Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers
|
|
|
- Homer Harrell
- 5 years ago
- Views:
Transcription
1 Supporting Information for Microwave Synthesis of Thionated Naphthalene Diimide-Based Small Molecules and Polymers Paniz Pahlavanlu, Andrew J. Tilley, Bryony T. McAllister, and Dwight S. Seferos* Department of Chemistry, University of Toronto 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada * Table of Contents 1. Synthesis of Parent Compounds 1.1 Substrate Scope S4 1.2 Representative Synthetic Schemes S5 2. Microwave Thionation 2.1 Supplementary Kinetic Studies S6 2.2 Post-Polymerization Thionation S Synthetic Scheme S Photographs and Optical Micrographs S7 3. Physical Characterization 3.1 Nuclear Magnetic Resonance Spectra S8 3.2 Thermogravimetric Analysis Plots S Infrared Spectra S34 4. Optical Characterization 4.1 Optical Absorption Spectra S Photoluminescence Spectra S36 5. Computational Data 5.1 Optimized Geometries and HOMO/LUMO Visualizations S Optimized Geometry Data S Br-TNDIT-Br (Me) S S1 Br-TNDIT-Br (Me) S trans-s2 Br-TNDIT-Br (Me) S41 Pahlavanlu, P. et al. S1
2 List of Schemes, Figures, and Tables Figure S1. Chemical structures and abbreviations of parent compounds. S4 Scheme S1. Synthesis of Br-TNDIT-Br (2-OD). S5 Scheme S2. Synthesis of NDI (2-OD). S5 Figure S2. Microwave thionation kinetics of Br-TNDIT-Br (2-OD) using 0.5 mol. eq. Lawesson s reagent at temperatures ranging from ºC. S6 Scheme S3. Microwave post-polymerization thionation of PNDIT2. S7 Figure S3. Photographs and optical micrographs of P100-PNDIT2. S7 Figure S4. a) 1 H NMR and b) 13 C NMR spectra of NDI (2-OD). S8 Figure S5. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (2-OD). S9 Figure S6. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (3-HU). S10 Figure S7. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (2-OD). S11 Figure S8. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (3-HU). S12 Figure S9. a) 1 H NMR and b) 13 C NMR spectra of SeNDISe (2-OD). S13 Figure S10. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (2-OD). S14 Figure S11. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (3-HU). S15 Figure S12. a) 1 H NMR and b) 13 C NMR spectra of Br-SeNDISe-Br (2-OD). S16 Figure S13. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (2-OD). S17 Figure S14. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (3-HU). S18 Figure S15. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-SeNDISe-Br (2-OD). S19 Figure S16. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (2-OD). S20 Figure S17. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (3-HU). S21 Figure S18. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-SeNDISe-Br (2-OD). S22 Figure S19. COSY NMR spectrum of Br-TNDIT-Br (2-OD). S23 Figure S20. COSY NMR spectrum of S1 Br-TNDIT-Br (2-OD). S24 Figure S21. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (2-OD). S25 Figure S22. COSY NMR spectrum of Br-TNDIT-Br (3-HU). S26 Figure S23. COSY NMR spectrum of S1 Br-TNDIT-Br (3-HU). S27 Figure S24. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (3-HU). S28 Figure S25. COSY NMR spectrum of Br-SeNDISe-Br (2-OD). S29 Figure S26. COSY NMR spectrum of S1 Br-SeNDISe-Br (2-OD). S30 Figure S27. COSY NMR spectrum of trans-s2 Br-SeNDISe-Br (2-OD). S31 Figure S28. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT- Br (3-HU). S32 Figure S29. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe- Br (2-OD). S32 Figure S30. Thermogravimetric analysis plots of P, S1, and trans-s2 Br-TNDIT-Br (2-OD). S33 Figure S31. DFT calculated vibrational frequency spectra. S34 Figure S32. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT-Br (3-HU). S34 Pahlavanlu, P. et al. S2
3 Figure S33. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe-Br (2-OD). S34 Figure S34. Normalized optical absorption spectra of a) P, b) S1, c) trans-s2 Br-TNDIT-Br (2- OD) in cyclohexane, CHCl 3, and tetrahydrofuran. S35 Figure S35. Normalized optical absorption spectra of a) P, S1, and trans-s2 Br-TNDIT-Br (3- HU) and b) P, S1, and trans-s2 Br-SeNDISe-Br (2-OD) in CHCl 3. S35 Figure S36. Photoluminescence spectra of P, S1, and trans-s2 of a) Br-TNDIT-Br (2-OD), b) Br- TNDIT-Br (3-HU), and c) Br-SeNDISe-Br (2-OD) in CHCl 3 (λ ex = 450 nm). S36 Figure S37. Optimized geometries and HOMO/LUMO visualizations of P, S1, and trans-s2 Br- TNDIT-Br (Me) calculated using DFT. S36 Table S1. Optimized geometry coordinates of Br-TNDIT-Br (Me). S37 Table S2. Optimized geometry coordinates of S1 Br-TNDIT-Br (Me). S39 Table S3. Optimized geometry coordinates of trans-s2 Br-TNDIT-Br (Me). S41 Pahlavanlu, P. et al. S3
4 1. Synthesis of Parent Compounds 1.1 Substrate Scope Figure S1. Chemical structures and abbreviations of parent compounds. Pahlavanlu, P. et al. S4
5 1.2 Representative Synthetic Schemes Scheme S1. Synthesis of Br-TNDIT-Br (2-OD). *Relative to 50% 2,6-BrNDABr in starting material. Scheme S2. Synthesis of NDI (2-OD). Pahlavanlu, P. et al. S5
6 2. Microwave Thionation 2.1 Supplementary Kinetic Studies Figure S2. Microwave thionation kinetics of Br-TNDIT-Br (2-OD) using 0.5 mol. eq. Lawesson s reagent at temperatures ranging from ºC, as measured through 1 H NMR analysis of naphthyl core protons. Pahlavanlu, P. et al. S6
7 2.2 Post-Polymerization Thionation Synthetic Scheme Scheme S3. Microwave post-polymerization thionation of PNDIT Photographs and Optical Micrographs Figure S3. a) Photograph of inverted microwave vial containing P100-PNDIT2 crude mixture, illustrating gel formation with extended thionation. b) Photograph of P100-PNDIT2 crude mixture swollen in toluene. c) Overlaid optical micrographs of purified and dried P100-PNDIT2, sliced with a razer blade. Pahlavanlu, P. et al. S7
8 3. Physical Characterization 3.1 Nuclear Magnetic Resonance Spectra Figure S4. a) 1 H NMR and b) 13 C NMR spectra of NDI (2-OD). Pahlavanlu, P. et al. S8
9 Figure S5. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (2-OD). Pahlavanlu, P. et al. S9
10 Figure S6. a) 1 H NMR and b) 13 C NMR spectra of Br-NDI-Br (3-HU). Pahlavanlu, P. et al. S10
11 Figure S7. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (2-OD). Pahlavanlu, P. et al. S11
12 Figure S8. a) 1 H NMR and b) 13 C NMR spectra of TNDIT (3-HU). Pahlavanlu, P. et al. S12
13 Figure S9. a) 1 H NMR and b) 13 C NMR spectra of SeNDISe (2-OD). Pahlavanlu, P. et al. S13
14 Figure S10. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S14
15 Figure S11. a) 1 H NMR and b) 13 C NMR spectra of Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S15
16 Figure S12. a) 1 H NMR and b) 13 C NMR spectra of Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S16
17 Figure S13. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S17
18 Figure S14. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S18
19 Figure S15. a) 1 H NMR and b) 13 C NMR spectra of S1 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S19
20 Figure S16. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S20
21 Figure S17. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S21
22 Figure S18. a) 1 H NMR and b) 13 C NMR spectra of trans-s2 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S22
23 Figure S19. COSY NMR spectrum of Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S23
24 Figure S20. COSY NMR spectrum of S1 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S24
25 Figure S21. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S25
26 Figure S22. COSY NMR spectrum of Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S26
27 Figure S23. COSY NMR spectrum of S1 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S27
28 Figure S24. COSY NMR spectrum of trans-s2 Br-TNDIT-Br (3-HU). Pahlavanlu, P. et al. S28
29 Figure S25. COSY NMR spectrum of Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S29
30 Figure S26. COSY NMR spectrum of S1 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S30
31 Figure S27. COSY NMR spectrum of trans-s2 Br-SeNDISe-Br (2-OD). Pahlavanlu, P. et al. S31
32 Figure S28. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT- Br (3-HU). Through-bond coupling between naphthyl protons (H A, H A ) and neighbouring carbons reflects the proximity of these protons to either carbonyl or thionyl carbons (~160 ppm and 190 ppm, respectively). α-protons on the imide substituent (H B, H B ) serve as a frame of reference, since they are proximal to both carbonyl and thionyl carbons. Here, R = 2-hexyldecyl. Figure S29. Low field portion of HMBC NMR spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe- Br (2-OD). Through-bond coupling between naphthyl protons (H A, H A ) and neighbouring carbons reflects the proximity of these protons to either carbonyl or thionyl carbons (~160 ppm and 190 ppm, respectively). α-protons on the imide substituent (H B, H B ) serve as a frame of reference, since they are proximal to both carbonyl and thionyl carbons. Here, R = 1-octylundecyl. Pahlavanlu, P. et al. S32
33 3.2 Thermogravimetric Analysis Plots Figure S30. Thermogravimetric analysis plots of P, S1, and trans-s2 Br-TNDIT-Br (2-OD). Pahlavanlu, P. et al. S33
34 3.3 Infrared Spectra Figure S31. DFT calculated vibrational frequency spectra (left). Calculated frequencies of P, S1, and trans-s2 Br-TNDIT-Br (Me) correspond to characteristic carbonyl (C=O) and/or thionyl (C=S) stretches (right). Figure S32. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-TNDIT-Br (3-HU), illustrating characteristic carbonyl (C=O) and/or thionyl (C=S) stretches. Figure S33. Infrared spectra of a) P, b) S1, and c) trans-s2 Br-SeNDISe-Br (2-OD), illustrating characteristic carbonyl (C=O) and/or thionyl (C=S) stretches. Pahlavanlu, P. et al. S34
35 4. Optoelectronic Characterization 4.1 Optical Absorption Spectra Figure S34. Normalized optical absorption spectra of a) P, b) S1, c) trans-s2 Br-TNDIT-Br (2- OD) in cyclohexane, CHCl 3, and tetrahydrofuran. Figure S35. Normalized optical absorption spectra of a) P, S1, and trans-s2 Br-TNDIT-Br (3- HU) and b) P, S1, and trans-s2 Br-SeNDISe-Br (2-OD) in CHCl 3. Pahlavanlu, P. et al. S35
36 4.2 Photoluminescence Spectra Figure S36. Photoluminescence spectra of P, S1, and trans-s2 of a) Br-TNDIT-Br (2-OD), b) Br- TNDIT-Br (3-HU), and c) Br-SeNDISe-Br (2-OD) in CHCl 3 (λ ex = 450 nm). 5. Computational Data 5.1 Optimized Geometries and HOMO/LUMO Visualizations Figure S37. Optimized geometries and HOMO/LUMO visualizations of P, S1, and trans-s2 Br- TNDIT-Br (Me) calculated using DFT (B3LYP functional, G(d) basis set). Pahlavanlu, P. et al. S36
37 5.2 Optimized Geometry Data Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S1. Optimized geometry coordinates of Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S37
38 Pahlavanlu, P. et al. S38
39 S1 Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S2. Optimized geometry coordinates of S1 Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S39
40 Pahlavanlu, P. et al. S40
41 trans-s2 Br-TNDIT-Br (Me) Method/Functional/Basis Set: DFT/B3LYP/6-311+G(d) Number of Imaginary Frequencies: 0 Total Energy of Optimized Structure: Hartrees Table S3. Optimized geometry coordinates of trans-s2 Br-TNDIT-Br (Me). Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Pahlavanlu, P. et al. S41
42 Pahlavanlu, P. et al. S42
Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view.
Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view. (b) Side view. All hydrogen atoms are omitted for clarity.
Department of Chemistry, University of Rhode Island, Kingston, RI USA
Supporting Information for Controlled Organocatalytic Ring-Opening Polymerization of - Thionocaprolactone Partha P. Datta and Matthew K. Kiesewetter Department of Chemistry, University of Rhode Island,
Introduction to Organic Spectroscopy
Introduction to rganic Spectroscopy Chem 8361/4361: Interpretation of rganic Spectra 2009 2013 Andrew Harned & Regents of the University of Minnesota What is spectroscopy?? From Wikipedia Spectroscopy:
Supplementary Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Supplementary Information Synthesis of hydrocarbon-soluble, methyl-substituted highly branched
Supplementary Information
Supplementary Information S1. Energy Minimization and ECD Calculations. Figure S1. HRESIMS spectrum of compound 1. Figure S2. IR spectrum of compound 1. Figure S3. 1 H NMR spectrum of compound 1 in CDCl
Supporting Information
Supporting Information Chemo-selectivity of IBX oxidation of hydroxybenzyl alcohols in the presence of Hemicucurbit[6]uril Hang Cong, a,b Takehiko Yamato* a and Zhu Tao b a Department of Applied Chemistry,
Epichlorohydrin coupling reactions with wood
Wood Science and Technology 28 (1994) 371-376 Springer-Verlag 1994 Epichlorohydrin coupling reactions with wood Part 1. Reaction with biologicallyactive alcohols R. M. Rowell, G. C. Chen Summary Properties
Principles of Molecular Spectroscopy: Electromagnetic Radiation and Molecular structure. Nuclear Magnetic Resonance (NMR)
Principles of Molecular Spectroscopy: Electromagnetic Radiation and Molecular structure Nuclear Magnetic Resonance (NMR) !E = h" Electromagnetic radiation is absorbed when the energy of photon corresponds
CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY]
![CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY]](/thumbs/83/88348834.jpg "CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY]")
CHEM 241 UNIT 5: PART A DETERMINATION OF ORGANIC STRUCTURES BY SPECTROSCOPIC METHODS [MASS SPECTROMETRY] 1 Introduction Outline Mass spectrometry (MS) 2 INTRODUCTION The analysis of the outcome of a reaction
Supporting Information for. an Equatorial Diadduct: Evidence for an Electrophilic Carbanion
Supporting Information for Controlled Synthesis of C 70 Equatorial Multiadducts with Mixed Addends from an Equatorial Diadduct: Evidence for an Electrophilic Carbanion Shu-Hui Li, Zong-Jun Li,* Wei-Wei
Supplementary Information
Supplementary Information Self-assembly of Metal-Polymer Analogues of Amphiphilic Triblock Copolymers 1 Zhihong Nie, 1 Daniele Fava, 1, 2, 3 Eugenia Kumacheva 1 Department of Chemistry, University of Toronto,
Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2008
Supplementary Information for: Scrambling Reaction between Polymers Prepared by Step-growth and Chain-growth Polymerizations: Macromolecular Cross-metathesis between 1,4-Polybutadiene and Olefin-containing
Synthesis and Properties of Endohedral Aza[60]fullerenes: and as Their Dimers and Monomers
![Synthesis and Properties of Endohedral Aza[60]fullerenes: and as Their Dimers and Monomers](/thumbs/87/96827117.jpg "Synthesis and Properties of Endohedral Aza[60]fullerenes: and as Their Dimers and Monomers")
Supporting Information Synthesis and Properties of Endohedral Aza[60]fullerenes: H2O@C59N and H2@C59N as Their Dimers and Monomers Yoshifumi Hashikawa, Michihisa Murata, Atsushi Wakamiya, and Yasujiro
A thermally remendable epoxy resin
Supplementary Information A thermally remendable epoxy resin Qiao Tian a, Yan Chao Yuan a, Min Zhi Rong *b, Ming Qiu Zhang b a Key Laboratory for Polymeric Composite and Functional Materials of Ministry
Modular P,S-Ligands for Pd-Catalyzed Asymmetric
Phosphinite-Thioethers derived from Chiral Epoxides. Modular P,S-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions Xisco Caldentey, and Miquel A. Pericàs,, * Institute of Chemical Research of Catalonia
Effect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
Supporting Information. Enlarging the π System of Phosphorescent (C^C*) Cyclometalated Platinum(II) NHC Complexes
Supporting Information Enlarging the π System of Phosphorescent (C^C*) Cyclometalated Platinum(II) NHC Complexes Alexander Tronnier #, Alexander Pöthig, # Stefan Metz $, Gerhard Wagenblast $, Ingo Münster
Module 20: Applications of PMR in Structural Elucidation of Simple and Complex Compounds and 2-D NMR spectroscopy
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper 12: Organic Spectroscopy Module 20: Applications of PMR in Structural Elucidation of Simple and Complex Compounds and 2-D NMR spectroscopy
Chemistry 51 Summer 2006 Final Exam
Chemistry 51 Summer 2006 Final Exam 1. This is a two-hour, closed book exam. All answers are to be put on the question sheets. 2. Use the backsides of these pages for scratch paper. None other permitted.
Calculate a rate given a species concentration change.
Kinetics Define a rate for a given process. Change in concentration of a reagent with time. A rate is always positive, and is usually referred to with only magnitude (i.e. no sign) Reaction rates can be
CHEM 3.2 (AS91388) 3 credits. Demonstrate understanding of spectroscopic data in chemistry
CHEM 3.2 (AS91388) 3 credits Demonstrate understanding of spectroscopic data in chemistry Spectroscopic data is limited to mass, infrared (IR) and 13 C nuclear magnetic resonance (NMR) spectroscopy. Organic
Supporting 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
Spectroscopy. Empirical Formula: Chemical Formula: Index of Hydrogen Deficiency (IHD)
Spectroscopy Empirical Formula: Chemical Formula: Index of Hydrogen Deficiency (IHD) A)From a structure: B)From a molecular formula, C c H h N n O o X x, Formula for saturated hydrocarbons: Subtract the
Supporting Information
Stereochemical nversion in Difunctionalized Pillar[5]arenes Nathan L. Strutt, Severin T. Schneebeli, J. Fraser Stoddart* Department of hemistry, Northwestern University, Evanston, L U.S.A. stoddart@northwestern.edu
Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides H 4. NH-CO- CH 3 i. ; X = Cl, CH 3
Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides and Substituted Acetamides, 2/3/4-YC 6 H 4 NH-CO- CH 3 i X i (Y=CH 3, F, Cl, Br, NO 2 ; X = Cl, CH 3 ; i =0,1,2,3)
Chem 2320 Exam 1. January 30, (Please print)
Chem 2320 Exam 1 January 30, 2006 Name: (first) (last) (Please print) Last 4 digits of I.D. I. Multiple Choice ( /20) Score /60 II /15 III /25 Total score /100 I. Multiple choice questions. (3 points each).
ORGANIC - EGE 5E CH NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
!! www.clutchprep.com CONCEPT: PURPOSE OF ANALYTICAL TECHNIQUES Classical Methods (Wet Chemistry): Chemists needed to run dozens of chemical reactions to determine the type of molecules in a compound.
12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy
12. Structure Determination: Mass Spectrometry and Infrared Spectroscopy Determining the Structure of an Organic Compound The analysis of the outcome of a reaction requires that we know the full structure
Anion 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
Supplementary Figure 1. SEM images of (a) 1, (b) 1 PSt/PMMA, and (c) polymer blend isolated from 1 PSt/PMMA. The size and morphology of the host
Supplementary Figure 1. SEM images of (a) 1, (b) 1 PSt/PMMA, and (c) polymer blend isolated from 1 PSt/PMMA. The size and morphology of the host crystals were the almost same to those of the blend polymer
Chapter 13 Spectroscopy
hapter 13 Spectroscopy Infrared spectroscopy Ultraviolet-Visible spectroscopy Nuclear magnetic resonance spectroscopy Mass Spectrometry 13.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation
Experiment 11: NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
Experiment 11: NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY Purpose: This is an exercise to introduce the use of nuclear magnetic resonance spectroscopy, in conjunction with infrared spectroscopy, to determine
Introduction. The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants
Introduction The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants Spectroscopy and the Electromagnetic Spectrum Unlike mass spectrometry,
Use the three tables of spectral data on the Data Sheet where appropriate.
Q1. Organic chemists use a variety of methods to identify unknown compounds. When the molecular formula of a compound is known, spectroscopic and other analytical techniques are used to distinguish between
Page 2. Q1.Consider the five cyclic compounds, A, B, C, D and E. The infrared spectra of compounds A, B, C and D are shown below.
Q1.Consider the five cyclic compounds, A, B, C, D and E. (a) The infrared spectra of compounds A, B, C and D are shown below. Write the correct letter, A, B, C or D, in the box next to each spectrum. You
CH Exam #4 (Take Home) Date Due: 11/25,26/2013
CH2710 - Exam #4 (Take Home) Date Due: 11/25,26/2013 Section I - Multiple Choice - Choose the BEST answer from the choices given and place the letter of you choice in the space provided. 1. Energy absorbed
EASTERN ARIZONA COLLEGE General Organic Chemistry I
EASTERN ARIZONA COLLEGE General Organic Chemistry I Course Design 2015-2016 Course Information Division Science Course Number CHM 235 (SUN# CHM 2235) Title General Organic Chemistry I Credits 4 Developed
Chemistry 213 Practical Spectroscopy
Chemistry 213 Practical Spectroscopy Dave Berg djberg@uvic.ca Elliott 314 A course in determining structure by spectroscopic methods Different types of spectroscopy afford different information about molecules
Final Exam Chem 3045x Wednesday, Dec. 17, 1997
Final Exam Chem 3045x Wednesday, Dec. 17, 1997 Instructions: This is a closed book examination. You may not use any notes, books or external materials during the course of the examination. Please print
7a. Structure Elucidation: IR and 13 C-NMR Spectroscopies (text , , 12.10)
2009, Department of Chemistry, The University of Western Ontario 7a.1 7a. Structure Elucidation: IR and 13 C-NMR Spectroscopies (text 11.1 11.5, 12.1 12.5, 12.10) A. Electromagnetic Radiation Energy is
Electronic Supplementary Information (ESI) A Green Miniemulsion-Based Synthesis of Polymeric Aggregation-Induced Emission.
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 215 Electronic Supplementary Information (ESI) A Green Miniemulsion-Based Synthesis of Polymeric
SUPPORTING INFORMATION. Stereomutation of Conformational Enantiomers of 9-Isopropyl-9-formyl fluorene and Related Acyl Derivatives.
SUPPORTING INFORMATION Stereomutation of Conformational Enantiomers of 9-Isopropyl-9-formyl fluorene and Related Acyl Derivatives. Daniele Casarini*, Lodovico Lunazzi, and Andrea Mazzanti* Department of
The rest of topic 11 INTRODUCTION TO ORGANIC SPECTROSCOPY
The rest of topic 11 INTRODUCTION TO ORGANIC SPECTROSCOPY 1. Mass spectrometry: SPECTROSCOPIC TECHNIQUES - A technique capable of identifying the presence of various mass segments of organic molecules.
Electronic 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
CHEM 344 Fall 2015 Final Exam (100 pts)
CHEM 344 Fall 2015 Final Exam (100 pts) Name: TA Name: DO NOT REMOVE ANY PAGES FROM THIS EXAM PACKET. Have a swell winter break. Directions for drawing molecules, reactions, and electron-pushing mechanisms:
NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY
NUCLEAR MAGNETIC RESONANCE AND INTRODUCTION TO MASS SPECTROMETRY A STUDENT SHOULD BE ABLE TO: 1. Identify and explain the processes involved in proton ( 1 H) and carbon-13 ( 13 C) nuclear magnetic resonance
(a) Name the alcohol and catalyst which would be used to make X. (2)
1 The chemical X is an ester with formula CH 3 COOC(CH 3 ) 3 which occurs in raspberries and pears. It can be prepared in the laboratory by refluxing ethanoic acid with an alcohol in the presence of a
Lecture 11. IR Theory. Next Class: Lecture Problem 4 due Thin-Layer Chromatography
Lecture 11 IR Theory Next Class: Lecture Problem 4 due Thin-Layer Chromatography This Week In Lab: Ch 6: Procedures 2 & 3 Procedure 4 (outside of lab) Next Week in Lab: Ch 7: PreLab Due Quiz 4 Ch 5 Final
Supporting Information for:
Supporting Information for: Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: The Effect of The Lifetime of the E Photoenol on the Photochemistry Armands Konosonoks, P. John Wright,
Supplementary Figures
Supplementary Figures Supplementary Figure 1. DFT optimized structure of the [Ag III (L 1 )](ClO 4 ) 2 (1 ClO4 ) complex (CCDC code 978368). Hydrogen atoms and the two perchlorate anions have been omitted
Keynotes in Organic Chemistry
Keynotes in Organic Chemistry Second Edition ANDREW F. PARSONS Department of Chemistry, University of York, UK Wiley Contents Preface xi 1 Structure and bonding 1 1.1 Ionic versus covalent bonds 1 1.2
Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2012
Ring Expansion of Alkynyl Cyclopropanes to Highly substituted Cyclobutenes via a N-Sulfonyl-1,2,3-Triazole Intermediate Renhe Liu, Min Zhang, Gabrielle Winston-Mcerson, and Weiping Tang* School of armacy,
Supporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling
Supporting information An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling X. Shang, 1 R. Lai, 1,3 X. Song, 1 H. Li, 1,3 W. Niu, 2 and J. Guo 1 * 1. Department of Chemistry,
L35 REVIEW OUTLINE. 1. Reactions. 2. Spectroscopy and Stereochemistry. 3. Preview of Final. CHEM2312: Spring 2008
L35 REVIEW UTLINE 1. Reactions 2. Spectroscopy and Stereochemistry 3. Preview of Final EM2312: Spring 2008 REVIEW F REATINS While the following schemes group reactions by type of functional group, recognize
SYSTEMWIDE CHEM 2425 FINAL EXAM. Department Of Physical Sciences
SYSTEMWIDE CHEM 2425 FINAL EXAM Department f Physical Sciences Morphine NAME: RGANIC CHEM 2425 FINAL EXAM DIRECTINS- A periodic table is attached at the end of this exam. Please answer all questions in
The resonance frequency of the H b protons is dependent upon the orientation of the H a protons with respect to the external magnetic field:
Spin-Spin Splitting in Alkanes The signal arising from a proton or set of protons is split into (N+1) lines by the presence of N adjacent nuclei Example 1: Bromoethane The resonance frequency of the H
CHEM 344 Fall 2016 Spectroscopy and WebMO Exam (75 pts)
CHEM 344 Fall 2016 Spectroscopy and WebMO Exam (75 pts) Name: TA Name: Exam Length = 90 min DO NOT REMOVE ANY PAGES FROM THIS EXAM PACKET. Directions for drawing molecules, reactions, and electron-pushing
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System
Regioselective Silylation of Pyranosides Using a Boronic Acid / Lewis Base Co-Catalyst System Doris Lee and Mark S. Taylor* Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St.
CHEM 344 Final Quiz Fall pts. Name: TA Name:
CHEM 344 Final Quiz Fall 2013 100 pts Name: TA Name: 1 CHEM 344 Final Quiz Fall 2013 100 pts 1) A multi-step synthesis of the NSAID ibuprofen is shown below. a) Fill in the boxes with the appropriate reagent(s)
(07) 2 (c) 2 (c) (i) Calculate the ph of this buffer solution at 25 oc (3 marks) (Extra space)
7 The value of Ka for methanoic acid is 1.78 10 4 mol dm 3 at 25 oc. A buffer solution is prepared containing 2.35 10 2 mol of methanoic acid and Question 1: N/A 1.84 10 2 mol of sodium methanoate in 1.00
All measurement has a limit of precision and accuracy, and this must be taken into account when evaluating experimental results.
Chapter 11: Measurement and data processing and analysis 11.1 Uncertainty and error in measurement and results All measurement has a limit of precision and accuracy, and this must be taken into account
1.1 Is the following molecule aromatic or not aromatic? Give reasons for your answer.
Page 1 QUESTION ONE 1.1 Is the following molecule aromatic or not aromatic? Give reasons for your answer. 1.2 List four criteria which compounds must meet in order to be considered aromatic. Page 2 QUESTION
Name: Student Number: University of Manitoba - Department of Chemistry CHEM Introductory Organic Chemistry II - Term Test 2
Name: Student Number: University of Manitoba - Department of Chemistry CHEM 2220 - Introductory Organic Chemistry II - Term Test 2 Thursday, March 12, 2015; 7-9 PM This is a 2-hour test, marked out of
Infrared Spectroscopy
Infrared Spectroscopy Introduction Spectroscopy is an analytical technique which helps determine structure. It destroys little or no sample. The amount of light absorbed by the sample is measured as wavelength
ORGANIC CHEMISTRY. Fifth Edition. Stanley H. Pine
ORGANIC CHEMISTRY Fifth Edition Stanley H. Pine Professor of Chemistry California State University, Los Angeles McGraw-Hill, Inc. New York St. Louis San Francisco Auckland Bogota Caracas Lisbon London
Technical Note. Introduction
Technical Note Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)- phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4- Methoxybenzyl Analogues - Part II Patrick A. Hays*,
Infrared Spectroscopy: Identification of Unknown Substances
Infrared Spectroscopy: Identification of Unknown Substances Suppose a white powder is one of the four following molecules. How can they be differentiated? H N N H H H H Na H H H H H A technique that is
Investigation of Cation Binding and Sensing by new Crown Ether core substituted Naphthalene Diimide systems
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 218 Supplementary Material Investigation
All-conjugated, all-crystalline donor-acceptor block. copolymers P3HT-b-PNDIT2 via direct arylation
upporting information for All-conjugated, all-crystalline donor-acceptor block copolymers P3HT-b-PNDIT2 via direct arylation polycondensation Fritz Nübling,, Hartmut Komber, Michael ommer,, Makromolekulare
Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy
Supporting Information: Dostie, Prévost and Guindon S-1 Diastereoselective Synthesis of C2 -Fluorinated Nucleoside Analogues using an Acyclic Strategy Starr Dostie,, Michel Prévost *,, Philippe Mochirian,
Thermal 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:
NMR and IR spectra & vibrational analysis
Lab 5: NMR and IR spectra & vibrational analysis A brief theoretical background 1 Some of the available chemical quantum methods for calculating NMR chemical shifts are based on the Hartree-Fock self-consistent
Organic Chemistry II (CHE ) Examination I February 11, Name (Print legibly): Key. Student ID#:
rganic hemistry II (HE 232-001) Examination I February 11, 2009 Name (Print legibly): Key (last) (first) Student ID#: PLEASE observe the following: You are allowed to have scratch paper (provided by me),
CHEMISTRY 341. Final Exam Tuesday, December 16, Problem 1 15 pts Problem 9 8 pts. Problem 2 5 pts Problem pts
CEMISTRY 341 Final Exam Tuesday, December 16, 1997 Name NAID Problem 1 15 pts Problem 9 8 pts Problem 2 5 pts Problem 10 21 pts Problem 3 26 pts Problem 11 15 pts Problem 4 10 pts Problem 12 6 pts Problem
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
Scope of the 2(5H)-Furanone Helicity Rule: A Combined ECD, VCD, and DFT Investigation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Scope of the 2(5H)-Furanone Helicity Rule: A Combined ECD, VCD, and DFT
Chem 213 Final 2012 Detailed Solution Key for Structures A H
Chem 213 Final 2012 Detailed Solution Key for Structures A H COMPOUND A on Exam Version A (B on Exam Version B) C 8 H 6 Cl 2 O 2 DBE = 5 (aromatic + 1) IR: 1808 cm 1 suggests an acid chloride since we
High-Conductance Pathways in Ring-Strained Disilanes by way of Direct σ-si Si to Au Coordination. Supporting Information
High-Conductance Pathways in Ring-Strained Disilanes by way of Direct σ- to Au Coordination Nathaniel T. Kim, Haixing Li, Latha Venkataraman,* and James L. Leighton* Department of Chemistry, Columbia University,
Measurement techniques
Measurement techniques 1 GPC GPC = gel permeation chromatography GPC a type of size exclusion chromatography (SEC), that separates analytes on the basis of size. The column used for GPC is filled with
Basic One- and Two-Dimensional NMR Spectroscopy
Horst Friebolin Basic One- and Two-Dimensional NMR Spectroscopy Third Revised Edition Translated by Jack K. Becconsall WILEY-VCH Weinheim New York Chichester Brisbane Singapore Toronto Contents XV 1 The
flowers, leaves and roots of roses rose oil heat
1 Rose oil can be extracted from the flowers, leaves and roots of roses using the apparatus below. coolant flowers, leaves and roots of roses rose oil heat (a) The rose oil contains a mixture of compounds,
Supporting Information for Ultra-narrow metallic armchair graphene nanoribbons
Supporting Information for Ultra-narrow metallic armchair graphene nanoribbons Supplementary Figure 1 Ribbon length statistics. Distribution of the ribbon lengths and the fraction of kinked ribbons for
1G (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
Supplementary Material
Supplementary Material Rongalite /PEG 400 as reducing system in the synthesis of new glycerol derived selenol esters using anhydrides and bis (2,2 dimethyl 1,3 dioxolanylmethyl)diselenide as substrates
CHAPTER 21 HW: ALDEHYDES + KETONES
CAPTER 21 W: ALDEYDES + KETES MECLATURE 1. Give the name for each compound (IUPAC or common name). C Structure 2 ame Structure ame 2. Draw each compound. Structure ame dicyclohexyl ketone 1,1,1-trifluoro-3-pentanone
CHEM4. (JAN12CHEM401) WMP/Jan12/CHEM4. General Certificate of Education Advanced Level Examination January 2012
Centre Number Surname Candidate Number For Examiner s Use Other Names Candidate Signature Examiner s Initials General Certificate of Education Advanced Level Examination January 2012 Question 1 2 Mark
ISATIN (PER-O-ACETYL- -D- GALACTOPYRANOSYL)THIOSEMICARBAZONES
ISATIN (PER--ACETYL- -D- GALACTPYRANSYL)THISEMICARBAZNES Nguyen Dinh Thanh*, Nguyen Thi Kim Giang Faculty of Chemistry, College of Science, Vietnam National University (Hanoi), 19 Le Thanh Tong, Hanoi
Certificate Of Analysis
Certificate f Analysis Compound: -Hydroxy Propranolol Molecular Formula: C H N. (mw base =.) Structure: MW =. base H 8 0 H C H N -Hydroxy Propranolol "FR CHEMICAL USE NLY" Synonyms: (CA index name) -[(-Methylethyl)amino]--(-{-hydroxy}-naphthalenyloxy)--Propanol
Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides
Suzuki-Miyaura Coupling of Heteroaryl Boronic Acids and Vinyl Chlorides Ashish Thakur, Kainan Zhang, Janis Louie* SUPPORTING INFORMATION General Experimental: All reactions were conducted under an atmosphere
Chemistry Instrumental Analysis Lecture 3. Chem 4631
Chemistry 4631 Instrumental Analysis Lecture 3 Quantum Transitions The energy of a photon can also be transferred to an elementary particle by adsorption if the energy of the photon exactly matches the
SUPPLEMENTARY INFORMATION
SUPPLEMENTARY INRMATIN doi:10.1038/nature16185 Improved Synthesis of P-CDP H H H 7 + 1 TH/DM: 9/1 K 2 C 3 / 85 o C 2 days / under N 2 45% H R R 7 P-CDP 2 n A flame dried 20 ml scintillation vial equipped
SUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
SUPPLEMENTARY INFORMATION
doi:10.1038/nature14137 1. Supplementary Methods 2. Supplementary Text 2.1 Physico-Chemical Properties and Structural Elucidation of Compound 1. 2.2 Physico-Chemical Properties and Structural Elucidation
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
Structural Elucidation of Sumanene and Generation of its Benzylic Anions
Structural Elucidation of Sumanene and Generation of its Benzylic Anions idehiro Sakurai, Taro Daiko, iroyuki Sakane, Toru Amaya, and Toshikazu irao Department of Applied Chemistry, Graduate School of
Electronic supplementary information for Synthetic details. Compound 1, PyG. Scheme S1. The synthesis of PyG.
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2014 Electronic supplementary information for Photoisomerization-Induced Gel-to-Sol Transition
Ping Pong Energy Transfer in a Bodipy-Containing Pt(II) Schiff Base Complex: Synthesis, Photophysical Studies, and Anti-
Supporting Information for: Ping Pong Energy Transfer in a Bodipy-Containing Pt(II) Schiff Base Complex: Synthesis, Photophysical Studies, and Anti- Stokes Shift Increase in Triplet Triplet Annihilation
Unit 11 Instrumentation. Mass, Infrared and NMR Spectroscopy
Unit 11 Instrumentation Mass, Infrared and NMR Spectroscopy Spectroscopic identification of organic compounds Qualitative analysis: presence but not quantity (i.e. PEDs) Quantitative analysis: quantity
Electronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information An efficient non-fullerene acceptor based on central and peripheral
PAPER No.12 :Organic Spectroscopy MODULE No.29: Combined problem on UV, IR, 1 H NMR, 13 C NMR and Mass - Part I
Subject Chemistry Paper No and Title Module No and Title Module Tag 12: rganic Spectroscopy 29: Combined problem on UV, IR, 1 H NMR, 13 C NMR and Mass - Part I CHE_P12_M29 TABLE F CNTENTS 1. Learning utcomes