The synthesis, density functional theory (DFT) molecular structure and Fourier transform infrared spectroscopy (FTIR) molecular recognition study of diethyl phenylenebis(methylene) dicarbamates with 1,2- and 1,3-benzenediols is described. The formation of the complexes was confirmed by the shift of the O-H stretching bands in the IR spectra of the complexes compared with the IR spectra of the noncomplexed benzenediols.
carbamates; xylylenediamines; molecular recognition; DFT
| δ 1H NMR (400 MHz, CDCl3), J in Hz | ||||||||||
| Compound | H2 | H3 | H4 | H5 | H6 | H7 | NH | H9 | H10 | |
| 1a | 7.22 | - | 7.19 | 7.30 | 7.19 | 4.36 3J = 5.6 |
5.03 | 4.16 3J = 7.2 |
1.27 3J = 7.2 |
|
| 2a | 7.27 | 7.27 | - | 7.27 | 7.27 | 4.35 3J = 6.0 |
5.01 | 4.15 3J = 7.2 |
1.25 3J = 7.2 |
|
| δ 13C NMR (100 MHz, CDCl3) | ||||||||||
| Compound | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 |
| 1a | 139.1 | 126.5 | 139.1 | 129.0 | 126.5 | 129.0 | 44.8 | 156.6 | 61.0 | 14.6 |
| 2a | 137.9 | 127.8 | 127.8 | 137.9 | 127.8 | 127.8 | 44.6 | 156.6 | 61.0 | 14.6 |
| IR frequencies, ν in cm-1 | ||||||||||
| Compound | N-H | =C-H (Ar) | C-H (Alk) | C=O | C-C (Ar) | C-O | ||||
| 1a | 3310 | 3065 | 2981 | 1687 | 1530 (s) | 1247,1045 | ||||
| 2a | 3308 | 3054 | 2986 | 1685 | 1527 (s) | 1248,1051 | ||||
| Compound | νO-H | Δ(νO-H) | νN-H | Δ(νN-H) | νC=O | Δ(νC=O) |
|---|---|---|---|---|---|---|
| 1a | - | - | 3310 | - | 1687 | - |
| 2a | - | - | 3308 | - | 1685 | - |
| 3 | 3183 | - | - | - | - | - |
| 1a3 | 3313 | +130 | 3313 | +3 | 1683 | -4 |
| 2a·3 | 3309 | +126 | 3309 | -1 | 1685 | 0 |
| 4 | 3227 | - | - | - | - | - |
| 1a·4 | 3312 | +85 | 3312 | +4 | 1685 | -2 |
| 2a·4 | 3308 | +81 | 3308 | 0 | 1685 | 0 |
| 5 | 3517, 3320 | - | - | - | - | - |
| 1a·5 | 3339 | -178, +19 | 3339 | +29 | 1689 | +2 |
| 2a·5 | 3309 | -136, +12 | 3382 | +1 | 1684 | -1 |
| 6 | 3444, 3320 | - | - | - | - | - |
| 1a·6 | 3311 | -133, -9 | 3311 | +1 | 1686 | -1 |
| 2a·6 | 3308 | -136, -12 | 3308 | 0 | 1684 | -1 |
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