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50. Analytical and Spectroscopic Data of New Compounds: 1,3-Bis(phenylethynyl)benzene
1
(4ag): Brown solid; Yield 89 %; H NMR (500 MHz, CDCl3) δ (ppm): 7.70-7.64 (m,
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1H), 7.52-7.42 (m, 6H), 7.34-7.32 (m, 7H), C NMR (125 MHz, CDCl3) δ (ppm):134.6,
131.6, 131.2, 128.4, 128.3, 88.5, GC-MS m/z 278 (M+1) Anal. Calc. for C22H14, (278.35):
C, 94.93; H, 5.07. Found: C, 95.01.61; H, 5.01; 6-phenylhex-5-ynenitrile (6ah): Yellow
oil; Yield 90 %; 1H NMR (500 MHz, CDCl3) δ (ppm): 7.34-7.32 (m, 2H), 7.24 – 7.22 (m,
3H), 2.53 (t, J = 6.7 Hz, 2H), 2.49 (t, J = 7.3 Hz, 2H), 1.89 (m, 2H); 13C NMR (125 MHz,
CDCl3) δ (ppm):131.5, 128.2, 127.9, 123.1, 119.1, 86.8, 82.3, 24.6, 18.5, 16.1, GC-MS
m/z 169 (M+1) Anal. Calc. for C12H11N (169.08): C, 85.17; H, 6.55; N, 8.28. Found: C,
85.21; H, 6.62; N, 8.73; 6, 6'-Benzene-1,4-diylbishex-5-ynenitrile (7gg):Yellow oil,
Yield 95 %; 1H NMR (500 MHz, CDCl3) δ (ppm): 7.29 (s, 4H), 2.59 (t, J = 6.7 Hz, 4H),
2.53 (t, J = 7.3 Hz, 4H), 1.94 (m, 4H); 13C NMR (125 MHz, CDCl3) δ (ppm):132.2,
123.5, 119.8, 89.4, 82.8, 25.2, 19.3, 16.9; IR (KBr, vcm-1) 2953, 2246, 1919, 1672, 1505,
1446, 1296, 1215, 1056, 838; GC-MS m/z 260 (M+). Anal. Calc. for C18H16N2 (260.13):
C, 83.04; H, 6.19; N, 10.76. Found: C, 83.24; H, 6.23; N, 10.92; 1,4-Bis(5-chloropent-1-
1
yn-1-yl)benzene (7gh): Yellow oil, Yield 96 %; H NMR (500 MHz, CDCl3) δ (ppm):
7.24 (s, 4H), 4.0 (t, J = 6.4 Hz, 4H), 2.54 (t, J = 6.7 Hz, 4H), 1.98 (m, 4H); 13C NMR (125
MHz, CDCl3) δ (ppm):131.3, 122.9, 89.7, 81.2, 43.7, 31.3, 16.9; IR (CH2Cl2, vcm-1)
2947, 2230, 1915, 1706, 1501, 1437, 1283, 1064; GC-MS m/z 279 (M+) Anal. Calc. for
C16H16Cl2 (279.21): C, 68.83; H, 5.78. Found: C, 68.51; H, 5.43; 1,4-Bis(3,5-dimethyl-1-
1
hex-1-yn-3-ol)benzene (7go): Yellow viscous oil, Yield 93 %; H NMR (500 MHz,
CDCl3) δ (ppm): 7.31 (s, 4H), 1.98 (m, 2H), 1.67 (d, J = 6.2 Hz, 4H), 1.55 (s, 6H); 1.03
(d, J = 4.6 Hz, 12H), 13C NMR (125 MHz, CDCl3) δ (ppm):131.4, 122.6, 95.0, 83.1,
68.5, 51.9, 30.9, 25.2, 24.2; IR (CH2Cl2, vcm-1) 3373, 2953, 2225, 1910, 1658, 1457,
1367, 1153, 926, 834; GC-MS m/z 326 (M+) Anal. Calc. for C22H30O2, (326.22): C,
80.94; H, 9.26. Found: C, 80.61; H, 9.33.
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