Supplementary Information. Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3
|
|
|
- Δάμαρις Μανιάκης
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Supplementary Information Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3 Lewis Pairs: Structures of Intermediates, Kinetics, and Mechanism Qianyi Wang, Wuchao Zhao, Jianghua He, and Yuetao Zhang *, and Eugene Y.-X. Chen State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, , China Department of Chemistry, Colorado State University, Fort Collins, Colorado , United States * Corresponding author. s:ytzhang2009@jlu.edu.cn S1
2 Table of Contents Figure S1. 1 H NMR spectrum of NHO1 (25 C, C 6 D 6 )...S4 Figure S2. 13 C NMR spectrum of NHO1 (25 C, C 6 D 6 )...S4 Figure S3. 1 H NMR spectrum of compound 1 (25 C, C 6 D 6 )...S5 Figure S4. 13 C NMR spectrum of compound 1 (25 C, CD 2 Cl 2 )...S5 Figure S5. 1 H NMR spectrum of compound 2 (25 C, C 6 D 6 )...S6 Figure S6. 13 C NMR spectrum of compound 2 (25 C, CD 2 Cl 2 )...S6 Figure S7. 1 H NMR spectrum of 1-hydroxynonan-5-one (25 C, CDCl 3 )...S6 Figure S8. 1 H NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S9. 19 F NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S C NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S11. 1 H NMR spectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S F NMR spectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S C NMRspectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S14. 1 H NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (25 C, C 6 D 6 )... S9 Figure S F NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (25 C, C 6 D 6 )... S9 Figure S16. 1 H NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S F NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S C NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S19. 1 H NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S F NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S C NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S22. 1 H NMR spectrum of INT3 (25 C, C 6 D 6 )... S12 S2
3 Figure S F NMRspectrum of INT3 (25 C, C 6 D 6 )... S12 Figure S C NMRspectrum of INT3 (25 C, CD 2 Cl 2 )...S12 Figure S25. Plots of M n and PDI for PCL and PVL vs [M] 0 /[NHO2] ratio... S13 Figure S26. Plots of M n and PDI of PCL vs ε-cl conversion... S13 Figure S27. 1 H NMR spectrum of Low MW PVL produced by NHO2/Al(C 6 F 5 ) 3 ) system..s14 Scheme S1. Structure of Lewis Base...S15 Table S1. ROP of ε-cl by different Al(C 6 F 5 ) 3 based Lewis pairs...s15 Table S2. Copolymerization of ε-cl and δ-vl by NHO2/Al(C 6 F 5 ) 3 system...s15 Table S3. Crystal data and structure refinement for compound 1, Al(C 6 F 5 ) 3 CL, and INT3...S16 Table S4. Bond lengths [Å] and angles [º] for compound 1...S17 Table S5. Bond lengths [Å] and angles [º] for adduct Al(C 6 F 5 ) 3 CL...S17 Table S6. Bond lengths [Å] and angles [º] for INT3...S19 S3
4 Figure S1. 1 H NMR spectrum of NHO1 (benzene-d 6, 500 MHz). Figure S2. 13 C NMR spectrum of NHO1 (benzene-d 6, 126 MHz). S4
5 Figure S3. 1 H NMR spectrum of compound 1 (benzene-d 6, 500 MHz). Figure S4. 13 C NMR spectrum of compound 1 (CD 2 Cl 2, 126 MHz). S5
6 Figure S5. 1 H NMR spectrum of compound 2 (benzene-d 6, 500 MHz). Figure S6. 13 C NMR spectrum of compound 2 (CD 2 Cl 2, 126 MHz). Figure S7. 1 H NMR spectrum of 1-hydroxynonan-5-one (CDCl 3, 500 MHz). S6
7 Figure S8. 1 H NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 500 MHz). Figure S9. 19 F NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 471 MHz). Figure S C NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 126 MHz). S7
8 Figure S11. 1 H NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 500 MHz). Figure S F NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 471 MHz). Figure S C NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 126 MHz). S8
9 Figure S14. 1 H NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (benzene-d 6, 500 MHz). Figure S F NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (benzene-d 6, 471 MHz). S9
10 Figure S16. 1 H NMR spectrum of INT1 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of reaction of INT1 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT1 (benzene-d 6, 126 MHz). S10
11 Figure S19. 1 H NMR spectrum of INT2 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of reaction of INT2 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT2 (benzene-d 6, 126 MHz). S11
12 Figure S22. 1 H NMR spectrum of INT3 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of INT3 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT3 (CD 2 Cl 2, 126 MHz). S12
13 M n (10 4 g/mol) PCL M n Ð PVL M n Ð R² = R² = [M] 0 /[NHO2] Ð Figure S25. Plots of M n and PDI for PCL and PVL vs [M] 0 /[NHO2] ratio M n (10 4 g/mol) M n Ð R² = Conv. (%) 2 Ð Figure S26. Plots of M n and PDI of PCL vs ε-cl conversion catalyzed by NHO2/ Al(C 6 F 5 ) 3 at room temperature. Conditions: [ε-cl] 0 /[Al(C 6 F 5 ) 3 ]/[NHO2] = 800:2:1. S13
14 Figure S27. 1 H NMR spectrum of Low MW PVL produced by NHO2/Al(C 6 F 5 ) 3 system in toluene at room temperature (benzene-d 6, 500 MHz). S14
15 N N t - Bu N N t - Bu N N N N Ph Ph N N DBU DMAP tbu NHC NHO1 NHO2 Scheme S1. Structure of Lewis Base Table S1. ROP of ε-cl by different Al(C 6 F 5 ) 3 based Lewis pairs a Run LA LB ε-cl :LA:LB Time (hr) Conv. (%) b 1 Al(C 6 F 5 ) 3 0.5Tol DBU 400:2: Al(C 6 F 5 ) 3 0.5Tol DMAP 400:2: Al(C 6 F 5 ) 3 0.5Tol PMes 3 400:2: Al(C 6 F 5 ) 3 0.5Tol tbu NHC 400:2: Al(C 6 F 5 ) 3 0.5Tol NHO1 400:2: Al(C 6 F 5 ) 3 0.5Tol NHO2 400:2: a Carried out at ambient temperature (~ 25 ºC) in toluene (Tol), where [ε-cl] 0 = 1.0 M, [Al(C 6 F 5 ) 3 ] 0 = 5 mm, and [LB] 0 = 2.5 mm for a [ε-cl]:[la]:[lb] ratio of 400:2:1. b Monomer conversions measured by 1 H NMR. Table S2. Copolymerization of ε-cl and δ-vl by NHO2/Al(C 6 F 5 ) 3 system a Run M1/M2 Conv c M w Đ (%) b (10 3 g/mol) 1 200CL/200CL CL: d 200CL and 200VL CL: VL: CL/200VL CL: VL: VL/200CL CL: VL: CL/200VL/200CL CL:100 VL: a Carried out at ambient temperature (~ 25 ºC) in toluene (Tol), where [M] 0 = 1.0 M. b Monomer conversions measured by 1 H NMR. c Absolute molecular weight (M w ) measured by GPC using light scattering detector. d both monomers were added in the same time. S15
16 Table S3. Crystal data and structure refinement for compound 1, Al(C 6 F 5 ) 3 CL, and INT3. Compound 1 Al(C 6 F 5 ) 3 CL INT3 empirical formula C 11 H 18 N 2 O 2 C 24 H 10 AlF 15 O 2 C 52.5 H 43 AlClF 15 N 2O 2 MW wavelength, Å crystal system Triclinic Orthorhombic Triclinic space group P-1 Pbca P-1 a, Å (13) (7) Å (8) b, Å (15) (5) (9) c, Å (16) (7) (15) α, deg (3) (2) β, deg (3) (2) γ, deg (3) (2) V, Å (17) (3) (3) Z D calc, g cm µ, mm F(000) crystal size, mm θ range, deg limiting indices 9 h 9 11 k 8 12 l h k l h k l 27 reflns collected independent reflns 2489 [R(int) = ] 5969 [R(int) = ] [R(int) = ] absorption correction Empirical Empirical Empirical data/restraints/para s 2489 / 0 / / 0 / / 114 / 658 goodness-of-fit on F final R indices R1 = [ I >2σ(I) ] [a] wr2 = R indices (all data) [a] R1 = ; wr2 = R1 = wr2 = R1 = wr2 = R1 = wr2 = R1 = ; wr2 = peak max /hole min (e Å 3 ) / / / [a] R1 = F o F c / F o ; wr2 = { [w(f o 2 F c 2 ) 2 ]/ [w(f o 2 ) 2 ]} 1/2 S16
17 Table S4. Bond lengths [Å] and angles [º] for compound 1. O(1)-C(7) 1.269(2) N(2)-C(5) 1.350(2) N(1)-C(5) 1.358(2) N(2)-C(3) 1.386(3) N(1)-C(2) 1.377(3) N(2)-C(4) 1.458(3) N(1)-C(1) 1.448(3) C(9)-C(8) 1.527(3) C(10)-C(11) 1.519(3) C(11)-O(2) 1.418(2) C(10)-C(9) 1.526(3) C(6)-C(5) 1.423(3) C(7)-C(6) 1.390(3) C(2)-C(3) 1.333(3) C(7)-C(8) 1.525(3) C(5)-N(1)-C(2) (17) C(10)-C(9)-C(8) (16) C(5)-N(1)-C(1) (17) O(2)-C(11)-C(10) (17) C(2)-N(1)-C(1) (17) C(7)-C(6)-C(5) (18) C(11)-C(10)-C(9) (16) N(2)-C(5)-N(1) (16) O(1)-C(7)-C(6) (18) N(2)-C(5)-C(6) (18) O(1)-C(7)-C(8) (17) N(1)-C(5)-C(6) (17) C(6)-C(7)-C(8) (17) C(3)-C(2)-N(1) (18) C(5)-N(2)-C(3) (17) C(2)-C(3)-N(2) (18) C(5)-N(2)-C(4) (17) C(7)-C(8)-C(9) (16) C(3)-N(2)-C(4) (17) Table S5. Bond lengths [Å] and angles [º] for adduct Al(C 6 F 5 ) 3 CL. Al(1)-O(1) (13) C(13)-C(18) 1.379(2) Al(1)-C(7) (16) C(13)-C(14) 1.385(2) Al(1)-C(19) (17) C(14)-F(5) 1.358(2) Al(1)-C(13) (18) C(14)-C(15) 1.380(3) O(1)-C(1) 1.252(2) C(15)-F(4) 1.347(2) O(2)-C(1) 1.294(2) C(15)-C(16) 1.369(3) O(2)-C(2) 1.484(2) C(16)-F(3) 1.341(2) C(1)-C(6) 1.488(2) C(16)-C(17) 1.380(3) C(2)-C(3) 1.510(3) C(17)-F(2) 1.345(2) C(3)-C(4) 1.525(3) C(17)-C(18) 1.377(2) C(4)-C(5) 1.518(3) C(18)-F(1) (19) C(5)-C(6) 1.537(3) C(19)-C(20) 1.382(2) C(7)-C(12) 1.383(2) C(19)-C(24) 1.382(2) C(7)-C(8) 1.388(2) C(20)-F(15) (19) C(8)-F(6) (18) C(20)-C(21) 1.383(2) C(8)-C(9) 1.384(2) C(21)-F(14) 1.347(2) C(9)-F(7) (18) C(21)-C(22) 1.373(2) C(9)-C(10) 1.373(2) C(22)-F(13) (19) C(10)-F(8) (19) C(22)-C(23) 1.374(3) S17
18 C(10)-C(11) 1.376(2) C(23)-F(12) (19) C(11)-F(9) 1.345(2) C(23)-C(24) 1.383(2) C(11)-C(12) 1.378(2) C(24)-F(11) (19) C(12)-F(10) (19) O(1)-Al(1)-C(7) (6) C(18)-C(13)-Al(1) (12) O(1)-Al(1)-C(19) (7) C(14)-C(13)-Al(1) (14) C(7)-Al(1)-C(19) (7) F(5)-C(14)-C(15) (16) O(1)-Al(1)-C(13) (7) F(5)-C(14)-C(13) (17) C(7)-Al(1)-C(13) (7) C(15)-C(14)-C(13) (18) C(19)-Al(1)-C(13) (7) F(4)-C(15)-C(16) (19) C(1)-O(1)-Al(1) (12) F(4)-C(15)-C(14) 120.8(2) C(1)-O(2)-C(2) (14) C(16)-C(15)-C(14) (17) O(1)-C(1)-O(2) (15) F(3)-C(16)-C(15) (18) O(1)-C(1)-C(6) (16) F(3)-C(16)-C(17) 119.8(2) O(2)-C(1)-C(6) (15) C(15)-C(16)-C(17) (17) O(2)-C(2)-C(3) (14) F(2)-C(17)-C(18) (17) C(2)-C(3)-C(4) (15) F(2)-C(17)-C(16) (17) C(5)-C(4)-C(3) (15) C(18)-C(17)-C(16) (18) C(4)-C(5)-C(6) (16) F(1)-C(18)-C(17) (16) C(1)-C(6)-C(5) (15) F(1)-C(18)-C(13) (15) C(12)-C(7)-C(8) (14) C(17)-C(18)-C(13) (16) C(12)-C(7)-Al(1) (12) C(20)-C(19)-C(24) (15) C(8)-C(7)-Al(1) (12) C(20)-C(19)-Al(1) (12) F(6)-C(8)-C(9) (14) C(24)-C(19)-Al(1) (12) F(6)-C(8)-C(7) (14) F(15)-C(20)-C(19) (15) C(9)-C(8)-C(7) (15) F(15)-C(20)-C(21) (15) F(7)-C(9)-C(10) (15) C(19)-C(20)-C(21) (15) F(7)-C(9)-C(8) (15) F(14)-C(21)-C(22) (15) C(10)-C(9)-C(8) (15) F(14)-C(21)-C(20) (15) F(8)-C(10)-C(9) (16) C(22)-C(21)-C(20) (15) F(8)-C(10)-C(11) (16) F(13)-C(22)-C(21) (16) C(9)-C(10)-C(11) (15) F(13)-C(22)-C(23) (15) F(9)-C(11)-C(10) (15) C(21)-C(22)-C(23) (15) F(9)-C(11)-C(12) (16) F(12)-C(23)-C(22) (16) C(10)-C(11)-C(12) (15) F(12)-C(23)-C(24) (16) F(10)-C(12)-C(11) (15) C(22)-C(23)-C(24) (15) F(10)-C(12)-C(7) (14) F(11)-C(24)-C(19) (15) C(11)-C(12)-C(7) (15) F(11)-C(24)-C(23) (15) C(18)-C(13)-C(14) (16) C(19)-C(24)-C(23) (16) S18
19 Table S6. Bond lengths [Å] and angles [º] for INT3. Al(1)-O(1) 1.732(2) Cl(1)-C(48)# (6) Al(1)-C(27) 2.017(3) Cl(1)-C(45) 1.686(6) Al(1)-C(39) 2.035(3) Cl(1)-C(49)# (7) Al(1)-C(33) 2.042(3) Cl(1)-C(47)# (9) F(1)-C(28) 1.360(4) C(45)-C(48)# (9) F(2)-C(29) 1.348(4 C(45)-C(49)# (16) F(3)-C(30) 1.344(4) C(45)-C(47)# (16) F(4)-C(31) 1.344(4) C(45)-C(46) F(5)-C(32) 1.351(4) C(45)-C(50) F(6)-C(34) 1.354(4) C(45)-C(50)# (10) F(7)-C(35) 1.346(4) C(45)-C(46)# (14) F(8)-C(36) 1.347(4) C(46)-C(49)# (12) F(9)-C(37) 1.342(4 C(46)-C(50)# (12) F(10)-C(38) 1.357(4) C(46)-C(47) F(11)-C(40) 1.361(4) C(46)-C(48)# (13) F(12)-C(41) 1.354(4) C(46)-C(45)# (13) F(13)-C(42) 1.342(4) C(47)-C(50)# (11) F(14)-C(43) 1.346(4) C(47)-C(45)# (13) F(15)-C(44) 1.349(4) C(47)-C(48) O(1)-C(1) 1.381(3) C(47)-C(49)# (12) O(2)-C(1) 1.422(4) C(47)-Cl(1)# (8) O(2)-C(2) 1.433(4) C(48)-C(45)# (8) N(1)-C(8) 1.354(4) C(48)-Cl(1)# (5) N(1)-C(9) 1.389(4) C(48)-C(49) N(1)-C(13) 1.468(4) C(48)-C(50)# (14) N(2)-C(8) 1.354(4) C(48)-C(46)# (11) N(2)-C(10) 1.400(4) C(49)-C(46)# (13) N(2)-C(14) 1.473(4) C(49)-C(45)# (12) C(1)-C(6) 1.549(4) C(49)-C(50) C(1)-C(7) 1.578(4) C(49)-C(47)# (13) C(2)-C(3) 1.517(5) C(49)-Cl(1)# (7) C(3)-C(4) 1.520(6) C(50)-C(47)# (11) C(4)-C(5) 1.524(6) C(50)-C(46)# (14) C(5)-C(6) 1.526(5) C(50)-C(48)# (16) C(7)-C(8) 1.534(4) C(50)-C(45)# (8) C(7)-C(12) 1.542(4) Cl(2)-C(54)# (5) C(7)-C(11) 1.543(4) Cl(2)-C(55)# (7) C(9)-C(10) 1.350(4) Cl(2)-C(51) 1.718(5) C(9)-C(15) 1.476(4) Cl(2)-C(53)# (7) C(10)-C(21) 1.476(4) C(51)-C(55)# (11) C(15)-C(20) 1.394(4) C(51)-C(54)# (8) C(15)-C(16) 1.397(4) C(51)-C(56)# (11) S19
20 C(16)-C(17) 1.389(5) C(51)-C(52) C(17)-C(18) 1.379(5) C(51)-C(56) C(18)-C(19) 1.391(5) C(51)-C(53)# (11) C(19)-C(20) 1.382(5) C(51)-C(51)# (8) C(21)-C(26) 1.386(5) C(51)-C(52)# (11) C(21)-C(22) 1.392(4) C(52)-C(56)# (9) C(22)-C(23) 1.389(5) C(52)-C(55)# (10) C(23)-C(24) 1.379(6) C(52)-C(53) C(24)-C(25) 1.390(6) C(52)-C(51)# (9) C(25)-C(26) 1.391(5) C(53)-C(56)# (10) C(27)-C(32) 1.381(5) C(53)-C(54) C(27)-C(28) 1.384(4) C(53)-C(51)# (10) C(28)-C(29) 1.378(4) C(53)-Cl(2)# (6) C(29)-C(30) 1.373(5) C(54)-Cl(2)# (4) C(30)-C(31) 1.366(5) C(54)-C(51)# (8) C(31)-C(32) 1.392(4) C(54)-C(55) C(33)-C(34) 1.383(5) C(55)-C(51)# (9) C(33)-C(38) 1.385(5) C(55)-C(52)# (10) C(34)-C(35) 1.381(5) C(55)-C(56) C(35)-C(36) 1.366(6) C(55)-Cl(2)# (6) C(36)-C(37) 1.380(5) C(56)-C(52)# (11) C(37)-C(38) 1.380(5) C(56)-C(53)# (10) C(39)-C(40) 1.387(4) C(56)-C(51)# (9) C(39)-C(44) 1.397(4) C(57)-C(58) 1.501(9) C(40)-C(41) 1.370(5) C(58)-C(59) 1.465(11) C(41)-C(42) 1.380(5) C(59)-C(60) 1.522(9) C(42)-C(43) 1.375(5) C(60)-C(61) 1.502(11) C(43)-C(44) 1.383(5) O(1)-Al(1)-C(27) (12) C(47)-C(46)-C(45)#1 40.8(3) O(1)-Al(1)-C(39) (12) C(48)#1-C(46)-C(45)#1 93.0(7) C(27)-Al(1)-C(39) (13) C(50)#1-C(47)-C(45)#1 84.6(12) O(1)-Al(1)-C(33) (12) C(50)#1-C(47)-C(48) 109.0(13) C(27)-Al(1)-C(33) (13) C(45)#1-C(47)-C(48) 24.4(4) C(39)-Al(1)-C(33) (14) C(50)#1-C(47)-C(46) 11.1(13) C(1)-O(1)-Al(1) 147.0(2) C(45)#1-C(47)-C(46) 95.6(4) C(1)-O(2)-C(2) 117.0(3) C(48)-C(47)-C(46) C(8)-N(1)-C(9) 110.2(2) C(50)#1-C(47)-C(49)#1 7.9(10) C(8)-N(1)-C(13) 129.0(3) C(45)#1-C(47)-C(49)#1 92.4(5) C(9)-N(1)-C(13) 120.7(2) C(48)-C(47)-C(49)# (5) C(8)-N(2)-C(10) 109.7(2) C(46)-C(47)-C(49)#1 3.3(5) C(8)-N(2)-C(14) 129.8(3) C(50)#1-C(47)-Cl(1)# (14) C(10)-N(2)-C(14) 120.5(3) C(45)#1-C(47)-Cl(1)#1 48.9(4) O(1)-C(1)-O(2) 111.5(2) C(48)-C(47)-Cl(1)#1 24.6(2) S20
21 O(1)-C(1)-C(6) 110.5(2) C(46)-C(47)-Cl(1)# (2) O(2)-C(1)-C(6) 111.5(3) C(49)#1-C(47)-Cl(1)# (5) O(1)-C(1)-C(7) 107.6(2) C(45)#1-C(48)-Cl(1)# (16) O(2)-C(1)-C(7) 102.5(2) C(45)#1-C(48)-C(47) 71.0(13) C(6)-C(1)-C(7) 112.8(2) Cl(1)#1-C(48)-C(47) 124.5(6) O(2)-C(2)-C(3) 112.2(3) C(45)#1-C(48)-C(49) 49.0(13) C(2)-C(3)-C(4) 114.0(3) Cl(1)#1-C(48)-C(49) 115.4(6) C(3)-C(4)-C(5) 114.8(3) C(47)-C(48)-C(49) C(4)-C(5)-C(6) 113.9(3) C(45)#1-C(48)-C(50)#1 51.9(11) C(5)-C(6)-C(1) 118.4(3) Cl(1)#1-C(48)-C(50)# (7) C(8)-C(7)-C(12) 111.1(3) C(47)-C(48)-C(50)#1 19.0(3) C(8)-C(7)-C(11) 110.6(3) C(49)-C(48)-C(50)# (3) C(12)-C(7)-C(11) 105.6(2) C(45)#1-C(48)-C(46)#1 35.2(9) C(8)-C(7)-C(1) 107.5(2) Cl(1)#1-C(48)-C(46)# (7) C(12)-C(7)-C(1) 111.1(3) C(47)-C(48)-C(46)# (5) C(11)-C(7)-C(1) 111.0(3) C(49)-C(48)-C(46)#1 13.8(5) N(1)-C(8)-N(2) 106.2(3) C(50)#1-C(48)-C(46)#1 87.1(4) N(1)-C(8)-C(7) 126.8(3) C(46)#1-C(49)-C(45)# (17) N(2)-C(8)-C(7) 127.0(3) C(46)#1-C(49)-C(48) 131.0(13) C(10)-C(9)-N(1) 107.0(3) C(45)#1-C(49)-C(48) 23.3(5) C(10)-C(9)-C(15) 129.2(3) C(46)#1-C(49)-C(50) 11.1(13) N(1)-C(9)-C(15) 123.8(3) C(45)#1-C(49)-C(50) 96.8(5) C(9)-C(10)-N(2) 107.0(3) C(48)-C(49)-C(50) C(9)-C(10)-C(21) 129.4(3) C(46)#1-C(49)-C(47)#1 7.9(10) N(2)-C(10)-C(21) 123.6(3) C(45)#1-C(49)-C(47)# (8) C(20)-C(15)-C(16) 119.5(3 C(48)-C(49)-C(47)# (5) C(20)-C(15)-C(9) 119.7(3) C(50)-C(49)-C(47)#1 3.3(5) C(16)-C(15)-C(9) 120.8(3) C(46)#1-C(49)-Cl(1)# (15) C(17)-C(16)-C(15) 119.4(3) C(45)#1-C(49)-Cl(1)#1 51.7(5) C(18)-C(17)-C(16) 120.7(3) C(48)-C(49)-Cl(1)#1 28.5(3) C(17)-C(18)-C(19) 120.1(3) C(50)-C(49)-Cl(1)# (3) C(20)-C(19)-C(18) 119.7(3) C(47)#1-C(49)-Cl(1)# (6) C(19)-C(20)-C(15) 120.6(3) C(47)#1-C(50)-C(46)#1 161(2) C(26)-C(21)-C(22) 119.3(3) C(47)#1-C(50)-C(49) 168.9(17) C(26)-C(21)-C(10) 120.2(3) C(46)#1-C(50)-C(49) 7.7(8) C(22)-C(21)-C(10) 120.4(3) C(47)#1-C(50)-C(45) 71.0(17) C(23)-C(22)-C(21) 120.3(3) C(46)#1-C(50)-C(45) 127.6(8) C(24)-C(23)-C(22) 120.1(3) C(49)-C(50)-C(45) C(23)-C(24)-C(25) 120.0(3) C(47)#1-C(50)-C(48)#1 51.9(13) C(24)-C(25)-C(26) 119.9(3) C(46)#1-C(50)-C(48)# (11) C(21)-C(26)-C(25) 120.4(3) C(49)-C(50)-C(48)# (5) C(32)-C(27)-C(28) 113.4(3) C(45)-C(50)-C(48)#1 19.0(5) C(32)-C(27)-Al(1) 126.2(2) C(47)#1-C(50)-C(45)#1 155(2) S21
22 C(28)-C(27)-Al(1) 120.4(2) C(46)#1-C(50)-C(45)#1 43.3(5) F(1)-C(28)-C(29) 116.1(3) C(49)-C(50)-C(45)#1 35.8(4) C(29)-C(28)-C(27) 124.9(3) C(45)-C(50)-C(45)#1 84.3(4) F(2)-C(29)-C(30) 119.3(3) C(48)#1-C(50)-C(45)# (7) F(2)-C(29)-C(28) 121.9(3) C(54)#2-Cl(2)-C(55)#2 57.2(9) C(30)-C(29)-C(28) 118.8(3) C(54)#2-Cl(2)-C(51) 14.3(12) F(3)-C(30)-C(31) 120.3(3) C(55)#2-Cl(2)-C(51) 44.0(3) F(3)-C(30)-C(29) 120.2(3) C(54)#2-Cl(2)-C(53)#2 35.1(9) F(4)-C(31)-C(30) 119.6(3) C(55)#2-Cl(2)-C(53)#2 92.2(2) F(4)-C(31)-C(32) 121.0(3) C(51)-Cl(2)-C(53)#2 48.3(3) C(30)-C(31)-C(32) 119.3(3) C(55)#2-C(51)-C(54)#2 67.3(5) F(5)-C(32)-C(27) 120.2(3) C(55)#2-C(51)-C(56)#2 63.7(5) F(5)-C(32)-C(31) 115.8(3) C(54)#2-C(51)-C(56)# (9) C(27)-C(32)-C(31) 124.0(3) C(55)#2-C(51)-C(52) 57.1(6) C(34)-C(33)-C(38) 113.2(3) C(54)#2-C(51)-C(52) 124.3(7) C(34)-C(33)-Al(1) 122.9(2) C(56)#2-C(51)-C(52) 7.2(4) C(38)-C(33)-Al(1) 123.9(2) C(55)#2-C(51)-C(56) 175.9(8) F(6)-C(34)-C(35) 115.8(3) C(54)#2-C(51)-C(56) 115.6(7) F(6)-C(34)-C(33) 119.9(3) C(56)#2-C(51)-C(56) 113.3(4) C(35)-C(34)-C(33) 124.3(3) C(52)-C(51)-C(56) F(7)-C(35)-C(36) 119.6(3) C(55)#2-C(51)-C(53)# (7) F(7)-C(35)-C(34) 120.8(3) C(54)#2-C(51)-C(53)#2 62.0(4) C(36)-C(35)-C(34) 119.6(3) C(56)#2-C(51)-C(53)# (8) F(8)-C(36)-C(35) 120.2(4) C(52)-C(51)-C(53)# (5) F(8)-C(36)-C(37) 120.5(3) C(56)-C(51)-C(53)#2 53.5(5) C(35)-C(36)-C(37) 119.3(3) C(55)#2-C(51)-C(51)# (9) F(9)-C(37)-C(38) 121.5(3) C(54)#2-C(51)-C(51)# (11) F(9)-C(37)-C(36) 119.8(3) C(56)#2-C(51)-C(51)#2 56.9(4) C(38)-C(37)-C(36) 118.6(3) C(52)-C(51)-C(51)#2 63.7(4) F(10)-C(38)-C(37) 114.8(3) C(56)-C(51)-C(51)#2 56.4(4) F(10)-C(38)-C(33) 120.3(3) C(53)#2-C(51)-C(51)# (8) C(37)-C(38)-C(33) 124.9(3) C(55)#2-C(51)-C(52)# (11) C(40)-C(39)-C(44) 113.1(3) C(54)#2-C(51)-C(52)# (8) C(40)-C(39)-Al(1) 125.6(2) C(56)#2-C(51)-C(52)# (5) C(44)-C(39)-Al(1) 121.1(2) C(52)-C(51)-C(52)# (4) F(11)-C(40)-C(41) 115.5(3) C(56)-C(51)-C(52)#2 3.3(4) F(11)-C(40)-C(39) 119.7(3) C(53)#2-C(51)-C(52)#2 55.8(4) C(41)-C(40)-C(39) 124.8(3) C(51)#2-C(51)-C(52)#2 53.9(4) F(12)-C(41)-C(40) 121.2(3) C(55)#2-C(51)-Cl(2) 62.4(4) F(12)-C(41)-C(42) 119.2(3) C(54)#2-C(51)-Cl(2) 5.3(4) C(40)-C(41)-C(42) 119.6(3) C(56)#2-C(51)-Cl(2) 126.1(5) F(13)-C(42)-C(43) 120.3(3) C(52)-C(51)-Cl(2) 119.5(3) F(13)-C(42)-C(41) 120.9(3) C(56)-C(51)-Cl(2) 120.5(3) S22
23 C(43)-C(42)-C(41) 118.8(3) C(53)#2-C(51)-Cl(2) 67.0(3) F(14)-C(43)-C(42) 119.5(3) C(51)#2-C(51)-Cl(2) 175.6(7) F(14)-C(43)-C(44) 120.9(3) C(52)#2-C(51)-Cl(2) 122.8(4) C(42)-C(43)-C(44) 119.5(3) C(56)#2-C(52)-C(55)#2 133(4) F(15)-C(44)-C(43) 115.8(3) C(56)#2-C(52)-C(53) 41(3) F(15)-C(44)-C(39) 120.1(3) C(55)#2-C(52)-C(53) 174.8(6) C(43)-C(44)-C(39) 124.1(3) C(56)#2-C(52)-C(51) 84(4) C(48)#1-Cl(1)-C(45) 5.2(8) C(55)#2-C(52)-C(51) 55.7(6) C(48)#1-Cl(1)-C(49)#1 36.1(4) C(53)-C(52)-C(51) C(45)-Cl(1)-C(49)#1 30.9(4) C(56)#2-C(52)-C(51)#2 28(4) C(48)#1-Cl(1)-C(47)#1 30.9(4) C(55)#2-C(52)-C(51)# (8) C(45)-Cl(1)-C(47)#1 36.2(4) C(53)-C(52)-C(51)#2 57.6(3) C(49)#1-Cl(1)-C(47)# (16) C(51)-C(52)-C(51)#2 62.4(3) C(48)#1-C(45)-C(49)#1 108(2) C(56)#2-C(53)-C(52) 5.2(4) C(48)#1-C(45)-C(47)#1 84.6(16) C(56)#2-C(53)-C(54) 115.6(4) C(49)#1-C(45)-C(47)# (9) C(52)-C(53)-C(54) C(48)#1-C(45)-C(46) 131.0(19) C(56)#2-C(53)-C(51)#2 62.0(4) C(49)#1-C(45)-C(46) 23.3(6) C(52)-C(53)-C(51)#2 66.5(3) C(47)#1-C(45)-C(46) 144.3(5) C(54)-C(53)-C(51)#2 53.5(3) C(48)#1-C(45)-C(50) 109.0(19) C(56)#2-C(53)-Cl(2)# (5) C(49)#1-C(45)-C(50) 143.2(6) C(52)-C(53)-Cl(2)# (2) C(47)#1-C(45)-C(50) 24.4(5) C(54)-C(53)-Cl(2)#2 11.3(2) C(48)#1-C(45)-Cl(1) 10.3(15) C(51)#2-C(53)-Cl(2)#2 64.7(3) C(49)#1-C(45)-Cl(1) 97.4(7) Cl(2)#2-C(54)-C(55) 106.2(9) C(47)#1-C(45)-Cl(1) 94.9(4) C(51)#2-C(54)-C(55) 55.7(4) C(46)-C(45)-Cl(1) 120.7(4) Cl(2)#2-C(54)-C(53) 133.6(9) C(50)-C(45)-Cl(1) 119.3(4) C(51)#2-C(54)-C(53) 64.4(4) C(48)#1-C(45)-C(50)#1 155(2) C(55)-C(54)-C(53) C(47)#1-C(45)-C(50)# (7) C(51)#2-C(55)-C(52)#2 67.3(4) C(46)-C(45)-C(50)#1 24.3(4) C(51)#2-C(55)-C(56) 63.0(4) C(50)-C(45)-C(50)#1 95.7(4) C(52)#2-C(55)-C(56) 5.2(5) Cl(1)-C(45)-C(50)# (6) C(51)#2-C(55)-C(54) 57.1(4) C(48)#1-C(45)-C(46)# (19) C(52)#2-C(55)-C(54) 124.3(4) C(49)#1-C(45)-C(46)# (6) C(56)-C(55)-C(54) C(47)#1-C(45)-C(46)#1 43.5(4) C(51)#2-C(55)-Cl(2)#2 73.6(4) C(46)-C(45)-C(46)# (3) C(52)#2-C(55)-Cl(2)# (6) C(50)-C(45)-C(46)#1 19.2(3) C(56)-C(55)-Cl(2)# (2) Cl(1)-C(45)-C(46)# (5) C(54)-C(55)-Cl(2)#2 16.6(2) C(50)#1-C(45)-C(46)#1 76.6(4) C(52)#2-C(56)-C(53)#2 133(3) C(49)#1-C(46)-C(50)#1 161(2) C(52)#2-C(56)-C(51)#2 89(3) C(49)#1-C(46)-C(45) 49.0(15) C(53)#2-C(56)-C(51)# (9) C(50)#1-C(46)-C(45) 112.4(8) C(52)#2-C(56)-C(55) 41(3) C(49)#1-C(46)-C(47) 168.9(15) C(53)#2-C(56)-C(55) 174.8(7) S23
24 C(50)#1-C(46)-C(47) 7.7(8) C(51)#2-C(56)-C(55) 53.4(4) C(45)-C(46)-C(47) C(52)#2-C(56)-C(51) 149(4) C(49)#1-C(46)-C(48)#1 35.2(10) C(53)#2-C(56)-C(51) 64.4(6) C(50)#1-C(46)-C(48)# (12) C(51)#2-C(56)-C(51) 66.7(4) C(45)-C(46)-C(48)#1 13.8(5) C(55)-C(56)-C(51) C(47)-C(46)-C(48)# (5) C(59)-C(58)-C(57) 114.0(6) C(49)#1-C(46)-C(45)# (17) C(58)-C(59)-C(60) 114.4(5) C(50)#1-C(46)-C(45)#1 33.3(6) C(61)-C(60)-C(59) 114.2(6) C(45)-C(46)-C(45)#1 79.2(3) Symmetry transformations used to generate equivalent atoms: #1 -x+1,-y-1,-z #2 -x-1,-y,-z+1 S24
Nickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings
ickel and Platinum PCP Pincer Complexes Incorporating an Acyclic Diaminoalkyl Central Moiety Connecting Imidazole or Pyrazole Rings Braulio M. Puerta Lombardi, Rudy M. Braun, Chris Gendy, Chia Yun Chang,
Enantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid
Enantioselective Synthesis of the Anti-inflammatory Agent ( )-Acanthoic Acid Taotao Ling, a Chinmay Chowdhury, a Bryan A. Kramer, a Binh G. Vong, a Michael A. Palladino b and Emmanuel A. Theodorakis a
Electronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) Cyclopentadienyl iron dicarbonyl (CpFe(CO) 2 ) derivatives
chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
σ-donor/acceptor confused ligands: The case of a chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX 77843-3255. *To whom correspondence
Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond
Photo-Induced Self-Assembly of Pt(II)-Linked Rings and Cages via the Photolabilization of a Pt(II) Pyridine Bond Ken-ichi Yamashita, Kei-ichi Sato, Masaki Kawano and Makoto Fujita* Contents; Figure S1.
Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles
![Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles](/thumbs/89/100111450.jpg "Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles")
X-Ray crystallographic data tables for paper: Supplementary Material (ESI) for Organic & Biomolecular Chemistry Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically
Supporting Information for Substituent Effects on the Properties of Borafluorenes
Supporting Information for Substituent Effects on the Properties of Borafluorenes Mallory F. Smith, S. Joel Cassidy, Ian A. Adams, Monica Vasiliu, Deidra L. Gerlach, David Dixon*, Paul A. Rupar* Department
Supporting Information. Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory
Supporting Information Dysiherbols A C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge Wei-Hua Jiao,, Guo-Hua Shi,, Ting-Ting Xu,, Guo-Dong Chen,
IV. ANHANG 179. Anhang 178
Anhang 178 IV. ANHANG 179 1. Röntgenstrukturanalysen (Tabellen) 179 1.1. Diastereomer A (Diplomarbeit) 179 1.2. Diastereomer B (Diplomarbeit) 186 1.3. Aldoladdukt 5A 193 1.4. Aldoladdukt 13A 200 1.5. Aldoladdukt
College of Life Science, Dalian Nationalities University, Dalian , PR China.
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Postsynthetic modification
Patrycja Miszczyk, Dorota Wieczorek, Joanna Gałęzowska, Błażej Dziuk, Joanna Wietrzyk and Ewa Chmielewska. 1. Spectroscopic Data.
; doi:10.3390/molecules22020254 S1 of S23 Supplementary Materials: Reaction of 3-Amino-1,2,4-Triazole with Diethyl Phosphite and Triethyl Orthoformate: Acid-Base Properties and Antiosteoporotic Activities
Table S1. Summary of data collections and structure refinements for crystals 1Rb-1h, 1Rb-2h, and 1Rb-4h.
Supporting Information [NH 3 CH 3 ] [In SbS 9 SH]: A novel methylamine-directed indium thioantimonate with Rb + ion-exchange property Kai-Yao Wang a,b, Mei-Ling Feng a, Jian-Rong Li a and Xiao-Ying Huang
Supporting Information
Supporting Information Vinylogous elimination/heck coupling/allylation domino reactions: access to 2- substituted 2,3-dihydrobenzofurans and indolines Jianguo Yang, *, Hanjie Mo, Xiuxiu Jin, Dongdong Cao,
Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads for low-energy photosensitization
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Electronic supplementary information (ESI) Bodipy functionalized ortho-carborane dyads
SUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
10.1071/CH17272_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(12), 1285-1290 SUPPLEMENTARY MATERIAL A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine
C H Activation of Cp* Ligand Coordinated to Ruthenium. Center: Synthesis and Reactivity of a Thiolate-Bridged
Supporting Information C H Activation of Cp* Ligand Coordinated to Ruthenium Center: Synthesis and Reactivity of a Thiolate-Bridged Diruthenium Complex Featuring Fulvene-like Cp* Ligand Xiaoxiao Ji, Dawei
Table of Contents 1 Supplementary Data MCD
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information for Magnetic circular dichroism and density functional theory
Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes
![Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes](/thumbs/92/108867714.jpg "Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes")
SUPPORTING INFORMATION Pyrrolo[2,3-d:5,4-d']bisthiazoles: Alternate Synthetic Routes and a Comparative Study to Analogous Fused-ring Bithiophenes Eric J. Uzelac, Casey B. McCausland, and Seth C. Rasmussen*
Supporting information. An unusual bifunctional Tb-MOF for highly sensing of Ba 2+ ions and remarkable selectivities of CO 2 /N 2 and CO 2 /CH 4
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A. This journal is The Royal Society of Chemistry 2015 Supporting information An unusual bifunctional Tb-MOF for highly sensing
Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ]
![Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ]](/thumbs/92/109256432.jpg "Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ]")
Supporting Information Multifunctinality and Crystal Dynamics of Highly Stable Porous Metal-Organic Framework [Zn 4 O(NTB) 2 ] Eun Young Lee, Seung Yeon Jang, and Myunghyun Paik Suh* School of Chemistry,
Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers. Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative
Fused Bis-Benzothiadiazoles as Electron Acceptors
Fused Bis-Benzothiadiazoles as Electron Acceptors Debin Xia, a,b Xiao-Ye Wang, b Xin Guo, c Martin Baumgarten,*,b Mengmeng Li, b and Klaus Müllen*,b a MIIT Key Laboratory of ritical Materials Technology
Zebra reaction or the recipe for heterodimeric zinc complexes synthesis
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 05 Supporting Information Zebra reaction or the recipe for heterodimeric zinc complexes synthesis
Electronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) CPh 3 as a functional group in P-heterocyclic
Supporting Information
Supporting Information Aluminum Complexes of N 2 O 2 3 Formazanate Ligands Supported by Phosphine Oxide Donors Ryan R. Maar, Amir Rabiee Kenaree, Ruizhong Zhang, Yichen Tao, Benjamin D. Katzman, Viktor
Supporting Information
SUPPORTING INFORMATION FOR: Trialkylstibine complexes of boron, aluminium, gallium and indium trihalides: synthesis, properties and bonding Victoria K. Greenacre, William Levason and Gillian Reid Chemistry,
Supplementary Material
Supplementary Material Synthesis of bis-oxathiaaza[3.3.3]propellanes via nucleophilic addition of (1,ω-alkanediyl)bis(N'-organylthioureas) on dicyanomethylene-1,3-indanedione Alaa A. Hassan, a * Kamal
SUPPORTING INFORMATION. Pyramidanes: The Covalent Form of the Ionic Compounds
SUPPORTING INFORMATION Pyramidanes: The Covalent Form of the Ionic Compounds Vladimir Ya. Lee, 1 * Olga A. Gapurenko, 2 Yuki Ito, 1 Takahiko Meguro, 1 Haruka Sugasawa, 1 Akira Sekiguchi, 1 *, Ruslan M.
Supporting Information. Palladium Complexes with Bulky Diphosphine. Synthesis of (Bio-) Adipic Acid from Pentenoic. Acid Mixtures.
Supporting Information Palladium Complexes with Bulky Diphosphine Ligands as Highly Selective Catalysts for the Synthesis of (Bio-) Adipic Acid from Pentenoic Acid Mixtures. Choon Heng Low, James D. Nobbs,*
Supporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Abnormal N-Heterocyclic Carbene Based Nickel Complex for Catalytic
Synthesis, Crystal Structure and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5- yl)benzenes
Supplementary information Synthesis, Crystal Structure and Supramolecular Understanding of 1,3,5-Tris(1-phenyl-1H-pyrazol-5- yl)benzenes Marcos A. P. Martins 1 *, Alexandre R. Meyer 1, Paulo R. S. Salbego
E-H (E = B, Si, C) Bond Activation by Tuning Structural and Electronic Properties of Phosphenium Cations
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 Email: drasko.vidovic@monash.edu
Supporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Supporting Information. Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the. Synthesis of Heteroaromatic Biaryls
Supporting Information Pd()-Catalyzed Decarboxylative Coupling and Tandem C H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls Debkumar andi, Yang-Ming Jhou, Jhen-Yi Lee, Bing-Chiuan
Supporting Information File 2. Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ;
Supporting Information File 2 Crystallographic data of syn-bis-quinoxaline, 16c CH 3 CO 2 C 2 H 5 ; Preparation, structures and host guest chemistry of fluorinated syn-bisquinoxaline molecular tweezers
Supporting Information
Supporting Information Chloroyttrium 2-(1-(arylimino)alkyl)quinolin-8-olate Complexes: Synthesis, Characterization, and Catalysis of the Ring-Opening Polymerization (ROP) of ε- Caprolactone (ε-cl) Wenjuan
Nitric oxide (NO) reactivity studies on mononuclear Iron(II) complexes supported by a tetradentate Schiff base Ligand
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Nitric oxide (NO) reactivity studies on mononuclear Iron(II) complexes supported by a tetradentate
Supporting Information. Generation Response. Physics & Chemistry of CAS, 40-1 South Beijing Road, Urumqi , China. China , USA
Supporting Information Pb 3 B 6 O 11 F 2 : A First Noncentrocentric Lead Fluoroborate with Large Second Harmonic Generation Response Hongyi Li, a Hongping Wu, a * Xin Su, a Hongwei Yu, a,b Shilie Pan,
Supporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Supporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Supporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Heterobimetallic Pd-Sn Catalysis: Michael Addition. Reaction with C-, N-, O-, S- Nucleophiles and In-situ. Diagnostics
Supporting Information (SI) Heterobimetallic Pd-Sn Catalysis: Michael Addition Reaction with C-, N-, -, S- Nucleophiles and In-situ Diagnostics Debjit Das, a Sanjay Pratihar a,b and Sujit Roy c * a rganometallics
SUPPLEMENTARY MATERIAL. In Situ Spectroelectrochemical Investigations of Ru II Complexes with Bispyrazolyl Methane Triarylamine Ligands
10.1071/CH16555_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(5), 546-555 SUPPLEMENTARY MATERIAL In Situ Spectroelectrochemical Investigations of Ru II Complexes with Bispyrazolyl Methane Triarylamine
Supplementary information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary information Hybrids of acylated homoserine lactone and nitric
L. Kaßner a, K. Nagel a, R. E. Grützner b, M. Korb c, T. Rüffer c, H. Lang c and S. Spange a
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information L. Kaßner a, K. Nagel a, R. E. Grützner b, M. Korb c, T. Rüffer
Stereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines
![Stereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines](/thumbs/83/87678994.jpg "Stereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines")
Stereochemistry and mechanistic insight in the [2 k +2 i +2 i ] annulations of ketenes and imines Zhanhui Yang, Wei He, Baoxiang Cheng and Jiaxi Xu* State Key Laboratory of Chemical Resource Engineering,
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2008 Copper Complexes of Mono- and Ditopic [(Methylthio)methyl]borates: Missing Links and Linked Systems En Route to Copper
Supporting Information
Supporting Information Molecular Cage Impregnated Palladium Nanoparticles: Efficient, Additive-Free Heterogeneous Catalysts for Cyanation of Aryl Halides. Bijnaneswar Mondal, Koushik Acharyya, Prodip Howlader
Supporting Information
Supporting Information 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and 1,4-Dinitriles - Sterically Constrained Examples by Incorporation into Cyclic Peripheries: Synthesis, Aggregation and
Supporting Information
Supporting Information for Pyrene nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies Artur Jabłoński 1, Yannic Fritz 2, Hans-Achim Wagenknecht 2, Rafał Czerwieniec
Synthesis, Characterization, and Computational Study of Three-Coordinate SNS-Copper(I) Complexes Based on Bis-Thione Precursors
For Synthesis, Characterization, and Computational Study of Three-Coordinate SNS-Copper(I) Complexes Based on Bis-Thione Precursors John R. Miecznikowski a *; Matthew A. Lynn b ; Jerry P. Jasinski c ;
NH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications
Supporting Information NH-Type of chiral Ni(II) complexes of glycine Schiff base: design, structural evaluation, reactivity and synthetic applications Mackenzie Bergagnini, a Kazunobu Fukushi, b Jianlin
Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties
Supporting Information Controlling Growth of Molecular Crystal Aggregates with Distinct Linear and Nonlinear Optical Properties Yusen Luo,,,# Chunqing Yuan,,# Jialiang Xu*, Yongjun Li*, Huibiao Liu, Sergey
Supporting Information
One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine Alexander V. Aksenov,* Dmitrii A. Aksenov, Naila A. Orazova, Nicolai A. Aksenov, Georgii D. Griaznov, Annelise
Supporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Supplementary Materials for. Kinetic and Computational Studies on Pd(I) Dimer- Mediated Halogen Exchange of Aryl Iodides
Supplementary Materials for Kinetic and Computational Studies on Pd(I) Dimer- Mediated Halogen Exchange of Aryl Iodides Indrek Kalvet, a Karl J. Bonney, a and Franziska Schoenebeck a * a Institute of Organic
Supporting Information. for
Supporting Information for A general synthetic route to [Cu(X)(NHC)] (NHC = N- heterocyclic carbene, X =Cl, Br, I) complexes Orlando Santoro, Alba Collado, Alexandra M. Z. Slawin, Steven P. Nolan and Catherine
Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
Electronic Supplementary Information
Electronic Supplementary Material (ESI) for Polymer hemistry This journal is The Royal Society of hemistry 2011 Phosphoric and Phosphoramidic Acids as Bifunctional atalysts for the Ring-pening Polymerization
Single Crystal X-Ray Structure Determination of Compounds 8a, 8b and 11a
Single Crystal X-Ray Structure Determination of Compounds 8a, 8b and 11a General: Preliminary examination and data collection were carried out on an area detecting system (Kappa-CCD; Nonius) using graphite-monochromated
and Trimethylene Carbonate
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2018 Supporting information for Preparation of Multiblock Copolymers via Step-wise Addition
Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: -S-aromatic heterocyclic podophyllum derivatives display antitumor activity
Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: -S-aromatic heterocyclic podophyllum derivatives display antitumor activity Jian-Long Li 1,a, Wei Zhao 1,a, Chen Zhou 1,a, Ya-Xuan
Supporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Faculty of Chemistry, University of Wrocław, Joliot-Curie 14, Wrocław, Poland
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2017 Synthesis, X-ray characterization, DFT calculations and Hirshfeld surface analysis of M n+
Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Electronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic, Crystal Chemistry, and Nonlinear Optical Property Relationships. or W, and D = P or V)
Electronic, Crystal Chemistry, and Nonlinear Optical Property Relationships in the Dugganite A 3 B 3 CD 2 O 14 Family (A = Sr, Ba or Pb; B = Mg or Zn; C = Te or W, and D = P or V) Hongwei Yu, Joshua Young,
Supporting information for
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting information for Palladium-Catalyzed Benzothieno[2,3-b]indole Formation via Dehydrative-Dehydrogenative
Palladium-Catalyzed Direct ortho-sulfonylation of. Azobenzenes with Arylsulfonyl Chlorides via C H. Table of Contents
Electronic upplementary Material (EI) for RC Advances. This journal is The Royal ociety of Chemistry 205 upporting Information Palladium-Catalyzed Direct ortho-ulfonylation of Azobenzenes with Arylsulfonyl
Synthesis of New Heteroscorpionate Iridium(I) and Iridium(III) Complexes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 ELECTRONIC SUPPORTING INFORMATION For Synthesis of New Heteroscorpionate Iridium(I)
Supporting Information
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2014 Supporting Information Heteroleptic Platinum(II) NHC Complexes with a C^C*
Supporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2017 Supporting Information Phosphorescent Pt(II) complexes bearing a monoanionic C^N^N luminophore
Electronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) Lanthanide metal-organic frameworks constructed by asymmetric 2-nitro-biphenyl-4,4 -dicarboxylate ligand: syntheses, structures, luminescence and magnetic investigations
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information Domino reaction of cyclic sulfamidate imines with
Electronic Supporting Information. 3-Aminothiophenecarboxylic acid (3-Atc)-induced folding in peptides
Electronic Supplementary Material (ESI for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Electronic Supporting Information
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Supporting Information
Supporting Information Wiley-VCH 27 69451 Weinheim, Germany Supplementary Figure 1. Synthetic results as detected by XRD (Cu-Kα). Simulation pattern of MCM-68 Relative Intensity / a.u. YNU-2P Conventional
Supplementary Information for
Supplentary Information for Aggregation induced blue-shifted ission molecular picture from QM/MM study Qunyan Wu, a Tian Zhang, a Qian Peng,* b Dong Wang, a and Zhigang Shuai* a a Key Loratory of Organic
Supporting Information
Supporting Information On the Ambiguity of 1,3,2-Benzodiazaboroles as Donor/Acceptor unctionalities in Luminescent Molecules Lothar Weber *[a], Johannes Halama [a], Kenny Hanke [a], Lena Böhling [a], Andreas
Four- and Five-membered Cobaltacycles by Regioselective Cyclometalation. of Benzylsulfide Derivatives via Co(V) intermediates
Electronic Supplementary Information for Dalton Transactions This journal is The Royal Society of Chemistry 2008 Supporting Information for: Four- and Five-membered Cobaltacycles by Regioselective Cyclometalation
Supporting Information
Supporting Information For A Highly Sensitive ESIPT Based Ratiometric Fluorescence Sensor for Selective Detection of Al 3+ Sanghamitra Sinha, Bijit Chowdhury and Pradyut Ghosh* Department of Inorganic
Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as
![Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as](/thumbs/92/107849210.jpg "Novel electroluminescent donor-acceptors based on dibenzo[a,c]phenazine as")
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Novel electroluminescent donor-acceptors
Divergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Supporting Information
Supporting Information rigin of the Regio- and Stereoselectivity of Allylic Substitution of rganocopper Reagents Naohiko Yoshikai, Song-Lin Zhang, and Eiichi Nakamura* Department of Chemistry, The University
Supporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Electronic Supplementary Information DFT Characterization on the Mechanism of Water Splitting Catalyzed by Single-Ru-substituted Polyoxometalates
Electronic Supplementary Information DFT Characterization on the Mechanism of Water Splitting Catalyzed by Single-Ru-substituted Polyoxometalates Zhong-Ling Lang, Guo-Chun Yang, Na-Na Ma, Shi-Zheng Wen,
Bloco A, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ, Brazil. Contents Pages
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information Copper(II) Catalyzed Synthesis of Novel Helical
Supporting Information. for. Single-molecule magnet behavior in 2,2 -bipyrimidinebridged
Supporting Information for Single-molecule magnet behavior in 2,2 -bipyrimidinebridged dilanthanide complexes Wen Yu 1*, Frank Schramm 1, Eufemio Moreno Pineda 1, Yanhua Lan 2, Olaf Fuhr 1, Jinjie Chen
Supporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
SUPPLEMENTARY MATERIAL
10.1071/CH16014_AC The Authors 2016 Australian Journal of Chemistry 2016, 69(9), 1049-1053 SUPPLEMENTARY MATERIAL A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4- e]isoxazolo[5,4-b]pyridin-6-one
Electronic Supplementary Information
Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*
An experimental and theoretical study of the gas phase kinetics of atomic chlorine reactions with CH 3 NH 2, (CH 3 ) 2 NH, and (CH 3 ) 3 N
Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics. This journal is the Owner Societies 2015 An experimental and theoretical study of the gas phase kinetics of atomic chlorine
Key Laboratory of Functional Materials and Devices for Special Environments, Xinjiang Technical
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 2016 KPb 2 (PO 3 ) 5 : A Novel Nonlinear Optical Lead Polyphosphate with Short
Supplementary Materials: Development of Amyloseand β-cyclodextrin-based Chiral Fluorescent Sensors Bearing Terthienyl Pendants
S1 of S12 Supplementary Materials: Development of Amyloseand β-cyclodextrin-based Chiral Fluorescent Sensors Bearing Terthienyl Pendants Tomoyuki Ikai, Changsik Yun, Yutaka Kojima, Daisuke Suzuki, Katsuhiro
Experimental. Crystal data
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Terephthalic acid 2,2 0 -dimethyl-1,1 0 - (butane-1,4-diyl)dibenzimidazole (2/3) Hui Jiang and Xian-Wu Dong* Department
Supplementary Material
Supplementary Material Efficient, mild synthesis of - unsubstituted 1,2,3- triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles Janeth Rodríguez-Florencio, Diego Martínez-tero, Marco A. García-Eleno,