Synthetic strategy for the incorporation of Bu2Sn(IV) into fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones and spectroscopic characterization of hexacoordinated complexes of Bu2Sn(IV)
-
Karuna Maheshwari
und
Sanjiv Saxena
Abstract
New complexes of dibutyltin(IV) of fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones having the general formula Bu2SnLL′ (where LH=RCOCH2COR′, R=-C6H5, R′=-CF3,L1H; R=-C4H3S, R′=-CF3, L2H; R=-C6H5, R′=-CH3,L3H and 
R″=-C6H5, L1′H; R″=-p-ClC6H4, L2′H; R″=-CH3, L3′H and R″=-C2H5, L4′H) were synthesized by the reaction of dibutyltin(IV)dichloride with sodium salts of fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones in 1:1:1 molar ratios in refluxing dry benzene solution. Plausible structures of these Bu2Sn(IV) complexes were suggested on the basis of physico-chemical and spectral [infrared and nuclear magnetic resonance (NMR)] studies. 119Sn NMR spectroscopic studies of some of these complexes revealed the presence of hexacoordinated tin centers.
Introduction
The chemistry of organotin(IV) complexes derived from oximes (Bhambhani et al., 1995; Singh and Tawade, 2001; Sharma et al., 2007), amino acid derivatives (Nath et al., 2003; Joshi et al., 2005; Assunta et al., 2010), Schiff bases (Dey et al., 1999; Sedaghat and Rahmani, 2008; Sharma et al., 2010; Sedaghat et al., 2011; Mun et al., 2012; Rehman et al., 2012), sulfa drug derivatives (Jain et al., 2004), β-diketones (Pettinari et al., 1997, 2011; Marchetti et al., 2002; Singh and Gupta, 2002; Gupta et al., 2010; Caruso et al., 2011), heterocyclic β-diketones (Pettinari et al., 1997; Marchetti et al., 2002; Joshi et al., 2004; Gupta et al., 2010; Caruso et al., 2011), semicarbazides (Belwal et al., 1997; Vieira et al., 2008),semicarbazone (Singh et al., 2012) and nonsteroidal anti-inflammatory drugs (Shahzadi et al., 2005), etc., has been prominently cited in the literature. Some organotin(IV) complexes are extensively used as bactericidal (Mishra et al., 2011; Shujah et al., 2011; Sedaghat et al., 2012; Salam et al., 2013),insecticidal (Jain et al., 1999, 2006), pesticidal (Dawara and Singh, 2011), fungicidal (Yousif et al., 2011), anti-inflammatory (Nath et al., 2009, 2010, 2011) and antineoplastic (Liang et al., 2012; Shang et al., 2012; Sobhanmanesh et al., 2012; Hong et al., 2013; Nath et al., 2013) agents. Some dibutyltin(IV) complexes (Shang et al., 2012; Sobhanmanesh et al., 2012; Nath et al., 2013) exhibit antitumor activity owing to the presence of R2Sn(IV)moiety. Incorporation of R2Sn(IV) moiety into various potential organic ligands may result in the design and development of possible tin-based anticancer drugs. The chemistry of organotin(IV) complexes has attracted much attention because these complexes possess superior properties as compared to their pure counterparts (Najafi et al., 2013).
In order to incorporate R2Sn(IV) moiety into potential organic ligands, the reactions of dibutyltin(IV)dichloride with sodium salts of fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones were carried out, which resulted in the formation of hexacoordinated complexes of Bu2Sn(IV).
Results and discussion
The reaction of dibutyltin(IV)dichloride with sodium salts of fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones in 1:1:1 molar ratios in refluxing dry benzene solution gave the corresponding complexes 1–10 (Scheme 1).
Synthesis of complexes 1–10.
1: R=C6H5, R′=CF3, R″=C6H5
2: R=C6H5, R′=CF3, R″=p-ClC6H4
3: R=C6H5, R′=CF3, R″=CH3
4: R=C6H5, R′=CF3, R″=C2H5
5: R=C4H3S, R′=CF3, R″=C6H5
6: R=C4H3S, R′=CF3, R″=p-ClC6H4
7: R=C6H5, R′=CH3, R″=C6H5
8: R=C6H5, R′=CH3, R″=p-ClC6H4
9: R=C6H5, R′=CH3, R″=CH3
10: R=C6H5, R′=CH3, R″=C2H5
Complexes 1 and 5 are red viscous products, while the other complexes are yellow- or red-colored solid materials. All of these compounds are soluble in common organic solvents like benzene, methanol, chloroform, tetrahydrofuran, etc.
IR spectra
The IR spectra of fluorinated β-diketones, benzoylacetone, sterically demanding heterocyclic β-diketones and complexes 1–10 derived from these ligands were recorded in KBr pellets in the range of 4000–400 cm-1.
For compounds 1–10, a medium-intensity band appeared in the region 620±10 cm-1. This band may be assigned to the Sn-O bond. The IR spectra of fluorinated β-diketones and benzoylacetone exhibit a strong band in the region 1550–1660 cm-1, which is attributed to (>C=O) stretching vibrations(Joshi et al., 2005). In the IR spectra of complexes 1–6, this band is shifted to a higher wave number, while in complexes 7–10, this band shifts towards a lower wave number. This significant shift in the carbonyl frequency clearly shows that the carbonyl oxygen atom is involved in bonding and that fluorinated β-diketones as well as benzoylacetone are behaving as bidentate ligands.
The IR spectra of the sterically demanding heterocyclic β-diketones display a band at 1545 cm-1, which is due to (>C=O) stretching vibrations. This band is shifted to a lower wave number and appeared in the region 1525–1530 cm-1 in the IR spectra of these dibutyltin(IV) complexes. This shift in the carbonyl frequency towards a lower wave number supports the bidentate nature of sterically demanding heterocyclic β-diketones in these complexes. The bands in the region 1560–1570 and 1580–1590 cm-1 may be assigned to (>C=C</>C=N-) and phenyl stretching vibrations, respectively.
1H NMR spectra
The 1H NMR spectra of 4,4,4-trifluoro-1-phenyl-1,3-butanedione, benzoylacetone, sterically demanding heterocyclic β-diketones and dibutyltin(IV) complexes 1–10 derived from these ligands are summarized in Table 1.
1H NMR spectroscopic data (in CDCl3) of the dibutyltin(IV) complexes 1–10 (in δ).
| Complex no. | Ligands and complexes | RCOCH2COR′(LH) |  | Sn-butyl | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| OH | CH | CH2 | CH3 | C6H5/C4H3S | OH | Ring CH3 | Ring C6H5 | Terminal | |||||
| C6H5/-p-ClC6H4 | CH3 | CH2 | |||||||||||
| L1H | 14.97 (bs) | 6.56 (s) | 3.40 (s) | 7.24–7.93 (m) | |||||||||
| L1′H | 11.25 (bs) | 2.10 (s) | 7.25–7.89 (m) | a | |||||||||
| 1 | Bu2SnL1L1′ | – | 6.44 (s) | – | a | – | b | 7.23–8.18 (m) | a | 0.74–1.85 (m) | |||
| L2′Hc | 11.37 (bs) | 2.14 (s) | 7.26–8.00 (m) | a | |||||||||
| L3′Hc | 11.51 (bs) | 2.51 (s) | 7.17–7.83 (m) | 2.45 (s) | |||||||||
| 3 | Bu2SnL1L3′ | – | 6.40 (s) | – | a | – | 2.48 (s) | 7.24–8.11 (m) | 2.46 (s) | 0.74–1.57 (m) | |||
| L4′Hc | 10.67 (bs) | 2.39 (s) | 7.23–7.86 (m) | 1.21 (t) | 2.73 (q) | ||||||||
| 4 | Bu2SnL1L4′ | – | 6.40 (s) | – | a | – | 2.48 (s) | 7.18–8.11 (m) | 1.27 (t) | 2.75 (q) | 0.74–1.57 (m) | ||
| 5 | Bu2SnL2L1′ | – | 6.29 (s) | – | a | – | 2.55 (s) | 7.09–8.17 (m) | a | 0.77–1.83 (m) | |||
| 6 | Bu2SnL2L2′ | – | 6.29 (s) | – | a | – | 2.57 (s) | 7.11–7.98 (m) | a | 0.73–1.86 (m) | |||
| L3H | 16.16 (bs) | 6.18 (s) | 4.10 (s) | 2.22 (s) | 7.25–7.95 (m) | ||||||||
| 7 | Bu2SnL3L1′ | – | 6.10 (s) | – | 2.17 (s) | a | – | 2.61 (s) | 7.19–8.03 (m) | a | 0.74–1.81 (m) | ||
| 8 | Bu2SnL3L2′ | – | 6.20 (s) | – | b | a | – | b | 7.22–7.97 (m) | a | 0.70–1.85 (m) | ||
| 9 | Bu2SnL3L3′ | – | 6.20 (s) | – | 2.48 (s) | a | – | 2.49 (s) | 7.14–7.91 (m) | 2.45 (s) | 0.73–1.79 (m) | ||
| 10 | Bu2SnL3L4′ | – | 6.10 (s) | – | b | a | – | 2.46 (s) | 7.15–7.95 (m) | b | 2.73 (q) | 0.74–1.63 (m) | |
s, singlet; t, triplet; q, quartet; m, multiplet; bs, broad singlet.
aMerged in the phenyl region.
bMerged in the butyl region.
cGupta et al. (2010).
Fluorinated β-diketone (L1H), benzoylacetone (L3H) and sterically demanding heterocyclic β-diketones (L1′H, L2′H, L3′H and L4′H) exhibit a broad signal of enolic –OH at δ 14.97, δ 16.16 and in the region δ 10.67–11.51, respectively. The disappearance of these broad signals from the 1H NMR spectra of compounds 1–10 indicates the deprotonation of fluorinated β-diketone (L1H) , benzoylacetone and sterically demanding heterocyclic β-diketones and the formation of Sn-O bond. The 1H NMR spectra of fluorinated β-diketone (L1H) and benzoylacetone (L3H) exhibit a singlet due to –CH2- protons at δ 3.40 and δ 4.10, respectively. This singlet was absent in the spectra of the complexes. There is a small shift in the position of the methine (=CH-) proton in the 1H NMR spectra of the complexes as compared to its position in fluorinated β-diketone (L1H) and benzoylacetone (L3H). The probable reason for this small shift may be the delocalization of electrons in the quasi-aromatic chelate ring. The butyl protons directly appended to the central tin atom in these complexes appeared as a complex pattern in the region δ 0.70–1.86. Aromatic protons were observed as a complex pattern in the region δ 7.09–8.18.
13C NMR spectra
The 13C NMR spectra of fluorinated β-diketones (L1H and L2H), benzoylacetone (L3H) and sterically demanding heterocyclic β-diketones (L′H) and dibutyltin(IV) complexes derived from these ligands are summarized in Table 2.
13C NMR spectroscopic data (in CDCl3) of the dibutyltin(IV) complexes 1–10 ( in δ).
| Ligands and complexes | RC(O)CH2C(O)R′ (LH) |  | Sn butyl | |||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| CO | CH | CH3 | -C6H5/-C4H3S | CH2 | CF3 | Terminal | Ring C6H5 | C3 | C4 | C5 | C6 | C7 | ||||
| -CH2 | -CH3 | -C6H5/-p-ClC6H4 | ||||||||||||||
| L1H | 186.23, 178.08, 177.59,177.16, 176.62 | 92.36 | 127.68, 129.07, 132.90, 134.14 | 115.32 | ||||||||||||
| L1′H | 137.17, 131.90, 128.42, 126.71 | 147.97, 129.13, 127.88, 120.77 | 161.43 | 103.58 | 137.57 | 192.04 | 15.82 | |||||||||
| 1. Bu2SnL1L1′ | 192.00, 190.11 | 92.06 | b | – | 120.68 | b | 149.32–120.81 | 162.60 | 104.64 | 138.45 | a | 16.49 | 13.58, 25.96, 27.11, 31.60 | |||
| L2′H | 137.05, 136.12, 131.52, 128.81 | 147.69, 129.38, 126.90, 120.90 | 161.07 | 103.46 | 138.23 | 191.23 | 15.90 | |||||||||
| 2. Bu2SnL1L2′ | 193.49, 193.09 | 91.99 | b | – | 120.67 | b | 148.88–120.87 | 161.98 | 104.70 | 138.46 | a | 17.32 | 13.57, 25.94, 26.70, 28.70 | |||
| L3′H | 26.66 | 147.69, 129.11, 126.60, 120.67 | 160.40 | 104.23 | 137.19 | 194.40 | 15.57 | |||||||||
| 3. Bu2SnL1L3′ | 193.11, 189.75 | 91.95 | b | 120.68 | 26.69 | 148.80–120.87 | 161.99 | 104.64 | 138.46 | 193.52 | 17.32 | 13.56, 26.61, 27.91, 28.80 | ||||
| L4′H | 32.53 | 8.18 | 147.40, 129.10, 126.59, 120.71 | 160.26 | 103.44 | 137.23 | 198.30 | 15.75 | ||||||||
| 4. Bu2SnL1L4′ | 197.17, 196.05 | 91.92 | b | 120.75 | 32.85 | 8.87 | 148.41–120.91 | 162.00 | 103.93 | 138.53 | a | 17.42 | 13.57, 25.99, 26.72, 28.78 | |||
| L2H | 191.88, 182.81, 171.39, 171.03 | 93.69 | 143.23–123.57 | 38.92 | 120.73 | |||||||||||
| 5(ma). Bu2SnL2L1′ | 191.54, 190.63 | 92.12 | b | 128.84 | b | 149.30–120.75 | 162.51 | 104.68 | 138.34 | a | 16.39 | 13.47, 26.67, 27.15, 29.21 | ||||
| 6. Bu2SnL2L2′ | 190.75, 190.14 | 92.24 | b | 128.75 | b | 148.98–120.49 | 162.81 | 104.76 | 138.30 | a | 16.68 | 13.59, 26.64, 27.03, 29.15 | ||||
| L3H | 193.75, 183.31 | 96.64 | 25.82 | 134.85, 132.25, 128.58, 126.97 | 54.70 | |||||||||||
| 7. Bu2SnL3L1′ | 193.51, 191.61 | 97.53 | 26.03 | b | b | 149.39–120.81 | 162.86 | 104.83 | 138.44 | a | 16.53 | 13.63, 26.61, 27.05, 29.35 | ||||
| 9. Bu2SnL3L3′ | 193.11, 191.57 | 97.17 | 26.01 | b | 26.61 | 149.37–120.86 | 161.93 | 104.70 | 138.42 | a | 16.53 | 13.63, 26.90, 27.31, 29.32 | ||||
| 10. Bu2SnL3L4′ | 196.96 | 100.0 | 26.13 | b | 32.87 | 9.17 | 148.41–120.90 | 162.37 | 104.00 | 138.50 | a | 17.54 | 13.65, 26.95, 27.22, 28.61 | |||
aMerged in the CO region of fluorinated β-diketones/benzoylacetone.
bMerged in the phenyl region.
(ma)= ESI-Full ms (150.00–2000.00) (m/z): 765.1 [M]+., 639.1 (base peak). Other peaks 416.8, 417.9, 511.0, 543.1, 545.1, 635.1, 641.1, 695.2, 750.1, 860.8, 898.8, 900.8, 902.8, 906.8, 916.8, 918.8, 1004.9, 1006.0, 1164.7, 1254.6, 1292.8, 1294.9, 1298.9, 1299.9, 1316.8, 1542.5, 1701.4, 1705.5, 1920.6.
The 13C NMR spectrum of fluorinated β-diketones (L1H and L2H) shows the splitting of the carbon signals of >CO in regions δ 186.23–176.62 and δ 191.88–171.03. In the case of benzoylacetone (L3H), the two signals for >CO carbon atom were observed at δ 193.75 and δ183.31. There is some shift in the position of the carbon signals of >CO, which shows that carbonyl oxygen participates in bonding and also reveals the bidentate nature of fluorinated β-diketones (L1H and L2H) and benzoylacetone (L3H). The delocalization of electrons in the quasi-aromatic chelate ring is supported by a small shift in the position of the carbon signal of methine (=CH-) in the 13C NMR spectra of these complexes as compared to its position in the parent ligands.
In the 13C NMR spectra of the dibutyltin(IV) complexes, the positions of C3, C4 and C6 carbon signals are slightly shifted as compared to their positions in sterically demanding heterocyclic β-diketones. These shifts support the delocalization of electrons in a six-membered quasi-aromatic chelate ring and the bidentate nature of sterically demanding heterocyclic β-diketones in these complexes. The carbon signals present in the region δ 13.47–31.60 in the spectra of these complexes are assigned to the butyl group attached to the central tin atom.
119Sn NMR spectra
The 119Sn NMR spectra of a few representative complexes of dibutyltin(IV) derived from fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones are given in Table 3.
119Sn NMR data (in CDCl3) of compounds 3, 7 and 8.
| Complex no. | 119Sn NMR chemical shift values in δ |
|---|---|
| 3 | -355, -366 |
| 7 | -355, -362 |
| 8 | -353, -360 |
The 119Sn NMR spectra of complexes 3, 7 and 8 show signals in the region from δ -352 to δ -366. These observed 119Sn NMR chemical shift values are consistent with the earlier cited values for six-coordinated tin (IV) complexes.
Conclusion
Some new dibutyltin(IV) complexes derived from fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones have been synthesized. All the compounds are colored solids/viscous and monomeric in nature. Spectroscopic data suggest the bidentate chelating manner of both the type of ligands and the six-coordinated octahedral geometry of the central tin atom. This work is useful for the design and development of possible tin-based antitumor drugs, which may be achieved by the synthetic strategy involving incorporation of Bu2Sn(IV) into various potential organic ligands.
Experimental
Strict precautions were taken to remove atmospheric moisture during the experimental work. Sterically demanding heterocyclic β-diketones were synthesized by the Jensen (1959) method. Bu2SnCl2, fluorinated β-diketones and benzoylacetone are commercially available.
The solvents such as methanol, benzene, chloroform and petrol ether were dried by standard methods. The melting points of these complexes were determined in sealed capillaries. The Rast camphor method was used for the determination of the molecular weights of these complexes. Tin present in these complexes was estimated as tin(IV) oxide. IR spectra of these complexes were recorded on a Fourier transform infrared spectrophotometer (FTIR-8400S, Shimadzu, Tokyo, Japan), and samples were prepared as KBr pellets. The 1H, 13C and 119Sn NMR spectra of these complexes were recorded in CDCl3 solution using tetramethylsilane as an internal standard on a JEOLFT AL300NMR spectrometer operating at 300 and 75.45 MHz, respectively.
Synthesis of compounds 1–10
A similar method was used for the preparation of the complexes of dibutyltin(IV) of fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones. The preparation of one representative complex of dibutyltin(IV) is given in detail. Analytical data for other dibutyltin(IV) complexes are summarized in Table 4.
Analytical and physical data of the dibutyltin(IV) complexes 1–10.
| Complex no. | Product formula | Reagents in mmol (mg) | NaCl in milligrams found (calculated) | % Yield | MP (°C) | % Sn found (calculated) | Molecular weight found (calculated) | |||
|---|---|---|---|---|---|---|---|---|---|---|
| Na | LH | L′H | Bu2SnCl2 | |||||||
| 1 | C35H37N2O4F3Sn (Bu2SnL1L1′) | 8.16 (187) | 4.08 (882) | 4.08 (1135) | 4.08 (1240) | 450 (470) | 70 | - | 16.34 (16.36) | (725.39) |
| 2 | C35H36N2O4ClF3Sn (Bu2SnL1L2′) | 8.13 (187) | 4.06 (879) | 4.06 (1267) | 4.06 (1236) | 460 (470) | 83 | 88 | 15.60 (15.62) | 658 (759.83) |
| 3 | C30H35N2O4F3Sn (Bu2SnL1L3′) | 8.33 (191) | 4.16 (900) | 4.16 (900) | 4.16 (1266) | 460 (480) | 92 | 92 | 17.87 (17.89) | 623 (663.32) |
| 4 | C31H37N2O4F3Sn (Bu2SnL1L4′) | 7.83 (180) | 3.91 (846) | 3.91 (901) | 3.91 (1190) | 430 (450) | 88 | 72 | 17.54 (17.55) | 658 (676.34) |
| 5 | C33H35N2O4SF3Sn (Bu2SnL2L1′) | 7.61 (175) | 3.80 (846) | 3.80 (1058) | 3.80 (1157) | 420 (440) | 76 | - | 16.22 (16.23) | (731.42) |
| 6 | C33H34N2O4ClSF3Sn (Bu2SnL2L2′) | 7.26 (167) | 3.63 (807) | 3.63 (1131) | 3.63 (1103) | 410 (420) | 81 | 136 | 15.53 (15.55) | 715 (765.86) |
| 7 | C35H40N2O4Sn (Bu2SnL3L1′) | 10.21 (235) | 5.10 (828) | 5.10 (1420) | 5.10 (1547) | 560 (580) | 51 | 78 | 17.66 (17.68) | 669 (671.42) |
| 8 | C35H39N2O4ClSn (Bu2SnL3L2′) | 7.51 (172) | 3.75 (606) | 3.75 (1170) | 3.75 (1139) | 410 (430) | 65 | 102 | 16.80 (16.81) | 698 (705.86) |
| 9 | C30H38N2O4F3Sn (Bu2SnL3L3′) | 7.59 (174) | 3.79 (615) | 3.79 (820) | 3.79 (1153) | 430 (440) | 52 | 132 | 19.47 (19.48) | 593 (609.35) |
| 10 | C31H40N2O4Sn (Bu2SnL3L4′) | 5.82 (134) | 2.91 (472) | 2.91 (670) | 2.91 (885) | 310 (330) | 53 | 128 | 19.02 (19.04) | 602 (629.37) |
L1H=C10H7O2F3,L2H=C8H5O2F3S, L3H=C10H10O2, L1′H=C17H14N2O2, L2′H=C17H13ClN2O2,L3′H=C12H12N2O2, L4′H=C13H14N2O2.
To a methanolic solution of sodium (191 mg, 8.33 mmol), the dry benzene solutions of the ligands 4,4,4-trifluoro-1-phenyl-1,3-butanedione (L1H) (900 mg, 4.16 mmol) and 4-acetyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one (L3′H) (900 mg, 4.16 mmol) were added. The reaction mixture was refluxed for about 7 h. A benzene solution of Bu2SnCl2 (1266 mg, 4.16 mmol) was added to this reaction mixture containing sodium salts of the two ligands, and the reaction contents were further refluxed for about 8 h.
The sodium chloride that formed in the reaction was filtered off. The excess solvent was removed under reduced pressure. A light yellow-colored solid product was obtained, which was purified by recrystallization from a dry chloroform-petroleum ether mixture. Analytical data and the results of this complex and other complexes are summarized in Table 4.
Acknowledgment
Dr. Asha Jain and Karuna Maheshwari are thankful to UGC, NewDelhi, India, for financial assistance.
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Artikel in diesem Heft
- Frontmatter
- Research articles
- Molecular structures of Sn(II) and Sn(IV) compounds with di-, tri- and tetramethylene bridged salen* type ligands
- Synthesis and structures of Cu-Cl-M adducts (M=Zn, Sn, Sb)
- Synthetic strategy for the incorporation of Bu2Sn(IV) into fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones and spectroscopic characterization of hexacoordinated complexes of Bu2Sn(IV)
- Reactivity of bis(cyclohexylammonium) 4-nitrophenylphosphate with SnMe3 Cl. X-ray structure of 4-NO2 C6 H4 PO4(SnMe3)2·H2 O
- Structural elucidation of novel mixed ligand complexes of 2-thiophene carboxylic acid [M(TCA)2(H2O)x(im)2] [x=2 M: Mn(II), Co(II) or Cd(II), x=0 Cu(II)]
- Short Communication
- Synthesis and structure of the first tin(II) amidinato-guanidinate [DippNC(nBu)NDipp]Sn{pTol-NC[N(SiMe3)2]N-pTol}
Artikel in diesem Heft
- Frontmatter
- Research articles
- Molecular structures of Sn(II) and Sn(IV) compounds with di-, tri- and tetramethylene bridged salen* type ligands
- Synthesis and structures of Cu-Cl-M adducts (M=Zn, Sn, Sb)
- Synthetic strategy for the incorporation of Bu2Sn(IV) into fluorinated β-diketones/benzoylacetone and sterically demanding heterocyclic β-diketones and spectroscopic characterization of hexacoordinated complexes of Bu2Sn(IV)
- Reactivity of bis(cyclohexylammonium) 4-nitrophenylphosphate with SnMe3 Cl. X-ray structure of 4-NO2 C6 H4 PO4(SnMe3)2·H2 O
- Structural elucidation of novel mixed ligand complexes of 2-thiophene carboxylic acid [M(TCA)2(H2O)x(im)2] [x=2 M: Mn(II), Co(II) or Cd(II), x=0 Cu(II)]
- Short Communication
- Synthesis and structure of the first tin(II) amidinato-guanidinate [DippNC(nBu)NDipp]Sn{pTol-NC[N(SiMe3)2]N-pTol}
