Electronic Supplementary Information for Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity
|
|
- Theresa Lorraine Whitehead
- 5 years ago
- Views:
Transcription
1 Electronic Supplementary Information for Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Contents Qi-Qiang Wang, Rowshan Ara Begum, Victor W. Day, Kristin Bowman-James* Department of Chemistry, University of Kansas, Lawrence, Kansas * General experimental procedure Figure S1. 1 H NMR changes of CEES in CD 3 OD over time. Figure S2. 1 H NMR changes of CEES in D 2 O over time. Figure S3. 1 H NMR changes of HN2 in DMSO-d 6 over time. Figure S4. 1 H NMR changes of HN2 in CD 3 OD over time. Figure S5. 1 H NMR changes of HN2 in D 2 O over time. Figure S6. 1 H NMR changes of HN3 in DMSO-d 6 over time. Figure S7. 1 H NMR changes of HN3 in CD 3 OD over time. Figure S8. 1 H NMR changes of HN3 in D 2 O over time. Figure S9. 1 H NMR monitoring of the reaction between BCEE and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data). Figure S10. 1 H NMR monitoring of the reaction between CEES and (CH 3 ) 2 NH in CDCl 3. Figure S11. 1 H NMR monitoring of the reaction between CEES and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data). Figure S12. 1 H NMR monitoring of the reaction between HN2 and CH 3 NH 2 in CDCl 3. Figure S13. 1 H NMR monitoring of the reaction between HN2 and CH 3 CH 2 NH 2 in CDCl 3. Figure S14. 1 H NMR monitoring of the reaction between HN2 and (CH 3 ) 2 NH in CDCl 3 (with ESI-MS data).
2 Figure S15. 1 H NMR monitoring of the reaction between HN2 and (CH 3 CH 2 ) 2 NH in CDCl 3 (with ESI-MS data). Figure S16. 1 H NMR monitoring of the reaction between HN2 and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data). Figure S17. 1 H NMR monitoring of the reaction between HN3 and (CH 3 ) 2 NH in CDCl 3 (with ESI-MS data). Figure S18. 1 H NMR monitoring of the reaction between HN3 and (CH 3 CH 2 ) 2 NH in CDCl 3 (with ESI-MS data). Figure S19. 1 H NMR monitoring of the reaction between HN3 and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data). Figure S20. 1 H NMR of the precipitates isolated from the reaction between BCEE and (CH 3 ) 2 NH in CDCl 3 (with ESI-MS data). Figure S21. 1 H NMR of the precipitates isolated from the reaction between HN3 and CH 3 NH 2 in CDCl 3 (with ESI-MS data). Table S1. Crystallographic data for 4,4-dimethylmorpholinium chloride (A) and 2,2 -oxybis(n,n,n-trimethylethanaminium) dichloride (B). General experimental procedure Oxygen mustard, bis(β-chloroethyl) ether (BCEE), and half mustard, 2-chloroethyl ethyl sulfide (CEES) were purchased from Aldrich and used as received. Nitrogen mustards HN2 and HN3 were purchased from Aldrich and received as hydrochloride form, mechlorethamine hydrochloride and tris(2-chloroethyl)amine hydrochloride. The hydrochloride was neutralized by NaOH in water and extracted rapidly with diethyl ether, dried over anhydrous Na 2 SO 4 to give the free amine form. Deuterated solvents CDCl 3, CD 3 CN, DMSO-d 6, CD 3 OD and D 2 O were purchased from Cambridge Isotope Laboratories, Inc. Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 spectrometer. Chemical shifts of the protons are expressed in ppm and calibrated against TMS as an internal reference or the residue solvent proton signals. Mass spectral data were obtained from the Mass Spectrometry Laboratory at the University of Kansas on a LCT Premier Mass spectrometer. For X-ray crystallography study, intensity data were collected at 100K using a Bruker APEX II CCD area detector mounted on a Bruker D8 goniometer. Monochromatic Cu K α radiation ( = Å) was provided with Helios multilayer optics and a Bruker MicroStar microfocus rotating anode operating at 45kV and 60mA. The crystallographic data and details of data collection for 4,4-dimethylmorpholinium chloride (A) and 2,2 -oxybis(n,n,n-trimethylethanaminium) dichloride (B) are given in Table S1.
3 Figure S1. 1 H NMR changes (400 MHz, rt) of CEES in CD 3 OD over time.
4 Figure S2. 1 H NMR changes (400 MHz, rt) of CEES in D 2 O over time.
5 Figure S3. 1 H NMR changes (400 MHz, rt) of HN2 in DMSO-d 6 over time.
6 Figure S4. 1 H NMR changes (400 MHz, rt) of HN2 in CD 3 OD over time.
7 Figure S5. 1 H NMR changes of HN2 in D 2 O over time.
8 Figure S6. 1 H NMR changes (400 MHz, rt) of HN3 in DMSO-d 6 over time.
9 Figure S7. 1 H NMR changes (400 MHz, rt) of HN3 in CD 3 OD over time.
10 Figure S8. 1 H NMR changes (400 MHz, rt) of HN3 in D 2 O over time.
11 < 10% conversion (7 d) C 7 H 17 ClNO + (ESI-MS) Calc Expt Figure S9. 1 H NMR monitoring (400 MHz, rt) of the reaction between BCEE and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data).
12 < 10% conversion (7 d) Figure S10. 1 H NMR monitoring (400 MHz, rt) of the reaction between CEES and (CH 3 ) 2 NH in CDCl 3.
13 < 10% conversion (7 d) C 7 H 18 NS + (ESI-MS) Calc Expt Figure S11. 1 H NMR monitoring (400 MHz, rt) of the reaction between CEES and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data).
14 ca. 25% conversion (7 d) Figure S12. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN2 and CH 3 NH 2 in CDCl 3.
15 < 10% conversion (7 d) Figure S13. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN2 and CH 3 CH 2 NH 2 in CDCl 3.
16 ca. 80% conversion (7 d) C 7 H 17 N 2 + (ESI-MS) Calc Expt Figure S14. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN2 and (CH 3 ) 2 NH in CDCl 3 (with ESI-MS data).
17 ca. 20% conversion (7 d) C 9 H 21 N 2 + (ESI-MS) Calc Expt Figure S15. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN2 and (CH 3 CH 2 ) 2 NH in CDCl 3 (with ESI-MS data).
18 ca. 35% conversion (7 d) C 8 H 20 ClN 2 + (ESI-MS) Calc Expt Figure S16. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN2 and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data).
19 ca. 50% conversion (7 d) C 8 H 18 ClN 2 + (ESI-MS) Calc Expt Figure S17. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN3 and (CH 3 ) 2 NH in CDCl 3 (with ESI-MS data).
20 < 10% conversion (7 d) C 10 H 22 ClN 2 + (ESI-MS) Calc Expt Figure S18. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN3 and (CH 3 CH 2 ) 2 NH in CDCl 3 (with ESI-MS data).
21 < 10% conversion (7 d) C 9 H 21 Cl 2 N 2 + (ESI-MS) Calc Expt Figure S19. 1 H NMR monitoring (400 MHz, rt) of the reaction between HN3 and (CH 3 ) 3 N in CDCl 3 (with ESI-MS data).
22 C 6 H 14 NO + (ESI-MS) Calc Expt Figure S20. 1 H NMR (400 MHz, rt, D 2 O) of the precipitates isolated from the reaction between BCEE and (CH 3 ) 2 NH in CDCl 3 (with ESI- MS data).
23 C 7 H 15 N 2 + (ESI-MS) Calc Expt Figure S21. 1 H NMR (400 MHz, rt, D 2 O) of the precipitates isolated from the reaction between HN3 and CH 3 NH 2 in CDCl 3 (with ESI-MS data).
24 Table S1. Crystallographic data for 4,4-dimethylmorpholinium chloride (A) and 2,2 -oxybis(n,n,n-trimethylethanammonium) dichloride (B) A Formula C 6 H 14 ClNO C 10 H 28 Cl 2 N 2 O 2 Formula weight Crystal size (mm 3 ) Crystal system Orthorhombic Monoclinic Space group P C c a (Å) (3) (7) b (Å) (4) (2) c (Å) (4) (4) ( o ) ( o ) (10) ( o ) V (Å 3 ) (5) (9) Z 4 4 calcd (g cm -3 ) (Å) T (K) 100(2) 100(2) F(000) (mm -1 ) Abs corr Multi-scan Multi-scan Max, min trans 1.000, , range ( o ) Reflns collected Indep reflns R(int) Data/restr/param 1438 / 0 / / 2 / 257 a R 1 ; wr ; ; GOF (F 2 ) Obsd data [I > 2 (I)] Largest diff. peak and hole (e Å - 3 ) 0.161, , a R 1 (obsd data) = F o F c / F o. wr 2 (all data) = { [w(f o 2 -F c 2 ) 2 ] / [w(f o 2 ) 2 ]} 1/2 B
Electronic Supplementary Information for: Gram-scale Synthesis of a Bench-Stable 5,5 -Unsubstituted Terpyrrole
Electronic Supplementary Information for: Gram-scale Synthesis of a Bench-Stable 5,5 -Unsubstituted Terpyrrole James T. Brewster II, a Hadiqa Zafar, a Matthew McVeigh, a Christopher D. Wight, a Gonzalo
More informationReaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O 2
Electronic Supplementary Information for: Reaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O - and H O Includes Conversion of a Peroxomanganese(III) Adduct to a Bis(µ- O)dimanganese(III,IV)
More informationSupplementary Materials for
www.advances.sciencemag.org/cgi/content/full/1/5/e1500304/dc1 Supplementary Materials for Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne click reaction This PDF file includes:
More informationThe oxide-route for the preparation of
Supporting Information for: The oxide-route for the preparation of mercury(ii) N-heterocyclic carbene complexes. Simon Pelz and Fabian Mohr* Fachbereich C-Anorganische Chemie, Bergische Universität Wuppertal,
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Over or under: Hydride attack at the metal versus the coordinated
More informationBiasing hydrogen bond donating host systems towards chemical
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Biasing hydrogen bond donating host systems towards chemical warfare agent
More informationSupporting information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Template-directed synthesis
More informationHydrophobic Ionic Liquids with Strongly Coordinating Anions
Supporting material Hydrophobic Ionic Liquids with Strongly Coordinating Anions Hasan Mehdi, Koen Binnemans*, Kristof Van Hecke, Luc Van Meervelt, Peter Nockemann* Experimental details: General techniques.
More informationReversible dioxygen binding on asymmetric dinuclear rhodium centres
Electronic Supporting Information for Reversible dioxygen binding on asymmetric dinuclear rhodium centres Takayuki Nakajima,* Miyuki Sakamoto, Sachi Kurai, Bunsho Kure, Tomoaki Tanase* Department of Chemistry,
More information2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2- b]pyrrole (AAPP) AIEgens: tunable RIR and TICT characteristics
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2017 2,5-bis(4-alkoxycarbonylphenyl)-1,4-diaryl-1,4-dihydropyrrolo[3,2- b]pyrrole (AAPP) AIEgens:
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationZero-field slow magnetic relaxation in a uranium(iii) complex with a radical ligand
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information for: Zero-field slow magnetic relaxation in a uranium(iii) complex with
More informationSupplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary Information A Novel Single-Side Azobenzene-Grafted Anderson-Type Polyoxometalate
More informationTotal Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol
. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry Total Synthesis of Gonytolides C and G, Lachnone C, and Formal Synthesis
More informationSupporting Information
Selective Hg 2+ sensing behaviors of rhodamine derivatives with extended conjugation based on two successive ring-opening processes Chunyan Wang a,b and Keith Man-Chung Wong a,b * a Department of Chemistry,
More informationAnion recognition in water by a rotaxane containing a secondary rim functionalised cyclodextrin stoppered axle
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information: Anion recognition in water by a rotaxane containing a secondary rim
More informationPrabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra*
Supporting Information Ferrocenyl BODIPYs: Synthesis, Structure and Properties Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra* Department of Chemistry, Indian Institute of Technology
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Quantitative evaluation of anion-π interactions in solution Guzmán Gil-Ramirez, a Eduardo C. Escudero-Adan, a Jordi
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H
More information,
2013. 54, 6. 1115 1120 UDC 548.737:547.12 CHARACTERIZATION AND CRYSTAL STRUCTURES OF SOLVATED N -(4-HYDROXY-3-NITROBENZYLIDENE)-3-METHYLBENZOHYDRAZIDE AND N -(4-DIMETHYLAMINOBENZYLIDENE)-3-METHYLBENZOHYDRAZIDE
More informationIron Complexes of a Bidentate Picolyl NHC Ligand: Synthesis, Structure and Reactivity
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supplementary Information for Iron Complexes of a Bidentate Picolyl HC Ligand: Synthesis,
More informationCu(I)-MOF: naked-eye colorimetric sensor for humidity and. formaldehyde in single-crystal-to-single-crystal fashion
Supporting Information for Cu(I)-MOF: naked-eye colorimetric sensor for humidity and formaldehyde in single-crystal-to-single-crystal fashion Yang Yu, Xiao-Meng Zhang, Jian-Ping Ma, Qi-Kui Liu, Peng Wang,
More informationSynthesis of two copper clusters and their catalysis towards the oxidation of benzene
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Synthesis of two copper clusters and their catalysis towards
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More information1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in
Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow
More informationZiessel a* Supporting Information (75 pages) Table of Contents. 1) General Methods S2
S1 Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes based on Boron Substituted Diisoindolomethene Frameworks Gilles Ulrich, a, * Sebastien Goeb a, Antoinette De Nicola a,
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Electronic Supplementary Information
More informationSynthesis of Tetra-ortho-Substituted, Phosphorus- Containing and Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach
Synthesis of Tetra-ortho-Substituted, Phosphorus- Containing and Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach Bradley O. Ashburn and Rich G. Carter* and Lev N. Zakharov Department of Chemistry,
More informationDavid L. Davies,*, 1 Charles E. Ellul, 1 Stuart A. Macgregor,*, 2 Claire L. McMullin 2 and Kuldip Singh. 1. Table of contents. General information
Experimental Supporting Information for Experimental and DFT Studies Explain Solvent Control of C-H Activation and Product Selectivity in the Rh(III)-Catalyzed Formation of eutral and Cationic Heterocycles
More informationSupplementary Figure S1 a, wireframe view of the crystal structure of compound 11. b, view of the pyridinium sites. c, crystal packing of compound
a b c Supplementary Figure S1 a, wireframe view of the crystal structure of compound 11. b, view of the pyridinium sites. c, crystal packing of compound 11. 1 a b c Supplementary Figure S2 a, wireframe
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Synthesis of New Copper(I) Based linear 1-D-Coordination
More informationSynthesis of Vinyl Germylenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Material for Synthesis of Vinyl Germylenes Małgorzata Walewska, Judith Baumgartner,*
More informationSupporting Information
Supporting Information Manuscript Title: Synthesis of Semibullvalene Derivatives via Co 2 (CO) 8 -Mediated Cyclodimerization of 1,4-Dilithio-1,3-butadienes Corresponding Author: Zhenfeng Xi Affiliations:
More informationSulfuric Acid-Catalyzed Conversion of Alkynes to Ketones in an Ionic Liquid Medium under Mild Reaction Conditions
Sulfuric Acid-Catalyzed Conversion of Alkynes to Ketones in an Ionic Liquid Medium under Mild Reaction Conditions Wing-Leung Wong, Kam-Piu Ho, Lawrence Yoon Suk Lee, Kin-Ming Lam, Zhong-Yuan Zhou, Tak
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Catalyst Design Based on Agostic Interaction: Synthesis, Characterization,
More informationSupporting Information
Supporting Information N-Heterocyclic Carbene-Catalyzed Chemoselective Cross-Aza-Benzoin Reaction of Enals with Isatin-derived Ketimines: Access to Chiral Quaternary Aminooxindoles Jianfeng Xu 1, Chengli
More informationSupporting Information
Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
More information1,4-Dihydropyridyl Complexes of Magnesium: Synthesis by Pyridine. Insertion into the Magnesium-Silicon Bond of Triphenylsilyls and
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information 1,4-Dihydropyridyl Complexes of Magnesium: Synthesis
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 208 Supporting Information Cobalt-Catalyzed Regioselective Syntheses of Indeno[2,-c]pyridines
More informationDiastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines
Supporting Information for Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines Alexander Penger, Cortney. von ahmann, Alexander S. Filatov and John T. Welch* Address:
More informationSupporting Information for the Article Entitled
Supporting Information for the Article Entitled Catalytic Production of Isothiocyanates via a Mo(II) / Mo(IV) Cycle for the Soft Sulfur Oxidation of Isonitriles authored by Wesley S. Farrell, Peter Y.
More informationSupporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino
More informationOrganocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at C3 position
Organocatalytic asymmetric synthesis of 3,3-disubstituted oxindoles featuring two heteroatoms at C3 position Feng Zhou, Xing-Ping Zeng, Chao Wang, Xiao-Li Zhao, and Jian Zhou* [a] Shanghai Key Laboratory
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationEnantioselectivity switch in copper-catalyzed conjugate addition. reaction under influence of a chiral N-heterocyclic carbene-silver complex
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supplementary Information Enantioselectivity switch in copper-catalyzed conjugate addition
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Carbene Activation of P 4 and Subsequent Derivatization Jason D. Masuda, Wolfgang W. Schoeller, Bruno Donnadieu, and Guy Bertrand * [*] Dr.
More informationSupporting Information
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 A rare case of a dye co-crystal showing better dyeing performance Hui-Fen Qian, Yin-Ge Wang,
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information (ESI) A Large Spin, Magnetically Anisotropic, Octanuclear
More informationSupporting Information for A Janus-type Bis(maloNHC) and its Zwitterionic Gold and Silver Metal Complexes
Supporting Information for A Janus-type Bis(maloNHC) and its Zwitterionic Gold and Silver Metal Complexes Ashley Carter, Alexander Mason, Michael A. Baker, Donald G. Bettler, Angelo Changas, Colin D. McMillen,
More informationSupporting Information for. Hydrogen-Bond Symmetry in Difluoromaleate Monoanion
S1 Supporting Information for Hydrogen-Bond Symmetry in Difluoromaleate Monoanion Charles L. Perrin,* Phaneendrasai Karri, Curtis Moore, and Arnold L. Rheingold Department of Chemistry, University of California
More informationSimple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their Labile Dimethylsulfide Adducts
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information for: Simple Solution-Phase Syntheses of Tetrahalodiboranes(4) and their
More informationAnti-Inflammatory Isoquinoline with Bis-seco-aporphine Skeleton from Dactylicapnos scandens
Anti-Inflammatory Isoquinoline with Bis-seco-aporphine Skeleton from Dactylicapnos scandens Bei Wang,,, Zi-Feng Yang,, Yun-Li Zhao, Ya-Ping Liu, Jun Deng, Wan-Yi Huang, Xiao-Nian Li, Xin-Hua Wang *, and
More informationHydrogen Bonded Dimer Stacking Induced Emission of Amino-Benzoic Acid Compounds
Electronic Supplementary Information (ESI) Hydrogen Bonded Dimer Stacking Induced Emission of Amino-Benzoic Acid Compounds Tianlei Zhou, Feng Li, Yan Fan, Weifeng Song, Xiaoyue Mu, Hongyu Zhang* and Yue
More informationSupporting Information
Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2018 Precursor Control Over the Self-Assembly of [2]Catenanes via Hydrazone Condensation
More informationElectronic Supplementary Informations
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Informations A radical approach for fluorescent
More informationDepartment of Chemistry, University of Basel, St. Johanns-Ring 19, Spitalstrasse 51, and Klingelbergstrasse 80, CH-4056 Basel, Switzerland
Charge Transfer Pathways in Three Isomers of Naphthalene-Bridged Organic Mixed Valence Compounds Hauke C. Schmidt, Mariana Spulber, Markus Neuburger, Cornelia G. Palivan, Markus Meuwly,* and Oliver S.
More informationSupporting Information
Supporting Information New Hexaphosphane Ligands 1,3,5-C 6 H 3 {p-c 6 H 4 N(PX 2 ) 2 } 3 [X = Cl, F, C 6 H 3 OMe(C 3 H 5 )]: Synthesis, Derivatization and, Palladium(II) and Platinum(II) Complexes Sowmya
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationSupporting Information:
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Sulfonato-imino copper(ii) complexes : fast and general Chan-
More informationStoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes to Borinic Esters Lauren E. Longobardi, Connie Tang, and Douglas W.
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Supplementary Data for: Stoichiometric Reductions of Alkyl-Substituted Ketones and Aldehydes
More informationSuper-Resolution Monitoring of Mitochondrial Dynamics upon. Time-Gated Photo-Triggered Release of Nitric Oxide
Supporting Information for Super-Resolution Monitoring of Mitochondrial Dynamics upon Time-Gated Photo-Triggered Release of Nitric Oxide Haihong He a, Zhiwei Ye b, Yi Xiao b, *, Wei Yang b, *, Xuhong Qian
More informationSupplementary Information
Supplementary Information Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl 3 /Al 2 O 3 and Analysis of Large 1 H NMR Diastereotopic Effect Isabel Monreal, a Mariano Sánchez-Castellanos,
More informationNickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol
Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol Ailing Zhang, Sakthi Raje, Jianguo Liu, Xiaoyan Li, Raja Angamuthu, Chen-Ho Tung, and Wenguang Wang* School of Chemistry and Chemical
More informationSupplementary Information. Two Cyclotriveratrylene Metal-Organic Frameworks as Effective Catalysts
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2018 Supplementary Information Two Cyclotriveratrylene Metal-Organic Frameworks as Effective
More informationCyclams with ambidentate methylthiazolyl pendants for a stable, inert and selective Cu(II) coordination
Supporting Information for: Cyclams with ambidentate methylthiazolyl pendants for a stable, inert and selective Cu(II) coordination Aurora Rodríguez-Rodríguez, Zakaria Halime, Luís M. P. Lima, Maryline
More informationHai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman
More informationElectronic Supporting Information. for. Group 13 Complexes of Dipyridylmethane, a Forgotten Ligand in Coordination Chemistry
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Electronic Supporting Information for Group 13 Complexes of Dipyridylmethane, a Forgotten
More informationReversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex.
Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex. Emmanuelle Despagnet-Ayoub, Michael K. Takase, Jay A. Labinger and John E. Bercaw Contents 1. Experimental
More informationSupporting Information
Supporting Information Unprecedented solvent-dependent sensitivities in highly efficient detection of metal ions and nitroaromatic compounds by a fluorescent Ba MOF Rongming Wang, Xiaobin Liu, Ao Huang,
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Crystal-to-Crystal Transformation between Three Cu(I) Coordination Polymers and Structural Evidence for Luminescence Thermochromism Tae Ho
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A New Melt Approach to the Synthesis of catena- Phosphorus Dications to Access the First Derivatives of 2+ ** [P 6 Ph 4 R 4 ] Jan J. Weigand*,
More informationElectronic Supplementary Information
Electronic Supplementary Information Early-Late Heterobimetallic Rh-Ti and Rh-Zr Complexes via Addition of Early Metal Chlorides to Mono- and Divalent Rhodium Dan A. Smith and Oleg V. Ozerov* Department
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationSupporting Information. for. Synthetic routes to [Au(NHC)(OH)] (NHC = N- heterocyclic carbene) complexes
Supporting Information for Synthetic routes to [Au(HC)(OH)] (HC = - heterocyclic carbene) complexes Adrián Gómez-Suárez, Rubén S, Alexandra M. Z. Slawin and Steven P. olan* EaStChem School of chemistry,
More informationElectronic Supplementary Information
Electronic Supplementary Information Regiodivergent Heterocyclization: A Strategy for the Synthesis of Substituted Pyrroles and Furans Using α-formyl Ketene Dithioacetals as Common Precursors Ting Wu,
More informationSupplementary Material (ESI) for CrystEngComm. An ideal metal-organic rhombic dodecahedron for highly efficient
Supplementary Material (ESI) for CrystEngComm An ideal metal-organic rhombic dodecahedron for highly efficient adsorption of dyes in an aqueous solution Yuan-Chun He, Jin Yang,* Wei-Qiu Kan, and Jian-Fang
More informationSupporting information. Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor
Supporting information Cooperatively Enhanced Ion Pair Binding with a Hybrid Receptor Toni Mäkelä, a Elina Kalenius a and Kari Rissanen a* a University of Jyvaskyla, Department of Chemistry, Nanoscience
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 Tuning the Lewis Acidity of Boranes in rustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationElectronic Supplementary Information (12 pages)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong
More informationThe Aldimine Effect in Bis(imino)pyridine Complexes: Non-Planar Nickel(I) Complexes of a Bis(aldimino)pyridine Ligand
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting Information for: The Aldimine Effect in Bis(imino)pyridine Complexes: Non-Planar Nickel(I)
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More informationSupporting Information. Crystal surface mediated structure transformation of kinetic framework. composed of multi-interactive ligand TPHAP and Co(II)
Supporting Information Crystal surface mediated structure transformation of kinetic framework composed of multi-interactive ligand TPHAP and Co(II) Yumi Yakiyama, Akira Ueda, Yasushi Morita,* Masaki Kawano*
More informationFluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium
Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing
More informationTransformations: New Approach to Sampagine derivatives. and Polycyclic Aromatic Amides
-1- An Unexpected Rearrangement which Disassembles Alkyne Moiety Through Formal Nitrogen Atom Insertion between Two Acetylenic Carbons and Related Cascade Transformations: New Approach to Sampagine derivatives
More informationLight-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
More informationSupplementary Figure 1 IR Spectroscopy. 1Cu 1Ni Supplementary Figure 2 UV/Vis Spectroscopy. 1Cu 1Ni
Supplementary Figure 1 IR Spectroscopy. IR spectra of 1Cu and 1Ni as well as of the starting compounds, recorded as KBr-pellets on a Bruker Alpha FTIR spectrometer. Supplementary Figure 2 UV/Vis Spectroscopy.
More informationSilver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous
More informationSpain c Departament de Química Orgànica, Universitat de Barcelona, c/ Martí I Franqués 1-11, 08080, Barcelona, Spain.
a Institute of Chemical Research of Catalonia, Av. Països Catalans, 16, 43007 Tarragona, Spain. b Departament de Química, Universitat Autònoma de Barcelona, Cerdanyola del Vallès, E-08193 Barcelona, Spain
More informationElectronic Supplementary Information
Electronic Supplementary Information Thermally Reversible Single-Crystal to Single-Crystal Transformation of Mononuclear to Dinuclear Zn(II) Complexes By[2+2] Cycloaddition Reaction Raghavender Medishetty,
More informationSupporting Information
Supporting Information Incorporation of a Sugar Unit into a C C N Pincer Pd Complex Using Click Chemistry and Its Dynamic Behavior in Solution and Catalytic Ability toward the Suzuki Miyaura Coupling in
More informationJuan Manuel Herrera, Enrique Colacio, Corine Mathonière, Duane Choquesillo-Lazarte, and Michael D. Ward. Supporting information
Cyanide-bridged tetradecanuclear Ru II 3M II 11 clusters (M II = Zn II and Cu II ) based on the high connectivity building block [Ru 3 (HAT)(CN) 12 ] 6+ : structural and photophysical properties Juan Manuel
More informationSupporting Information
Supporting Information Wiley-VCH 2012 69451 Weinheim, Germany Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles** Kohei Fuchibe, Masaki Takahashi,
More informationCollege of Materials Science and Engineering, Nanjing Tech University, Nanjing , P. R. China
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Extra thermostable one-dimensional organic-inorganic hybrid perovskite [N-methyldabconium]PbI 3
More informationDepartment of Chemistry, Zhejiang University, Hangzhou , P. R. China.
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2014 Responsive cross-linked supramolecular polymer network: hierarchical supramolecular polymerization
More informationSupplementary Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supplementary Information Coordination structure and extraction behavior of a silver
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 ROS-mediated Carbon Monoxide and Drug Release from Drug-conjugated Carboxyboranes Theppawut
More informationThermal and nonlinear optical studies of newly synthesized EDOT based bent-core and hockey-stick like liquid crystals
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Electronic supplementary information:
More informationSupporting Information. A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions
Supporting Information A Structure-Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki-Miyaura Coupling Reactions Thomas Di Franco, Marko Stojanovic, Sébastien Keller, Rosario
More information