Synthesis and Characterization of Novel Organotin-Phosphorous Compounds II
Abstract
:1. Introduction
2. Results and Discussion
Compound | R | Melting point (°C) | Yield (%) |
---|---|---|---|
IVa | 4-Cl | 81-82 | 87 |
IVb | 3-CF3 | 87.5 | 58 |
IVc | 3-OCH3 | 50-53 | 53 |
Compound | Calculated | Measured | ||||
---|---|---|---|---|---|---|
%C | %H | %N | %C | %H | %N | |
II | 57.43 | 8.26 | - | 57.63 | 8.33 | - |
III | 61.09 | 8.72 | - | 61.18 | 8.64 | - |
IVa | 60.14 | 6.41 | 1.90 | 60.02 | 6.37 | 1.93 |
IVb | 59.09 | 6.13 | 1.81 | 58.79 | 6.21 | 1.87 |
IVc | 62.14 | 6.86 | 1.91 | 62.21 | 6.93 | 1.94 |
2.1. 13C-NMR Spectra
R group | δ (ppm) | ||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Sn-CH2- | -CH2CH2- | -CH3 | C0 | C1 | C2 | C3 | C4 | C5 | C6 | ||||||||||
4-Cl | 29.0 | 27.8 | 9.6 | 59.2 | 136.0 | 136.5 | 146.8 | 143.3 | 128.2 | 129.5 | |||||||||
13.6 | 53.0 | ||||||||||||||||||
3-CF3 | 29.0 | 27.3 | 9.6 | 59.4 | 136.4 | 137.0 | 142.4 | 142.4 | 128.3 | 129.5 | |||||||||
13.6 | 53.2 | ||||||||||||||||||
3-OCH3 | 29.0 | 27.3 | 9.6 | 60.1 | 134.3 | 136.3 | 142.4 | 142.4 | 127.9 | 128.3 | |||||||||
13.5 | 54.0 | ||||||||||||||||||
R group | δ (ppm) | ||||||||||||||||||
C'1 | C'2 | C'3 | C'4 | C'5 | C'6 | ||||||||||||||
4-Cl | 147.4 | 113.9 | 135.0 | 118.1 | 129.7 | 112.2 | |||||||||||||
3-CF3 | 146.4 | 115.1 | 139.0 | 119.3 | 129.0 | 120.8 | |||||||||||||
3-OCH3 | 142.6 | 91.9 | 153.8 | 120.4 | 153.8 | 91.9 | |||||||||||||
R group | δ (ppm) | ||||||||||||||||||
C''1 | C''2,6a | C''3,5a | C''4 | ||||||||||||||||
4-Cl | 150.4 | 120.7 | 130.2 | 127.3 | |||||||||||||||
149.8 | 120.5 | 130.2 | |||||||||||||||||
3-CF3 | 150.5 | 120.6 | 129.5 | 127.9 | |||||||||||||||
150.1 | 120.4 | 129.5 | |||||||||||||||||
3-OCH3 | 150.5 | 120.7 | 130.9 | 127.8 | |||||||||||||||
150.4 | 120.6 | 130.9 |
Compound | δ (ppm) | |||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Sn-CH2- | -CH2CH2- | -CH3 | C0 | C1 | C2 | C3 | C4 | C5 | C6 | |||||
Sn-(CH2-CH2-CH2-CH3)3 | 27.8 | 26.8 | 13.6 | - | - | - | - | - | - | - | ||||
18.0 | ||||||||||||||
III | 29.1 | 27.4 | 9.7 | 192.2 | 135.6 | 137.7 | 143.6 | 142.6 | 128.4 | 129.5 | ||||
13.7 | ||||||||||||||
Compound | δ (ppm) | |||||||||||||
C'1 | C'2 | C'3 | C'4 | C'5 | C'6 | |||||||||
4-Chloroaniline | 147.7 | 114.8 | 134.7 | 118.2 | 130.3 | 113.2 | ||||||||
3-Trifluoromethaneaniline | 146.4 | 115.8 | 138.9 | 119.3 | 129.7 | 112.2 | ||||||||
3-Methoxyaniline | 143.3 | 98.8 | 152.9 | 119.0 | 152.9 | 98.8 | ||||||||
Compound | δ (ppm) | |||||||||||||
C''1 | C''2,6a | C''3,5a | C''4 | |||||||||||
Diphenyl phosphite | 149.3 | 120.8 | 131.8 | 127.6 | ||||||||||
149.0 | 120.5 | 131.8 |
2.2. 1H-NMR Spectra
Compound | δ (ppm) | ||||
---|---|---|---|---|---|
3(-(C H2)3CH3) | Ar-H | -O-CH-O- | -O(C H2)2O- | -C HO | |
II | 1.2 (m, 27H) | 7.5 (m, 4H) | 5.8 (s, 1H) | 4.1 (d, 4H) | - |
III | 1.2 (m, 27H) | 7.7 (m, 4H) | - | - | 10.3 (s, 1H) |
Compound | δ (ppm) | ||||
3(-(CH2)3CH3) | -P-CH-N- | -NH- | Ar-H | ||
IVa | 0.6-1.8 (m, 27H) | 4.7 (m, 1H) | 5.4 (d, 1H) | 6.5-6.7 (m, 18H) | |
IVb | 0.6-1.7 (m, 27H) | 4.8-5.0 (d, 1H) | 5.3-5.4 (m, 1H) | 6.6-7.6 (m, 18H) | |
IVc | 0.6-1.6 (m, 27H) | 3.8 (s, 1H) | 5.4 (d, 1H) | 6.25-7.6 (s, 18H) |
2.3. FT-IR Spectra
Compound | Wavenumber (cm-1) | |||||||
---|---|---|---|---|---|---|---|---|
-(CH2)3CH3 | Aromatic ring | P-O-Aryl | -P=O | C-O-C | -C=O | |||
C-H stretching | C-H bending | C=C stretching | Stretching | |||||
II | 2860, 2910, 2940 | 1350, 1370 | 1420, 1455 | - | - | 1080 | - | |
III | 2840, 2910, 2950 | 1360 | 1450 | - | - | - | 1700 | |
IVa | 2900, 2940 | 1290 | 1480 | 1180 | 1200 | - | - | |
IVb | 2840, 2900, 2960 | 1340 | 1480 | 1100 | 1200 | - | - | |
IVc | 2920, 2940 | 1300 | 1470 | 1040 | 1200 | - | - |
3. Experimental
3.1. Instruments
3.2. Methods
3.2.1. Preparation of 2-[3-(tri-n-butylstannyl)]1,3-dioxolane (II)
3.2.2. Preparation of 3-(tri-n-butylstannyl)-benzaldehyde (III)
3.2.3. Preparation of organotin substituted α-anilinomethyl phosphonates IV
4. Conclusions
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Al-Deyab, S.S.; El-Newehy, M.H. Synthesis and Characterization of Novel Organotin-Phosphorous Compounds II. Molecules 2010, 15, 1425-1432. https://doi.org/10.3390/molecules15031425
Al-Deyab SS, El-Newehy MH. Synthesis and Characterization of Novel Organotin-Phosphorous Compounds II. Molecules. 2010; 15(3):1425-1432. https://doi.org/10.3390/molecules15031425
Chicago/Turabian StyleAl-Deyab, Salem S., and Mohamed H. El-Newehy. 2010. "Synthesis and Characterization of Novel Organotin-Phosphorous Compounds II" Molecules 15, no. 3: 1425-1432. https://doi.org/10.3390/molecules15031425
APA StyleAl-Deyab, S. S., & El-Newehy, M. H. (2010). Synthesis and Characterization of Novel Organotin-Phosphorous Compounds II. Molecules, 15(3), 1425-1432. https://doi.org/10.3390/molecules15031425