Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts
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1 Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry Supporting Information Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts Kathiravan Murugesan, Thirusangumurugan Senthamarai, Manzar Sohial, Ahmad S. Alshammari, Marga-Martina Pohl, Matthias Beller* and Rajenahally V. Jagadeesh* Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. a, Rostock, Germany. *Corresponding authors: and
2 Supplementary figures R (I) N Catalyst Catalyst H R NH R NH H (II) (III) R NH -NH Catalyst R N R R N R H (IV) H (V) Fig. S. Reaction pathway for the catalytic hydrogenation of nitriles: Formation of desired and un-desired products. Fig.. Studies on the effect of ammonia (A), reaction time (B), amount of catalyst (C) and pressure of hydrogen (D) on the hydrogenation of benzonitrile. Reaction conditions: A:. mmol benzonitrile, mg catalyst (. mol% Co), ml toluene, bar H, - bar NH, C, h. B: same as A with bar NH, o C, - h. C: Same as A with - mg catalyst and bar NH. D: Same as A with - bar H and bar NH.
3 Fig. S. HAADF-STEM/EDX images of cobalt-terephthalic acid catalyst. Fig. S. TEM images cobalt
4 Fig. S: HAADF-STEM images (A-C) and ABF-STEM image (D) of used catalyst. (A) and (B) show the new Co O structures grown during reaction on the surface of the carbon support. (C) shows Co metal and Co O particles. (D) shows a high resolution ABF image of a metal Co particle (see EDXS from S) highlighting the encapsulation with several layers of graphenes.
5 Fig. S: HAADF-STEM images with EDX spectra from marked areas showing morphology comparable to the fresh specimen in the case of metallic Co particles (A, area ) and changes in the case of cobalt oxide structures (A, area ). Additionally a cobalt oxide phase has grown on the surface of carbon support (B, area ).
6 Fig. S. XRD spectra of cobalt-terephthalic acid catalyst. Fig. S. XRD spectra of (A) Cobalt-terephthalic acid MOF and cobalt-terephthalic acid MOF-carbon template. Fig. S. EPR spectra of cobalt-terephthalic acid catalyst.
7 Fig. S. XPS of Cop (A) and Os (B) electrons for cobalt-terephthalic acid
8 Fig. S. Sorption isotherm of cobalt-terephthalic acid catalyst.
9 Fig. S. Pore-size distribution calculated from the desorption isotherm for Cobalt-terephthalic acid catalyst.
10 NMR Data KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (dd, J =.,. Hz, H),. (dd, J =.,. Hz, H),.. (m, H),.. (m, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.,.,..off white solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),.. (m, H),.. (m, H),.. (m, H),. (t, J =. Hz, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.. Brown solid. KM- Br NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),.. (m, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.. White solid. KM- H N NH + Cl - O H NMR ( MHz, DMSO-d ) δ. (br s, H),. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. White solid.
11 KM- F F F NH + Cl - N O H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (s, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d ) δ.,.,. (q, J =. Hz),. (q, J =. Hz),. (q, J =. Hz),. (q, J =. Hz),.,.,.,.. Off white solid. KM- F NH + Cl - NH H NMR ( MHz, DMSO-d ) δ. (br s, H),. (br s, H),. (dd, J =.,. Hz, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ. (d, J =. Hz),.,. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.. Off white solid. KM- F NH + Cl - F F H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ. (ddd, J =.,.,. Hz),. (dt, J =.,. Hz),. (td, J =.,. Hz),.. (m),.. Off white solid. KM- HO F NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),. (br s, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.,.. Off white solid.
12 KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. White solid. KM- O NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. White solid. KM- F NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),. (d, J =. Hz),.. White solid. KM- Cl NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. White solid. KM- Br NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. White solid.
13 KM- NH H NMR ( MHz, DMSO-d ) δ.. (m, H),. (br s, H),.. (m, H),. (t, J =. Hz, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.. Brown oil. KM- F F F F NH + Cl - F F H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),. (s, H). F NMR ( MHz, DMSO-d ) δ -.. White solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (t, J =. Hz, H),.-. (m, H),.-. (m, H),. (t, J =. Hz, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.. Off white solid. KM- O H N Cl O NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),.. (m, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.. Yellow solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (t, J =. Hz, H),. (t, J =. Hz, H),. (d, J =. Hz, H),.. (m, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.. Brown gum.
14 KM- O NH + Cl - O H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (dd, J =.,. Hz, H),. (s, H),. (s, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d) δ.,.,.,.,.,.,.,.,.,..yellow solid. KM- N NH + Cl - H NMR ( MHz, DMSO-d ) δ. (m, H),.. (m, H),. (s, H). C NMR ( MHz, DMSOd ) δ.,.,.,.. Brown solid. KM- O NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. - (m, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. Brown solid. KM- O NH + Cl - O H NMR ( MHz, DMSO-d ) δ. (br s, H),. (s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.. White solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,..
15 KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),. (s, H),.. (m, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. White solid. KM- O NH + Cl - O H NMR ( MHz, DMSO-d ) δ. (br s, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.. White solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (t, J =. Hz, H),. (d, J =. Hz, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. Off white solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),. (dd, J =.,. Hz, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.,.. Off white solid.
16 KM- NH + Cl - N H H NMR ( MHz, DMSO-d ) δ. (s, H),. (br s, H),.. (m, H),.. (m, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.. Off white solid. KM- O NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (d, J =. Hz, H),. (s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.. White solid. KM- O NH + Cl - F H NMR ( MHz, DMSO-d ) δ. (br s, H),. (s, H),.. (m, H),.. (m, H),. (d, J =. Hz, H),. (s, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (s, H). C NMR ( MHz, DMSO-d ) δ. (d, J =. Hz),.,.,. (d, J =. Hz),.,.,. (d, J =. Hz),.,.,. (d, J =. Hz),.,.,.. White solid. KM- NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),.. (m, H),.. (m, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. White solid.
17 KM- N NH + Cl - H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (d, J =. Hz, H),.. (m, H),.. (m, H),.. (m, H),.. (m, H),. (t, J =. Hz, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.. Off white solid. KM- F NH + Cl - F F H NMR ( MHz, DMSO-d ) δ. (br s, H),.. (m, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,. (q, J =. Hz),.,. (d, J =. Hz),.. White solid. KM- H N H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (d, J =. Hz, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.,.. Yellow solid. KM- H N O O H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (q, J =. Hz, H),. (br s, H),. (t, J =. Hz, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.. Yellow solid.
18 KM- NH O HN S O O H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),.. (m, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.,.,.. Brown solid. KM- N NH H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),. (br s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.. Brown gum. KM- H N O O H NMR ( MHz, DMSO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.. Yellow solid. KM- NH S H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.. Brown gum.
19 KM- F F F NH O O S O H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),.. (m, H),.. (m, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,. (q, J =. Hz),. (q, J =. Hz),.,.,.,. (q, J =. Hz),. (q, J =. Hz),.. Yellow gum. KM- NH O S O NH H NMR ( MHz, DMSO-d ) δ. (d, J =. Hz, H),.. (m, H),. (dd, J =.,. Hz, H),.. (m, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. Off white solid. KM- Cl NH H N Cl H NMR ( MHz, Chloroform-d) δ. (s, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.. Brown solid. KM- NH N H NMR ( MHz, Chloroform-d) δ. (dd, J =.,. Hz, H),. (dd, J =.,. Hz, H),.. (m, H),. (dd, J =.,. Hz, H),. (dd, J =.,. Hz, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.. Brown solid.
20 KM- NH H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),.. (m, H),. (dd, J =.,. Hz, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.,.. Brown solid. KM- NH O H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.. Off white solid. KM- HN N NH H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. -. (m, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.. Brown gum. KM- Cl NH Cl Cl H NMR ( MHz, Chloroform-d) δ. (s, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.. Brown solid. KM- NH NH Cl H NMR ( MHz, Chloroform-d) δ.. (m, H),. (d, J =. Hz, H),.. (m, H),. (dt, J =.,. Hz, H),. (d, J =. Hz, H),. (br s, H),. (br s, H). C NMR ( MHz,
21 Chloroform-d) δ.,.,.,.,.,.,.,.,.,.. Brown solid. KM- O H N H NMR ( MHz, Chloroform-d) δ. (d, J =. Hz, H),. (d, J =. Hz, H),.. (m, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.,.,.. Yellow solid. KM- NH H NMR ( MHz, Chloroform-d) δ.. (m, H),.. (m, H),.. (m, H),. (dt, J =.,. Hz, H),. (br s, H). C NMR ( MHz, Chloroform-d) δ.,.,.,.,.,.,.,.,.,.. Colorless gum. KM- NH OH H NMR ( MHz, DMSO-d ) δ. (br s, H),. (ddd, J =.,.,. Hz, H),.. (m, H),. (ddd, J =.,.,. Hz, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. Brown solid. KM- Cl O NH NH H NMR ( MHz, DMSO-d ) δ.. (m, H),. (dd, J =.,. Hz, H),. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.,.,.,.,.,.,.,.. Pale brown solid.
22 KM- NH O NH H NMR ( MHz, DMSO-d ) δ. (m, H),. (br s, H),. (d, J =. Hz, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. Off white solid. KM- NH O O H NMR ( MHz, DMSO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H),. (s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.,.. Off white solid. KM- Br NH N NH H NMR ( MHz, DMSO-d ) δ. (d, J =. Hz, H),. (d, J =. Hz, H),. (br s, H),. (br s, H). C NMR ( MHz, DMSO-d ) δ.,.,.,.,.. Brown solid.
23 NMR spectra.f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) -
24 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) -
25 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl}..... f (ppm) f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) -
26 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) -
27 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) MeOH f (ppm) -
28 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl}......f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) -
29 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl}....f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) -
30 .f..fid Kathir KMID- PROTON DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir KMID- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) -
31 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl}......f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) -
32 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) -
33 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl}.....f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) -
34 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) -
35 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl}.....f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) -
36 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) -
37 .f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl}.....f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) -
38 ...fid Kathir KM- AuF DMSO {C:\Bruker\TopSpin.pl} -..f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
39 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
40 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
41 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
42 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) -... f (ppm) - - -
43 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}.....f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
44 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl}......f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
45 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
46 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
47 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} fid Kathir KMIO- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
48 ...fid Kathir KMIO- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KMIO- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
49 ...fid Kathir KMIO- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KMIO- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
50 ...fid Kathir KMIO- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
51 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
52 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
53 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
54 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
55 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} fid Kathir KM- AuH DMSO {C:\Bruker\TopSpin.pl}.... f (ppm) f (ppm) - - -
56 ...fid Kathir KM- AuC DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm)
57 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
58 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
59 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
60 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
61 .f..fid Kathir/ KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl}.. f (ppm) f (ppm) - - -
62 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl}......f..fid Kathir/ KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
63 .f..fid Kathir/ KM- CCPD CDCl {C:\Bruker\TopSpin.pl} f..fid Kathir KM- PROTON DMSO {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
64 .f..fid Kathir KM- CCPD DMSO {C:\Bruker\TopSpin.pl} f..fid Kathir KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) -.. f (ppm) - - -
65 .f..fid Kathir KM- CCPD CDCl {C:\Bruker\TopSpin.pl}.....f..fid Kathir KM- PROTON CDCl {C:\Bruker\TopSpin.pl} f (ppm) f (ppm) - - -
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