaH2 and vacuum distilled before use.
Abrecht D.G., Muñoz J.A., Smith H.L, & Fultz B. (2014). Spin-State Effects on the Thermal Dihydrogen Release from Solid-State [MH(η2-H2)dppe2]+ (M = Fe, Ru, Os) Organometallic Complexes for Hydrogen Storage Applications. The Journal of Physical Chemistry. C, Nanomaterials and Interfaces, 118(4), 1783-1792.
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10

Purification and Characterization of Compound 1

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Proton NMR spectra were recorded in CDCl3 on a 400 MHz Bruker (Billerica, MA, USA) NMR spectrometer using the residual solvent signals (δH at 7.28 ppm) as internal standards. High-performance liquid chromatography isolation and purification of compound 1 was conducted on a Shimadzu (Nakagyo-ku, Kyoto, Japan) LC-8A preparative LC coupled to a Shimadzu SPD-M10A VP diode array detector. The UPLC-HRMS/MS analysis was conducted on a Waters (Milford, MA, USA) Xevo G2-XS qTOF with an ESI positive ion mode and data-dependent acquisition mode to obtain MS and MS/MS data. The HPLC-MS/MS analysis was conducted on a Thermo–Finnigan (San Jose, CA, USA) LCQ Advantage ion trap mass spectrometer with an ESI positive ion mode and data-dependent manner to obtain MS and MS/MS data. High-performance liquid chromatography preparative and analytical columns was obtained from Phenomenex (Torrance, CA, USA), and a UPLC analytical column was obtained from Waters. All solvents were HPLC-grade purchased from Thermo-Fisher Scientific (Waltham, MA, USA) and HPLC-grade water obtained by filtration using a Milli-Q Direct water purification system from Millipore (Billerica, MA, USA) unless otherwise stated. Deuterated NMR solvents were purchased from Cambridge Isotope Laboratories (Tewksbury, MA, USA).
Ding C.Y., Pang L.M., Liang Z.X., Goh K.K., Glukhov E., Gerwick W.H, & Tan L.T. (2018). MS/MS-Based Molecular Networking Approach for the Detection of Aplysiatoxin-Related Compounds in Environmental Marine Cyanobacteria. Marine Drugs, 16(12), 505.
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