Palladate Salts from Chiral Pyridinium Ionic Liquids: Synthesis and Crystal Structures
Abstract
:Introduction
Results and Discussion
Conclusions
Experimental
General
Synthesis of (R)– or (S)–1-phenylethylpyridinium chloride (1R and 1S)
Synthesis of (R)– or (S)–bis(1-phenylethylpyridinium) tetrachloropalladate (2R and 2S)
Crystal data for 1R and 2R
Identification code | [py*][Cl] (1R) | [py*]2[PdCl4] (2R) |
Empirical formula | C13H14.50ClNO0.25 | C26H28Cl4N2Pd |
Formula weight | 224.21 | 616.70 |
Temperature | 193(2) K | 173(2) K |
Wavelength | 0.71073 Å | 0.71073 Å |
Crystal system | Tetragonal | Orthorhombic |
Space group | P41 | P212121 |
Unit cell dimensions | a = 22.369(1) Å | a = 8.059(1) Å |
b = 22.369(1) Å | b = 12.211(1) Å | |
c = 9.570(1) Å | c = 27.872(2) Å | |
Volume | 4788.9(4) Å3 | 2742.7(3) Å3 |
Z | 16 | 4 |
Density (calculated) | 1.244 Mg/m3 | 1.494 Mg/m3 |
Absorption coefficient | 0.29 mm-1 | 1.08 mm-1 |
F(000) | 1896 | 1248 |
Crystal size | 0.5 x 0.6 x 0.6 mm3 | 0.1 x 0.1 x 0.5 mm3 |
Theta range for data collection | 5.1 to 23.3°. | 1.5 to 26.4°. |
Index ranges | -24<=h<=24
-23<=k<=24 -10<=l<=8 | -10<=h<=9 -12<=k<=15 -30<=l<=34 |
Reflections collected | 21441 | 16203 |
Independent reflections | 6428 [R(int) = 0.0184] | 5600 [R(int) = 0.0225] |
Completeness to theta | (=23.3°) 98.5 % | (=26.4°) 99.8 % |
Absorption correction | Semi-empirical | Semi-empirical |
Ratio Tmin/Tmax | 0.694 | 0.776 |
Refinement method | Full-matrix least-squares on F2 | Full-matrix least-squares on F2 |
Data / restraints / parameters | 6428 / 1 / 569 | 5600 / 0 / 300 |
Goodness-of-fit on F2 | 1.18 | 1.05 |
Final R indices [I>2sigma(I)] | R1
a = 0.070 wR2b = 0.175 | R1 = 0.021 wR2 = 0.046 |
R indices (all data) | R1 = 0.072
wR2 = 0.176 | R1 = 0.024 wR2 = 0.047 |
Absolute structure parameter | 0.00(10) | -0.019(19) |
Largest diff. peak and hole | 0.76 and -1.24 e.Å-3 | 0.30 and -0.23 e.Å-3 |
D-H...A | d(D-H) | d(H...A) | d(D...A) | <(DHA) |
C(2)-H(2B)...Cl(1) | 0.98 | 2.80 | 3.687(8) | 151 |
C(12)-H(12)...Cl(1)#1 | 0.95 | 2.75 | 3.528(7) | 139 |
C(23)-H(23)...Cl(1)#1 | 0.95 | 2.63 | 3.562(7) | 166 |
C(27)-H(27)...Cl(1) | 1.00 | 2.49 | 3.478(7) | 168 |
C(41)-H(41C)...Cl(1) | 0.98 | 2.98 | 3.944(9) | 167 |
C(44)-H(44)...Cl(1)#2 | 0.95 | 2.90 | 3.823(7) | 163 |
C(52)-H(52)...Cl(1) | 0.95 | 2.51 | 3.419(7) | 161 |
C(1)-H(1)...Cl(2) | 1.00 | 2.54 | 3.499(6) | 161 |
C(13)-H(13)...Cl(2) | 0.95 | 2.99 | 3.811(7) | 146 |
C(15)-H(15C)...Cl(2) | 0.98 | 2.96 | 3.909(8) | 162 |
C(17)-H(17)...Cl(2) | 0.95 | 2.97 | 3.914(7) | 173 |
C(22)-H(22)...Cl(2) | 0.95 | 2.52 | 3.444(7) | 165 |
C(28)-H(28B)...Cl(2)#3 | 0.98 | 2.75 | 3.665(8) | 156 |
C(38)-H(38)...Cl(2) | 0.95 | 2.80 | 3.578(7) | 139 |
C(51)-H(51)...Cl(2) | 0.95 | 2.65 | 3.540(7) | 156 |
C(14)-H(14)...Cl(3)#4 | 1.00 | 2.80 | 3.710(7) | 151 |
C(43)-H(43)...Cl(3)#5 | 0.95 | 2.80 | 3.691(7) | 157 |
C(48)-H(48)...Cl(3)#5 | 0.95 | 2.66 | 3.595(7) | 168 |
C(49)-H(49)...Cl(3) | 0.95 | 2.74 | 3.559(8) | 145 |
O(1)-H(1O)...Cl(3)#4 | 0.97(5) | 2.32(6) | 3.234(6) | 157 |
O(1)-H(2O)...Cl(3)#6 | 1.02(5) | 2.37(7) | 3.226(6) | 141 |
C(19)-H(19)...Cl(4)#7 | 0.95 | 2.90 | 3.662(7) | 137 |
C(35)-H(35)...Cl(4)#4 | 0.95 | 2.99 | 3.593(7) | 122 |
C(36)-H(36)...Cl(4) | 0.95 | 2.85 | 3.766(8) | 162 |
C(10)-H(10)...Cl(5)#6 | 0.95 | 2.82 | 3.737(8) | 163 |
C(45)-H(45)...Cl(5)#8 | 0.95 | 2.86 | 3.608(8) | 136 |
O(1)-H(2O)...Cl(3)#6 | 1.02(5) | 2.37(7) | 3.226(6) | 141 |
O(1)-H(1O)...Cl(3)#4 | 0.97(5) | 2.32(6) | 3.234(6) | 157 |
C(21)-H(21)...O(1) | 0.95 | 2.47 | 3.395(9) | 164 |
C(25)-H(25)...O(1)#9 | 0.95 | 2.88 | 3.506(9) | 124 |
C(26)-H(26)...O(1) | 0.95 | 2.75 | 3.672(9) | 164 |
C(40)-H(40)...O(1)#10 | 1.00 | 2.57 | 3.396(9) | 139 |
2R | |
---|---|
Cl(1)-Pd(1)-Cl(2) | 90.57(2) |
Cl(1)-Pd(1)-Cl(3) | 90.39(3) |
Cl(2)-Pd(1)-Cl(4) | 89.08(2) |
Cl(3)-Pd(1)-Cl(4) | 90.03(2) |
D-H...A | d(D-H) | d(H...A) | d(D...A) | <(DHA) |
C(1)-H(1)...Cl(4)#1 | 1.00 | 2.69 | 3.641(2) | 158 |
C(3)-H(3)...Cl(2)#2 | 0.95 | 2.55 | 3.463(3) | 160 |
C(5)-H(5)...Cl(4)#3 | 0.95 | 3.00 | 3.614(3) | 123 |
C(6)-H(6)...Cl(3)#3 | 0.95 | 2.72 | 3.504(3) | 140 |
C(7)-H(7)...Cl(2)#1 | 0.95 | 2.70 | 3.486(3) | 140 |
C(14)-H(14)...Cl(4)#4 | 1.00 | 2.88 | 3.744(3) | 144 |
C(16)-H(16)...Cl(1)#5 | 0.95 | 2.72 | 3.580(2) | 150 |
C(16)-H(16)...Cl(3)#5 | 0.95 | 2.73 | 3.374(3) | 126 |
C(17)-H(17)...Cl(2) | 0.95 | 2.84 | 3.559(3) | 133 |
C(18)-H(18)...Cl(1) | 0.95 | 2.77 | 3.668(3) | 157 |
C(25)-H(25)...Cl(4)#3 | 0.95 | 3.00 | 3.648(3) | 126 |
Acknowledgements
References and Notes
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Tourneux, E.; Gornitzka, H.; Marty, J.-D.; Viguerie, N.L.-d. Palladate Salts from Chiral Pyridinium Ionic Liquids: Synthesis and Crystal Structures. Molecules 2007, 12, 1940-1949. https://doi.org/10.3390/12081940
Tourneux E, Gornitzka H, Marty J-D, Viguerie NL-d. Palladate Salts from Chiral Pyridinium Ionic Liquids: Synthesis and Crystal Structures. Molecules. 2007; 12(8):1940-1949. https://doi.org/10.3390/12081940
Chicago/Turabian StyleTourneux, Emmanuel, Heinz Gornitzka, Jean-Daniel Marty, and Nancy Lauth-de Viguerie. 2007. "Palladate Salts from Chiral Pyridinium Ionic Liquids: Synthesis and Crystal Structures" Molecules 12, no. 8: 1940-1949. https://doi.org/10.3390/12081940