Job/Unit: O30507
/KAP1
Date: 25-06-13 17:19:26
Pages: 6
Y.-S. Lan, B.-S. Liao, Y.-H. Liu, S.-M. Peng, S.-T. Liu
FULL PAPER
N-(3-Phenylallylidene)aniline: 35 mg, 47%. 1H NMR (400 MHz,
CDCl3): δ = 8.27 (m, 1 H, H-C=N), 7.54 (m, 2 H, Ar-H), 7.34–
7.43 (m, 5 H, Ar-H), 7.11–7.24 (m, 5 H, Ar-H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 161.7, 151.7, 144.1, 135.6, 129.7, 129.3,
129.0, 128.6, 127.6, 126.2, 121.0 ppm.
Acknowledgments
The authors thank the National Science Council, Taiwan for finan-
cial support (NSC-100-2113-M002-001-MY3).
N-Benzylidene-1-hexanamine: 36.8 mg, 54%. 1H NMR (CDCl3,
400 MHz): δ = 8.17 (s, 1 H, H-C=N), 7.63 (m, 2 H, Ar-H), 7.31
(m, 3 H, Ar-H), 3.52 (t, J = 7.0 Hz, 2 H, -CH2-), 1.62 (m, 2 H,
-CH2-), 1.24–1.30 (m, 6 H, -CH2-), 0.82 (m, 3 H, -Me) ppm. 13C
NMR (CDCl3, 100 MHz): δ = 160.7, 136.4, 130.5, 128.7, 128.1,
62.1, 32.0, 31.2, 27.4, 23.0, 14.4 ppm.
N-Benzylidene-1-octanamine: 53 mg, 68%. 1H NMR (400 MHz,
CDCl3): δ = 8.26 (s, 1 H, H-C=N), 7.73 (m, 2 H, Ar-H), 7.40 (m,
3 H, Ar-H), 3.61 (t, J = 7.0 Hz, 2 H, -CH2-), 1.71–1.73 (m, 2 H,
-CH2-), 1.30–1.36 (m, 10 H, -CH2-), 0.91 (t, J = 6.4 Hz, 3 H, -CH3)
ppm. 13C NMR (100 MHz, CDCl3): δ = 160.2, 136.0, 130.1, 128.3,
127.8, 62.0, 32.3, 31.4, 30.1, 29.8, 27.9, 23.2, 14.7 ppm.
N,NЈ-Bisbenzylidenebenzene-1,4-diamine: 74.7 mg, 73%. 1H NMR
(400 MHz, CDCl3): δ = 8.50 (s, 2 H, H-C=N), 7.90–7.92 (m, 4 H,
Ar-H), 7.47–7.48 (m, 6 H, Ar-H), 7.28 (s, 4 H, Ar-H) ppm. 13C
NMR (100 MHz, CDCl3): δ = 159.7, 149.9, 136.3, 131.4, 128.9,
122.0 ppm.
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N,NЈ-Bis(4-methoxybenzylidene)benzene-1,4-diamine: 73 mg, 59%.
1H NMR (400 MHz, CDCl3): δ = 8.43 (s, 2 H, H-C=N), 7.84 (d,
J = 8.8 Hz, 4 H, Ar-H), 7.24 (s, 4 H, Ar-H), 6.98 (d, J = 8.8 Hz, 4
H, Ar-H), 3.88 (s, 6 H, -CH3) ppm. 13C NMR (100 MHz, CDCl3):
δ = 162.2, 159.0, 150.0, 130.6, 130.5, 129.4, 121.9, 114.3, 55.6 ppm.
N,NЈ-Bis(4-trifluoromethylbenzylidene)benzene-1,4-diamine:
1
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106 mg, 70%. H NMR (400 MHz, CDCl3): δ = 8.54 (s, 2 H, H-
C=N), 8.01 (d, J = 8 Hz, 4 H, Ar-H), 7.72 (d, J = 8 Hz, 4 H, Ar-
H), 7.31 (s, 4 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ =
158.1, 149.8, 139.3, 132.9 (q, JC,F = 31.9 Hz), 129.1, 128.6 125.8
(q, JC,F = 52.5 Hz), 125.3, 122.1 ppm.
N-Benzylidene-3-iodoaniline: 60 mg, 54%. 1H NMR (400 MHz,
CDCl3): δ = 8.24 (s, 1 H, H-C=N), 7.74–7.76 (m, 2 H, Ar-H), 7.41–
7.43 (m, 2 H, Ar-H), 7.33–7.37 (m, 3 H, Ar-H), 6.97–7.05 (m, 2 H,
Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 161.2, 153.3, 135.8,
134.7, 131.8, 130.6, 129.6, 129.5, 129.0, 128.8, 120.7 ppm. HRMS
(ESI-TOF): calcd. for C13H9IN [M
307.9930.
–
H]+ 307.9931; found
Crystallography: A crystal of 1·3H2O was obtained by recrystalli-
zation from water/acetone. The cell parameters were determined
with a Siemens SMART CCD diffractometer. The structure was
solved using the SHELXS-97 program[13a] and refined using the
SHELXL-97 program[13b] by full-matrix least-squares on F2 values.
Crystal data: C21H22Cu2N4O10, Fw = 617.51, monoclinic, P21/c, a
= 7.1182(2) Å, b = 15.9813(3) Å, c = 20.0535(5) Å, α = 90, β =
94.306(2)°, γ = 90, V = 2274.81(10) Å3, Z = 4, Dcalcd.
=
1.803 Mgm–3, F(000) = 1256, crystal size: 0.25ϫ0.20ϫ0.15 mm3,
2.87 to 27.50°, 20256 reflections collected, 5088 reflections [R(int)
= 0.0335], Final R indices [IϾ2σ(I)]: R1 = 0.0288, wR2 = 0.0625,
for all data R1 = 0.0410, wR2 = 0.690, goodness-of-fit on F2: 1.022.
CCDC-909663 (for 1) contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from
The Cambridge Crystallographic Data Centre via www.ccdc.cam.
ac.uk/data_request/cif.
[13] a) SHELXS-97: G. M. Sheldrick, Acta Crystallogr., Sect. A:
Found. Crystallogr. 1990, 46, 467–474; b) G. M. Sheldrick,
SHELXL-97, University of Göttingen, Germany, 1997.
Received: April 9, 2013
Supporting Information (see footnote on the first page of this arti-
cle): NMR spectroscopic data, NMR spectra, and crystallographic
data.
Published Online:
6
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