Supplementary Figure S1 Stable structures of I, I', II, and II' optimized at the
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1 H C Si (2.348) (2.005) Fe O (2.077) (2.497) N (1.115) (2.175) I quintet (triplet) 0.0 (+4.1) kcal/mol II triplet (quintet) 0.0 (+4.3) kcal/mol (2.076) (2.351) Cl I' (2.239) quintet (triplet) 0.0 (+5.4) kcal/mol (2.286) (2.508) II' triplet (quintet) 0.0 (+1.9) kcal/mol (1.112) Supplementary Figure S1 Stable structures of I, I', II, and II' optimized at the B3LYP*/6-311+G** level of theory.
2 Si Si Fe Si N 2 thf Si 12.1 (no barrier) Fe thf N N Si 21.3 (3.1) Si Si Fe thf N N Si Si 36.6 (0.9) Si Si Fe thf N N Si Si Si 1.6 (12.0) Si Si Fe thf N NSi 3 I (triplet) II (triplet) III (quartet) IV (triplet) V (quartet) N(SiMe 3 ) (0.4) N N cleavage Si migration (4.1) Si Fe NSi 3 Si thf X (quintet) Si 22.3 (0.6) Si Fe NSi 3 thf IX (quartet) Si migration +7.6 (19.0) Si Si Fe NSi 2 thf VIII (quartet) Si 22.3 (0.6) Si Fe NSi 2 thf VII (quintet) Si 35.6 (no barrier) thf Fe NSi 2 VI (quartet) N(SiMe 3 ) 3 Supplementary Figure S2 Energy profile of a possible catalytic cycle on the transformation of N 2 into N(SiMe 3 ) 3 catalyzed by [Fe(SiMe 3 ) 2 (thf)] (I). Si represents trimethylsilyl radical. The energy change and activation energy (in parenthesis) for each reaction step were calculated at the B3LYP*/6-311+G** level of theory. The energies are presented in kcal/mol. 2
3 Fe O N N Si C II SiMe 3 TS (123i) III quartet quartet quartet kcal/mol 21.3 kcal/mol Supplementary Figure S3 Energy profile and optimized structures for the addition of Me 3 Si radical to II. 3
4 1.741 (1.731) (1.818) (1.325) III SiMe 3 TS (34i) IV quintet quintet quintet (triplet) kcal/mol 32.6 ( 36.5) kcal/mol Supplementary Figure S4 Energy profile and optimized structures for the addition of Me 3 Si radical to III. 4
5 IV SiMe 3 TS (148i) V quartet quartet quartet kcal/mol 1.6 kcal/mol Supplementary Figure S5 Energy profile and optimized structures for the addition of Me 3 Si radical to IV. 5
6 V TS (461i) VI N(SiMe 3 ) 3 quartet quartet quartet kcal/mol kcal/mol Supplementary Figure S6 Energy profile and optimized structures for the N-N bond cleavage of V and the generation of N(SiMe 3 ) 3. 6
7 VII SiMe 3 TS (18i) VIII quartet quartet quartet kcal/mol 22.3 kcal/mol Supplementary Figure S7 Energy profile and optimized structures for the addition of Me 3 Si radical to VII. 7
8 N Fe Si = VIII quartet 0.0 TS (150i) quartet 19.0 kcal/mol IX quartet 7.6 kcal/mol Supplementary Figure S8 Energy profile and optimized structures for the Me 3 Si migration of VIII yielding IX. 8
9 IX SiMe 3 TS (41i) X quintet quintet quintet kcal/mol 23.3 kcal/mol Supplementary Figure S9 Energy profile and optimized structures for the addition of Me 3 Si radical to IX. 9
10 X TS (46i) I N(SiMe 3 ) 3 quintet quintet quintet kcal/mol 16.6 kcal/mol Supplementary Figure S10 Energy profile and optimized structures for the release of N(SiMe 3 ) 3 from X. 10
11 Supplementary Table S1 [Fe(CO) 5 ]-catalyzed formation of N(SiMe 3 ) 3 from N 2. a N Na (1 atm) (60 mmol) [Fe(CO) 5 ] (0.10 mmol) + 6 Me 3 SiCl 2 N(SiMe 3 ) 3 + (60 mmol) solvent 1 temp 20 h 6 NaCl Me 3 SiSiMe 3 CH 3 CH 2 CH 2 CH 2 OSiMe 3 Me 3 SiCH 2 CH 2 CH 2 CH 2 OSiMe Fe(CO)5 solvent temp. amount (mmol) b equiv of 1 based run (mmol) (ml) ( C) on Fe atom THF (40) rt THF (40) rt THF (40) rt THF (20) rt THF (60) rt THF (40) THF (40) c 0.10 THF (40) rt hexane (40) rt benzene (40) rt Et2O (40) rt DME (40) rt dioxane (40) rt d 0.10 THF (40) rt e 0.10 THF (40) rt f 0.10 THF (40) rt g 0.10 THF (40) rt a All reactions using Na (60 mmol) and Me3SiCl (60 mmol) were carried out in the presence of [Fe(CO)5] under atmospheric pressure of N2. b Determined by GLC analysis. c For 100 h. d Li was used in place of Na. e The reaction was carried out under argon atmosphere. f The reaction was carried out under dry air. g The reaction was carried out in the presence of galvinoxyl (0.10 mmol). 11
12 Supplementary Table S2 Fe-catalyzed formation of N(SiMe 3 ) 3 from N 2. a N 2 (1 atm) + 6 Na (60 mmol) catalyst (0.10 mmol) + 6 Me 3 SiCl 2 N(SiMe 3 ) 3 + (60 mmol) THF 1 rt 20 h 6 NaCl Me 3 SiSiMe 3 CH 3 CH 2 CH 2 CH 2 OSiMe 3 Me 3 SiCH 2 CH 2 CH 2 CH 2 OSiMe amount (mmol) b equiv of 1 based run catalyst on Fe atom 1 [Fe(CO)5] [Fe2(CO)9] c [Fe3(CO)12] d [Fe(SiMe3)2(CO)4] [CpFe(CO)2]2 e [CpFe(CO)2I] [Cp2Fe] [Cp'2Fe] f [Cp''2Fe] g a All reactions using Na (60 mmol) and Me3SiCl (60 mmol) were carried out in the presence of a catalyst (0.10 mmol) under atmospheric pressure of N2 at room temperature for 20 h in THF (40 ml). b Determined by GLC analysis. c [Fe2(CO)9] (0.05 mmol) was used. d [Fe3(CO)12] (0.033 mmol) was used. e [CpFe(CO)2]2 (0.05 mmol) was used. f [Cp'2Fe] = [(η 5 -C5H4SiMe3)2Fe]. g [Cp''2Fe] = [{η 5 -C5H2(SiMe3)3}2Fe]. 12
13 Supplementary Table S3 Time profile of [Fe(CO) 5 ]-catalyzed formation of N(SiMe 3 ) 3 from N 2. a [Fe(CO) 5 ] (0.10 mmol) N Na + 6 Me 3 SiCl 2 N(SiMe 3 ) 3 + (1 atm) (60 mmol) (60 mmol) THF 1 rt 20 h 6 NaCl Me 3 SiSiMe 3 CH 3 CH 2 CH 2 CH 2 OSiMe 3 Me 3 SiCH 2 CH 2 CH 2 CH 2 OSiMe amount (mmol) b t (h) a Reaction using Na (60 mmol) and Me3SiCl (60 mmol) were carried out in the presence of Fe(CO)5 (0.10 mmol) under atmospheric pressure of N2 at room temperature in THF (40 ml). b Determined by GLC analysis. 13
14 Supplementary Table S4 Cartesian coordinate of I in the triplet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe C C C O C H H H H H H H H Si C H H H C H H H C H H H Si C H H H C H H H C H H H
15 Supplementary Table S5 Cartesian coordinate of I in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe C C C O C H H H H H H H H Si C H H H C H H H C H H H Si C H H H C H H H C H H H
16 Supplementary Table S6 Cartesian coordinate of I' in the triplet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H Cl
17 Supplementary Table S7 Cartesian coordinate of I' in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H Cl
18 Supplementary Table S8 Cartesian coordinate of II in the triplet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H
19 Supplementary Table S9 Cartesian coordinate of II in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H
20 Supplementary Table S10 Cartesian coordinate of II' in the triplet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H Cl N N
21 Supplementary Table S11 Cartesian coordinate of II' in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H Cl N N
22 Supplementary Table S12 Cartesian coordinate of II-SiMe 3 in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H Si C H H H C H
23 H H C H H H
24 Supplementary Table S13 Cartesian coordinate of TS between II-SiMe 3 and III in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Imaginary frequency: 123i Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H Si C H H H C
25 H H H C H H H
26 Supplementary Table S14 Cartesian coordinate of III in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H Si C H H H C H
27 H H C H H H
28 Supplementary Table S15 Cartesian coordinate of III-SiMe 3 in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H Si C H H H C H
29 H H C H H H Si C H H H C H H H C H H H
30 Supplementary Table S16 Cartesian coordinate of TS between III-SiMe 3 and IV in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Imaginary frequency: 34i Atom Coordinates (Angstroms) X Y Z Fe Si Si N N C H H H C H H H C H H H C H H H C H H H C H H H C C C O C H H H H H H H H Si C H H H C
31 H H H C H H H Si C H H H C H H H C H H H
32 Supplementary Table S17 Cartesian coordinate of IV in the quintet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C H
33 H H C H H H C C C O C H H H H H H H H
34 Supplementary Table S18 Cartesian coordinate of IV in the triplet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C H
35 H H C H H H C C C O C H H H H H H H H
36 Supplementary Table S19 Cartesian coordinate of IV-SiMe 3 in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C H
37 H H C H H H C C C O C H H H H H H H H Si C H H H C H H H C H H H
38 Supplementary Table S20 Cartesian coordinate of TS between IV-SiMe 3 and V in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Imaginary frequency: 148i Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C
39 H H H C H H H C C C O C H H H H H H H H Si C H H H C H H H C H H H
40 Supplementary Table S21 Cartesian coordinate of V in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C H
41 H H C H H H C C C O C H H H H H H H H Si C H H H C H H H C H H H
42 Supplementary Table S22 Cartesian coordinate of TS between V and VI in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Imaginary frequency: 461i Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C
43 H H H C H H H C C C O C H H H H H H H H Si C H H H C H H H C H H H
44 Supplementary Table S23 Cartesian coordinate of VI-N(SiMe 3 ) 3 in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N N Si Si C H H H C H H H C H H H C H H H C H
45 H H C H H H C C C O C H H H H H H H H Si C H H H C H H H C H H H
46 Supplementary Table S24 Cartesian coordinate of VII in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N C C C O C H H H H H H H H Si C H H H C H H
47 H C H H H
48 Supplementary Table S25 Cartesian coordinate of VII-SiMe 3 in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N Si C H H H C H H H C H H H C C C O C H H H
49 H H H H H Si C H H H C H H H C H H H
50 Supplementary Table S26 Cartesian coordinate of TS between VII-SiMe 3 and VIII in the quartet state. Units are presented in Å. SCF energy = hartree ZPE = hartree Imaginary frequency: 18i Atom Coordinates (Angstroms) X Y Z Fe Si C H H H C H H H C H H H Si C H H H C H H H C H H H N Si C H H H C H H H C H H H C C C O C H H
51 H H H H H H Si C H H H C H H H C H H H
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