Synthesis of 5-Substituted-1H-Tetrazole Derivatives Using Monodisperse Carbon Black Decorated Pt Nanoparticles
Baskaya et al.
all the products observation of belonging to the proposed
structure [M–H]− peak and then the loss of 28 units mass
that resulted from the loss of N2 from a tetrazole ring sup-
ports the tetrazole formation.
2.4.6. 5-(4-Chlorophenyl) 1H-Tetrazole (h)
ꢁ
ꢁ
As a white powder, M.p.: 250–251 C (lit. 250–252 C)4,
FT–IR (cm−1ꢂ: 3063, 2973, 2902, 2680, 2540, 1606, 1561,
1
1276, 1255, 1097, H NMR (300 MHz, DMSO-d6ꢂ: ꢆ =
7ꢅ70 (d, J = 8ꢅ56 Hz, 2H, Ar–H), 8.06 (d, J = 8ꢅ57 Hz,
2H, Ar–H), 16.95 (br, 1H, –NH) ppm, 13C NMR (75
MHz, DMSO-d6ꢂ: ꢆ = 123ꢅ67, 129.18, 130.03, 136.37,
155.92 ppm, HRMS (QTOF-ESI): m/z [M–H]− calcd. for
C7H4ClN4: 179.0124; found [M–H]−: 179.0123.
2.4.1. 5-Phenyl 1H-Tetrazole (a)
ꢁ
ꢁ
As a white powder, M.p.: 216–218 C (lit. 215–216 C),1
FT–IR (cm−1ꢂ: 3053, 2979, 2906, 2833, 2682, 2601, 1607,
1
1561, 1285, 1254 H NMR (300 MHz, DMSO-d6ꢂ: ꢆ =
7ꢅ60 − 7ꢅ65 (m, 3H, Ar–H), 8.03–8.07 (m, 2H, Ar–H),
16.85 (br, 1H, –NH) ppm, 13C NMR (75 MHz, DMSO-d6):
ꢆ = 124ꢅ60, 127.40, 129.79, 131.62, 155.77 ppm, HRMS
(QTOF-ESI): m/z [M–H]− calcd. for C7H5N4: 145.0514;
found [M–H]−: 145.0517.
2.4.7. 4-(1H-Tetrazol-5-yl)Benzaldehyde (i)
ꢁ
ꢁ
As a white powder, M.p.: 185–187 C (lit. 183–185 C)5,
FT–IR (cm−1ꢂ: 3065, 2978, 2912, 2817, 2686, 2542, 1698,
1
1565, 1557, 1289, 1255, H NMR (300 MHz, DMSO-
d6ꢂ: ꢆ = 8ꢅ13 (d, J = 8ꢅ42 Hz, 2H, Ar–H), 8.27 (d,
J = 8ꢅ22 Hz, 2H, Ar–H), 10.10 (s, 1H, –CHO), 17.15
(br, 1H, –NH) ppm, 13C NMR (75 MHz, DMSO-d6ꢂ:
ꢆ = 128ꢅ07, 130.00, 130.82, 138.07, 155.77, 193.13 ppm,
HRMS (QTOF-ESI): m/z [M–H]− calcd. for C8H6N4O:
173.0463; found [M–H]−: 173.0465.
2.4.2. 4-(1H-Tetrazol-5-yl)Pyridineꢁ(b)
ꢁ
As a white powder, M.p.: 255–257 C (lit. 254–255 C)1,
FT–IR (cm−1ꢂ: 3055, 2969, 2885, 2410, 1627, 1526, 1291,
1
1237, 1041, H NMR (300 MHz, DMSO-d6ꢂ: ꢆ = 8ꢅ05
(s, 2H, Ar–H), 8.90 (s, 2H, Ar–H), 15.60 (br, 1H, –NH)
ppm, 13C NMR (75 MHz, DMSO-d6ꢂ: ꢆ = 121ꢅ60, 133.91,
150.51, 155.64 ppm, HRMS (QTOF-ESI): m/z [M–H]−
calcd. for C6H5N5: 146.0467; found [M–H]−: 146.0468.
3. RESULTS AND DISCUSSION
Monodisperse Pt NPs@VC has been synthesized by using
optimized sonochemical double solvent reduction protocol
as given experimental section. Atomic force microscopy
(AFM), X-ray diffraction (XRD), transmission electron
2.4.3. 5-(P-Tolyl) 1H-Tetrazole (c)
ꢁ
ꢁ
As a white powder, M.p.: 247–248 C (lit. 248–249 C)2,
FT–IR (cm−1ꢂ: 3044, 2979, 2916, 2846, 2767, 2679, 2608,
1612, 1569, 1285, 1256, 1162, 1085, H NMR (300 MHz,
Delivered by Ingenta
microscopy (TEM), X-ray photoelectron spectroscopy
(XPS), and high resolution electron microscopy (HRTEM)
have been used for the characterization of monodisperse
Pt NPs@VC.
1
IP: 146.185.205.191 On: Mon, 19 Feb 2018 11:26:28
Copyright: American Scientific Publishers
DMSO-d6ꢂ: ꢆ = 2ꢅ40 (s, 3H, –CH3ꢂ, 7.42 (d, J = 8ꢅ09 Hz,
2H, Ar–H), 7.93 (d, J = 8ꢅ17 Hz, 2H, Ar–H), 16.75
(br, 1H, –NH) ppm, 13C NMR (75 MHz, DMSO-d6ꢂ:
ꢆ = 21ꢅ47, 121.71, 127.34, 130.40, 141.69, 155.53 ppm,
HRMS (QTOF-ESI): m/z [M–H]− calcd. for C8H7N4:
159.0671; found [M–H]−: 159.0674.
As shown in Figure 1, Pt NPs@VC exhibit distinct
diffraction patterns at 2ꢇ = 39ꢅ82, 46.22, 67.62, 81.22 and
85.91 which are mainly due to Pt (111), (200), (220),
(311), and (320), respectively, planes of the face-centered
cubic (fcc) crystal lattice of platinum. The lattice parame-
ter (ꢄPt) values and average crystallite of the Pt nanopar-
ticles were calculated to be 3.908 Å25 which is in good
agreement with 3.923 Å and 3ꢅ75 0ꢅ41 nm using the
2.4.4. N-(4-(1H-Tetrazol-5-yl)Phenyl)Acetamide (d)
As a white powder, M.p.: 285–287 ꢁC (lit. 287 ꢁC)3, FT–IR
(cm−1ꢂ: 3264, 3132, 3078, 2325, 2201, 2151, 1600, 1544,
1
1322, 1290, 1263, H NMR (300 MHz, DMSO-d6ꢂ: ꢆ =
2ꢅ07 (s, 3H, –CH3ꢂ, 7.58 (d, J = 8ꢅ21 Hz, 2H, Ar–H), 7.88
(d, J = 8ꢅ26 Hz, 2H, Ar–H), 9.95 (s, 1H, –NH) ppm, 13C
NMR (75 MHz, DMSO-d6ꢂ: ꢆ = 24ꢅ47, 119.40, 126.59,
127.91, 138.74, 155.92, 168.73 ppm, HRMS (QTOF-
ESI): m/z [M–H]− calcd. for C9H8N5O: 202.0729; found
[M–H]−: 202.0732.
2.4.5. 5-(4-Nitrophenyl) 1H-Tetrazole (f)
ꢁ
ꢁ
As a grey powder, M.p.: 219–220 C (lit. 219–221 C)1,
FT–IR (cm−1ꢂ: 3078, 2913, 2845, 2770, 1605, 1551, 1291,
1
1222, H NMR (300 MHz, DMSO-d6ꢂ: ꢆ = 8ꢅ31 (d, J =
9ꢅ01 Hz, 2H, Ar–H), 8.46 (d, J = 9ꢅ00 Hz, 2H, Ar–H),
17.15 (br, 1H, –NH) ppm, 13C NMR (75 MHz, DMSO-
d6ꢂ: ꢆ = 125ꢅ03, 128.63, 131.10, 149.16, 155.92 ppm,
HRMS (QTOF-ESI): m/z [M–H]− calcd. for C7H4N5O2:
190.0365; found [M–H]−: 190.0367.
Figure 1. XRD of catalyst monodisperse Pt NPs@VC.
J. Nanosci. Nanotechnol. 17, 1992–1999, 2017
1994