Molecules 2015, 20
4541
(
500 MHz, CDCl
3JHH = 7.5, 4JHH = 1.3 Hz, p-ArH), 7.43 (br. t, 2H, 3JHH = 7.9, m-ArH), 4.45 (t, 2H, 3JHH = 7.0 Hz,
CH -CH
O(CO)-), 2.64 (tt, 2H, 3JHH = 7.0 Hz, 4JHH = 2.4 Hz, -C≡CCH -), 2.17 (qt, 2H, 3JHH = 7.6 Hz,
4JHH = 2.3 Hz, Me-CH
). B-NMR (160 MHz, CDCl , 298 K,
, 298 K, 0.04 M): −129.60 (s, 2F, o-F), −146.36 (s, 1F,
3
, 298 K, 0.04 M): 8.0 (dd, 2H, 3JHH = 8.5 Hz, 4JHH = 1.1 Hz, o-ArH), 7.57 (br. tt, 1H,
-
2
2
2
-C≡), 1.12 (t, 3H, 3JHH = 7.5 Hz, -CH
.04 M): 46.88. F-NMR (376 MHz, CDCl
p-F), −160.73 (m, 2F, m-F).
11
2
3
3
1
9
0
3
3
.4.2. NMR Experiments of 2b
Samples of 0.4, 0.2, 0.1 and 0.04 M concentration were prepared by dissolving the required amount
1
of a 2b and B(C
6
F
5
)
3
in a 1:1 ratio in CDCl
3
(0.5 mL). H-NMR (500 MHz, CDCl
3
, 298 K, 0.4 M):
7
.75 (d, 2H, 3JHH = 8.3 Hz, o-ArH), 7.18 (d, 2H, 3JHH = 8.0 Hz, m-ArH), 4.58 (t, 2H, 3JHH = 6.9 Hz,
CH -CH -), 2.39 (s, 3H, Ar-CH ), 2.17
O(CO)-), 2.68 (tt, 2H, 3JHH = 6.9 Hz, 4JHH = 2.4 Hz, -C≡CCH
qt, 2H, 3JHH = 7.5 Hz, 4JHH = 2.3 Hz, Me-CH -C≡), 1.12 (t, 3H, 3JHH = 7.5 Hz, -CH ). 11B-NMR
160 MHz, CDCl , 298 K, 0.4 M):
, 298 K, 0.4 M): 18.09, −16.63. 19F-NMR (376 MHz, CDCl
-
(
(
2
2
2
3
2
3
3
3
−
133.11 (d, 2F, 3JFF = 19.7 Hz, o-F), −153.76 (t, 1F, 3JFF = 20.1 Hz, p-F), −162.85 (td, 2F, 3JFF = 20.9 Hz,
4JFF = 6.9 Hz, m-F). H-NMR (500 MHz, CDCl
1
, 298 K, 0.2 M): 7.76 (d, 2H, 3JHH = 8.2 Hz,
O(CO)-), 2.67 (tt, 2H,
), 2.17 (qt, 2H, 3JHH = 7.6 Hz,
, 298 K,
3
o-ArH), 7.19 (d, 2H, 3JHH = 8.2 Hz, m-ArH), 4.55 (t, 2H, 3JHH = 6.9 Hz, -CH
3JHH = 6.9 Hz, 4JHH = 2.3 Hz, -C≡CCH
4JHH = 2.4 Hz, Me-CH
2
2
-CH
2
-), 2.39 (s, 3H, Ar-CH
3
-C≡), 1.12 (t, 3H, 3JHH = 7.5 Hz, -CH
). B-NMR (160 MHz, CDCl
11
2
3
3
0
.2 M): 23.07. 19F-NMR (376 MHz, CDCl
152.60 (t, 1F, 3JFF = 19.8 Hz, p-F), −162.46 (td, 2F, 3JFF = 20.7 Hz, 4JFF = 6.9 Hz, m-F). H-NMR
3
, 298 K, 0.2 M): −132.58 (d, 2F, 3JFF = 18.4 Hz, o-F),
1
−
(
500 MHz, CDCl
3
, 298 K, 0.1 M): 7.80 (br. d, 2H, 3JHH = 8.4 Hz, o-ArH), 7.20 (d, 2H, 3JHH = 8.0 Hz,
O(CO)-), 2.65 (tt, 2H, 3JHH = 7.0 Hz, 4JHH = 2.4 Hz,
), 2.17 (qt, 2H, 3JHH = 7.6 Hz, 4JHH = 2.4 Hz, Me-CH
-C≡), 1.11
, 298 K, 0.1 M): 27.34. F-NMR (376 MHz,
m-ArH), 4.50 (t, 2H, 3JHH = 7.0 Hz, -CH
2
-
(
C≡CCH
2
-CH
2
-), 2.40 (s, 3H, Ar-CH
3
2
t, 3H, 3JHH = 7.5 Hz, -CH
). B-NMR (160 MHz, CDCl
11
19
3
3
CDCl
3
, 298 K, 0.1 M): −132.13 (d, 2F, 3JFF = 19.7 Hz, o-F), −152.60 (br. s, 1F, p-F), −162.16 (td, 2F,
3JFF = 21.8 Hz, 4JFF = 6.8 Hz, m-F). H-NMR (500 MHz, CDCl
1
, 298 K, 0.04 M): 7.84 (br. d, 2H,
O(CO)-),
), 2.17 (qt, 2H,
3
3JHH = 8.4 Hz, o-ArH), 7.21 (d, 2H, 3JHH = 8.1 Hz, m-ArH), 4.46 (t, 2H, 3JHH = 6.9 Hz, -CH
2
2
.64 (tt, 2H, 3JHH = 6.9 Hz, 4JHH = 2.3 Hz, -C≡CCH
3JHH = 7.6 Hz, 4JHH = 2.4 Hz, Me-CH
CDCl
, 298 K, 0.04 M): 43.58. 19F-NMR (376 MHz, CDCl
3JFF = 16.4 Hz, o-F), −147.64 (br. s, 1F, p-F), −161.08 (br. t, 2F, 3JFF = 17.4 Hz, m-F).
2
-CH
2
-), 2.40 (s, 3H, Ar-CH
3
-C≡), 1.11 (t, 3H, 3JHH = 7.5 Hz, -CH
). B-NMR (160 MHz,
11
2
3
3
3
, 298 K, 0.04 M): −130.20 (d, 2F,
3
.4.3. NMR Experiments of 2c
Samples of 0.4, 0.2, 0.1 and 0.04 M concentration were prepared by dissolving the required amount
1
of 2c and B(C
6
F
5
)
3
in a 1:1 ratio in CDCl
3
(0.5 mL). H-NMR (500 MHz, CDCl
3
, 298 K, 0.4 M): 7.86
(
-
d, 2H, 3JHH = 8.9 Hz, o-ArH), 6.84 (d, 2H, 3JHH = 9.0 Hz, m-ArH), 4.55 (t, 2H, 3JHH = 6.9 Hz,
CH O(CO)-), 3.85 (s, 3H, -OCH -CH -),
), 2.67 (br. tt, 2H, 3JHH = 6.9 Hz, 4JHH = 2.2 Hz, -C≡CCH
.17 (qt, 2H, 3JHH = 7.5 Hz, 4JHH = 2.3 Hz, Me-CH
). B-NMR
2
3
2
2
2
2
-C≡), 1.11 (t, 3H, 3JHH = 7.5 Hz, -CH
3
11
1
9
(160 MHz, CDCl
3
, 298 K, 0.4 M): 40.16, 10.33. F-NMR (376 MHz, CDCl
3
, 298 K, 0.4 M): −133.70
d, 2F, 3JFF = 19.2 Hz, o-F), 154.94 (br. s, 1F, p-F), −163.16 (t, 2F, 3JFF = 17.5 Hz, m-F). H-NMR
1
(