Chem. J. Chinese Universities ›› 2015, Vol. 36 ›› Issue (5): 831.doi: 10.7503/cjcu20141142
• Articles: Inorganic Chemistry • Previous Articles Next Articles
LIU Chao1,*(), ZHUO Xin1, CHENG Hui1, LIU Chuang1, LIU Xinhua2
Received:
2014-12-29
Online:
2015-05-10
Published:
2015-04-17
Contact:
LIU Chao
E-mail:ahliuchao333@163.com
Supported by:
CLC Number:
TrendMD:
LIU Chao, ZHUO Xin, CHENG Hui, LIU Chuang, LIU Xinhua. Synthesis, Crystal Structure and Homogeneous Catalytic Performance of Zinc Complex Based on Diethylenetriamine Ligand†[J]. Chem. J. Chinese Universities, 2015, 36(5): 831.
Empirical formula | C8 H21N3O5Zn | Z | 4 |
---|---|---|---|
Formula weight | 304.65 | Dc/(g·cm-3) | 1.453 |
Crystal system | Monoclinic | μ/mm-1 | 1.777 |
Space group | P21/c | F(000) | 640 |
Temperature/K | 296(2) | Reflections collected/unique(Rint) | 7896/2593(0.029) |
a/nm | 1.2433(7) | Data/restraints/parameters | 2593/0/156 |
b/nm | 1.3378(7) | Goodness-of-fit on F2 | 1.085 |
c/nm | 0.8676(5) | Final R indices[I>2σ(I)] | R1=0.0274, wR2=0.0696 |
β/(°) | 105.213(8) | R indices(all data) | R1=0.0320, wR2=0.0725 |
Volume/nm3 | 1.3924(13) |
Table 1 Crystallographic data and structure refinement parameters for the complex
Empirical formula | C8 H21N3O5Zn | Z | 4 |
---|---|---|---|
Formula weight | 304.65 | Dc/(g·cm-3) | 1.453 |
Crystal system | Monoclinic | μ/mm-1 | 1.777 |
Space group | P21/c | F(000) | 640 |
Temperature/K | 296(2) | Reflections collected/unique(Rint) | 7896/2593(0.029) |
a/nm | 1.2433(7) | Data/restraints/parameters | 2593/0/156 |
b/nm | 1.3378(7) | Goodness-of-fit on F2 | 1.085 |
c/nm | 0.8676(5) | Final R indices[I>2σ(I)] | R1=0.0274, wR2=0.0696 |
β/(°) | 105.213(8) | R indices(all data) | R1=0.0320, wR2=0.0725 |
Volume/nm3 | 1.3924(13) |
Compound | 1H NMR(400 MHz, CDCl3) |
---|---|
2 | 7.40-7.33(m, 5H, Ar-H), 5.41(dd, J=3.2, 9.6 Hz, 1H, ArCH), 4.56(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.47(dd, J=3.2, 13.2 Hz, 1H, CH2), 3.04(br, 1H, OH) |
3 | 7.28-7.21(m, 4H, Ar-H), 5.41(dd, J=2.8, 9.6 Hz, 1H, ArCH), 4.57(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.47(dd, J=2.8, 13.2 Hz, 1H, CH2), 2.88(br, 1H, OH), 2.37(s, 3H, CH3) |
4 | 7.52-7.17(m, 4H, Ar-H), 5.63(dd, J=2.4, 9.7 Hz, 1H, ArCH), 4.52(dd, J=9.7, 13.3 Hz, 1H, CH2), 4.41(dd, J=2.4, 13.3 Hz, 1H, CH2), 2.93(br, 1H, OH), 2.38(s, 3H, CH3) |
5 | 7.38-7.28(m, 4H, Ar-H), 5.45(dd, J=9.6, 3.2 Hz, 1H, ArCH), 4.56(dd, 1H, J=9.6, 13.6 Hz, 1H, CH2), 4.48(dd, 1H, J=3.2, 13.6 Hz, 1H, CH2), 3.05(br, 1H, OH) |
6 | 7.64-7.32(m, 4H, Ar-H), 5.75(dd, 1H, J=2.4, 9.6 Hz, 1H, ArCH), 4.59(dd, J=9.6, 13.5 Hz, 1H, CH2), 4.35(dd, J=2.4, 13.5 Hz, 1H, CH2), 3.03(br, 1H, OH) |
7 | 8.28-7.63(m, 4H, Ar-H ), 5.60(dd, J=3.2, 8.0 Hz, 1H, ArCH), 4.61(dd, J=8.0, 13.6 Hz, 1H, CH2), 4.57(dd, J=3.2, 13.6 Hz, 1H, CH2), 3.23(br, 1H, OH) |
8 | 8.07-7.52(m, 4H, Ar-H), 6.03(dd, J=3.2, 9.6 Hz, 1H, ArCH), 4.82(dd, J=9.2, 13.6 Hz, 1H, CH2), 4.53(dd, J=2.4, 13.6 Hz, 1H, CH2), 3.36(br, 1H, OH) |
9 | 4.40(dd, J=3.6, 7.6 Hz, 1H, ArCH), 4.36(dd, J=7.6, 13.2 Hz, 1H, CH2), 4.31(dd, J=3.6, 13.2 Hz, 1H, CH2), 2.60(br, 1H, OH), 1.63-1.27(m, 4H, CH2CH2), 0.98-0.93(t, 3H, CH3) |
10 | 4.50(dd, J=8.9, 13.1 Hz, 1H, CH2NO2), 4.42(dd, J=3.0, 13.1 Hz, 1H, CH2NO2), 4.12-4.08[m, 1H, CH(OH)], 2.52(br, 1H, OH), 1.84-1.06(m, 11H, cHex-H) |
11 | 7.41-6.38(m, 3H, Furan-H), 5.44(dd, J=3.6, 9.2 Hz, 1H, Furan-CH), 4.78(dd, J=9.2, 13.6 Hz, 1H, CH2), 4.67(dd, J=3.6, 13.6 Hz, 1H, CH2), 3.19(br, 1H, OH) |
12 | 8.55-7.26(m, 4H, Py-H), 5.48(dd, J=3.4, 9.6 Hz, 1H, Py-CH), 4.78(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.64(dd, J=3.4, 13.2 Hz, 1H, CH2), 3.56(br, 1H, OH) |
Table 2 Characterization of the catalytic products
Compound | 1H NMR(400 MHz, CDCl3) |
---|---|
2 | 7.40-7.33(m, 5H, Ar-H), 5.41(dd, J=3.2, 9.6 Hz, 1H, ArCH), 4.56(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.47(dd, J=3.2, 13.2 Hz, 1H, CH2), 3.04(br, 1H, OH) |
3 | 7.28-7.21(m, 4H, Ar-H), 5.41(dd, J=2.8, 9.6 Hz, 1H, ArCH), 4.57(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.47(dd, J=2.8, 13.2 Hz, 1H, CH2), 2.88(br, 1H, OH), 2.37(s, 3H, CH3) |
4 | 7.52-7.17(m, 4H, Ar-H), 5.63(dd, J=2.4, 9.7 Hz, 1H, ArCH), 4.52(dd, J=9.7, 13.3 Hz, 1H, CH2), 4.41(dd, J=2.4, 13.3 Hz, 1H, CH2), 2.93(br, 1H, OH), 2.38(s, 3H, CH3) |
5 | 7.38-7.28(m, 4H, Ar-H), 5.45(dd, J=9.6, 3.2 Hz, 1H, ArCH), 4.56(dd, 1H, J=9.6, 13.6 Hz, 1H, CH2), 4.48(dd, 1H, J=3.2, 13.6 Hz, 1H, CH2), 3.05(br, 1H, OH) |
6 | 7.64-7.32(m, 4H, Ar-H), 5.75(dd, 1H, J=2.4, 9.6 Hz, 1H, ArCH), 4.59(dd, J=9.6, 13.5 Hz, 1H, CH2), 4.35(dd, J=2.4, 13.5 Hz, 1H, CH2), 3.03(br, 1H, OH) |
7 | 8.28-7.63(m, 4H, Ar-H ), 5.60(dd, J=3.2, 8.0 Hz, 1H, ArCH), 4.61(dd, J=8.0, 13.6 Hz, 1H, CH2), 4.57(dd, J=3.2, 13.6 Hz, 1H, CH2), 3.23(br, 1H, OH) |
8 | 8.07-7.52(m, 4H, Ar-H), 6.03(dd, J=3.2, 9.6 Hz, 1H, ArCH), 4.82(dd, J=9.2, 13.6 Hz, 1H, CH2), 4.53(dd, J=2.4, 13.6 Hz, 1H, CH2), 3.36(br, 1H, OH) |
9 | 4.40(dd, J=3.6, 7.6 Hz, 1H, ArCH), 4.36(dd, J=7.6, 13.2 Hz, 1H, CH2), 4.31(dd, J=3.6, 13.2 Hz, 1H, CH2), 2.60(br, 1H, OH), 1.63-1.27(m, 4H, CH2CH2), 0.98-0.93(t, 3H, CH3) |
10 | 4.50(dd, J=8.9, 13.1 Hz, 1H, CH2NO2), 4.42(dd, J=3.0, 13.1 Hz, 1H, CH2NO2), 4.12-4.08[m, 1H, CH(OH)], 2.52(br, 1H, OH), 1.84-1.06(m, 11H, cHex-H) |
11 | 7.41-6.38(m, 3H, Furan-H), 5.44(dd, J=3.6, 9.2 Hz, 1H, Furan-CH), 4.78(dd, J=9.2, 13.6 Hz, 1H, CH2), 4.67(dd, J=3.6, 13.6 Hz, 1H, CH2), 3.19(br, 1H, OH) |
12 | 8.55-7.26(m, 4H, Py-H), 5.48(dd, J=3.4, 9.6 Hz, 1H, Py-CH), 4.78(dd, J=9.6, 13.2 Hz, 1H, CH2), 4.64(dd, J=3.4, 13.2 Hz, 1H, CH2), 3.56(br, 1H, OH) |
Zn1-O1 | 0.2072(2) | Zn1-O3 | 0.2001(2) | Zn1-N1 | 0.2157(2) |
---|---|---|---|---|---|
Zn1-N2 | 0.2136(2) | Zn1-N3 | 0.2177(2) | O1-C5 | 0.1268(3) |
O2-C5 | 0.1239(3) | O3-C7 | 0.1276(3) | O4-C7 | 0.1215(3) |
O1-Zn1-O3 | 99.14(7) | O1-Zn1-N1 | 90.98(7) | O1-Zn1-N2 | 137.95(6) |
O1-Zn1-N3 | 95.19(8) | O3-Zn1-N1 | 101.15(7) | O3-Zn1-N2 | 122.90(7) |
O3-Zn1-N3 | 99.27(8) | N1-Zn1-N2 | 80.88(6) | N1-Zn1-N3 | 157.43(8) |
N2-Zn1-N3 | 80.01(7) |
Table 3 Selected bond lengths(nm) and bond angles(°) of the complex
Zn1-O1 | 0.2072(2) | Zn1-O3 | 0.2001(2) | Zn1-N1 | 0.2157(2) |
---|---|---|---|---|---|
Zn1-N2 | 0.2136(2) | Zn1-N3 | 0.2177(2) | O1-C5 | 0.1268(3) |
O2-C5 | 0.1239(3) | O3-C7 | 0.1276(3) | O4-C7 | 0.1215(3) |
O1-Zn1-O3 | 99.14(7) | O1-Zn1-N1 | 90.98(7) | O1-Zn1-N2 | 137.95(6) |
O1-Zn1-N3 | 95.19(8) | O3-Zn1-N1 | 101.15(7) | O3-Zn1-N2 | 122.90(7) |
O3-Zn1-N3 | 99.27(8) | N1-Zn1-N2 | 80.88(6) | N1-Zn1-N3 | 157.43(8) |
N2-Zn1-N3 | 80.01(7) |
D-H…A | d(D-H ) | d(H…A) | d(D…A) | ∠(DHA) |
---|---|---|---|---|
O1W-H1WB…O1#1 | 0.0920 | 0.1960 | 0.2852(3) | 163.00 |
N1-H1A…O1W#2 | 0.0900 | 0.2080 | 0.2971(3) | 172.00 |
N1-H1B…O3#3 | 0.0900 | 0.2280 | 0.3135(3) | 158.00 |
O1W-H1WA…O2 | 0.0970 | 0.1830 | 0.2802(3) | 177.00 |
N2-H2C…O4#4 | 0.0910 | 0.2330 | 0.3067(3) | 138.00 |
N3-H3A…O3#5 | 0.0900 | 0.2520 | 0.3372(3) | 159.00 |
Table 4 Hydrogen bond lengths(nm) and bond angles(°) of the complex*
D-H…A | d(D-H ) | d(H…A) | d(D…A) | ∠(DHA) |
---|---|---|---|---|
O1W-H1WB…O1#1 | 0.0920 | 0.1960 | 0.2852(3) | 163.00 |
N1-H1A…O1W#2 | 0.0900 | 0.2080 | 0.2971(3) | 172.00 |
N1-H1B…O3#3 | 0.0900 | 0.2280 | 0.3135(3) | 158.00 |
O1W-H1WA…O2 | 0.0970 | 0.1830 | 0.2802(3) | 177.00 |
N2-H2C…O4#4 | 0.0910 | 0.2330 | 0.3067(3) | 138.00 |
N3-H3A…O3#5 | 0.0900 | 0.2520 | 0.3372(3) | 159.00 |
Entry | Solvent | Time/h | Catalystb | Catalyst loading (molar fraction, %) | Yield(%) |
---|---|---|---|---|---|
1 | Methanol | 24 | Complex 1+Et3N | 4 | 29.0 |
2 | Methanol | 24 | Complex 1+Et3N | 6 | 48.5 |
3 | Methanol | 24 | Complex 1+Et3N | 8 | 77.0 |
4 | Methanol | 24 | Complex 1+Et3N | 10 | 85.0 |
5 | Methanol | 24 | Complex 1+Et3N | 12 | 85.0 |
6 | Methanol | 24 | Complex 1+Et3N | 14 | 85.5 |
7 | Methanol | 20 | Complex 1+Et3N | 10 | 61.5 |
8 | Methanol | 22 | Complex 1+Et3N | 10 | 79.5 |
9 | Methanol | 26 | Complex 1+Et3N | 10 | 85.5 |
10 | Methanol | 28 | Complex 1+Et3N | 10 | 86.0 |
11 | Ethanol | 24 | Complex 1+Et3N | 10 | 82.5 |
12 | THF | 24 | Complex 1+Et3N | 10 | 79.0 |
13 | CH2Cl2 | 24 | Complex 1+Et3N | 10 | 69.5 |
14 | Toluene | 24 | Complex 1+Et3N | 10 | 77.5 |
15 | Methanol | 24 | Complex 1 | 10 | 31.0 |
16 | Methanol | 24 | Zn(OAc)2·2H2O | 10 | 15.5 |
17 | Methanol | 24 | Et3N | 10 | 35.0 |
18 | Methanol | 24 | Complex 1+Et2NH | 10 | 78.0 |
19 | Methanol | 24 | Complex 1+Pyridine | 10 | 65.5 |
20 | Methanol | 24 | Complex 1+(Me3Si)3N | 10 | 73.0 |
Table 5 Optimization of the reaction conditions of benzaldehyde to nitromethane*
Entry | Solvent | Time/h | Catalystb | Catalyst loading (molar fraction, %) | Yield(%) |
---|---|---|---|---|---|
1 | Methanol | 24 | Complex 1+Et3N | 4 | 29.0 |
2 | Methanol | 24 | Complex 1+Et3N | 6 | 48.5 |
3 | Methanol | 24 | Complex 1+Et3N | 8 | 77.0 |
4 | Methanol | 24 | Complex 1+Et3N | 10 | 85.0 |
5 | Methanol | 24 | Complex 1+Et3N | 12 | 85.0 |
6 | Methanol | 24 | Complex 1+Et3N | 14 | 85.5 |
7 | Methanol | 20 | Complex 1+Et3N | 10 | 61.5 |
8 | Methanol | 22 | Complex 1+Et3N | 10 | 79.5 |
9 | Methanol | 26 | Complex 1+Et3N | 10 | 85.5 |
10 | Methanol | 28 | Complex 1+Et3N | 10 | 86.0 |
11 | Ethanol | 24 | Complex 1+Et3N | 10 | 82.5 |
12 | THF | 24 | Complex 1+Et3N | 10 | 79.0 |
13 | CH2Cl2 | 24 | Complex 1+Et3N | 10 | 69.5 |
14 | Toluene | 24 | Complex 1+Et3N | 10 | 77.5 |
15 | Methanol | 24 | Complex 1 | 10 | 31.0 |
16 | Methanol | 24 | Zn(OAc)2·2H2O | 10 | 15.5 |
17 | Methanol | 24 | Et3N | 10 | 35.0 |
18 | Methanol | 24 | Complex 1+Et2NH | 10 | 78.0 |
19 | Methanol | 24 | Complex 1+Pyridine | 10 | 65.5 |
20 | Methanol | 24 | Complex 1+(Me3Si)3N | 10 | 73.0 |
Entry | Compound | R-CHO | Yield(%) | |
---|---|---|---|---|
This work | Ref. | |||
1 | 2 | C6H5CHO | 85.0 | 71.0[ |
2 | 3 | p-CH3C6H4CHO | 82.0 | 79.0[ |
3 | 4 | o-CH3C6H4CHO | 79.5 | 72.5[ |
4 | 5 | p-ClC6H4CHO | 89.5 | 74.0[ |
5 | 6 | o-ClC6H4CHO | 93.0 | 65.0[ |
6 | 7 | p-NO2C6H4CHO | 95.5 | 88.0[ |
7 | 8 | o-NO2C6H4CHO | 90.5 | 83.0[ |
8 | 9 | CH3CH2CH2CHO | 71.0 | 57.0[ |
9 | 10 | 66.0 | 79.0[ | |
10 | 11 | 83.5 | 71.0[ | |
11 | 12 | 87.0 | 80.0[ |
Table 6 Henry reaction of nitromethane with different aldehydes
Entry | Compound | R-CHO | Yield(%) | |
---|---|---|---|---|
This work | Ref. | |||
1 | 2 | C6H5CHO | 85.0 | 71.0[ |
2 | 3 | p-CH3C6H4CHO | 82.0 | 79.0[ |
3 | 4 | o-CH3C6H4CHO | 79.5 | 72.5[ |
4 | 5 | p-ClC6H4CHO | 89.5 | 74.0[ |
5 | 6 | o-ClC6H4CHO | 93.0 | 65.0[ |
6 | 7 | p-NO2C6H4CHO | 95.5 | 88.0[ |
7 | 8 | o-NO2C6H4CHO | 90.5 | 83.0[ |
8 | 9 | CH3CH2CH2CHO | 71.0 | 57.0[ |
9 | 10 | 66.0 | 79.0[ | |
10 | 11 | 83.5 | 71.0[ | |
11 | 12 | 87.0 | 80.0[ |
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