E-H (E = B, Si, C) Bond Activation by Tuning Structural and Electronic Properties of Phosphenium Cations
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1 E-H (E = B, Si, C) Bond Activation by Tuning Structural and Electronic Properties of Phosphenium Cations Nemanja Đorđević, Rakesh Ganguly, Milena Petković, and Dragoslav Vidović drasko.vidovic@monash.edu SUPPORTING INFORMATION
2 1. Multinuclear NMR Spectra [( i Pr2N)2P][BAr Cl 4], [1][BAr Cl 4]: Figure S1. 1 H NMR Spectrum of [1][BAr Cl 4] 2
3 Figure S2. 13 C{ 1 H} NMR Spectrum of [1][BAr Cl 4] Figure S3. 31 P NMR Spectrum of [1][BAr Cl 4] 3
4 [{C6H4(MeN)2C}2C. P(N i Pr2)Cl][X], [2a-Cl][X], X = Cl, SbF6: Figure S4. 1 H NMR Spectrum of [2a-Cl]Cl Figure S5. 13 C{ 1 H} NMR Spectrum of [2a-Cl]Cl 4
5 Figure S6. 31 P NMR Spectrum of [2a-Cl]Cl 5
6 [{C6H4(MeN)2C}2C. P(Ph)Cl][X], [2b-Cl][X], X = Cl, SbF6: Figure S7. 1 H NMR Spectrum of [2b-Cl]Cl 6
7 Figure S8. 13 C{ 1 H} NMR Spectrum of [2b-Cl]Cl Figure S9. 31 P NMR Spectrum of [2b-Cl]Cl 7
8 [{C6H4(MeN)2C}2C. PN i Pr2][BAr Cl 4]2, [2a][BAr Cl 4]2: Figure S10. 1 H NMR Spectrum of [2a][BAr Cl 4] 2 8
9 Figure S C{ 1 H} NMR Spectrum of [2a][BAr Cl 4] 2 Figure S P NMR Spectrum of [2a][BAr Cl 4] 2 9
10 [{C6H4(MeN)2C}2C. PPh][X]2, [2b][X]2, X = AlCl4 and BAr Cl 4: Figure S13. 1 H NMR Spectrum of [2b][AlCl 4] 2 Figure S C{ 1 H} NMR Spectrum of [2b][AlCl 4] 2 10
11 Figure S P NMR Spectrum of [2b][AlCl 4] 2 11
12 [{C6H4(MeN)2C}2C. P(CH2CCH3)2Ph][AlCl4]2, [2b(CH2CCH3)2][AlCl4]2: Figure S16. 1 H NMR Spectrum of [2b(CH2CCH3)2][AlCl 4] 2 Figure S C{ 1 H} NMR Spectrum of [2b(CH2CCH3)2][AlCl 4] 2 12
13 ppm Figure S P{ 1 H} NMR Spectrum of [2b(CH2CCH3)2][AlCl 4] 2 Figure S P NMR Spectrum of [2b(CH2CCH3)2][AlCl 4] 2 13
14 [( i Pr2N)2P(H)(BH2. Py)][BAr Cl 4], [1(H)(BH2. Py)][BAr Cl 4]: Figure S20. 1 H NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] Figure S C{ 1 H} NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] 14
15 Figure S B NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] 15
16 Figure S B{ 1 H} NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] Figure S P NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] 16
17 Figure S P{ 1 H} NMR Spectrum of [1(H)(BH2. Py)][BAr Cl 4] 17
18 [( i Pr2N)2P(H)(BH2. NMe3)][BAr Cl 4], [1(H)(BH2. NMe3)][BAr Cl 4]: Figure S26. 1 H NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] Figure S C{ 1 H} NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] 18
19 Figure S B NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] Figure S B{ 1 H} NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] 19
20 Figure S P NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] Figure S P{ 1 H} NMR Spectrum of [1(H)(BH2. NMe3)][BAr Cl 4] 20
21 Reactions of [2a][BAr Cl 4]2 with H3B. LB (LB = NMe3, Pyridine): Figure S P{ 1 H} NMR Spectrum of the reaction between in situ formed [2a][BAr Cl 4] 2 and H 3B. NMe 3 21
22 Figure S P NMR Spectrum of the reaction between in situ formed [2a][BAr Cl 4] 2 and H 3B. NMe 3 Figure S P NMR Spectrum of the reaction between in situ formed [2a][BAr Cl 4] 2 and H 3B. Py 22
23 Figure S P{ 1 H} NMR Spectrum of the reaction between in situ formed [2a][BAr Cl 4] 2 and H 3B. Py 23
24 x10 4 +ESI Scan (rt: min) Frag=200.0V Sept ND9.d Counts vs. Mass-to-Charge (m/z) Figure S36. HR-MS Spectrum (experimental bottom, and theoretical top right) of [2a(H)(BH2. Py)][BAr Cl 4] 2 24
25 [{C6H4(MeN)2C}2C. P(H)(BH2. NMe3)N i Pr2][BAr Cl 4]2, [2a(H)(BH2. NMe3)][BAr Cl 4]2: Figure S37. 1 H NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 25
26 Figure S B NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 Figure S B{ 1 H} NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 26
27 Figure S C{ 1 H} NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 Figure S P NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 27
28 Figure S P{ 1 H} NMR Spectrum of [2a(H)(BH2. NMe3)][BAr Cl 4] 2 28
29 x10 6 +ESI Scan (rt: min) Frag=150.0V Sept ND7.d Figure S43. HR-MS Spectrum (experimental bottom, and theoretical top right) of [2a(H)(BH2. NMe3)][BAr Cl 4] Counts vs. Mass-to-Charge (m/z) 29
30 [{C6H4(MeN)2C}2C. PH2][X], [2. PH2][X], [X] = [AlCl4], [BAr Cl 4]: Figure S44. 1 H NMR Spectrum of [2. PH2][BAr Cl 4] 30
31 Figure S P NMR Spectrum of [2. PH2][BAr Cl 4] Figure S P{ 1 H} NMR Spectrum of [2. PH2][BAr Cl 4] 31
32 Reactions of [2b][BAr Cl 4]2 with BH3. LB (LB = NMe3, Pyridine): Figure S P NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and H 3B. NMe 3 32
33 Figure S P{ 1 H} NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and H 3B. NMe 3 Figure S P NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and H 3B. Py 33
34 Figure S P{ 1 H} NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and H 3B. Py 34
35 x10 4 +ESI Scan (rt: min) Frag=100.0V Sept ND10.d Counts vs. Mass-to-Charge (m/z) Figure S51. HR-MS Spectrum (experimentally obtained bottom, and theoretically predicted top right) of [2b(H)(BH2. Py)][BAr Cl 4]
36 [{C6H4(MeN)2C}2C. P(H)(BH2. NMe3)Ph][X]2, [2b(H)(BH2. NMe3)][X]2, X = AlCl4, BAr Cl 4: Figure S52. 1 H NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 36
37 Figure S B NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 Figure S B{ 1 H} NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 37
38 Figure S C{ 1 H} NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 Figure S P NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 38
39 Figure S P{ 1 H} NMR Spectrum of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 39
40 x10 5 +ESI Scan (rt: min) Frag=50.0V Sept ND3.d Counts vs. Mass-to-Charge (m/z) Figure S58. HR-MS Spectrum (experimental bottom, and theoretical top right) of [2b(H)(BH2. NMe3)][BAr Cl 4] 2 40
41 Reactions of [2a][BAr Cl 4]2 with R3SiH (R = Et, Ph): Figure S P NMR Spectrum of the reaction mixture between in situ formed [2a][BAr Cl 4] 2 and Et 3SiH 41
42 Figure S P{ 1 H} NMR Spectrum of the reaction mixture between in situ formed [2a][BAr Cl 4] 2 and Et 3SiH 42
43 [{C6H4(MeN)2C}2C. P(N i Pr2)H][BAr Cl 4], [2a-H][BAr Cl 4]: Figure S P NMR Spectrum of the reaction mixture between in situ formed [2a][BAr Cl 4] 2 and n Bu 3SnH 43
44 Figure S P{ 1 H} NMR Spectrum of the reaction mixture between in situ formed [2a][BAr Cl 4] 2 and nbu 3SnH 44
45 Reaction of [2a][BAr Cl 4]2 with H2O. When [2a][BAr Cl 4]2 reacted with silanes and stannane (Figures S59-62), apart from the formation of [2a-H][BAr Cl 4], a new signal at P 12 ppm with coupling constant value of 1 JP-H = 560 Hz was observed in the 31 P/ 31 P{ 1 H} NMR spectrum. The following peak resembles the compound [{C6H4(MeN)2C}2C. P(O)(H)N i Pr2][BAr Cl 4], [2a(O)(H)][BAr Cl 4] derived from slight hydrolysis (less than 10% in abundance) of [2a][BAr Cl 4]2. The product of hydrolysis was synthesized independently according to the following procedure: 256 mg (0.40 mmol, 2 equiv) of Na[BAr Cl 4] was added to the solution of 100 mg (0.19 mmol, 1 equiv) of [2a- Cl]Cl in 40 ml of 1,2-difluorobenzene, and the resulting mixture was stirred for 5 minutes at ambient temperature. Then, 4 μl (0.19 mmol, 1 equiv) of H2O was added followed by additional 2 hours of stirring at ambient temperature. NaCl was removed by filtration, and the resulting solution treated with n-pentane (around 100 ml) to give [2a(O)(H)][BAr Cl 4] as a light yellow solid that was isolated by filtration and dried under vacuum. Yield: 186 mg (93%). 1 H NMR (400 MHz, CD2Cl2, 298 K): 0.90 (br s, 6H, (CH3)2CH), 1.39 (br s, 6H, (CH3)2CH), 3.42 (br s, 12H, NCH3), 3.78 (br m, 2H, CH(CH3)2), 6.89 (t, 4 JHH = 2 Hz, 8H, p-h, BAr Cl 4), 7.03 (m, 16H, BAr Cl 4), 7.31 (br s, 4H), 8.13 (d, 1 JHP = 560 Hz, PH), 7.57 (m, 4H). 13 C{ 1 H} NMR (100 MHz, CD2Cl2, 298 K): 23.0 (s, (CH3)2CH), 23.6 (s, (CH3)2CH), 32.9 (br s, NCH3), 47.2 (s, CH(CH3)2), (s, CH arom.), (s, p-c, BAr Cl 4), (s, CH arom.), (s, CH arom.), (br s, o-c, BAr Cl 4), (s, m-c, BAr Cl 4), (br s, NCN), (q, 1 JCB = 49 Hz, ipso-c, BAr Cl 4). 31 P NMR (160 MHz, CD2Cl2, 298 K): δ 12.3 (d, 1 JPH = 560 Hz). 31 P{ 1 H} NMR (160 MHz, CD2Cl2, 298 K): δ 12.9 (s). HR- MS Calculated for [C25H35N5OP] + [2a(O)(H)] + : m/z Found:
46 Figure S63. 1 H NMR Spectrum of [2a(O)(H)][BAr Cl 4] Figure S C{ 1 H} NMR Spectrum of [2a(O)(H)][BAr Cl 4] 46
47 Figure S P NMR Spectrum of [2a(O)(H)][BAr Cl 4] Figure S P{ 1 H} NMR Spectrum of [2a(O)(H)][BAr Cl 4] 47
48 x10 7 +ESI Scan (rt: min) Frag=100.0V Sept ND8.d Counts vs. Mass-to-Charge (m/z) Figure S67. HR-MS Spectrum (experimental bottom, and theoretical top right) of [2a(O)(H)][BAr Cl 4] 48
49 [{C6H4(MeN)2C}2C. P(Ph)H][X], [2b-H][X], [X] = [AlCl4] and [BAr Cl 4]: Figure S68. 1 H NMR Spectrum of [2b-H][BAr Cl 4] Figure S C{ 1 H} NMR Spectrum of [2b-H][BAr Cl 4] 49
50 Figure S P NMR Spectrum of [2b-H][BAr Cl 4] Figure S P{ 1 H} NMR Spectrum of [2b-H][BAr Cl 4] 50
51 x10 4 +ESI Scan (rt: min) Frag=50.0V Sept ND2.d Counts vs. Mass-to-Charge (m/z) Figure S72. HR-MS Spectrum (experimental bottom, and theoretic top right) of [2b-H][BAr Cl 4] 51
52 Reaction of [2b][BAr Cl 4]2 with 1,3,5-cycloheptatriene: Figure S P NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and cycloheptatriene 52
53 Figure S P{ 1 H} NMR Spectrum of the reaction between in situ formed [2b][BAr Cl 4] 2 and cycloheptatriene 53
54 [{C6H4(MeN)2C}2C. P{(CH)6CH2}Ph][BAr Cl 4]2, [2b{(CH)6CH2}][BAr Cl 4]2: Figure S75. 1 H NMR Spectrum of [2b{(CH)6CH2}][BAr Cl 4] 2 54
55 Figure S C{ 1 H} NMR Spectrum of [2b{(CH)6CH2}][BAr Cl 4] 2 Figure S P NMR Spectrum of [2b{(CH)6CH2}][BAr Cl 4] 2 55
56 x10 6 +ESI Scan (rt: min) Frag=100.0V Sept ND4.d Counts vs. Mass-to-Charge (m/z) Figure S78 HR-MS Spectrum (experimental bottom, and theoretical top right) of [2b{(CH)6CH2}][BAr Cl 4] 2 56
57 Reaction of [2b-H][BAr Cl 4] with tropylium tetrafluoroborate ([C7H7][BF4]): Figure S P NMR Spectrum of the reaction mixture between [2b][BAr Cl 4] 2 and [C 7H 7][BF 4] 57
58 Figure S P{ 1 H} NMR Spectrum of the reaction mixture between [2b][BAr Cl 4] 2 and [C 7H 7][BF 4] 58
59 [{C6H4(MeN)2C}2C. P(H)(CH{C6H4}2O)Ph][BAr Cl 4]2, [2b(H)(CH{C6H4}2O)][BAr Cl 4]2: Figure S81. 1 H NMR Spectrum of [2b(H)(CH{C6H4}2O)][BAr Cl 4] 2 59
60 Figure S82. 1 H NMR Spectra of [2b(H)(CH{C6H4}2O)][BAr Cl 4] 2 recorded using different effective frequencies 300 (top), 400 (middle), and 500 (bottom) MHz Figure S C{ 1 H} NMR Spectrum of [2b(H)(CH{C6H4}2O)][BAr Cl 4] 2 60
61 Figure S P{ 1 H} NMR Spectrum of [2b(H)(CH{C6H4}2O)][BAr Cl 4] 2 Figure S P NMR Spectrum of [2b(H)(CH{C6H4}2O)][BAr Cl 4] 2 61
62 x10 5 +ESI Scan (rt: min) Frag=50.0V Sept ND2.d Counts vs. Mass-to-Charge (m/z) Figure S86. HR-MS Spectrum (experimental bottom, and theoretical top right) of [2b(CH{C6H4}2O)] + 62
63 x10 6 +ESI Scan (rt: min) Frag=175.0V Sept ND5.d Counts vs. Mass-to-Charge (m/z) Figure S87. HR-MS Spectrum (experimental bottom, and theoretical top right) of [CH{C6H4}2O] + 63
64 2. Crystallographic Data Crystallographic data for [1][BAr Cl 4]: C36H40BCl8N2P, M r , monoclinic, P 1 21/n 1, a = (3) Å, b = (4) Å, and c = (8) Å, α = 90, β = (14), and γ = 90, V = (2) Å 3, Z = 4, ρ = c gcm-3, T = 103(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2a-Cl][SbF6]: C52H72Cl6F12N10P2Sb2, M r , triclinic, P - 1, a = (2) Å, b = (5) Å, and c = (4) Å, α = (11), β = (12), and γ = (14), V = (13) Å 3, Z = 2, ρ = c gcm-3, T = 153(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2b-Cl][SbF6]: C53H56Cl8F12N8P2Sb2, M r , triclinic, P -1, a = (8) Å, b = (15) Å, and c = (2) Å, α = (19), β = (19), and γ = (2), V = (5) Å 3, Z = 2, ρ = c gcm-3, T = 103(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå - 3 and eå -3. CCDC Crystallographic data for [2b][BAr Cl 4]2: C85H57B2Cl16F4N4P, M r , triclinic, P -1, a = (11) Å, b = (12) Å, and c = (19) Å, α = (3), β = (3), and γ = (3), V = (6) Å 3, Z = 2, ρ = c gcm-3, T = 103(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2b(CH2CCH3)2][AlCl4]2: C32H37Al2Cl10N4P, M r , monoclinic, P 1 21/n 1, a = (4) Å, b = (17) Å, and c = (7) Å, α = 90, β = (3), and γ = 90, V = (4) Å 3, Z = 4, ρ c = gcm-3, T = 153(2) K, λ = Å; reflections collected, 8081 independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [1(H)(BH2. Py)][BAr Cl 4]: C41H48B2Cl8N3P, M r , monoclinic, P 1 21/c 1, a = (6) Å, b = (5) Å, and c = (9) Å, α = 64
65 90, β = (14), and γ = 90, V = (3) Å 3, Z = 4, ρ c = gcm-3, T = 103(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå - 3 and eå -3. CCDC Crystallographic data for [1(H)(BH2. NMe3)][BAr Cl 4]: C39H52B2Cl8N3P, M r , triclinic, P -1, a = (5) Å, b = (5) Å, and c = (6) Å, α = (14), β = (14), and γ = (14), V = (15) Å 3, Z = 2, ρ c = gcm-3, T = 153(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2b(H)(BH2. NMe3)][AlCl4]2: C28H37Al2BCl8N5P, M r , triclinic, P -1, a = (7) Å, b = (13) Å, and c = (13) Å, α = (3), β = (3), and γ = (3), V = (5) Å 3, Z = 4, ρ c = gcm-3, T = 153(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå - 3 and eå -3. CCDC Crystallographic data for [2. PH2][AlCl4]: C19H22AlCl4N4P, M r , monoclinic, P 1 21/n 1, a = (9) Å, b = (15) Å, and c = (15) Å, α = 90, β = (3), and γ = 90, V = (4) Å 3, Z = 4, ρ = c gcm-3, T = 103(2) K, λ = Å; reflections collected, 5364 independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2b-H][AlCl4]: C50H53Al2Cl8N8P2, M r , orthorhombic, P c a 21, a = (16) Å, b = (16) Å, and c = (9) Å, α = 90, β = 90, and γ = 90, V = (7) Å 3, Z = 4, ρ = c gcm-3, T = 103(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystallographic data for [2b{(CH)6CH2}][BAr Cl 4]2: C92H67B2Cl16F4N4P, M r , triclinic, P -1, a = (11) Å, b = (12) Å, and c = (2) Å, α = (5), β = (5), and γ = (5), V = (7) Å 3, Z = 2, ρ c = gcm -3, T = 153(2) K, λ = Å; reflections collected, independent [Rint = ], which were used in all calculations; R1 = , wr2 = for I > 2σ(I), 65
66 and R1 = , wr2 = for all unique reflections; max and min residual electron densities eå -3 and eå -3. CCDC Crystal structures Figure S88. Molecular view of [1][BAr Cl 4]2 set at 50% probability. Counterion and hydrogen atoms were omitted for clarity. Selected bond lengths [Å] and angle [ ]: N1-P1, (10), N2-P1, (10), N1-P1-N2, (5). 66
67 Figure S89. Molecular view of [2b{(CH)6CH2}][BAr Cl 4]2 set at 50% probability. Counterions and hydrogen atoms were omitted for clarity. Selected bond lengths [Å] and angles [ ]: P1-C1, 1.674(16), P1-C2, 1.796(10), C1-P1-C2, 107.2(8). 67
68 3. Cartesian Coordinates for Phosphenium Cations [1] [2a]
69 [2b]
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