PP-ART-12-2009-000206 Supporting Information-revised · Title: Microsoft Word -...

Supporting information

Photochemical deuterium exchange in phenyl-

substituted pyrroles and indoles in CD3CN-D2O

Nikola Basarić,*a Alfredo Franco-Cea,b Marija Alešković,a Kata Mlinarić-

Majerski,a and Peter Wan*b

a Department of Organic Chemistry and Biochemistry, Bijenička cesta 54, 10 000 Zagreb,

Croatia. Fax: + 385 1 4680 195; Tel: +385 1 4561 141; E-mail: nbasaric@irb.hr

b Department of Chemistry, University of Victoria, Box 3065 Stn CSC, Victoria BC,

V8W3V6, Canada, Fax: + 1 (250) 721-7147, Tel: + 1 (250) 721-8976;

E-mail: pwan@uvic.ca

Electronic Supplementary Material (ESI) for Photochemical & Photobiological SciencesThis journal is © The Royal Society of Chemistry and Owner Societies 2010

Table of contents:

1. Experimental procedure for the preparation of compounds S3

2. 1H NMR spectra after photolyses in deuterated solvents S5

3. Fluorescence study S23

4. Laser flash photolysis S40

1. Experimental procedure for the preparation of compounds N-tert-Butoxycarbonyl-2-phenylpyrrole: To a stirred solution of iodobenzene (193 mg, 0.95

mmol), cesium carbonate (620 mg, 1.89 mmol) and tetrakis(triphenylphosphine)palladium (5

% mol) in toluene (20 mL) at reflux under nitrogen was added a solution of (1-tert-

butyloxycarbonylpyrrol-2-yl)boronic acid1 (200 mg, 0.95 mmol) in the mixture of toluene (10

mL) and methanol (3 mL) during 7 h. The mixture was stirred at reflux for 17 h, cooled and

methanol was evaporated under reduced pressure. To a toluene suspension was added water

(30 mL) and the layers were separated, the water layer was extracted with dichloromethane (3

× 25 mL). Combined organic extracts were washed with water (30 mL) and dried over

anhydrous MgSO4, and evaporated under reduced pressure. The resulting crude product was

purified by chromatography on silica eluting with the mixture of dichloromethane and hexane

(10 → 30%) to yield 185 mg (86 %) of N-tert-Butoxycarbonyl-2-phenylpyrrole as a clear oil.

The 1H NMR and 13C NMR spectra were identical to the literature data.2

2-Phenylpyrrole (8): A suspension of sodium methoxide (freshly prepared by reacting 84 mg

of sodium with 10 mL of methanol) was added to a stirred solution of N-tert-butoxycarbonyl-

2-phenylpyrrole (280 mg, 1.22 mmol) in methanol (40 mL) and stirred at reflux for 3h, and at

25 °C for 15 h. The solvent was evaporated and the residue was portioned between

dichloromethane and water. Water layer was extracted with dichloromethane (2 × 25 mL),

and the combined organic extracts were washed with brine (30 ml). Organic extracts were

dried over anhydrous MgSO4, solvent was evaporated to give 158 mg (90 %) of the product as

a white crystalline solid. The 1H NMR and 13C NMR spectra were identical to the literature

data.2

7-Phenylindole (12): A round bottom flask (50 mL) was charged with 7-bromoindole (255

mg, 1.3 mmol), phenylboronic acid (158 mg, 1.3 mmol),

tetrakis(triphenylphsophine)palladium (40 mg), K2CO3 (300 mg), toluene (10 mL) and

methanol (5 mL). The mixture was heated to reflux for 24 h under N2. During this time, the

orange solution turned to deep purple. After cooling to rt, 30 mL of HCl (1M) was added and

the mixture was extracted with CH2Cl2 (4 × 15 mL). The resulting deep-red organic extracts

were combined and dried over anhydrous MgSO4. The solvent was evaporated on a rotary

evaporator to yield the crude product in the form of dark oil that was purified by column

chromatography on silica gel eluting with a mixture of CH2Cl2 - Hexanes (1:3). The resulting

clear oil crystallized spontaneously upon storage at 10 ºC.

1. S. Martina, V. Enkelmann, G. Wegner, A.-D. Schlüter, Synthesis 1991 613-615.

2. A. Burghart, H. Kim, M. B. Welch, L. H. Thorensen, J. Reibenspies, K. Burgess, J.

Org. Chem. 1999, 64, 7813-7819.

1H NMR spectra after photolyses in deuterated solvents

1H NMR (CD3CN + D2O) after thermal (“dark“) experiment for 7 in CD3CN – D2O SpinWorks 2.3: Nikola NB-159 + D2O

PPM 7.70 7.60 7.50 7.40 7.30 7.20 7.10 7.00 6.90 6.80 6.70 6.60 6.50 6.40 6.30

file: D:\PODACI-Nikola\NMR-Zagreb\N-159\2\fid expt: <zg30>transmitter freq.: 600.133901 MHztime domain size: 32768 pointswidth: 9541.98 Hz = 15.899760 ppm = 0.291198 Hz/ptnumber of scans: 16

freq. of 0 ppm: 600.130013 MHzprocessed size: 32768 complex pointsLB: 0.000 GB: 0.0000

1H NMR (CD3CN + D2O) after photolysis (45min) of 7 at 254 nm in a quartz NMR tube SpinWorks 2.3: Nikola NB-159 + D2O na kraju

PPM 7.70 7.60 7.50 7.40 7.30 7.20 7.10 7.00 6.90 6.80 6.70 6.60 6.50 6.40 6.30

file: D:\PODACI-Nikola\NMR-Zagreb\N-159\4\fid expt: <zg30>transmitter freq.: 600.133901 MHztime domain size: 32768 pointswidth: 9541.98 Hz = 15.899760 ppm = 0.291198 Hz/ptnumber of scans: 24

freq. of 0 ppm: 600.130013 MHzprocessed size: 32768 complex pointsLB: 0.000 GB: 0.0000

1H NMR (CDCl3) after photolysis (2h) of 8 in CH3CN – D2O (1M)

1H NMR (CDCl3) after thermal (“dark“) experiment (2h) for 8 in CH3CN – D2O (1M)

1H NMR (CD3CN) after photolysis (30 min) of 8 in CD3CN – D2O (1M)

1H NMR (CDCl3) after thermal (“dark“) experiment for 8 in CD3CN – D2O (1M)

1H NMR (CD3CN) after photolysis (4h) of 9 in CH3CN – D2O (1M)

1H NMR (CD3CN) after thermal (“dark“) experiment (4h) for 9 in CH3CN – D2O (1M)

1H NMR (CD3CN) after thermal (“dark“) experiment (30 min) for 9 in CD3CN – D2O (1M)

1H NMR (CD3CN) after photolysis (30 min) of 9 in CD3CN

1H NMR (CD3CN) after thermal (“dark“) experiment (30 min) for 9 in CD3CN

1H NMR (CD3CN) after photolysis (4 h) of 12 in CH3CN – D2O (1M)

1H NMR (CD3CN) after thermal (“dark“) experiment (4 h) for 12 in CH3CN – D2O (1M)

3. Fluorescence study UV-vis spectra of 2-phenylpyrrole (8), 2-phenylindole (9) and 7-phenylindole (12) in CH3CN.

200 225 250 275 300 325 3500

Absorption spectra in CH3CN

Wavelength λ / nm

2-phenylpyrrole 2-phenylindole 7-phenylindole

Excitation and emission spectrum of 2-phenylpyrrole (8) in cyclohexane.

240 260 280 300 320 340 360 380 400 420

2-Phenylpyrrole in cyclohexane

Wavelength λ / nm

λem = 350 nm λex = 290 nm

Excitation and emission spectrum of 2-phenylpyrrole (8) in CH3CN.

240 260 280 300 320 340 360 380 400 420 440

2-phenylpyrrole in CH3CN

Wavelength λ / nm

Excitation and emission spectrum of 2-phenylpyrrole (8) in CH3OH.

240 260 280 300 320 340 360 380 400 420 440 460

2-Phenylpyrrole in CH3OH

Wavelength λ / nm

Emission spectra of 2-phenylpyrrole (8) in different solvents.

300 325 350 375 400 425 450

2-Phenylpyrrole in different solvents

Wavelength λ / nm

cyclohexane CH3CN CH3OH

Fluorescence spectra of 2-phenylpyrrole (8) in CH3CN at different H2O content and Stern-Volmer plot of fluorescence quenching by H2O.

300 350 400 450 500

Fluorescece in CH3CN at different H2O content

Wavelength λ / nm

c(H2O) = 0 M c(H2O) = 20.8 M

0 5 10 15 200,90

Φ0/Φ

c (H2O ) / M

Fluorescence quenching of 2-phenylpyrrole (8) in CH3CN-H2O (1:4) by HClO4, and Stern-Volmer plot of the fluorescence quenching by HClO4.

300 350 400 450 500

Wavelength λ / nm0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,0030

Φ0/Φ

c (H+) / M

Y = A + B * X

Parameter Value Error------------------------------------------------------------A 1,01204 0,00611B 180,78237 3,10335------------------------------------------------------------

R SD N P------------------------------------------------------------0,99721 0,01295 21 <0.0001------------------------------------------------

Relative fluorescence intensity of 2-phenylpyrrole (8) in CH3CN-H2O (4:1) at 358 nm as a function of HClO4 concentration. Red line represents the fitting of the model to the experimental values (black dots) obtained by the factor analysis in the SPECFIT program.

0,000 0,001 0,002 0,003

c (HClO4) / M

Relative fluorescence intensity of 2-phenylpyrrole (8) in CH3CN-H2O (4:1) in the protonated and non-protonated form, obtained by the factor analysis in the SPECFIT program.

300 350 400 450 500

Wavelenght λ/nm

Fluorescence quenching of 2-phenylpyrrole (8) in CH3CN-H2O (1:4) by NaOH, and Stern-Volmer plot of the fluorescence quenching by NaOH.

300 350 400 450 500

c(OH-)

Wavelength λ / nm

0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,0030

0 / Φ

c (NaOH) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,99755 0,02039 21 <0.0001-----------------------------------------------------------

Relative fluorescence intensity of 2-phenylpyrrole (8) in CH3CN-H2O (4:1) at 356 nm as a function of NaOH concentration. Red line represents the fitting of the model to the experimental values (black dots), obtained by the factor analysis in the SPECFIT program.

0,0000 0,0005 0,0010 0,0015 0,0020

c (NaOH) / M

Excitation and emission spectrum of 2-phenylindole (9) in cyclohexane.

250 300 350 400 450

Wavelength λ / nm

2-phenylindole in cyclohexane

Excitation and emission spectrum of 2-phenylindole (9) in chloroform.

250 300 350 400 450 500

Wavelength λ / nm

2-phenylindole in CHCl3

Excitation and emission spectrum of 2-phenylindole (9) in CH3CN.

250 300 350 400 450 500

2-phenylindole in CH3CN

Wavelength λ / nm

Excitation and emission spectrum of 2-phenylindole (9) in CH3OH.

250 300 350 400 450 500

Wavelength λ / nm

2-phenylindole in CH3OH

Emission spectra of 2-phenylindole (9) in different solvents.

350 400 450 500

Wavelength λ / nm

2-phenylindole in different solvents

cyclohexane CHCl3 CH3CN CH3OH

Fluorescence spectra of 2-phenylindole (9) in CH3CN at different H2O content and Stern-Volmer plot of fluorescence quenching by H2O.

350 400 450 500

Wavelength λ / nm

Fluorescece in CH3CN different H2O content2-phenylindole

c(H2O) = 0 M c(H2O) = 20.8 M

0 5 10 15 200,93

1,00 2-phenylindole in CH3CN

c (H2O ) / M

Fluorescence quenching of 2-phenylindole (9) in CH3CN-H2O (1:4) by HClO4, and Stern-Volmer plot of the fluorescence quenching by HClO4.

350 400 450 500

2-phenylindole

Wavelength λ / nm0,0 0,1 0,2 0,3 0,4 0,5

1,202-phenylindole

c(HClO4) / M

Stern-Volmer plot of the fluorescence quenching of 2-phenylindole (9) in CH3CN-H2O (1:4) by HClO4.

0,00 0,05 0,10 0,15 0,20 0,25 0,30

c (HClO4) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,9894 0,004 9 <0.0001-----------------------------------------------------

Fluorescence quenching of 2-phenylindole (9) in CH3CN-H2O (1:4) by NaOH, and Stern-Volmer plot of the fluorescence quenching by NaOH.

350 400 450 500

Wavelength λ / nm

c (OH-)

0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,0030

2-phenylindole

Φ0/Φ

c(NaOH) / M

Stern-Volmer plot of the fluorescence quenching of 2-phenylindole (9) in CH3CN-H2O (1:4) by NaOH.

0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,0030

c(NaOH) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,99689 0,00458 21 <0.0001----------------------------------------------------------

Relative fluorescence intensity of 2-phenylindole (9) in CH3CN-H2O (4:1) at 377 nm as a function of NaOH concentration. Red line represents the fitting of the model to the experimental values (black dots), obtained by the factor analysis in the SPECFIT program.

0,000 0,001 0,002 0,003

c (NaOH) / M

Excitation and emission spectrum of N-methyl-2-phenylindole (10) in cyclohexane.

250 300 350 400 450 500

Wavelength λ / nm

N-methyl-2-phenylindolecyclohexane

Excitation and emission spectrum of N-methyl-2-phenylindole (10) in CHCl3.

250 300 350 400 450 500

Wavelength λ / nm

N-methyl-2-phenylindoleCHCl3

Excitation and emission spectrum of N-methyl-2-phenylindole (10) in CH3CN.

250 300 350 400 450 500

N-methyl-2-phenylindoleCH3CN

Wavelength λ / nm

Excitation and emission spectrum of N-methyl-2-phenylindole (10) in CH3OH.

250 300 350 400 450 500

Wavelength λ / nm

N-methyl-2-phenylindoleCH3OH

Emission spectra of N-methyl-2-phenylindole (10) in different solvents.

350 400 450 500

Wavelength λ / nm

N-methyl-2-phenylindole

Stern-Volmer plot of the fluorescence quenching of N-methyl-2-phenylindole (10) in CH3CN by H2O.

0 5 10 15 20

1,00 N-methyl-2-phenylindole

c(H2O) / M

Fluorescence quenching of N-methyl-2-phenylindole (10) in CH3CN-H2O (1:4) by HClO4, and Stern-Volmer plot of the fluorescence quenching by HClO4.

350 400 450 500

Wavelength λ / nm

0,0 0,1 0,2 0,3 0,4 0,5

Φc (HClO4) / M

Stern-Volmer plot of the fluorescence quenching of N-methyl-2-phenylindole (10) in CH3CN-H2O (1:4) by HClO4.

0,00 0,05 0,10 0,15 0,20 0,25

0 / Φ

c (HClO4) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,99587 0,00657 7 <0.0001------------------------------------------------------------

Relative fluorescence intensity of N-methyl-2-phenylindole (10) in CH3CN-H2O (4:1) at 384 nm as a function of HClO4 concentration. Red line represents the fitting of the model to the experimental values (black dots), obtained by the factor analysis in the SPECFIT program.

0,00 0,05 0,10 0,15 0,20 0,25 0,30 0,35

c (HClO4) / M

Fluorescence quenching of N-methyl-2-phenylindole (10) in CH3CN-H2O (1:4) by NaOH, and Stern-Volmer plot of the fluorescence quenching by NaOH.

350 400 450 500

c(OH-)

Wavelength λ / nm

ity N-methyl-2-phenylindole

0,000 0,001 0,002 0,003

c(NaOH) / M

Stern-Volmer plot of the fluorescence quenching of N-methyl-2-phenylindole (10) in CH3CN-H2O (1:4) by NaOH.

0,000 0,001 0,002 0,003

c(NaOH) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,99349 0,00267 21 <0.0001------------------------------------------------------------

Excitation and emission spectrum of 7-phenylindole (12) in cyclohexane.

250 275 300 325 350 375 400 425

7-phenylindole in cyclohexane

Wavelength λ / nm

λ em = 360 nm λ ex = 290 nm

Excitation and emission spectrum of 7-phenylindole (12) in CHCl3.

250 275 300 325 350 375 400 425 450

Wavelength λ / nm

λ em = 350 nm λ ex = 290 nm

7-phenylindole in CHCl3

Excitation and emission spectrum of 7-phenylindole (12) in CH3CN.

250 300 350 400 450 500

Wavelength λ / nm

λ em = 375 nm λ ex = 290 nm

7-phenylindole in CH3CN

Excitation and emission spectrum of 7-phenylindole (12) in CH3OH.

250 300 350 400 450 500

Wavelength λ / nm

λ em = 350 nm λ ex = 290 nm

7-phenylindole in CH3OH

Emission spectra of 7-phenylindole (12) in different solvents.

300 325 350 375 400 425 450Wavelength λ / nm

nsity 7-phenylindole

Fluorescence spectra of 7-phenylindole (12) in CH3CN at different H2O content and Stern-Volmer plot of fluorescence quenching by H2O.

350 400 450 500

7-phenylindole / CH3CN

Wavelength λ / nm

c (H2O) = 0 M c (H2O) = 21 M

0 5 10 15 200,90

7-phenylindole / CH3CN

Φ 0 /

c (H2O) / M

Stern-Volmer plot of the fluorescence quenching of 7-phenylindole (12) in CH3CN-H2O (1:4) by HClO4.

0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,0030

c(H+) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,98825 0,00226 21 <0.0001------------------------------------------------------------

Relative fluorescence intensity of 7-phenylindole (12) in CH3CN-H2O (4:1) at 381 nm as a function of HClO4 concentration. Red line represents the fitting of the model to the experimental values (black dots), obtained by the factor analysis in the SPECFIT program.

0,000 0,001 0,002 0,003

c (HClO4) / M

Relative fluorescence intensity of 7-phenylindole (12) in CH3CN-H2O (4:1) in the protonated and non-protonated form, obtained by the factor analysis in the SPECFIT program.

350 400 450 500 550

Wavelength λ / nm

12 12H+

Fluorescence quenching of 7-phenylindole (12) in CH3CN-H2O (1:4) by NaOH, and Stern-Volmer plot of the fluorescence quenching by NaOH.

350 400 450 500 550

c (OH-)

Wavelength λ / nm

0,0000 0,0005 0,0010 0,0015 0,0020 0,0025 0,00300,9

1,7 7-phenylindole

c(NaOH) / M

Stern-Volmer plot of the fluorescence quenching of 7-phenylindole (12) in CH3CN-H2O (1:4) by NaOH.

0,0000 0,0002 0,0004 0,0006 0,0008 0,00100,95

7-phenylindole

Φ0/Φ

c(NaOH) / M

Y = A + B * X

R SD N P------------------------------------------------------------0,99573 0,01444 5 3,35277E-4---------------------------------------------------------

Relative fluorescence intensity of 7-phenylindole (12) in CH3CN-H2O (4:1) at 378 nm as a function of NaOH concentration. Red line represents the fitting of the model to the experimental values (black dots), obtained by the factor analysis in the SPECFIT program.

0,000 0,001 0,002 0,003

c (NaOH) / M

Relative fluorescence intensity of 7-phenylindole (12) in CH3CN-H2O (4:1) in the neutral and deprotonated form, obtained by the factor analysis in the SPECFIT program.

350 400 450 500 550

Wavelength λ / nm

12NH 12N-

4. Laser flash photolysis

Transient absorption spectra of 2-phenylpyrrole (8) in N2-purged CH3CN solution.

300 400 500 600 700 800-0,10

0,20 2-phenylpyrrole in CH3CNN2 purged

Wavelength λ / nm

0.55 μs 2.4 μs 5.0 μs 8.0 μs

Transient absorption spectra of 2-phenylpyrrole (8) in O2-purged CH3CN solution.

300 400 500 600 700 800

0.55 μs 2.4 μs 5.0 μs 8.0 μs

2-phenylpyrrole in CH3CNO2 purged

Wavelength λ / nm

Transient absorption spectrum of 2-phenylpyrrole (8) in O2-purged CH3CN solution 550 ns after the laser pulse.

400 500 600 700 8000,000

Wavelength λ / nm

2-phenylpyrrole in CH3CNO2 purged 550 ns after the pulse

300 400 500 600 700 800

400 500 600 700 8000,000

Wavelength λ / nm

2-phenylpyrrole in CH3CN

O2 purged

550 ns after the pulse

2-phenylpyrrole in CH3CNO2 purged

Wavelength λ / nm

Transient absorption spectra of 2-phenylpyrrole (8) in N2-purged CH3CN-H2O (1:1) solution, pH = 7.

300 400 500 600 700 800-0,05

0,25 Ph-py / CH3CN-H

2O 1:1 pH = 7

N2 purged

Wavelength λ / nm

0.5 μs 2.2 μs 7.2 μs 16 μs

Transient absorption spectra of 2-phenylpyrrole (8) in O2-purged CH3CN-H2O (1:1) solution, pH = 7.

300 400 500 600 700 800

Ph-py / CH3CN-H2O 1:1 pH = 7O2 purged

400 450 500 550 6000,000

Wavelength λ / nm

0.5 μs 3.1 μs 8.6 μs 16 μs

Wavelength λ / nm

0.5 μs 3.1 μs 8.6 μs 16 μs

Transient absorption spectra of 2-phenylpyrrole (8) in N2-purged CH3CN-H2O (1:1) solution, pH = 12.

300 400 500 600 700-0,050

-0,025

0.6 μs 3.1 μs 7.9 μs 16 μs

Wavelength λ / nm

Ph-py / CH3CN-H2O 1:1 pH = 12N2 purged

Transient absorption spectra of 2-phenylpyrrole (8) in O2-purged CH3CN-H2O (1:1) solution, pH = 12.

300 400 500 600

0,20Ph-py / CH3CN-H2O 1:1 pH = 12O2 purged

0.6 μs 3.5 μs 9.3 μs 16 μs

350 400 450 500 550 6000,00

Wavelength λ / nm

Transient absorption spectra of 2-phenylindole (9) in N2-purged CH3CN solution.

300 400 500 600 700 800

0,20 2-phenylindole / acnN2 purged

Wavelength λ / nm

0.51 μs 2.1 μs 4.9 μs 8.0 μs

Transient absorption spectra of 2-phenylindole (9) in O2-purged CH3CN solution.

300 400 500 600 700 800

Wavelength λ / nm

0.20 μs 1.1 μs 3.7 μs 8.0 μs

2-phenylindole / acnO2 purged

Transient absorption spectra of 2-phenylindole (9) in N2-purged CH3CN-H2O (1:1) solution.

300 400 500 600 700-0,05

2-phenylindole / CH3CN-H2O 1:1N2 purged

Wavelength λ / nm

0.30 μs 1.3 μs 4.1 μs 7.7 μs

Transient absorption spectra of 2-phenylindole (9) in O2-purged CH3CN-H2O (1:1) solution.

300 400 500 600 700-0,04

Wavelength λ / nm

2-phenylindole / CH3CN-H2O 1:1O2 purged

0.30 μs 1.4 μs 4.2 μs 7.8 μs

Transient absorption spectra of N-methyl-2-phenylindole (10) in N2-purged CH3CN-H2O (1:1) solution.

300 400 500 600 700 800-0,05

0,20N-methyl-2-phenylindole in CH3CN - H2O 1:1N2 purged

Wavelength λ / nm

1.1 μs 7.5 μs 23 μs 40 μs

Transient absorption spectra of N-methyl-2-phenylindole (10) in O2-purged CH3CN-H2O (1:1) solution.

300 400 500 600 700-0,04

Wavelength λ / nm

1.1 μs 7.5 μs 23 μs 40 μs

N-methyl-2-phenylindole in CH3CN - H2O 1:1O2 purged

Transient absorption spectra of 7-phenylindole (12) in N2-purged CH3CN solution.

300 350 400 450 500 550 600 650 700 750-0,05

0,157-phenylindole in CH3CNN2 purged

Wavelength λ / nm

1.1 μs 5.1 μs 10 μs 16 μs

Transient absorption spectra of 7-phenylindole (12) in O2-purged CH3CN solution.

300 350 400 450 500 550 600 650 700 750-0,010

-0,005

7-phenylindole in CH3CNO2 purged

Wavelength λ / nm

1.0 μs 5.1 μs 10 μs 16 μs

PP-ART-12-2009-000206 Supporting Information-revised · Title: Microsoft Word -...

Documents

ENTRIX Report Templatebaydeltalive.com/.../application/msword/...REVISED.doc · Web viewChurchwell, R., R. Padilla, K. Enstrom, K. Clark, D. Dorratcague, C. Hanson, T. Finnegan, and

PP Dwu Pp Dwst Pp c

GENERAL GOVERNMENT FACILITIES 2021-2025 …D-650006 BARC Sanitary Line Replacement 23 D-650007 BARC Warehouse Replacement 24 D-000174 City Hall - Drinking Fountains 3 D-000206 City

NWA Digital Duplicator- Revised - Next Wave … Microsoft Word - NWA Digital Duplicator- Revised.doc Author albri_000 Created Date 8/25/2017 2:27:46 PM

Origins of Wrestling revised - Loomis Chaffee School · Microsoft Word - Origins_of_Wrestling revised.doc Author: BobbiMoran Created Date: 11/30/2010 5:13:45 PM

cover page 326 revised.doc - econweb.umd.edueconweb.umd.edu/~sweeting/garmon.pdf · Revised: February 2016 FTC Bureau of Economics working papers are preliminary materials circulated

lesson 4 revised.doc

Department of Mathematics - Kutztown University of ...faculty.kutztown.edu/mcloughl/revised.doc · Web viewThe Department of Mathematics ... the student should be able to work basic

› documents › FIMA › Final Doc revised.doc · Web viewCUSTOMER MASTER INFORMATION MODULE (Inquiry)These are operational expenses such as catering charges from Student Union,

Garment Costing revised.doc

OPERTIONS RESEARCH Note from Ch I-V Revised.doc

Introduction to Molecular Genetics COPYRIGHTED MATERIAL€¦ · 4 Introduction to Molecular Genetics Pink parent White parent x x PP PP pp pp Pp Pp Pp Pp Pp Pp Pp Pp Gametes: F 1

1-6 kenji revised.doc

301-376 Tablolar.pdf · edu pp pp pp pp pp pp pp 7deor v i ] ] ] u o ] À ] ] u ]

HsNr - Dietramszelldietramszell.de/images/DZ Plan 8 VE 500_Vor11.8.17_end.pdf · N PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP PP OD Leistenstein Leistenstein

8 Sag The head the head revised.doc

Chapter - I - Environmental Law Alliance Worldwide III revised.doc · Web viewCHAPTER – III Baseline ... Isopod, Copepod, Crab, Shrimp and Foraminifera. During high tide and low

Microsoft Word - Romich Std CrtThnkg REVISED.doc · Web viewChapter 1 Search in the research section, then go to the fast ... Title Microsoft Word - Romich Std CrtThnkg REVISED.doc

BEFORE KUHN PETTIGREW AND KLINE JJ CA 0192...policies against piecemeal appeals Id 000206 at pp 56808 So2dat 483 Although the trial court designated the judgment as final the court

Additional Exercises - Department of Economics Sciences Poecon.sciences-po.fr/sites/default/files/file/additional_exercises.pdf · 6 Q C Q W PP PP PP PPP PP PP PPP PP PP PP PPP PP