Literature DB >> 21522267

[(1R*,2S*)-N-Benzyl-2-phenyl-1-(pyridin-2-yl)-N-(pyridin-2-ylmeth-yl)ethane-1,2-diamine]-dichloridozinc(II).

Adailton J Bortoluzzi1, Sandro L Mireski, Antonio C Joussef.   

Abstract

In the mononuclear zinc title complex, [ZnCl(2)(C(26)H(26)N(4))], the Zn(II) ion is surrounded by three N atoms from a (1R*,2S*)-N(1)-benzyl-2-phenyl-1-(pyridin-2-yl)-N(2)-(pyridin-2-ylmeth-yl)ethane-1,2-diamine (BPPPEN) ligand and two terminal chloride ligands, resulting in a highly distorted environment around the metal atom. The calculated τ parameter of 0.42 indicates that the coordination geometry is approximately square-pyramidal. Hydrogen bonds involving centrosymmetric N-H⋯Cl inter-actions form dimeric structures. The mol-ecules are stacked along the a and b axes.

Entities:  

Year:  2011        PMID: 21522267      PMCID: PMC3052059          DOI: 10.1107/S1600536811004314

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For general background to the chemistry and biological properties of vicinal diamines, see: Bennani & Hanessian (1997 ▶); Lucet et al. (1998 ▶); Fache et al. (2000 ▶); Saibabu Kottiet al. (2006) ▶ Alexakis & Andrey (2002 ▶); Andrey et al. (2003 ▶); Ma et al. (2003 ▶); Notz et al. (2004 ▶); Bassindale et al. (2004 ▶); Mealy et al. (2004 ▶). For a related structure, see: Mikata et al. (2009 ▶). For coordination geom­etries, see: Addison et al. (1984 ▶). For hydrogen bonds, see: Steiner (2002 ▶).

Experimental

Crystal data

[ZnCl2(C26H26N4)] M = 530.78 Monoclinic, a = 9.1716 (14) Å b = 28.888 (2) Å c = 10.4304 (12) Å β = 109.541 (8)° V = 2604.3 (5) Å3 Z = 4 Mo Kα radiation μ = 1.17 mm−1 T = 293 K 0.46 × 0.43 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan [PLATON (Spek, 2009 ▶); North et al. (1968 ▶)] T min = 0.615, T max = 0.751 4899 measured reflections 4632 independent reflections 2892 reflections with I > 2σ(I) R int = 0.048 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.169 S = 1.05 4632 reflections 298 parameters H-atom parameters constrained Δρmax = 0.74 e Å−3 Δρmin = −0.39 e Å−3 Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004314/zj2001sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004314/zj2001Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[ZnCl2(C26H26N4)]F(000) = 1096
Mr = 530.78Dx = 1.354 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.1716 (14) Åθ = 8.4–13.9°
b = 28.888 (2) ŵ = 1.17 mm1
c = 10.4304 (12) ÅT = 293 K
β = 109.541 (8)°Disc, colorless
V = 2604.3 (5) Å30.46 × 0.43 × 0.26 mm
Z = 4
Enraf–Nonius CAD-4 diffractometer2892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
graphiteθmax = 25.1°, θmin = 1.4°
ω–2θ scansh = −10→10
Absorption correction: ψ scan [PLATON (Spek, 2009); North et al. (1968)]k = −34→0
Tmin = 0.615, Tmax = 0.751l = −12→0
4899 measured reflections3 standard reflections every 200 reflections
4632 independent reflections intensity decay: 1%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0767P)2 + 4.3127P] where P = (Fo2 + 2Fc2)/3
4632 reflections(Δ/σ)max < 0.001
298 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = −0.39 e Å3
xyzUiso*/Ueq
Zn10.46704 (7)0.07907 (2)−0.11615 (6)0.0407 (2)
Cl10.4754 (2)0.13915 (6)−0.24916 (18)0.0689 (5)
Cl20.26694 (16)0.02852 (5)−0.17505 (17)0.0541 (4)
N10.4102 (5)0.12227 (17)0.0387 (4)0.0422 (11)
H10.40330.1480−0.01520.051*
C20.5396 (6)0.1186 (2)0.1695 (5)0.0423 (13)
H20.52780.08980.21460.051*
C30.6918 (6)0.11640 (18)0.1384 (5)0.0376 (12)
H30.69860.14470.08880.045*
N40.6810 (5)0.07700 (17)0.0455 (4)0.0412 (10)
H40.67230.04920.08410.049*
C100.2536 (7)0.1176 (2)0.0553 (6)0.0527 (16)
H10A0.21600.08630.03280.063*
H10B0.26360.12330.14960.063*
C110.1394 (7)0.1508 (2)−0.0336 (7)0.0578 (17)
C120.0595 (8)0.1409 (3)−0.1672 (8)0.073 (2)
H120.07850.1129−0.20270.088*
C13−0.0465 (11)0.1704 (4)−0.2503 (10)0.107 (3)
H13−0.10070.1622−0.33980.128*
C14−0.0720 (13)0.2124 (4)−0.1994 (14)0.126 (4)
H14−0.14100.2332−0.25620.151*
C150.0021 (14)0.2238 (4)−0.0674 (14)0.131 (4)
H15−0.01670.2521−0.03320.158*
C160.1102 (10)0.1915 (3)0.0184 (10)0.097 (3)
H160.16040.19850.10970.116*
C210.5408 (6)0.1586 (2)0.2628 (5)0.0439 (14)
N220.5383 (8)0.1999 (2)0.2084 (6)0.0710 (17)
C230.5386 (11)0.2370 (3)0.2849 (8)0.089 (3)
H230.53900.26610.24730.106*
C240.5384 (11)0.2342 (3)0.4158 (8)0.085 (2)
H240.53470.26070.46550.102*
C250.5437 (11)0.1911 (3)0.4705 (8)0.086 (2)
H250.54680.18760.56000.103*
C260.5446 (9)0.1531 (3)0.3938 (6)0.0666 (19)
H260.54780.12360.43030.080*
C310.8333 (6)0.1148 (2)0.2652 (6)0.0462 (14)
C320.9515 (8)0.1457 (3)0.2857 (8)0.081 (2)
H320.94410.16860.22110.097*
C331.0832 (10)0.1437 (4)0.4016 (10)0.103 (3)
H331.16220.16520.41460.124*
C341.0948 (10)0.1104 (4)0.4943 (9)0.094 (3)
H341.18270.10930.57150.112*
C350.9809 (9)0.0781 (3)0.4783 (7)0.082 (2)
H350.99050.05530.54360.099*
C360.8510 (7)0.0802 (2)0.3625 (6)0.0588 (16)
H360.77380.05810.34930.071*
C400.8042 (6)0.0759 (2)−0.0161 (6)0.0516 (15)
H40A0.90180.06760.05250.062*
H40B0.81540.1063−0.05110.062*
C410.7654 (6)0.0413 (2)−0.1293 (6)0.0451 (14)
N420.6161 (5)0.03297 (17)−0.1926 (5)0.0456 (12)
C430.5756 (8)0.0035 (2)−0.2951 (6)0.0565 (16)
H430.4708−0.0019−0.33920.068*
C440.6810 (9)−0.0196 (3)−0.3402 (7)0.068 (2)
H440.6488−0.0404−0.41240.082*
C450.8357 (9)−0.0108 (3)−0.2740 (7)0.070 (2)
H450.9104−0.0257−0.30110.084*
C460.8785 (7)0.0199 (2)−0.1688 (7)0.0590 (17)
H460.98250.0263−0.12410.071*
U11U22U33U12U13U23
Zn10.0376 (3)0.0438 (4)0.0395 (3)−0.0025 (3)0.0115 (2)0.0016 (3)
Cl10.0804 (12)0.0628 (11)0.0625 (10)−0.0105 (9)0.0225 (9)0.0193 (9)
Cl20.0394 (8)0.0452 (9)0.0764 (11)−0.0050 (6)0.0176 (7)−0.0015 (8)
N10.038 (3)0.051 (3)0.041 (2)0.004 (2)0.017 (2)0.001 (2)
C20.049 (3)0.042 (3)0.038 (3)0.001 (3)0.017 (3)0.004 (2)
C30.039 (3)0.034 (3)0.043 (3)−0.003 (2)0.019 (2)0.000 (2)
N40.037 (2)0.050 (3)0.038 (2)0.001 (2)0.0144 (19)−0.002 (2)
C100.046 (3)0.071 (4)0.047 (3)−0.001 (3)0.023 (3)−0.003 (3)
C110.048 (4)0.061 (4)0.072 (4)0.008 (3)0.029 (3)0.006 (4)
C120.068 (5)0.074 (5)0.073 (5)0.018 (4)0.017 (4)0.006 (4)
C130.091 (7)0.120 (9)0.097 (7)0.040 (6)0.014 (5)0.010 (6)
C140.107 (8)0.129 (10)0.133 (10)0.062 (7)0.028 (7)0.021 (8)
C150.131 (10)0.107 (9)0.165 (12)0.057 (8)0.062 (9)−0.009 (8)
C160.091 (6)0.099 (7)0.105 (7)0.026 (5)0.040 (5)−0.012 (6)
C210.049 (3)0.048 (4)0.039 (3)0.003 (3)0.020 (3)0.008 (3)
N220.121 (5)0.050 (4)0.055 (3)0.002 (3)0.047 (4)−0.001 (3)
C230.162 (9)0.037 (4)0.087 (6)0.003 (5)0.068 (6)−0.005 (4)
C240.135 (7)0.067 (5)0.070 (5)0.004 (5)0.057 (5)−0.026 (4)
C250.137 (7)0.083 (6)0.056 (4)−0.012 (5)0.059 (5)−0.007 (4)
C260.106 (6)0.055 (4)0.048 (4)−0.002 (4)0.037 (4)0.000 (3)
C310.043 (3)0.048 (4)0.048 (3)0.000 (3)0.015 (3)−0.014 (3)
C320.063 (5)0.092 (6)0.078 (5)−0.020 (4)0.013 (4)−0.011 (4)
C330.069 (6)0.134 (9)0.092 (7)−0.028 (6)0.008 (5)−0.036 (7)
C340.067 (6)0.133 (9)0.063 (5)0.011 (6)−0.002 (4)−0.032 (6)
C350.076 (5)0.108 (7)0.050 (4)0.023 (5)0.004 (4)−0.017 (4)
C360.054 (4)0.067 (4)0.048 (3)0.011 (3)0.006 (3)−0.008 (4)
C400.037 (3)0.065 (4)0.053 (3)0.000 (3)0.017 (3)−0.006 (3)
C410.042 (3)0.054 (4)0.042 (3)0.002 (3)0.017 (3)−0.004 (3)
N420.039 (3)0.056 (3)0.043 (3)0.000 (2)0.015 (2)−0.006 (2)
C430.055 (4)0.065 (4)0.047 (3)−0.007 (3)0.015 (3)−0.006 (3)
C440.082 (5)0.073 (5)0.055 (4)0.002 (4)0.030 (4)−0.013 (4)
C450.067 (5)0.088 (6)0.063 (4)0.014 (4)0.031 (4)−0.010 (4)
C460.043 (3)0.081 (5)0.056 (4)0.007 (3)0.022 (3)−0.006 (4)
Zn1—N42.118 (4)N22—C231.334 (9)
Zn1—N12.236 (4)C23—C241.369 (10)
Zn1—N422.238 (5)C23—H230.9300
Zn1—Cl12.2393 (17)C24—C251.366 (11)
Zn1—Cl22.2635 (16)C24—H240.9300
N1—C21.482 (7)C25—C261.359 (10)
N1—C101.509 (7)C25—H250.9300
N1—H10.9223C26—H260.9300
C2—C211.509 (8)C31—C321.364 (9)
C2—C31.537 (7)C31—C361.395 (9)
C2—H20.9800C32—C331.396 (11)
C3—N41.476 (7)C32—H320.9300
C3—C311.513 (8)C33—C341.342 (13)
C3—H30.9800C33—H330.9300
N4—C401.476 (7)C34—C351.369 (12)
N4—H40.9146C34—H340.9300
C10—C111.492 (9)C35—C361.386 (9)
C10—H10A0.9700C35—H350.9300
C10—H10B0.9700C36—H360.9300
C11—C161.358 (10)C40—C411.496 (8)
C11—C121.371 (10)C40—H40A0.9700
C12—C131.362 (11)C40—H40B0.9700
C12—H120.9300C41—N421.328 (7)
C13—C141.375 (14)C41—C461.384 (8)
C13—H130.9300N42—C431.318 (8)
C14—C151.356 (15)C43—C441.381 (9)
C14—H140.9300C43—H430.9300
C15—C161.436 (13)C44—C451.378 (10)
C15—H150.9300C44—H440.9300
C16—H160.9300C45—C461.362 (9)
C21—N221.318 (8)C45—H450.9300
C21—C261.365 (8)C46—H460.9300
N4—Zn1—N179.54 (16)N22—C21—C26121.9 (6)
N4—Zn1—N4275.71 (17)N22—C21—C2114.8 (5)
N1—Zn1—N42155.13 (16)C26—C21—C2123.3 (5)
N4—Zn1—Cl1107.49 (14)C21—N22—C23118.2 (6)
N1—Zn1—Cl194.56 (14)N22—C23—C24123.4 (7)
N42—Zn1—Cl195.09 (14)N22—C23—H23118.3
N4—Zn1—Cl2130.48 (14)C24—C23—H23118.3
N1—Zn1—Cl2101.09 (12)C25—C24—C23117.2 (7)
N42—Zn1—Cl293.20 (13)C25—C24—H24121.4
Cl1—Zn1—Cl2121.64 (7)C23—C24—H24121.4
C2—N1—C10112.8 (4)C26—C25—C24119.8 (7)
C2—N1—Zn1108.5 (3)C26—C25—H25120.1
C10—N1—Zn1119.6 (3)C24—C25—H25120.1
C2—N1—H1119.3C25—C26—C21119.5 (7)
C10—N1—H1105.6C25—C26—H26120.3
Zn1—N1—H189.7C21—C26—H26120.3
N1—C2—C21111.7 (4)C32—C31—C36117.5 (6)
N1—C2—C3108.2 (4)C32—C31—C3121.5 (6)
C21—C2—C3110.9 (5)C36—C31—C3121.0 (5)
N1—C2—H2108.6C31—C32—C33121.4 (9)
C21—C2—H2108.6C31—C32—H32119.3
C3—C2—H2108.6C33—C32—H32119.3
N4—C3—C31113.6 (4)C34—C33—C32119.4 (9)
N4—C3—C2107.7 (4)C34—C33—H33120.3
C31—C3—C2113.0 (4)C32—C33—H33120.3
N4—C3—H3107.4C33—C34—C35121.9 (8)
C31—C3—H3107.4C33—C34—H34119.1
C2—C3—H3107.4C35—C34—H34119.1
C3—N4—C40114.2 (4)C34—C35—C36118.3 (8)
C3—N4—Zn1110.0 (3)C34—C35—H35120.9
C40—N4—Zn1107.1 (3)C36—C35—H35120.9
C3—N4—H4112.7C35—C36—C31121.5 (7)
C40—N4—H4111.4C35—C36—H36119.2
Zn1—N4—H4100.4C31—C36—H36119.2
C11—C10—N1111.7 (5)N4—C40—C41110.1 (5)
C11—C10—H10A109.3N4—C40—H40A109.6
N1—C10—H10A109.3C41—C40—H40A109.6
C11—C10—H10B109.3N4—C40—H40B109.6
N1—C10—H10B109.3C41—C40—H40B109.6
H10A—C10—H10B108.0H40A—C40—H40B108.2
C16—C11—C12118.5 (7)N42—C41—C46121.5 (6)
C16—C11—C10119.9 (7)N42—C41—C40116.5 (5)
C12—C11—C10121.6 (6)C46—C41—C40122.0 (5)
C13—C12—C11122.8 (8)C43—N42—C41118.9 (5)
C13—C12—H12118.6C43—N42—Zn1129.3 (4)
C11—C12—H12118.6C41—N42—Zn1111.5 (4)
C12—C13—C14118.9 (10)N42—C43—C44123.3 (6)
C12—C13—H13120.6N42—C43—H43118.3
C14—C13—H13120.6C44—C43—H43118.3
C15—C14—C13121.0 (10)C45—C44—C43117.4 (6)
C15—C14—H14119.5C45—C44—H44121.3
C13—C14—H14119.5C43—C44—H44121.3
C14—C15—C16118.8 (10)C46—C45—C44119.7 (6)
C14—C15—H15120.6C46—C45—H45120.2
C16—C15—H15120.6C44—C45—H45120.2
C11—C16—C15120.0 (9)C45—C46—C41119.2 (6)
C11—C16—H16120.0C45—C46—H46120.4
C15—C16—H16120.0C41—C46—H46120.4
N4—Zn1—N1—C2−9.2 (3)C26—C21—N22—C23−0.4 (11)
N42—Zn1—N1—C2−3.6 (6)C2—C21—N22—C23179.7 (7)
Cl1—Zn1—N1—C2−116.2 (3)C21—N22—C23—C24−1.3 (14)
Cl2—Zn1—N1—C2120.3 (3)N22—C23—C24—C252.4 (15)
N4—Zn1—N1—C10−140.5 (4)C23—C24—C25—C26−1.9 (14)
N42—Zn1—N1—C10−134.9 (4)C24—C25—C26—C210.3 (13)
Cl1—Zn1—N1—C10112.5 (4)N22—C21—C26—C250.9 (11)
Cl2—Zn1—N1—C10−11.0 (4)C2—C21—C26—C25−179.3 (7)
C10—N1—C2—C21−66.1 (6)N4—C3—C31—C32110.5 (7)
Zn1—N1—C2—C21159.1 (4)C2—C3—C31—C32−126.4 (6)
C10—N1—C2—C3171.6 (5)N4—C3—C31—C36−66.3 (7)
Zn1—N1—C2—C336.7 (5)C2—C3—C31—C3656.8 (7)
N1—C2—C3—N4−56.4 (5)C36—C31—C32—C33−1.9 (11)
C21—C2—C3—N4−179.2 (4)C3—C31—C32—C33−178.8 (7)
N1—C2—C3—C31177.3 (4)C31—C32—C33—C340.7 (14)
C21—C2—C3—C3154.5 (6)C32—C33—C34—C350.2 (14)
C31—C3—N4—C40−65.8 (6)C33—C34—C35—C360.2 (13)
C2—C3—N4—C40168.2 (4)C34—C35—C36—C31−1.5 (10)
C31—C3—N4—Zn1173.7 (4)C32—C31—C36—C352.3 (9)
C2—C3—N4—Zn147.7 (5)C3—C31—C36—C35179.2 (6)
N1—Zn1—N4—C3−21.3 (3)C3—N4—C40—C41−168.0 (5)
N42—Zn1—N4—C3161.2 (4)Zn1—N4—C40—C41−46.0 (6)
Cl1—Zn1—N4—C370.3 (3)N4—C40—C41—N4227.5 (8)
Cl2—Zn1—N4—C3−117.0 (3)N4—C40—C41—C46−154.3 (6)
N1—Zn1—N4—C40−145.9 (4)C46—C41—N42—C430.2 (9)
N42—Zn1—N4—C4036.5 (4)C40—C41—N42—C43178.5 (6)
Cl1—Zn1—N4—C40−54.4 (4)C46—C41—N42—Zn1−173.9 (5)
Cl2—Zn1—N4—C40118.4 (4)C40—C41—N42—Zn14.4 (7)
C2—N1—C10—C11139.8 (5)N4—Zn1—N42—C43163.2 (6)
Zn1—N1—C10—C11−90.9 (6)N1—Zn1—N42—C43157.5 (5)
N1—C10—C11—C16−97.6 (7)Cl1—Zn1—N42—C43−90.0 (5)
N1—C10—C11—C1283.7 (8)Cl2—Zn1—N42—C4332.2 (5)
C16—C11—C12—C130.7 (13)N4—Zn1—N42—C41−23.4 (4)
C10—C11—C12—C13179.3 (8)N1—Zn1—N42—C41−29.1 (7)
C11—C12—C13—C141.7 (15)Cl1—Zn1—N42—C4183.3 (4)
C12—C13—C14—C15−2.6 (18)Cl2—Zn1—N42—C41−154.5 (4)
C13—C14—C15—C161(2)C41—N42—C43—C440.4 (10)
C12—C11—C16—C15−2.3 (13)Zn1—N42—C43—C44173.3 (5)
C10—C11—C16—C15179.0 (8)N42—C43—C44—C45−0.5 (11)
C14—C15—C16—C111.5 (17)C43—C44—C45—C46−0.1 (11)
N1—C2—C21—N22−52.8 (7)C44—C45—C46—C410.7 (11)
C3—C2—C21—N2268.1 (7)N42—C41—C46—C45−0.8 (10)
N1—C2—C21—C26127.3 (6)C40—C41—C46—C45−179.0 (6)
C3—C2—C21—C26−111.8 (7)
D—H···AD—HH···AD···AD—H···A
N4—H4···Cl2i0.912.433.304 (5)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
N4—H4⋯Cl2i0.912.433.304 (5)160

Symmetry code: (i) .

  12 in total

1.  trans-1,2-Diaminocyclohexane Derivatives as Chiral Reagents, Scaffolds, and Ligands for Catalysis: Applications in Asymmetric Synthesis and Molecular Recognition.

Authors:  Youssef L. Bennani; Stephen Hanessian
Journal:  Chem Rev       Date:  1997-12-18       Impact factor: 60.622

2.  The hydrogen bond in the solid state.

Authors:  Thomas Steiner
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-04       Impact factor: 15.336

3.  Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene.

Authors:  Alexandre Alexakis; Olivier Andrey
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

4.  Asymmetric transfer hydrogenation of prochiral ketones in aqueous media with new water-soluble chiral vicinal diamine as ligand.

Authors:  Yaping Ma; Hui Liu; Li Chen; Xin Cui; Jin Zhu; Jingen Deng
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

5.  Asymmetric Michael addition of alpha-hydroxyketones to nitroolefins catalyzed by chiral diamine.

Authors:  Olivier Andrey; Alexandre Alexakis; Gérald Bernardinelli
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

6.  Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Authors:  Wolfgang Notz; Fujie Tanaka; Carlos F Barbas
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

Review 7.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

8.  Effect of ligand structure on the asymmetric cyclization of achiral olefinic organolithiums.

Authors:  Michael J Mealy; Matthew R Luderer; William F Bailey; Michael Bech Sommer
Journal:  J Org Chem       Date:  2004-09-03       Impact factor: 4.354

9.  Bisquinoline-based fluorescent zinc sensors.

Authors:  Yuji Mikata; Azusa Yamashita; Ayano Kawamura; Hideo Konno; Yuka Miyamoto; Satoshi Tamotsu
Journal:  Dalton Trans       Date:  2009-03-27       Impact factor: 4.390

10.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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