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1 Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2019 Supporting information for the manuscript Facile N-functionalization and strong magnetic communication in a diuranium(v) bis-nitride complex Luciano Barluzzi a, Lucile Chatelain a, Farzaneh Fadaei-Tirani a, Ivica Zivkovic b and Marinella Mazzanti* a a Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland. b Laboratory for Quantum Magnetism, Institute of Physics, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland.
2 Contents A) NMR SPECTRA... 3 B) IR SPECTRA C) X-RAY CRYSTALLOGRAPHIC DATA D) MAGNETIC DATA E) UV-VIS DATA... 35
3 A) NMR spectra thf [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-n 3 )}], 3 [K{[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)}], 2 [U(OSi(O t Bu) 3 ) 3 ] 2, Fig. S1: 1 H-NMR (400 MHz) at 298 K in d 8-thf of the crude reaction mixture between [U(OSi(O t Bu) 3) 3] 2, 1 and one equivalent of KN 3 in thf after 4 days at -40 C leading to a mixture of complex [K{[U(OSi(O t Bu) 3) 3] 2(μ-N)}], 2 and complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], thf [K{[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)}], Fig. S2: 1 H-NMR (400 MHz) at 298 K in d 8-thf of isolated [K{[U(OSi(O t Bu) 3) 3] 2(μ-N)}], 2
4 -1.58 thf [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-n 3 )}], Fig. S3: 1 H-NMR (400 MHz) at 298 K in d 8-thf of the reaction mixture between [U(OSi(O t Bu) 3) 3] 2, 1 and two equivalents of KN 3 in thf at -40 C for 5 days forming complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], thf [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-n 3 )}], Fig. S4: 1 H-NMR (400 MHz) at 298 K in d 8-thf of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3
5 Fig. S5: 13 C-NMR (400 MHz) at 298 K in d 8-thf of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3 5d tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], 4 [U(OSi(O t Bu) 3 ) 4 ] [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-n 3 )}], 3 3d 24h 7h immediately Fig. S6: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3 at room temperature
6 -1.76 tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], Fig. S7: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3 after 24h at 70 C affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], 4 [U(OSi(O t Bu) 3 ) 4 ] [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-n 3 )}], 3 after 5d at RT after 24h at 70 C Fig. S8: 1 H-NMR (400 MHz) at 298 K in d 8-tol of [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3, after 5 days at RT (top) and after 24h at 70 C (bottom)
7 tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], Fig. S9: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 Fig. S10: 13 C-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4
8 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-s)(µ-ncs)}], Fig. S11: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture 6h after the addition of one equivalent of CS 2 to [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-S)(µ-NCS)}], [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-s)(µ-ncs)}], Fig. S12: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-S)(µ-NCS)}], 5
9 Fig. S13: 13 C-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-S)(µ-N 13 CS)}], 13 C-5 Fig. S14: 13 C-NMR (400MHz) at 298 K in d 6-dmso of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-S)(µ-N 13 CS)}], 13 C-5
10 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-s)(µ-ncs)}], 5 24h immediately Fig. S15: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- N) 2}], 4 and 10 equivalents of 13 CS 2 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-S)(µ-N 13 CS)}], 13 C-5 and an unidentified precipitate siloxide (C(CH 3 ) 3 ) siloxide (C(CH 3 ) 3 ) NCS in complex 5 unknown CS Fig. S16: 13 C-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 10 equivalents of 13 CS
11 d 6 -dmso KNCS CH 13 3 COONa Fig. S17: Quantitative 13 C-NMR (600 MHz) at 298 K in d 6-dmso of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- N) 2}], 4 and 10 equivalents of 13 CS 2 Fig. S18: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of one equivalent of CO 2 to [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-O)(µ-NCO)}], 6
12 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-o)(µ-nco)}], Fig. S19: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-O)(µ-NCO)}], 6 Fig. S20: 13 C-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-O)(µ-N 13 CO)}], 13 C-6
13 Fig. S21: 13 C-NMR (400 MHz) at 298 K in D 2O using d 6-dmso as a reference of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(µ-O)(µ- N 13 CO)}], 13 C [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-o)(µ-nco)}], 6 [U(OSi(O t Bu) 3 ) 4 ] Fig. S22: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 2 equivalents of CO 2 to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4
14 Fig. S23: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 10 equivalents of 13 CO 2 to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], Fig. S24: 13 C-NMR (400 MHz) at 298 K in d 6-dmso of the reaction mixture after the addition of 10 eqvs of 13 CO 2 to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4
15 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-cn)(µ-o)(µ-nco)}], 7 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], Fig. S25: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 1 eqv of CO to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-cn)(µ-o)(µ-nco)}], Fig. S26: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 3 eqvs of CO to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(µ-CN)(μ-O)(µ-NCO)}],
16 0.78 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-cn)(µ-o)(µ-nco)}], Fig. S27: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 1 atm of CO to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(µ-CN)(μ-O)(µ-NCO)}], [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-cn)(µ-o)(µ-nco)}], 7 [U(OSi(O t Bu) 3 ) 4 ] Fig. S28: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture immediately after the addition of 6 atm of CO to complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}],
17 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-cn)(µ-o)(µ-nco)}], Fig. S29: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(µ-CN)(μ-O)(µ-NCO)}], siloxide (C(CH 3 ) 3 ) siloxide (C(CH 3 ) 3 ) CN NCO or or Fig. S30: 13 C-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(µ- 13 CN)(μ-O)(µ-N 13 CO)}], 13 C-7
18 d 6 -dmso KNCO KCN Fig. S31: Quantitative 13 C-NMR (600 MHz) at 298 K in d 6-dmso of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(µ- 13 CN)(μ-O)(µ-N 13 CO)}], 13 C-7 Fig. S32: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction between complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 1 atm of H 2 heated up at 60 C for 1h affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8
19 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], 4 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], h 8h immediately Fig. S33: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- N) 2}], 4 and 1 atm of H 2 affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], Fig. S34: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction between complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 1 atm of H 2 after 16h at RT affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8
20 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], Fig. S35: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], 8 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], Fig. S36: 1 H-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8 on a broader spectral window
21 [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nd) 2 }], Fig. S37: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction between complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and D 2 heated up at 60 C for 1h affording complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-ND) 2}], 8 Fig. S38: 13 C-NMR (400 MHz) at 298 K in d 8-tol of isolated [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8
22 Fig. S39: 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction between complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 5.5 atm of H 2 after 3h at RT Et 2 O dmso Fig. S40: 1 H-NMR (400 MHz) at 298 K in d 6-dmso of the volatiles and the headspace of the reaction between complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 5.5 atm of H 2 after 3h at RT collected in a frozen 2M solution of HCl in Et 2O
23 NH 4 Cl dimethylsulfone dmso Fig. S41: 1 H-NMR (400 MHz) at 298 K in d 6-dmso of the reaction mixture between solid complex 4 and an excess of a 2M solution of HCl in Et 2O NH 4 Cl dimethylsulfone dmso Fig. S42: 1 H-NMR (400 MHz) at 298 K in d 6-dmso of the reaction mixture between solid complex 8 and an excess of a 2M solution of HCl in Et 2O
24 NH 4 Cl dimethylsulfone dmso Fig. S43: 1 H-NMR (400 MHz) at 298 K in d 6-dmso of the reaction mixture between solid complex 8 and an excess of a 2M solution of HCl in Et 2O in presence of excess KC 8 tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], 4 10d 7d 6d 5d 4d 3d 24h immediately Fig. S44: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- N) 2}], 4 and 1 eq of PyHOTf
25 tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-nh) 2 }], 8 72h 60h 48h 36h 24h 12h immediately Fig. S45: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- NH) 2}], 8 and 1 eq of PyHOTf NH 4 Cl dimethylsulfone dmso Fig. S46: 1 H-NMR (400 MHz) at 298 K in d 6-dmso of the volatiles and the headspace of the reaction mixture between between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4 and 30 eq of H 2O in thf collected in a frozen 2M solution of HCl in Et 2O
26 immediately tol [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n) 2 }], 4 Si 2 Me 6 30 min 1h 2h 6h 12h 18h Fig. S47: Evolution of the 1 H-NMR (400 MHz) at 298 K in d 8-tol of the reaction mixture between [K 2{[U(OSi(O t Bu) 3) 3] 2(μ- N) 2}], 4 and 1 eq of Si 2Me 6. The formation of an unidentified yellow precipitate is also observed. B) IR spectra 1977 Fig. S48: IR spectrum of isolated complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-S)(µ-N)(μ-NCS)}], 5 in a Nujol suspension measured on KBr windows.
27 IR spectrum of complex [K 2 {[U(OSi(O t Bu) 3 ) 3 ] 2 (μ-n)(µ-s)(µ-n 13 CS)}] %T Wavenumber (cm -1 ) Fig. S49: IR spectrum of isolated complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-O)(µ-N)(μ-N 13 CS)}], 5 in a Nujol suspension measured on KBr windows. Fig. S50: IR spectrum of isolated complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-O)(µ-N)(μ-NCO)}], 6 in a Nujol suspension measured on KBr windows.
28 Fig. S51: IR spectrum of isolated complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-O)(µ-N)(μ-N 13 CO)}], 13 C-6 in a Nujol suspension measured on KBr windows. C) X-Ray crystallographic data Formula C72H162KNO24Si6U2 C72H162K2N4O24Si6U2 C73H162K2N2O24S2Si6U2 Crystal size (mm ) x x crystal system Monoclinic Monoclinic monoclinic space group P21/c P21/n P21 volume (Å ) (2) (16) (4) a (Å) (3) (2) (4) b (Å) (19) (3) (7) c (Å) (3) (4) (9) α (deg) β (deg) (8) (9) (4) γ (deg) Z formula weight (g/mol) density (g cm ) absorption coefficient (mm ) F(000) temp (K) 100(2) 100(2) (10) total no. reflections unique reflections [R(int)] [0.1089] [0.0447] [0.0881]
29 Final R indices [I > 2σ(I)] R1 = , wr2 = R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole (e.a ) and and and GOOF Formula C73H162K2N2O26Si6U2 C81H170K2N2O26Si6U2 C79H172K2N2O24Si6U2 Crystal size (mm ) cryst syst Monoclinic Monoclinic Monoclinic space group P21 P21 P21/n volume (Å ) (3) (9) (3) a (Å) (5) (15) (4) b (Å) (5) (12) (5) c (Å) (6) (2) (6) α (deg) β (deg) (3) (7) (3) γ (deg) Z formula weight (g/mol) density (g cm ) absorption coefficient (mm ) F(000) temp (K) (10) 120(2) (10) total no. reflections unique reflections [R(int)] [0.0796] [0.0523] [0.0618] Final R indices [I > 2σ(I)] R1 = , wr2 = R1 = , wr2 = R1 = , wr2 = Largest diff. peak and hole (e.a ) and and and GOOF
30 D) Magnetic data (emu/mol Oe) Temperature (K) Fig. S52: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N) 2}], 4
31 (emu/mol Oe) Temperature (K) Fig. S53: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-S)(µ-N)(μ-NCS)}], (emu/mol Oe) Temperature (K) Fig. S54: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-O)(µ-N)(μ-NCO)}], 6
32 (emu/mol Oe) Temperature (K) Fig. S55: c vs T plot for complex [K{[U(OSi(O t Bu) 3) 3] 2(μ-N)}], 2
33 (emu/mol Oe) Temperature (K) Fig. S56: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], (emu/mol Oe) Temperature (K) Fig. S57: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(µ-CN)(μ-O)(µ-NCO)}], 7
34 (emu/mol Oe) Temperature (K) Fig. S58: c vs T plot for complex [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8
35 N4 a) b) N3 O1A C1A N2 N1 U1 91.5(4) 124.6(7) U1 U1 90.7(6) O2A 115.8(6) U2 N (6) Å 92.5(7) N2 C2A c) H1 N (7)Å U (12) U (2) Å Fig. S59: Ortep diagram of the core showing the metrical parameters for the bridging atoms in complexes a) [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-N)(μ-N 3)}], 3; b) [K 2{[U(OSi(O t Bu) 3) 3] 2(µ-CN)(μ-O)(µ-NCO)}], 7; c) [K 2{[U(OSi(O t Bu) 3) 3] 2(μ-NH) 2}], 8 E) UV-Vis data ε (M -1 cm -1 ) wavelenght (nm) Fig. S60: UV-Vis absorption spectra in solution of complexes 3-8.
36 ε (M -1 cm -1 ) wavelenght (nm) Fig. S61: NIR absorption spectra in solution of complexes 3-8.
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