The CB[n] Family: Prime Components for Self-Sorting Systems Supporting Information

Size: px
Start display at page:

Download "The CB[n] Family: Prime Components for Self-Sorting Systems Supporting Information"

Transcription

1 The CB[n] Family: Prime Components for Self-Sorting Systems Supporting Information by Simin Liu, Christian Ruspic, Pritam Mukhopadhyay,Sriparna Chakrabarti, Peter Y. Zavalij, and Lyle Isaacs* Department of Chemistry and Biochemistry, University of Maryland College Park, MD 074 Table of Contents Pages Table of Contents. S1 Figure S1. S 1 H and 13 C NMR spectra for new compounds 3 and 11. S3 S6 Details of the x-ray structures of CB[8] 3 and CB[8] 11. S7 S1 Selected 1 H NMR spectra from the K a and K rel measurements S13 S Sample Determination of K rel for the Competition Between 5 and 1 for CB[7]. S3 Sample Error Analysis Calculation for CB[7] 4. S3 S6 S1

2 Figure S1. Cross-eyed stereoview of the CB[7] 11 complex from MMFF calculations. Atom colors: C, gray; N, blue; O, red; H, aqua; H-bonds, aqua-red striped. S

3 Figure S. 1 H NMR spectrum (400 MHz, D O, RT) of 3. S3

4 Figure S3. 13 C NMR spectrum (100 MHz, D O, RT) of 3. S4

5 Figure S4. 1 H NMR spectrum (400 MHz, D O, RT) of 11. S5

6 Figure S5. 13 C NMR spectrum (100 MHz, D O, 70 C) of 11. S6

7 Crystal Structure Information for CB[8]*3*(I) *nh O Issued by: Peter Y. Zavalij Crystal No. & ID : 0518: Lyle CB8-3 crystal#4 flat Compound name : (CB8)*(3)*(I,Cl)4*34HO Chemical formula : (C48 H48 N3 O16), (C16 H33 N), (I3.33 Cl0.67), 34.63(HO) Empirical formula : C18 H31.6 Cl0.67 I3.33 N68 O66.3 Final R 1 [I>σ(I)] : 8.6 % A colorless plate of CB8*3*I *nh O, approximate dimensions mm 3, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured at 110() K on a threecircle diffractometer system equipped with Bruker SmartApex CCD area detector using a graphite monochromator and a MoKα fine-focus sealed tube (λ= Å) operated at 50 kv and 30 ma. The detector was placed at a distance of cm from the crystal. A total of 59 frames were collected with a scan width of 0. in and an exposure time of 0 sec/frame using SMART (Bruker, 1999). The total data collection time was hours. The frames were integrated with SAINT software package using a narrow-frame integration algorithm. The integration of the data using a Orthorhombic unit cell yielded a total of reflections to a maximum angle of 5.03, of which 9754 were independent (completeness = 97.9%, R int = 11.38%, R sig = 16.67%) and were greater than σ(i). The final cell dimensions of a = 5.478(3) Å, b = 5.873(3) Å, c = 6.538(3) Å, α= 90, β= 90, γ= 90, V = 17494(3) Å 3, are based upon the refinement of the XYZcentroids of 6903 reflections with. < θ < 4.9 using SAINT. Analysis of the data showed 0.07 % decay during data collection. Data were corrected for absorption effects with the Semi-empirical from equivalents method using XPREP (Sheldrick, 1997). The minimum and maximum transmission coefficients were and The structure was solved and refined using the SHELXS-97 (Sheldrick, 1990) and SHELXL-97 (Sheldrick, 1997) software in the space group P with Z = 4 for the formula unit CB8*3*I *nh O. The final anisotropic full-matrix least-squares refinement on F with 430 variables converged at R 1 = 8.6 % for the observed data and wr = 1.11 % for all data. The goodness-of-fit was The largest peak on the final difference map was 1.75 e/å 3 and the largest hole was e/å 3. On the basis of the final model, the calculated density was g/cm 3 and F(000), 8785 e. S7

8 Figure S6. A view of a molecule of CB8*3*I *nh O from the crystal structure. Anisotropic atomic displacement ellipsoids for the non-hydrogen atoms are shown at the 50% probability level. Hydrogen atoms are displayed with an arbitrarily small radius. Table S1. Sample and crystal data for CB8*3*I *nh O. X-ray labbook No Crystal ID Lyle CB8-3 crystal#4 flat Empirical formula C18 H31.6 Cl0.67 I3.33 N68 O66.3 Formula weight Temperature 110() K Wavelength Å Crystal size mm 3 Crystal habit colorless plate Crystal system Orthorhombic Space group P Unit cell dimensions a = 5.478(3) Å α = 90 b = 5.873(3) Å β = 90 c = 6.538(3) Å γ = 90 Volume 17494(3) Å 3 Z 4 Density, ρ calc g/cm 3 Absorption coefficient, μ mm -1 F(000) 8785 e S8

9 S9

10 Table S. Data collection and structure refinement for CB8*3*I *nh O. Diffractometer Bruker SmartApex CCD area detector Radiation source fine-focus sealed tube, MoKα Generator power 50 kv, 30 ma Detector distance cm Detector resolution 8.33 pixels/mm Total frames 59 Frame size 51 pixels Frame width 0. Exposure per frame 0 sec Total measurement time hours Data collection method ω scans θ range for data collection 1.10 to 5.03 Index ranges -30 h 30, -30 k 30, -31 l 31 Reflections collected Independent reflections 9754 Observed reflection, I>σ(I) Coverage of independent reflections 97.9 % Variation in check reflections 0.07 % Absorption correction Semi-empirical from equivalents XPREP (Sheldrick, 1997) Max. and min. transmission and Structure solution technique direct Structure solution program SHELXS-97 (Sheldrick, 1990) Refinement technique Full-matrix least-squares on F Refinement program SHELXL-97 (Sheldrick, 1997) Function minimized Σw(F o - F c ) Data / restraints / parameters 9754 / 1633 / 430 Goodness-of-fit on F Δ/σ max Final R indices: R 1, I>σ(I) wr, all data R int R sig Weighting scheme w = 1/[σ (F o ) + (0.08P) +.P], P = [max(f o,0) + F o ]/3 Absolute structure parameter 0.49() Largest diff. peak and hole 1.75 and e/å 3 R 1 = Σ F o - F c /Σ F o, wr = [Σw(F o -F c ) /Σw(F o ) ] 1/ S10

11 Crystal Structure Information for Complex CB[8] 11 Issued by: Peter Y. Zavalij Crystal No. & ID : 114: Isaacs Compound name : CB[8] 11 Chemical formula : (C48 H48 N3 O16), (C17 H1 N7 O), I.4, (H O)13., (H3 O)0.4 Final R 1 [I>σ(I)] : 6.38 % A colorless pyramid of C65 H96.54 I.41 N39 O30.56, approximate dimensions mm 3, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured at 193() K on a three-circle diffractometer system equipped with Bruker Smart1000 CCD area detector using a graphite monochromator and a MoKα fine-focus sealed tube (λ= Å) operated at 50 kv and 40 ma. The detector was placed at a distance of cm from the crystal. A total of 1868 frames were collected with a scan width of 0.3 in ω and an exposure time of 3 sec/frame using SMART (Bruker, 1999). The total data collection time was 15.6 hours. The frames were integrated with SAINT software package using a narrow-frame integration algorithm. The integration of the data using a Orthorhombic unit cell yielded a total of 4731 reflections to a maximum θ angle of 5.00, of which were independent (completeness = 99.9%, R int = 0.00%, R sig = 5.36%) and were greater than σ(i). The final cell dimensions of a = (1) Å, b = 7.964(3) Å, c = 5.43() Å, α= 90, β= 90, γ= 90, V = 8898.(14) Å 3, are based upon the refinement of the XYZ-centroids of 746 reflections with.3 < θ < 4.0 using SAINT. Analysis of the data showed 0.16 % decay during data collection. Data were corrected for absorption effects with the Semi-empirical from equivalents method using SADABS (Sheldrick, 1996). The minimum and maximum transmission coefficients were 0.70 and The structure was solved and refined using the SHELXS-97 (Sheldrick, 1990) and SHELXL-97 (Sheldrick, 1997) software in the space group Pna 1 with Z = 4 for the formula unit C65 H96.54 I.41 N39 O The final anisotropic full-matrix least-squares refinement on F with 1138 variables converged at R 1 = 6.38 % for the observed data and wr = % for all data. The goodness-of-fit was The largest peak on the final difference map was e/å 3 and the largest hole was e/å 3. On the basis of the final model, the calculated density was g/cm 3 and F(000), 457 e. Comments: - non-merohedral twinning: rotation around [011] in 0.57:0.43 ratio; - pseudo-centrosymmetric: CB8 shows centrosymmetric arrangement but diamine, iodide and most of the water don't. - disorder: diamine is disordered inside CB8 in about :1 ratio; - occupation disorder of water - modeled with partially occupied oxygen atoms. S11

12 Figure S7. A view of a molecule of [CB8*11]I*18HO from the crystal structure showing the numbering scheme employed. Anisotropic atomic displacement ellipsoids for the non-hydrogen atoms are shown at the 50% probability level. Hydrogen atoms are displayed with an arbitrarily small radius. Table S3. Sample and crystal data for [CB[8] 11]I.4*0.4H3O*13.HO. X-ray labbook No. 114 Crystal ID Isaacs Empirical formula C65 H96.54 I.41 N39 O30.56 Formula weight Temperature 193() K Wavelength Å Crystal size mm 3 Crystal habit colorless pyramid Crystal system Orthorhombic Space group Pna 1 Unit cell dimensions a = (1) Å α = 90 b = 7.964(3) Å β = 90 c = 5.43() Å γ = 90 Volume 8898.(14) Å 3 Z 4 Density, ρ calc g/cm 3 Absorption coefficient, μ mm -1 F(000) 457 e S1

13 Table S4. Data collection and structure refinement for [CB[8] 11]I.4*0.4H3O*13.HO. Diffractometer Bruker Smart1000 CCD area detector Radiation source fine-focus sealed tube, MoKα Generator power 50 kv, 40 ma Detector distance cm Detector resolution 8.33 pixels/mm Total frames 1868 Frame size 51 pixels Frame width 0.3 Exposure per frame 3 sec Total measurement time 15.6 hours Data collection method ω scans θ range for data collection 1.78 to 5.00 Index ranges 0 h 14, 0 k 33, -30 l 30 Reflections collected 4731 Independent reflections Observed reflection, I>σ(I) Coverage of independent reflections 99.9 % Variation in check reflections 0.16 % Absorption correction Semi-empirical from equivalents SADABS (Sheldrick, 1996) Max. and min. transmission and 0.70 Structure solution technique direct Structure solution program SHELXS-97 (Sheldrick, 1990) Refinement technique Full-matrix least-squares on F Refinement program SHELXL-97 (Sheldrick, 1997) Function minimized Σw(F o - F c ) Data / restraints / parameters / 340 / 1138 Goodness-of-fit on F 1.0 Δ/σ max Final R indices: R 1, I>σ(I) wr, all data R int R sig Weighting scheme w = 1/[σ (F o ) + (0.04P) P], P = [MAX(F o,0) + F o ]/3 Absolute structure parameter 0.33() Largest diff. peak and hole and e/å 3 R 1 = Σ F o - F c /Σ F o, wr = [Σw(F o -F c ) /Σw(F o ) ] 1/ S13

14 The following spectra are representative examples of those acquired during the determination of the various K a and K rel values. In the spectra presented here only some of the resonances are integrated to focus attention on those uncluttered regions of the spectrum where good integrals can be obtained. Although we have fully analyzed and assigned all of the spectra, we have not depicted those assignments here for reasons of clarity. The resonance at 1.9 ppm is due to residual H-atoms present in the CD 3 CO D used to make the buffer. Figure S8. One of the 1 H NMR spectra used in the direct determination of K a for CB[6] 8. S14

15 Figure S9. One of the 1 H NMR spectra used in the direct determination of K a for CB[6] 0. S15

16 Figure S10. One of the 1 H NMR spectra used in the determination of K rel for CB[6] 16 and CB[7] 16. S16

17 Figure S11. One of the 1 H NMR spectra used in the determination of K rel for CB[7] 1 and CB[7] 17. S17

18 Figure S1. One of the 1 H NMR spectra used in the determination of K rel for CB[7] 14 and CB[8] 14. S18

19 Figure S13. 1 H NMR spectrum of a :1 mixture of 14 and CB[8] used to establish the exclusive formation of a 1:1 complex in this case. S19

20 Figure S14. One of the 1 H NMR spectra used in the determination of K rel for CB[8] 14 and CB[8] 3. S0

21 Figure S15. One of the 1 H NMR spectra used in the determination of K rel for CB[8] 11 and CB[8] 3. S1

22 Figure S16. One of the 1 H NMR spectra used in the determination of K rel for CB[8] 11 and CB[8] 1. S

23 Figure S17. One of the 1 H NMR spectra used in the determination of K rel for CB[7] 5 and CB[7] 1. S3

24 Sample Determination of K rel for the Competition Between 5 and 1 for CB[7]. We use equation 1 to determine K rel for the interaction of 5 and 1 for CB[7]. For this purpose, we prepared a solution containing CB[7] (40 μm), 5 (840 μm), and 1 (137.7 mm) and allowed it to reach equilibrium (Figure S17). Next, we determined the relative concentrations of 1 and CB[7] 1 by integration of the appropriate resonances in the 1 H NMR spectrum (Figure 1: ppm; CB[7] 1: ppm). Using the relative concentrations and the mass balance expression (equation ) allowed us to calculate [1] free = μm and [CB[7] 1] = μm. Equation 3 is then used to calculate [CB[7] 5] (109.4 μm) using the known value of CB[7] 1. Lastly, equation 4 is used to calculate [5] free ( mm) using the known value of [CB[7] 5]. K rel = ([CB[7] 1][5] free ) / ([CB[7] 5][1] free ) (1) [1] Total = 840 μm = [1] free + [CB[7] 1] () [CB[7]] Total = 40 μm = [CB[7] 1] + [CB[7] 5] (3) [5] Total = mm = [5] free + [CB[7] 5] (4) Substitution of the values of [CB[7] 1], [1] free, [CB[7] 5], and [5] free into equation 1 gave K rel = These determinations were done in triplicate from independently prepared stock solutions and the average values were used in the calculations of K a and the error analysis shown below. In preparing the solutions for the above determinations we used a small excess of 1 (to ensure there is no free CB[7]) and a large excess of 5; under those conditions the errors in [5] free, [1] free are small and both [1] and [CB[7] 1] are kept in a good range for accurate measurement of their ratio by 1 H NMR. Sample Error Analysis Calculation for CB[7] 4. Since the binding constants in this paper are determined by several levels of 1 H NMR competition experiments referenced to an absolute K a measured for CB[7] 5 measured by UV/Vis titration, a proper error analysis is critical. In this section we give a sample calculation of the error analysis used to determine the uncertainty associated with the K a value for CB[7] 4. Step 1 Estimation of the accuracy of 1 H NMR methods for the determination of guest and host guest concentrations. We used 1 H NMR to repeatedly determine the concentration of samples of known concentration of guest and host guest complex by monitoring guest resonances. The 1 H NMR based method was accurate with a standard deviation of ± 3%. Step Determination of the Uncertainty Associated with a Single Level of Competition (K rel ). We propagated the above uncertainty associated with the NMR determination of concentrations (e.g. {(σ [CB[n] guest] )/[CB[n] guest]} = 0.03 and {(σ [Guest] )/[Guest]} = 0.03) of using equations 5 and equations 6 7 (Bevington eq. 4-11, pages 61 6). Equation 6 delivers the uncertainty associated with the weighted product (x) of two values (u and v) (e.g. x = ±a u v). Similarly, equation 7 delivers the uncertainty for dividing two numbers (e.g. x = ±(a u) / v). We make the assumption that the fluctuations in u and v are not correlated (σ uv = 0) which when substituted into equations 6 and 7 delivers equation 8. Rearranging slightly yields equation 9 which allows us to directly use the 3% uncertainty determined for our NMR method. K rel = ([CB[n] G][G1]) / ([CB[n] G1][G]) (5) S4

25 σ x = σ u σ v σ + + uv x u v uv (6) σ x = σ u σ v σ + - uv x u v uv (7) σ x = σ u σ + v x u v (8) σ x = x σ u u + σ v v (9) We break the uncertainty determination in K rel (equation 1) into three steps: 1) Multiplying [CB[n] G][G1], ) multiplying [CB[n] G1][G], and 3) dividing the two results. Substituting (σ[cb[n] G] / [CB[n] G]) = 0.03 and (σ[g1]/[g1]) = 0.03 into equation 9 gives equation 10 and an uncertainty of 4.4% for [CB[n] G][G1] (equation 11). Similarly, the uncertainty of [CB[n] G1][G] is 4.4%. σ [CB[n] G][G1] = [CB[n] G][G1] (0.03) + (0.03) (10) σ [CB[n] G][G1] [CB[n] G][G1] = (11) With the two values of the uncertainties of [CB[n] G][G1] and [CB[n] G1][G] (4.4%) in hand we next substituted these values into equation 9 to give the uncertainty in K rel (eq. 1 13) of 6%. σ Krel K rel = σ [CB[n] G][G1] [CB[n] G1][G] [CB[n] G][G1] [CB[n] G1][G] = (0.044) + (0.044) (1) σ Krel K rel = 0.06 (13) Step 3 Determination of the Uncertainty in the K a value for CB[7] 5. We obtained an uncertainty in the value of K a for CB[7] 5 (K a = 8.07 ± 0.60 x 10 4 M -1 ) (7.43 %) from the nonlinear least squares fit of the UV/Vis titration data to a 1:1 binding model. Step 4 Determination of K a for CB[7] 1 by competition of 5 and 1 for a limiting quantity of CB[7]. We used 1 H NMR competition experiments to determine K rel = 5.5 for these two guests. Substitution of K CB[7] 5 = M -1 and K rel into equation 14 gave K CB[7] 1 = M -1 (equation 15). The uncertainty in K CB[7] 1 can be determined using equation 16. Substituting σ(k CB[7] 5 )/K CB[7] 5 = and σ(k rel )/K rel = 0.10 [Note that we are using the even more conservative 10% error in this analysis] gives the percent error in K CB[7] 1 (equation 17). Substituting eq. 15 into eq. 17 gives σ(k CB[7] 5 ) (equation 18) which can be combined with eq. 15 to give a final value for K CB[7] 1 (equation 19). K G = (K G1 )(K rel ) (14) K CB[7] 1 = M -1 (15) σ KCB[7] 1 K CB[7] 1 = σ K CB[7] 5 K CB[7] 5 + σ Krel K rel (16) σ KCB[7] 1 = (1.46%) K CB[7] 1 (17) S5

26 σ K = (0.146) (1.8 x 10 7 M -1 ) =. x 10 6 M -1 CB[7] 1 (18) K CB[7] 1 = 1.8 ± M -1 (19) Step 5 Determination of K a for CB[7] 19 by competition of 1 and 19 for a limiting quantity of CB[7]. We used 1 H NMR competition experiments to determine K rel = 48.8 for these two guests. Substitution of K CB[7] 1 = 1.8 ± M -1 and K rel into equation 0 gave K CB[7] 19 = M -1 (equation 1). The uncertainty in K CB[7] 19 can be determined using equation. Substituting σ(k CB[7] 1 )/K CB[7] 1 = and σ(k rel )/K rel = 0.10 gives the percent error in K CB[7] 19 (15.97%, equation 3). Substituting eq. 1 into eq. 3 gives σ(k CB[7] 19 ) (equation 4) which can be combined with eq. 1 to give a final value for K CB[7] 19 (equation 5) K CB[7] 19 = (K CB[7] 1 )(K rel ) (0) K CB[7] 19 = M -1 (1) σ KCB[7] 19 K CB[7] 19 = σ K CB[7] 1 K CB[7] 1 + σ Krel K rel () σ KCB[7] 19 = (15.97%) K CB[7] 19 (3) σ K = (0.1597) (8.88 x 10 8 M -1 ) = 1.41 x 10 8 M -1 CB[7] 19 (4) K CB[7] 19 = 8.88 ± M -1 (5) Step 6 Determination of K a for CB[7] 1 by competition of 19 and 1 for a limiting quantity of CB[7]. We used 1 H NMR competition experiments to determine K rel = 37 for these two guests. Substitution of K CB[7] 19 = 8.88 ± M -1 and K rel into equation 6 gave K CB[7] 1 = M -1 (equation 7). The uncertainty in K CB[7] 1 can be determined using equation 8. Substituting σ(k CB[7] 19 )/K CB[7] 19 = and σ(k rel )/K rel = 0.10 gives the percent error in K CB[7] 1 (18.84%, equation 9). Substituting eq. 7 into eq. 9 gives σ(k CB[7] 1 ) (equation 30) which can be combined with eq. 7 to give a final value for K CB[7] 1 (equation 31) K CB[7] 1 = (K CB[7] 19 )(K rel ) (6) K CB[7] 1 = M -1 (7) σ KCB[7] 1 K CB[7] 1 = σ K CB[7] 19 K CB[7] 19 + σ Krel K rel (8) σ KCB[7] 1 = (18.84%) K CB[7] 1 (9) σ K = (0.1884) (3.31 x M -1 ) = 0.6 x M -1 CB[7] 1 (30) K CB[7] 1 = 3.31 ± M -1 (31) Step 7 Determination of K a for CB[7] 4 by competition of 1 and 4 for a limiting quantity of CB[7]. We used 1 H NMR competition experiments to determine K rel = 5.98 for these two guests. Substitution of K CB[7] 1 = 3.31 ± M -1 and K rel into equation 3 gave K CB[7] 4 = M -1 (equation 33). The uncertainty in K CB[7] 4 can be determined using equation 34. S6

27 Substituting σ(k CB[7] 1 )/K CB[7] 1 = and σ(k rel )/K rel = 0.10 gives the percent error in K CB[7] 4 (1.33%, equation 35). Substituting eq. 33 into eq. 35 gives σ(k CB[7] 4 ) (equation 36) which can be combined with eq. 35 to give a final value for K CB[7] 1 (equation 37) K CB[7] 4 = (K CB[7] 1 )(K rel ) (3) K CB[7] 4 = M -1 (33) σ KCB[7] 4 K CB[7] 4 = σ K CB[7] 1 K CB[7] 1 + σ Krel K rel (34) σ KCB[7] 4 = (1.33%) K CB[7] 4 (35) σ K = (0.133) (1.98 x 10 1 M -1 ) = 4. x M -1 CB[7] 4 (36) K CB[7] 4 = 1.98 ± M -1 (37) S7

Supporting Information for the Article Entitled

Supporting Information for the Article Entitled Supporting Information for the Article Entitled Catalytic Production of Isothiocyanates via a Mo(II) / Mo(IV) Cycle for the Soft Sulfur Oxidation of Isonitriles authored by Wesley S. Farrell, Peter Y.

More information

Recognition Properties of Acyclic Glycoluril Oligomers. Supporting Information

Recognition Properties of Acyclic Glycoluril Oligomers. Supporting Information Recognition Properties of Acyclic Glycoluril Oligomers Supporting Information by Derick Lucas and Lyle Isaacs* Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742 Table

More information

A Clipped [3]Rotaxane Derived From Bis-nor-seco-Cucurbit[10]uril

A Clipped [3]Rotaxane Derived From Bis-nor-seco-Cucurbit[10]uril A Clipped [3]Rotaxane Derived From Bis-nor-seco-Cucurbit[10]uril Supplementary Information by James B. Wittenberg, Matthew G. Costales, Peter Y. Zavalij, and Lyle Isaacs* Department of Chemistry and Biochemistry,

More information

Supporting Information. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper*

Supporting Information. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper* Supporting Information Regioselective base-mediated cyclizations of mono-n-acylpropargylguanadines. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper* * Department of Chemistry, University

More information

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK 73019-5251 Sample: KP-XI-cinnamyl-chiral alcohol Lab ID: 12040 User:

More information

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK

Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK 73019-5251 Sample: KP-XI-furan-enzymatic alcohol Lab ID: 12042 User:

More information

Supporting Information Strong Luminescent Copper(I)-halide Coordination Polymers and Dinuclear Complexes with Thioacetamide and N,N-donor ligands

Supporting Information Strong Luminescent Copper(I)-halide Coordination Polymers and Dinuclear Complexes with Thioacetamide and N,N-donor ligands Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Supporting Information Strong Luminescent Copper(I)-halide Coordination Polymers and Dinuclear

More information

Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin

Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin Page S16 Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin Tarek Sammakia,* Deidre M. Johns, Ganghyeok Kim, and Martin

More information

CALIFORNIA INSTITUTE OF TECHNOLOGY BECKMAN INSTITUTE X-RAY CRYSTALLOGRAPHY LABORATORY

CALIFORNIA INSTITUTE OF TECHNOLOGY BECKMAN INSTITUTE X-RAY CRYSTALLOGRAPHY LABORATORY APPENDIX F Crystallographic Data for TBA Tb(DO2A)(F-DPA) CALIFORNIA INSTITUTE OF TECHNOLOGY BECKMAN INSTITUTE X-RAY CRYSTALLOGRAPHY LABORATORY Date 11 January 2010 Crystal Structure Analysis of: MLC23

More information

Synthetic, Structural, and Mechanistic Aspects of an Amine Activation Process Mediated at a Zwitterionic Pd(II) Center

Synthetic, Structural, and Mechanistic Aspects of an Amine Activation Process Mediated at a Zwitterionic Pd(II) Center Synthetic, Structural, and Mechanistic Aspects of an Amine Activation Process Mediated at a Zwitterionic Pd(II) Center Supporting Information Connie C. Lu and Jonas C. Peters* Division of Chemistry and

More information

Copyright WILEY-VCH Verlag GmbH, D Weinheim, 2000 Angew. Chem Supporting Information For Binding Cesium Ion with Nucleoside Pentamers.

Copyright WILEY-VCH Verlag GmbH, D Weinheim, 2000 Angew. Chem Supporting Information For Binding Cesium Ion with Nucleoside Pentamers. Copyright WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2000 Angew. Chem. 2000 Supporting Information For Binding Cesium Ion with Nucleoside Pentamers. Templated Self-Assembly of an Isoguanosine Decamer.**

More information

Supporting Information for A Janus-type Bis(maloNHC) and its Zwitterionic Gold and Silver Metal Complexes

Supporting Information for A Janus-type Bis(maloNHC) and its Zwitterionic Gold and Silver Metal Complexes Supporting Information for A Janus-type Bis(maloNHC) and its Zwitterionic Gold and Silver Metal Complexes Ashley Carter, Alexander Mason, Michael A. Baker, Donald G. Bettler, Angelo Changas, Colin D. McMillen,

More information

Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (-)-GSK

Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (-)-GSK Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (-)-GSK1360707 Vassil I. Elitzin, Kimberly A. Harvey, Hyunjung Kim, Matthew Salmons, Matthew J. Sharp*, Elie

More information

Orthorhombic, Pbca a = (3) Å b = (15) Å c = (4) Å V = (9) Å 3. Data collection. Refinement

Orthorhombic, Pbca a = (3) Å b = (15) Å c = (4) Å V = (9) Å 3. Data collection. Refinement organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N 0 -(3,4-Dimethylbenzylidene)furan-2- carbohydrazide Yu-Feng Li a and Fang-Fang Jian b * a Microscale Science

More information

APPENDIX E. Crystallographic Data for TBA Eu(DO2A)(DPA) Temperature Dependence

APPENDIX E. Crystallographic Data for TBA Eu(DO2A)(DPA) Temperature Dependence APPENDIX E Crystallographic Data for TBA Eu(DO2A)(DPA) Temperature Dependence Temperature Designation CCDC Page 100 K MLC18 761599 E2 200 K MLC17 762705 E17 300 K MLC19 763335 E31 E2 CALIFORNIA INSTITUTE

More information

Supporting Information

Supporting Information Submitted to Cryst. Growth Des. Version 1 of August 22, 2007 Supporting Information Engineering Hydrogen-Bonded Molecular Crystals Built from 1,3,5-Substituted Derivatives of Benzene: 6,6',6''-(1,3,5-Phenylene)tris-1,3,5-triazine-2,4-diamines

More information

Sigma Bond Metathesis with Pentamethylcyclopentadienyl Ligands in Sterically. Thomas J. Mueller, Joseph W. Ziller, and William J.

Sigma Bond Metathesis with Pentamethylcyclopentadienyl Ligands in Sterically. Thomas J. Mueller, Joseph W. Ziller, and William J. Sigma Bond Metathesis with Pentamethylcyclopentadienyl Ligands in Sterically Crowded (C 5 Me 5 ) 3 M Complexes Thomas J. Mueller, Joseph W. Ziller, and William J. Evans * Department of Chemistry, University

More information

Supporting Information. for. Advanced Functional Materials, adfm Wiley-VCH 2007

Supporting Information. for. Advanced Functional Materials, adfm Wiley-VCH 2007 Supporting Information for Advanced Functional Materials, adfm.200601202 Wiley-VCH 2007 69451 Weinheim, Germany [Supporting Information] Optical Sensor Based on Nanomaterial for the Selective Detection

More information

Structure Report for J. Reibenspies

Structure Report for J. Reibenspies X-ray Diffraction Laboratory Center for Chemical Characterization and Analysis Department of Chemistry Texas A & M University Structure Report for J. Reibenspies Project Name: Sucrose Date: January 29,

More information

Supporting Information

Supporting Information Supporting Information Methanetrisamidines in Coordination Chemistry - Syntheses, Structures and CH-NH Tautomerism Benjamin Gutschank, Stephan Schulz,* Dieter Bläser and Christoph Wölper Crystallographic

More information

Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of ( )-9a-epi-Hippocasine

Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of ( )-9a-epi-Hippocasine Supporting Information for: Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of ( )-9a-epi-Hippocasine Sílvia Alujas-Burgos, Cristina Oliveras-González, Ángel Álvarez-Larena, Pau

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2016 Supporting Information Over or under: Hydride attack at the metal versus the coordinated

More information

Electronic Supplementary Information for: Gram-scale Synthesis of a Bench-Stable 5,5 -Unsubstituted Terpyrrole

Electronic Supplementary Information for: Gram-scale Synthesis of a Bench-Stable 5,5 -Unsubstituted Terpyrrole Electronic Supplementary Information for: Gram-scale Synthesis of a Bench-Stable 5,5 -Unsubstituted Terpyrrole James T. Brewster II, a Hadiqa Zafar, a Matthew McVeigh, a Christopher D. Wight, a Gonzalo

More information

Ethylene Trimerization Catalysts Based on Chromium Complexes with a. Nitrogen-Bridged Diphosphine Ligand Having ortho-methoxyaryl or

Ethylene Trimerization Catalysts Based on Chromium Complexes with a. Nitrogen-Bridged Diphosphine Ligand Having ortho-methoxyaryl or Ethylene Trimerization Catalysts Based on Chromium Complexes with a Nitrogen-Bridged Diphosphine Ligand Having ortho-methoxyaryl or ortho-thiomethoxy Substituents: Well Defined Catalyst Precursors and

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Poly[tetra-l-cyanido-dipyridinecadmium(II)zinc(II)] Sheng Li,* Kun Tang and Fu-Li Zhang College of Medicine,

More information

Decomposition of Ruthenium Olefin Metathesis. Catalysts

Decomposition of Ruthenium Olefin Metathesis. Catalysts Supporting Information for: Decomposition of Ruthenium Olefin Metathesis Catalysts Soon Hyeok Hong, Anna G. Wenzel, Tina T. Salguero, Michael W. Day and Robert H. Grubbs* The Arnold and Mabel Beckman Laboratory

More information

b = (13) Å c = (13) Å = (2) V = (19) Å 3 Z =2 Data collection Refinement

b = (13) Å c = (13) Å = (2) V = (19) Å 3 Z =2 Data collection Refinement organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 b = 12.4861 (13) Å c = 12.9683 (13) Å = 90.748 (2) V = 1051.10 (19) Å 3 Z =2 Mo K radiation = 3.87 mm 1 T = 193

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 = 86.130 (2) = 81.155 (2) = 76.289 (3) V = 699.69 (4) Å 3 Z =2 Mo K radiation = 1.58 mm 1 T = 293 (2) K

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Dichloridotris(trimethylphosphine)- nickel(ii) Ruixia Cao, Qibao Wang and Hongjian Sun* School of Chemistry

More information

Supporting Information for

Supporting Information for Supporting Information for Tris(carbene)borate ligands featuring imidazole-2-ylidene, benzimidazol-2-ylidene and 1,3,4-triazol-2-ylidene donors. Evaluation of donor properties in four-coordinate {NiNO}

More information

Supplementary Information. Single Crystal X-Ray Diffraction

Supplementary Information. Single Crystal X-Ray Diffraction Supplementary Information Single Crystal X-Ray Diffraction Single crystal diffraction data were collected on an Oxford Diffraction Gemini R Ultra diffractometer equipped with a Ruby CCD-detector with Mo-K

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2015 Supporting Information Single-Crystal-to-Single-Crystal Transformation of an Anion Exchangeable

More information

Supporting Information

Supporting Information Supporting Information One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations Moumita Jash, Bimolendu Das, and Chinmay Chowdhury* Organic & dicinal Chemistry Division,

More information

Supporting Information

Supporting Information Selective Hg 2+ sensing behaviors of rhodamine derivatives with extended conjugation based on two successive ring-opening processes Chunyan Wang a,b and Keith Man-Chung Wong a,b * a Department of Chemistry,

More information

Efficient, scalable and solvent-free mechanochemical synthesis of the OLED material Alq 3 (q = 8-hydroxyquinolinate) Supporting Information

Efficient, scalable and solvent-free mechanochemical synthesis of the OLED material Alq 3 (q = 8-hydroxyquinolinate) Supporting Information Efficient, scalable and solvent-free mechanochemical synthesis of the OLED material Alq 3 (q = 8-hydroxyquinolinate) Xiaohe Ma, Gin Keat Lim, Kenneth D.M. Harris, David C. Apperley, Peter N. Horton, Michael

More information

SUPPLEMENTARY MATERIAL

SUPPLEMENTARY MATERIAL 10.1071/CH16716_AC CSIRO 2017 Australian Journal of Chemistry 2017, 70(5), 601-607 SUPPLEMENTARY MATERIAL New Heterodinuclear Zn/Ln (Ln = Gd, Tb, Er, Yb) Complexes of Hexadentate N,N -Bis(3-alkoxy-2-hydroxybenzyl)cyclohexane-

More information

electronic reprint 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited David Shin and Peter Müller

electronic reprint 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited David Shin and Peter Müller Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Editors: W.T. A. Harrison, H. Stoeckli-Evans, E. R.T. Tiekink and M. Weil 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited

More information

Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex.

Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex. Reversible 1,2-Alkyl Migration to Carbene and Ammonia Activation in an NHC-Zirconium Complex. Emmanuelle Despagnet-Ayoub, Michael K. Takase, Jay A. Labinger and John E. Bercaw Contents 1. Experimental

More information

White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule

White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule www.sciencemag.org/cgi/content/full/324/5935/1697/dc1 Supporting Online Material for White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule Prasenjit Mal, Boris Breiner, Kari Rissanen,

More information

Synthesis, Characterization and Reactivities of Molybdenum and Tungsten PONOP Pincer Complexes

Synthesis, Characterization and Reactivities of Molybdenum and Tungsten PONOP Pincer Complexes Synthesis, Characterization and Reactivities of Molybdenum and Tungsten PONOP Pincer Complexes Ruth Castro-Rodrigo, Sumit Chakraborty, Lloyd Munjanja, William W. Brennessel, and William D. Jones* Department

More information

= (1) V = (12) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

= (1) V = (12) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 S-Benzylisothiouronium nitrate P. Hemalatha a and V. Veeravazhuthi b * a Department of Physics, PSG College of

More information

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol

Total Synthesis of Gonytolides C and G, Lachnone C, and. Formal Synthesis of Blennolide C and Diversonol . This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry Total Synthesis of Gonytolides C and G, Lachnone C, and Formal Synthesis

More information

Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 92 parameters

Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 92 parameters organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1,1 0 -(Butane-1,4-diyl)dipyridinium dibromide dihydrate Ming-Qiang Wu, a Xin Xiao, a Yun-Qian Zhang, a * Sai-Feng

More information

Supporting Information. Table of Contents

Supporting Information. Table of Contents Supporting Information Cyclo-P 3 Complexes of Vanadium. Redox Properties and Origin of the 31 P NMR Chemical Shift. Balazs Pinter,, Kyle T. Smith, Masahiro Kamitani, Eva M. Zolnhofer,ǁ Ba L. Tran, Skye

More information

Understanding the relationship between crystal structure, plasticity and compaction behavior of theophylline, methyl gallate and their 1:1 cocrystal

Understanding the relationship between crystal structure, plasticity and compaction behavior of theophylline, methyl gallate and their 1:1 cocrystal Understanding the relationship between crystal structure, plasticity and compaction behavior of theophylline, methyl gallate and their 1:1 cocrystal Sayantan Chattoraj, Limin Shi and Changquan Calvin Sun

More information

Manganese-Calcium Clusters Supported by Calixarenes

Manganese-Calcium Clusters Supported by Calixarenes Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Manganese-Calcium Clusters Supported by Calixarenes Rebecca O. Fuller, George A. Koutsantonis*,

More information

Supplementary Materials for

Supplementary Materials for advances.sciencemag.org/cgi/content/full/3/5/e1603193/dc1 Supplementary Materials for Molecular surgery on a 23-gold-atom nanoparticle Qi Li, Tian-Yi Luo, Michael G. Taylor, Shuxin Wang, Xiaofan Zhu, Yongbo

More information

Supporting Information. Table of Contents

Supporting Information. Table of Contents Supporting Information Selective Anion Exchange and Tunable Luminescent Behaviors of Metal-Organic Framework Based Supramolecular Isomers Biplab Manna, Shweta Singh, Avishek Karmakar, Aamod V.Desai and

More information

oligomerization to polymerization of 1-hexene catalyzed by an NHC-zirconium complex

oligomerization to polymerization of 1-hexene catalyzed by an NHC-zirconium complex Mechanistic insights on the controlled switch from oligomerization to polymerization of 1-hexene catalyzed by an NHC-zirconium complex Emmanuelle Despagnet-Ayoub, *,a,b Michael K. Takase, c Lawrence M.

More information

Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol

Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol Nickel-Mediated Stepwise Transformation of CO to Acetaldehyde and Ethanol Ailing Zhang, Sakthi Raje, Jianguo Liu, Xiaoyan Li, Raja Angamuthu, Chen-Ho Tung, and Wenguang Wang* School of Chemistry and Chemical

More information

(+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate

(+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate From the SelectedWorks of Kraig A. Wheeler 2009 (+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate Sara A. Reeb, Eastern Illinois University Marlesa C. Shields, Eastern Illinois University Kraig A. Wheeler,

More information

High-Throughput in Chemical Crystallography from an industrial point of view

High-Throughput in Chemical Crystallography from an industrial point of view High-Throughput in Chemical Crystallography from an industrial point of view Ina Dix Novartis Institutes for Biomedical Research, Basel Analytics at Novartis (Basel) staff # spectra NMR 8 10.000 1.500

More information

= (8) V = (8) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

= (8) V = (8) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1-(3-Amino-1H-inden-2-yl)ethanone Dong-Yue Hu and Zhi-Rong Qu* Ordered Matter Science Research Center, College

More information

International Journal of Innovative Research in Science, Engineering and Technology. (An ISO 3297: 2007 Certified Organization)

International Journal of Innovative Research in Science, Engineering and Technology. (An ISO 3297: 2007 Certified Organization) ISSN(Online) 2319-8753 ISSN (Print) 2347-6710 (An ISO 3297 2007 Certified Organization) Website www.ijirset.com X-Ray Crystallographic Investigation and Crystal Structure of 6-(2-Hydroxy-4,6- dimethyl-phenyl)-4-(2-methoxy-phenyl)5-

More information

,

, 2013. 54, 6. 1115 1120 UDC 548.737:547.12 CHARACTERIZATION AND CRYSTAL STRUCTURES OF SOLVATED N -(4-HYDROXY-3-NITROBENZYLIDENE)-3-METHYLBENZOHYDRAZIDE AND N -(4-DIMETHYLAMINOBENZYLIDENE)-3-METHYLBENZOHYDRAZIDE

More information

Reversible dioxygen binding on asymmetric dinuclear rhodium centres

Reversible dioxygen binding on asymmetric dinuclear rhodium centres Electronic Supporting Information for Reversible dioxygen binding on asymmetric dinuclear rhodium centres Takayuki Nakajima,* Miyuki Sakamoto, Sachi Kurai, Bunsho Kure, Tomoaki Tanase* Department of Chemistry,

More information

1,4-Dihydropyridyl Complexes of Magnesium: Synthesis by Pyridine. Insertion into the Magnesium-Silicon Bond of Triphenylsilyls and

1,4-Dihydropyridyl Complexes of Magnesium: Synthesis by Pyridine. Insertion into the Magnesium-Silicon Bond of Triphenylsilyls and Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information 1,4-Dihydropyridyl Complexes of Magnesium: Synthesis

More information

Cu(I)-MOF: naked-eye colorimetric sensor for humidity and. formaldehyde in single-crystal-to-single-crystal fashion

Cu(I)-MOF: naked-eye colorimetric sensor for humidity and. formaldehyde in single-crystal-to-single-crystal fashion Supporting Information for Cu(I)-MOF: naked-eye colorimetric sensor for humidity and formaldehyde in single-crystal-to-single-crystal fashion Yang Yu, Xiao-Meng Zhang, Jian-Ping Ma, Qi-Kui Liu, Peng Wang,

More information

organic papers Acetone (2,6-dichlorobenzoyl)hydrazone: chains of p-stacked hydrogen-bonded dimers Comment Experimental

organic papers Acetone (2,6-dichlorobenzoyl)hydrazone: chains of p-stacked hydrogen-bonded dimers Comment Experimental organic papers Acta Crystallographica Section E Structure Reports Online Acetone (2,6-dichlorobenzoyl)hydrazone: chains of p-stacked hydrogen-bonded dimers ISSN 1600-5368 Solange M. S. V. Wardell, a Marcus

More information

Microporous Manganese Formate: A Simple Metal-Organic Porous Material with High Framework Stability and Highly Selective Gas Sorption Properties

Microporous Manganese Formate: A Simple Metal-Organic Porous Material with High Framework Stability and Highly Selective Gas Sorption Properties Supporting Information Microporous Manganese Formate: A Simple Metal-Organic Porous Material with High Framework Stability and Highly Selective Gas Sorption Properties Danil N. Dybtsev, Hyungphil Chun,

More information

Juan Manuel Herrera, Enrique Colacio, Corine Mathonière, Duane Choquesillo-Lazarte, and Michael D. Ward. Supporting information

Juan Manuel Herrera, Enrique Colacio, Corine Mathonière, Duane Choquesillo-Lazarte, and Michael D. Ward. Supporting information Cyanide-bridged tetradecanuclear Ru II 3M II 11 clusters (M II = Zn II and Cu II ) based on the high connectivity building block [Ru 3 (HAT)(CN) 12 ] 6+ : structural and photophysical properties Juan Manuel

More information

Eur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2013 ISSN SUPPORTING INFORMATION

Eur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2013 ISSN SUPPORTING INFORMATION Eur. J. Inorg. Chem. 2013 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 ISSN 1099 0682 SUPPORTING INFORMATION DOI: 10.1002/ejic.201300309 Title: Hydrogen Evolution Catalyzed by Aluminum-Bridged

More information

Reaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O 2

Reaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O 2 Electronic Supplementary Information for: Reaction Landscape of a Pentadentate N5-Ligated Mn II Complex with O - and H O Includes Conversion of a Peroxomanganese(III) Adduct to a Bis(µ- O)dimanganese(III,IV)

More information

Electronic Supplementary Information (ESI)

Electronic Supplementary Information (ESI) Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supplementary Information (ESI) A Large Spin, Magnetically Anisotropic, Octanuclear

More information

Supplementary File. Modification of Boc-protected CAN508 via acylation and Suzuki-Miyaura Coupling

Supplementary File. Modification of Boc-protected CAN508 via acylation and Suzuki-Miyaura Coupling Supplementary File Modification of Boc-protected CA508 via acylation and Suzuki-Miyaura Coupling Martin Pisár, Eva Schütznerová 2, Filip Hančík, Igor Popa 3, Zdeněk Trávníček 3 and Petr Cankař, * Department

More information

Electronic Supplementary Information (ESI)

Electronic Supplementary Information (ESI) Electronic Supplementary Information (ESI) S1 Experimental Section: Materials and methods: All commercially available chemicals were used as supplied without further purification. The Q[5] was synthesized

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2009 69451 Weinheim, Germany Total Synthesis of Spirastrellolide F thyl Ester Part 2: Macrocyclization and Completion of the Synthesis** Stefan Benson, Marie-Pierre Collin,

More information

Supporting information. (+)- and ( )-Ecarlottones, Uncommon Chalconoids. from Fissistigma latifolium with Proapoptotic

Supporting information. (+)- and ( )-Ecarlottones, Uncommon Chalconoids. from Fissistigma latifolium with Proapoptotic Supporting information (+)- and ( )-Ecarlottones, Uncommon Chalconoids from Fissistigma latifolium with Proapoptotic Activity Charlotte Gény, Alma Abou Samra, Pascal Retailleau, Bogdan I. Iorga, Hristo

More information

Synthesis, Structure and Reactivity of O-Donor Ir(III) Complexes: C-H Activation Studies with Benzene

Synthesis, Structure and Reactivity of O-Donor Ir(III) Complexes: C-H Activation Studies with Benzene Synthesis, Structure and Reactivity of O-Donor Ir(III) Complexes: C-H Activation Studies with Benzene Gaurav Bhalla, Xiang Yang Liu, Jonas Oxgaard, William A. Goddard, III, Roy A. Periana* Loker Hydrocarbon

More information

Z =8 Mo K radiation = 0.35 mm 1. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections

Z =8 Mo K radiation = 0.35 mm 1. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 4-Amino-3-(4-pyridyl)-1,2,4-triazole- 5(4H)-thione Fang Zou, Wei-Min Xuan, Xue-Ming Fang and Hui Zhang* State

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Tetraaquabis(nicotinamide-jN 1 )nickel(ii) bis(2-fluorobenzoate) Tuncer Hökelek, a * Hakan Dal, b Barış

More information

Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra*

Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra* Supporting Information Ferrocenyl BODIPYs: Synthesis, Structure and Properties Prabhat Gautam, Bhausaheb Dhokale, Shaikh M. Mobin and Rajneesh Misra* Department of Chemistry, Indian Institute of Technology

More information

Magnetic Ordering in TCNQ-Based Metal-Organic Frameworks With Host-Guest Interactions

Magnetic Ordering in TCNQ-Based Metal-Organic Frameworks With Host-Guest Interactions Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers. This journal is the Partner Organisations 215 Magnetic Ordering in TCNQ-Based Metal-Organic Frameworks With Host-Guest Interactions

More information

Fluorous Metal Organic Frameworks with Superior Adsorption and Hydrophobic Properties toward Oil Spill Cleanup and Hydrocarbon Storage

Fluorous Metal Organic Frameworks with Superior Adsorption and Hydrophobic Properties toward Oil Spill Cleanup and Hydrocarbon Storage SUPPORTING INFORMATION Fluorous Metal Organic Frameworks with Superior Adsorption and Hydrophobic Properties toward Oil Spill Cleanup and Hydrocarbon Storage Chi Yang, a Ushasree Kaipa, a Qian Zhang Mather,

More information

Electronic Supplementary Information for: Effect of 1,3-adamantane bridging units within the surrounding macrocycle of squaraine rotaxanes

Electronic Supplementary Information for: Effect of 1,3-adamantane bridging units within the surrounding macrocycle of squaraine rotaxanes 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 2014 Electronic Supplementary Information

More information

Spain c Departament de Química Orgànica, Universitat de Barcelona, c/ Martí I Franqués 1-11, 08080, Barcelona, Spain.

Spain c Departament de Química Orgànica, Universitat de Barcelona, c/ Martí I Franqués 1-11, 08080, Barcelona, Spain. a Institute of Chemical Research of Catalonia, Av. Països Catalans, 16, 43007 Tarragona, Spain. b Departament de Química, Universitat Autònoma de Barcelona, Cerdanyola del Vallès, E-08193 Barcelona, Spain

More information

Oxidation of cobalt(ii) bispidine complexes with dioxygen

Oxidation of cobalt(ii) bispidine complexes with dioxygen 10.1071/CH16674_AC CSIRO 2017 1 2 3 Australian Journal of Chemistry 2017, 70(5), 576-580 Supplementary Material Oxidation of cobalt(ii) bispidine complexes with dioxygen 4 5 6 Peter Comba *, Bianca Pokrandt

More information

Supplementary Figure S1 a, wireframe view of the crystal structure of compound 11. b, view of the pyridinium sites. c, crystal packing of compound

Supplementary Figure S1 a, wireframe view of the crystal structure of compound 11. b, view of the pyridinium sites. c, crystal packing of compound a b c Supplementary Figure S1 a, wireframe view of the crystal structure of compound 11. b, view of the pyridinium sites. c, crystal packing of compound 11. 1 a b c Supplementary Figure S2 a, wireframe

More information

Electronic Supplementary Information

Electronic Supplementary Information 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 Electronic Supplementary Information

More information

Supporting Information

Supporting Information Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Unmasking Representative Structures of TMP-Active Hauser and Turbo Hauser Bases Pablo García-Álvarez, David V. Graham,

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2-Oxo-1,2-dihydropyrimidin-3-ium di-l- chlorido-bis{dichloridobis[pyrimidin- 2(1H)-one-jN 3 ]cuprate(ii)}

More information

Ziessel a* Supporting Information (75 pages) Table of Contents. 1) General Methods S2

Ziessel a* Supporting Information (75 pages) Table of Contents. 1) General Methods S2 S1 Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes based on Boron Substituted Diisoindolomethene Frameworks Gilles Ulrich, a, * Sebastien Goeb a, Antoinette De Nicola a,

More information

1. X-ray crystallography

1. X-ray crystallography From Selenidostannates to Silver-Selenidostannate: Structural Variation of Chalcogenidometallates Synthesized in Ionic Liquids Jian-Rong Li a, Wei-Wei Xiong a, Zai-Lai Xie a, Cheng-Feng Du a, Guo-Dong

More information

SUPPLEMENTARY INFORMATION

SUPPLEMENTARY INFORMATION doi: 10.1038/nature05669 SUPPLEMENTARY INFORMATION Reversible Shape Changes of Molecular Crystals by Photoirradiation Seiya Kobatake 1, Shizuka Takami, Hiroaki Muto, Tomoyuki Ishikawa 1 & Masahiro Irie

More information

Synthesis of Vinyl Germylenes

Synthesis of Vinyl Germylenes Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Material for Synthesis of Vinyl Germylenes Małgorzata Walewska, Judith Baumgartner,*

More information

Supporting Information. for. Angew. Chem. Int. Ed Wiley-VCH 2004

Supporting Information. for. Angew. Chem. Int. Ed Wiley-VCH 2004 Supporting Information for Angew. Chem. Int. Ed. 246736 Wiley-VCH 24 69451 Weinheim, Germany 1 Challenges in Engineering Spin Crossover. Structures and Magnetic Properties of six Alcohol Solvates of Iron(II)

More information

Reactivity of (Pyridine-Diimine)Fe Alkyl Complexes with Carbon Dioxide. Ka-Cheong Lau, Richard F. Jordan*

Reactivity of (Pyridine-Diimine)Fe Alkyl Complexes with Carbon Dioxide. Ka-Cheong Lau, Richard F. Jordan* Supporting Information for: Reactivity of (Pyridine-Diimine)Fe Alkyl Complexes with Carbon Dioxide Ka-Cheong Lau, Richard F. Jordan* Department of Chemistry, The University of Chicago, 5735 South Ellis

More information

Supporting information for Eddaoudi et al. (2002) Proc. Natl. Acad. Sci. USA 99 (8), ( /pnas ) Supporting Information

Supporting information for Eddaoudi et al. (2002) Proc. Natl. Acad. Sci. USA 99 (8), ( /pnas ) Supporting Information Supporting information for Eddaoudi et al. (2002) Proc. Natl. Acad. Sci. USA 99 (8), 4900 4904. (10.1073/pnas.082051899) Supporting Information Table 1. Syntheses of MOF-102 112 MOFn MOF- 102 Link and

More information

CIF access. Redetermination of biphenylene at 130K. R. Boese, D. Bläser and R. Latz

CIF access. Redetermination of biphenylene at 130K. R. Boese, D. Bläser and R. Latz CIF access Acta Cryst. (1999). C55, IUC9900067 [ doi:10.1107/s0108270199099163 ] Redetermination of biphenylene at 130K R. Boese, D. Bläser and R. Latz Abstract Biphenylene is one of the key compounds

More information

Supporting Information

Supporting Information Supporting Information for Gold(I) Alkynyls Supported by Mono- and Bidentate NHC Ligands: Luminescence and Isolation of Unprecedented Ionic Complexes Alexander A. Penney, Galina L. Starova, Elena V. Grachova,

More information

Scandium and Yttrium Metallocene Borohydride Complexes: Comparisons of (BH 4 ) 1 vs (BPh 4 ) 1 Coordination and Reactivity

Scandium and Yttrium Metallocene Borohydride Complexes: Comparisons of (BH 4 ) 1 vs (BPh 4 ) 1 Coordination and Reactivity Scandium and Yttrium Metallocene Borohydride Complexes: Comparisons of (BH 4 ) 1 vs (BPh 4 ) 1 Coordination and Reactivity Selvan Demir, Nathan A. Siladke, Joseph W. Ziller, and William J. Evans * Department

More information

UV INITIATED BUBBLE FREE FRONTAL POLYMERIZATION IN AQUEOUS

UV INITIATED BUBBLE FREE FRONTAL POLYMERIZATION IN AQUEOUS Supporting Information UV INITIATED BUBBLE FREE FRONTAL POLYMERIZATION IN AQUEOUS CONDITIONS Paul Michael Potzmann, Francisco Javier Lopez Villanueva, Robert Liska, Institute of Applied Synthetic Chemistry,

More information

Redox-Responsive Complexation between a. Pillar[5]arene with Mono ethylene oxide Substituents. and Paraquat

Redox-Responsive Complexation between a. Pillar[5]arene with Mono ethylene oxide Substituents. and Paraquat Redox-Responsive Complexation between a Pillar[5]arene with Mono ethylene oxide Substituents and Paraquat Xiaodong Chi, Min Xue, Yong Yao and Feihe Huang* MOE Key Laboratory of Macromolecular Synthesis

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Propane-1,2-diammonium bis(pyridine- 2,6-dicarboxylato-j 3 O,N,O 0 )nickelate(ii) tetrahydrate Hossein Aghabozorg,

More information

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Supporting Information Synthesis and Structures of N-Arylcyano-β-diketiminate Zinc Complexes

More information

Coordination Behaviour of Calcocene and its Use as a Synthon for Heteroleptic Organocalcium Compounds

Coordination Behaviour of Calcocene and its Use as a Synthon for Heteroleptic Organocalcium Compounds Supporting Information Coordination Behaviour of Calcocene and its Use as a Synthon for Heteroleptic Organocalcium Compounds Reinald Fischer, Jens Langer, Sven Krieck, Helmar Görls, Matthias Westerhausen*

More information

Electronic Supplementary Information. Iridium(III) phosphors with bis(diphenylphorothioyl)amide ligand for

Electronic Supplementary Information. Iridium(III) phosphors with bis(diphenylphorothioyl)amide ligand for Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 218 Electronic Supplementary Information Iridium(III) phosphors with bis(diphenylphorothioyl)amide

More information

metal-organic compounds

metal-organic compounds metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis{tris[3-(2-pyridyl)-1H-pyrazole]- zinc(ii)} dodecamolybdosilicate hexahydrate Xiutang Zhang, a,b * Peihai

More information

Direct observation of key intermediates by negative-ion electrospray ionization mass spectrometry in palladium-catalyzed cross-coupling

Direct observation of key intermediates by negative-ion electrospray ionization mass spectrometry in palladium-catalyzed cross-coupling Direct observation of key intermediates by negative-ion electrospray ionization mass spectrometry in palladium-catalyzed cross-coupling Krista L. Vikse, a Matthew A. Henderson, a Allen G. Oliver b and

More information

organic papers 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Comment

organic papers 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Comment organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Richard D. Gilardi a * and Ray J. Butcher b a Laboratory for the Structure

More information