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SOURCE
Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").
*First name | *Last name | Organization | Role | ||
Author 2 | Francesco | Giustiniano | University of Southampton | Doer | |
Author 3 | Richard | Whitby | University of Southampton | Conceiver | |
Author 4 |
TEXT
*Procedure or Transformation | Bidirectional Sonogashira Coupling |
*Compound(s) being made | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene |
*Chemicals used (delimited by semicolons ;) | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene; 4-bromobenzonitrile; PdCl2; PPh3; CuI; benzene; Triethylamine |
*Procedure | A small Schlenk tube containing 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene(40 mg, 46 μmol), 4-bromobenzonitrile (20 mg, 0.11 mmol, 2.40 eq.), PdCl2 (1 mg, 5.00 μmol, 10 mol%), PPh3 (3 mg, 0.01 mmol, 20 mol%) and CuI (2 mg, 0.01 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding benzene (1.0 mL: ~ 20 mL/mmol) and triethylamine, TEA (0.04 mL, 28 mg, 0.28 mmol, 6.00 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 22 h. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude product (mostly yellow solid, 91 mg). The pure title compound (Rf 0.36; yellow solid, 18 mg, 17 μmol, yield 37%) was obtained by column chromatography on silica gel using as eluent (2/1) DCM/hexane. |
*Authors Comments |
Similar approach has been taken: Using 1-(2-(2,5-Didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene as starting material and distilled benzene (in step ii) afforded 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-cyanophenyl)ethynyl)phenyl)ethynyl) benzene in 41% yield. |
Lead Reference | Taken from: F. Giustiniano, 2010, "Directed Assembly of Functional Patterns",PhD thesis, University of Southampton. Pages 13, 114 |
Other References | |
Multimedia Content | |
*Data | 1H NMR (400 MHz, CDCl3, D1 5 s); 13C NMR (100 MHz, CDCl3, NS 6144) |
#Data file 1 | H NMR 16 - ju1606fg1 .jdx |
#Data file 2 | C NMR 16 - ju1606fg1 .jdx |
#Data file 3 | |
#Data file 4 | |
#Data file 5 |
SCHEME
*#Structure file (ChemDraw, ChemSketch or RXN file) | reactionscheme_16 .cdx |
*#Image file (GIF or PNG) | reactionscheme_16 .gif |
Keywords
Compounds Keywords | Aromatics; alkynes |
Reactions Keywords | substitution |
Other Keywords |
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Compound
ChemSpider ID | 29289767 |
*#Name of Compound mol file | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene.mol |
Description and Tags
Description | |
Tags (separated by comma) |
Identifiers
*Chemical Name | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene |
Common Name | |
Synonym |
Spectra
*#Spectrum jcamp file | *Spectrum Type | Comments | OpenData | Image or PDF | |
Spectrum 1 | H NMR 16 - ju1606fg1 .jdx |
H NMR | 1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.63 (8H, m, Ar4), 7.54-7.52 (16H, m, Ar3-Ar2), 7.37 (2H, s, Ar1), 2.81 (4H, t, J = 7.8, C1), 1.71 (4H, pent J = 7.4, C2), 1.43-1.25 (36H, m, C3-C11), 0.87 (6H, t, J = 6.9, C12) | Y | H NMR 16 .pdf |
Spectrum 2 | C NMR 16 - ju1606fg1 .jdx |
C NMR | 13C NMR (100 MHz, CDCl3, NS 6144): δ 142.75 (C, Ar1R), 132.77, 132.45 (double intensity), 132.12, 132.02, 131.99, 131.81 (7CH, Ar1-Ar2-Ar3-Ar4), 128.32 (C, Ar4CC), 124.21, 124.04, 123.05, 122.90, 122.53 (5C, CCAr3CCAr2-CCAr1), 118.80 (C, Ar4CN), 112.11 (C, Ar4CN), 94.09, 93.71, 91.90, 91.12, 90.97, 89.93 (6C, Ar4CCAr3CCAr2CCAr1), 34.49 (CH2, C1), 32.29 (CH2, C10), 31.03 (CH2, C2), 30.06-29.71 (7CH2, C3-C9), 23.05 (CH2, C11), 14.46 (CH3, C12) | Y | C NMR 16 .pdf |
Spectrum 3 | C NMR DEPT135 - 16 - ju1606fg1 .jdx |
C NMR | DEPT 135 | Y | C NMR DEPT135 - 16 .pdf |
Spectrum 4 | MALDI-TOF | LRMS (MALDI-TOF): m/z 1065 ([M+], 100 %) | Y | 16-MALDI.JPG |
|
Spectrum 5 | Infrared | IR (film): 2921, 2848 (m, CH stretch), 2357, 2337 (m, CC stretch, alkyne) | Y | 16-IR.JPG |
|
Spectrum 6 | |||||
Spectrum 7 | |||||
Spectrum 8 | |||||
Spectrum 9 | |||||
Spectrum 10 |
Properties
Experimental Physico-chemical Properties
Property | Value | Unit | Comments |
Experimental Boiling Point | |||
Experimental Flash Point | |||
Experimental Freezing Point | |||
Experimental Gravity | |||
Experimental Ionization Potent | |||
Experimental LogP | |||
Experimental Melting Point | 168 | °C | |
Experimental Optical Rotation | |||
Experimental Refraction Index | |||
Experimental Solubility | |||
Experimental Vapor Pressure | |||
Non Water Solubility | |||
Non Water Solubility |
Spectroscopy
Property | Value | Unit | Comments |
Lambda Max | 373 | nm | (CHCl3); (ε 61000) |
Miscellaneous
Property | Value | Unit | Comments |
Appearance | Yellow Solid | ||
Bio Activity | |||
Chemical Class | |||
Compound Source | |||
Drug Status | |||
Exposure Limits | |||
Exposure Limits Niosh Rel | |||
Exposure Routes | |||
First-Aid | |||
Incompatability | |||
Personal Protection | |||
Safety | |||
Stability | |||
Symptoms | |||
Target Organs | |||
Therapeutical Effect | |||
Toxicity |
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SOURCE
Author 1 is the author of this LabTrove post (and has contributor role of "Abstracter").
*First name | *Last name | Organization | Role | ||
Author 2 | Francesco | Giustiniano | University of Southampton | Doer | |
Author 3 | Richard | Whitby | University of Southampton | Conceiver | |
Author 4 |
TEXT
*Procedure or Transformation | Deprotection of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene |
*Compound(s) being made | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene |
*Chemicals used (delimited by semicolons ;) | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene; THF; TBAF |
*Procedure | In a 50 mL rbf a solution of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene(58 mg, 0.06 mmol) in THF (10 mL: large excess) was stirred for 15 min, at r.t., in presence of TBAF (0.84 mL of a solution 1 M in THF; 14.00 eq.); the disappearance of starting material (Rf 0.00, (20/1) hexane/DCM) was monitored by TLC. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine, dried over anhydrous MgSO4 and evaporated, to afford the crude product (bright yellow solid, 56 mg, 0.06 mmol, yield 93%). No further purification was carried out. |
*Authors Comments | The deprotection with K2CO3 and methanol/DCM was not viable because of the too low solubility of the starting material in methanol/DCM. |
Lead Reference | Taken from: F. Giustiniano, 2010, "Directed Assembly of Functional Patterns",PhD thesis, University of Southampton. Pages 13, 113 |
Other References | |
Multimedia Content | |
*Data | 1H NMR (400 MHz, CDCl3, D1 5 s); 13C NMR (100 MHz, CDCl3, NS 3072) |
#Data file 1 | H NMR 15 - fe1506sd2 .jdx |
#Data file 2 | C NMR 15 - fe1506sd2 .jdx |
#Data file 3 | |
#Data file 4 | |
#Data file 5 |
SCHEME
*#Structure file (ChemDraw, ChemSketch or RXN file) | reactionscheme_15 .cdx |
*#Image file (GIF or PNG) | reactionscheme_15 .gif |
Keywords
Compounds Keywords | Aromatics; alkynes |
Reactions Keywords | substitution |
Other Keywords |
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Compound
ChemSpider ID | 29289769 |
*#Name of Compound mol file | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene .mol |
Description and Tags
Description | |
Tags (separated by comma) |
Identifiers
*Chemical Name | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene |
Common Name | |
Synonym |
Spectra
*#Spectrum jcamp file | *Spectrum Type | Comments | OpenData | Image or PDF | |
Spectrum 1 | H NMR 15 - fe1506sd2 .jdx |
H NMR | 1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.51 (8H, m, Ar3), 7.48 (8H, m, Ar2), 7.37 (2H, s, Ar1), 3.18 (2H, s, CCH), 2.81 (4H, t, J = 7.8, C1), 1.70 (4H, pent, J = 7.5, C2), 1.42-1.23 (36H, m, C3-C11), 0.87 (6H, t, J = 6.8, C12) | Y | H NMR 15 .pdf |
Spectrum 2 | C NMR 15 - fe1506sd2 .jdx |
C NMR | 13C NMR (100 MHz, CDCl3, NS 3072): δ 142.54 (C, Ar1R), 132.56, 132.27, 131.78, 131.64, 131.59 (5CH, Ar3-Ar2-Ar1), 123.75, 123.70, 122.92, 122.70, 122.28 (5C, Ar1CCAr2CCAr3CCH), 93.89, 91.25, 90.89, 90.70 (4C, Ar3CCAr2CCAr1), 83.39 (C, Ar3CCH), 79.18 (CH, Ar3CCH; low intensity in DEPT), 34.29 (CH2, C1), 32.10 (CH2, C10), 30.83 (CH2, C2), 29.86-29.52 (7CH2, C3-C9), 22.85 (CH2, C11), 14.26 (CH3, C12) | Y | C NMR 15 .pdf |
Spectrum 3 | C NMR DEPT135 15 - fe1506sd2 .jdx |
C NMR | DEPT 135 | Y | C NMR DEPT135 - 15 .pdf |
Spectrum 4 | MALDI-TOF | LRMS (MALDI-TOF, DHB): m/z 862 ([M+], 100) | Y | 15-MALDI.JPG |
|
Spectrum 5 | Infrared | IR (film): 3290 (w, CH stretch, alkyne), 2958 (w), 2918, 2853 (m, CH stretch) | Y | 15-IR.JPG |
|
Spectrum 6 | |||||
Spectrum 7 | |||||
Spectrum 8 | |||||
Spectrum 9 | |||||
Spectrum 10 |
Properties
Experimental Physico-chemical Properties
Property | Value | Unit | Comments |
Experimental Boiling Point | |||
Experimental Flash Point | |||
Experimental Freezing Point | |||
Experimental Gravity | |||
Experimental Ionization Potent | |||
Experimental LogP | |||
Experimental Melting Point | 115-120 | °C | |
Experimental Optical Rotation | |||
Experimental Refraction Index | |||
Experimental Solubility | |||
Experimental Vapor Pressure | |||
Non Water Solubility | |||
Non Water Solubility |
Spectroscopy
Property | Value | Unit | Comments |
Lambda Max | 361 | nm | (CHCl3); (ε 70600) |
Miscellaneous
Property | Value | Unit | Comments |
Appearance | bright yellow solid | ||
Bio Activity | |||
Chemical Class | |||
Compound Source | |||
Drug Status | |||
Exposure Limits | |||
Exposure Limits Niosh Rel | |||
Exposure Routes | |||
First-Aid | |||
Incompatability | |||
Personal Protection | |||
Safety | |||
Stability | |||
Symptoms | |||
Target Organs | |||
Therapeutical Effect | |||
Toxicity |
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Compound
ChemSpider ID | 29289433 |
*#Name of Compound mol file | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene .mol |
Description and Tags
Description | |
Tags (separated by comma) |
Identifiers
*Chemical Name | 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene |
Common Name | |
Synonym |
Spectra
*#Spectrum jcamp file | *Spectrum Type | Comments | OpenData | Image or PDF | |
Spectrum 1 | H NMR 14 - fe1106sd1 .jdx |
H NMR | 1H NMR (400 MHz, CDCl3, D1 5 s): δ 7.50 (8H, m, Ar3), 7.45 (8H, m, Ar2), 7.37 (2H, s, Ar1), 2.81 (4H, t, J = 7.8, C1), 1.70 (4H, pent, J = 7.5, C2), 1.43-1.25 (36H, m, C3-C11), 0.87 (6H, t, J = 6.9, C12), 0.26 (18H, s, TMS). | Y | H NMR - 14 .pdf |
Spectrum 2 | C NMR - 14 - fe1106sd1 .jdx |
C NMR | 13C NMR (100 MHz, CDCl3, NS 3072): δ 142.54 (C, Ar1R), 132.55, 132.09, 131.75, 131.58, 131.56 (5CH, Ar1-Ar2-Ar3), 123.68, 123.32, 123.25, 123.00, 122.70 (5C, Ar1CCAr2CCAr3CC), 104.75 (C, TMSCCAr3), 96.62 (C, TMSCC), 93.90, 91.18, 91.11, 90.67 (4C, Ar3CCAr2CCAr1), 34.29 (CH2, C1), 32.09 (CH2, C10), 30.83 (CH2, C2), 29.85-29.53 (7CH2, C3-C9), 22.85 (CH2, C11; not visible in DEPT), 14.26 (CH3, C12), 0.07 (CH3, TMS) | Y | C NMR 14 .pdf |
Spectrum 3 | C NMR DEPT135 - 14 - fe1106sd1 .jdx |
C NMR | DEPT 135 | Y | C NMR DEPT135 - 14 .pdf |
Spectrum 4 | MALDI-TOF | LRMS (MALDI-TOF, alpha): m/z 1008 ([M+H]+, 100), 885 (13), 699 (16) | Y | 14-MALDI.JPG |
|
Spectrum 5 | Infrared | IR (film): 2950 (w), 2919 (m), 2851 (w, CH stretch), 2154 (w, CC stretch, alkyne) | Y | 14-IR.JPG |
|
Spectrum 6 | |||||
Spectrum 7 | |||||
Spectrum 8 | |||||
Spectrum 9 | |||||
Spectrum 10 |
Properties
Experimental Physico-chemical Properties
Property | Value | Unit | Comments |
Experimental Boiling Point | |||
Experimental Flash Point | |||
Experimental Freezing Point | |||
Experimental Gravity | |||
Experimental Ionization Potent | |||
Experimental LogP | |||
Experimental Melting Point | 168-171 | °C | |
Experimental Optical Rotation | |||
Experimental Refraction Index | |||
Experimental Solubility | |||
Experimental Vapor Pressure | |||
Non Water Solubility | |||
Non Water Solubility |
Spectroscopy
Property | Value | Unit | Comments |
Lambda Max |
Miscellaneous
Property | Value | Unit | Comments |
Appearance | White Solid | ||
Bio Activity | |||
Chemical Class | |||
Compound Source | |||
Drug Status | |||
Exposure Limits | |||
Exposure Limits Niosh Rel | |||
Exposure Routes | |||
First-Aid | |||
Incompatability | |||
Personal Protection | |||
Safety | |||
Stability | |||
Symptoms | |||
Target Organs | |||
Therapeutical Effect | |||
Toxicity |