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GlcN residue), 4.25 (s, 6H, 2 ꢂ CH3 of MeIm), 3.84 (t, J ¼ 7.2 Hz, 1660 (s, sh, n(C]O)acetyl), 1634 (vs, sh, n(C]N)azomethine), 1558 (m,
5H, GlcN and GlcNHAc residue), 3.56 (s, 1H, GlcN residue), 3.17 sh, amide II), 1370 (m, sh, amide III), 1285 (m, sh, n(Ar–O)), 1155
(br, s, 6H, GlcN and GlcNHAc residue), 2.76 (t, J ¼ 8.2 Hz, 2H, (s, sh, n(H–C]C+H–C]N)bend, Im), 1066 (m, sh, n(C–O–C)str), 895 (m,
ꢁ
GlcN and GlcNHAc residue), 2.40 (tt, J ¼ 15.4, 7.4 Hz, 3H, sh, n(C–O–C), b-glycosidic linkage), 836 (s, sh, n(PF )), 761 (m, sh,
6
NHAc). 13C NMR (151 MHz, 1% CD3COOD/D2O)60
d (ppm): Im). 1H NMR (600 MHz, 1% CD3COOD/D2O)60 C d (ppm): 10.35
ꢀ
ꢀC
177.14, 168.29, 155.10, 153.27, 141.89, 137.77, 133.84, 126.20, (s, 1H, OH), 10.28 (s, 1H, OH), 9.06 (d, J ¼ 11.5 Hz, 2H, 2 ꢂ H–
124.50, 122.66, 118.78, 111.90, 101.96, 98.53, 88.15, 84.77, C]N), 8.17 (s, 1H, NH of GlcNHAc residue), 8.10 (d, J ¼ 8.7 Hz,
70.65, 61.16, 57.76, 50.71, 45.27, 42.29, 38.72, 36.27, 31.22, 29.79 1H, Ar-H), 7.96 (dd, J ¼ 8.5, 2.1 Hz, 2H, 2 ꢂ Ar-H), 7.89–7.75 (m,
and 22.51.
2H, 2 ꢂ Ar-H), 7.61–7.42 (m, 1H, Ar-H), 5.76 (s, 4H, 2 ꢂ CH2 of
5-(N,N,N-Triethylammonium chloride)-salicylidene chitosan CH2Ar), 5.25 (s, 1H, GlcN residue), 4.25 (s, 6H, 2 ꢂ CH3 of
(ILCSB2). Yellow crystals, yield (1.54 g, 98.1%). FTIR (KBr, MeIm), 3.85 (t, J ¼ 7.0 Hz, 5H, GlcN and GlcNHAc residue), 3.53
cmꢁ1): 3451 (vs, br, n(O–H+NH )), 3150 (m, br, n(N–H)), 1661 (s, sh, (s, 1H, GlcN residue), 3.16 (br, s, 6H, GlcN and GlcNHAc
2
n(C]O)acetyl), 1638 (vs, sh, n(C]N)azomethine), 1556 (m, sh, amide residue), 2.76 (t, J ¼ 8.2 Hz, 2H, GlcN and GlcNHAc residue),
II), 1377 (m, sh, amide III), 1283 (m, sh, n(Ar–O)), 1073 (m, sh, 2.40 (m, 3H, NHAc). 13C NMR (151 MHz, 1% CD3COOD/
1
ꢀ
n(C–O–C)str), 896 (m, sh, n(C–O–C), b-glycosidic linkage). H NMR D2O)60 C d (ppm): 176.24, 168.56, 154.95, 152.87, 141.89, 138.02,
ꢀ
(600 MHz, 1% CD3COOD/D2O)60
d (ppm): 10.35 (s, 2H, 2 ꢂ 133.84, 126.22, 124.51, 122.53, 118.89, 111.90, 102.12, 98.13,
C
OH), 9.08 (d, J ¼ 11.9 Hz, 2H, 2 ꢂ H–C]N), 8.24 (d, J ¼ 11.9 Hz, 87.25, 84.48, 70.65, 61.61, 57.32, 50.71, 45.26, 41.99, 38.72,
1H, NH of GlcNHAc residue), 8.14 (d, J ¼ 2.4 Hz, 1H, Ar-H), 7.98 35.87, 31.22, 30.13, 22.56.
(d, J ¼ 8.7 Hz, 1H, Ar-H), 7.86–7.80 (m, 3H, 3 ꢂ Ar-H), 7.47 (d, J ¼
5-(N,N,N-Triethylammonium hexauorophosphate)-salicyli-
8.7 Hz, 1H, Ar-H), 5.77 (s, 4H, 2 ꢂ CH2 of CH2Ar), 5.27 (d, J ¼ 7.3 dene chitosan (ILCSB5). Yellow plates, yield (1.79 g, 98.8%).
Hz, 1H, GlcN residue), 4.28–4.22 (m, 6H, GlcN and GlcNAc FTIR (KBr, cmꢁ1): 3425 (vs, br, n(O–H+NH )), 3163 (m, br, n(N–H)),
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residue), 4.11 (s, 2H, GlcNAc residue), 3.84 (t, J ¼ 7.2 Hz, 4H, 2 ꢂ 1659 (s, sh, n(C]O)acetyl), 1633 (vs, sh, n(C]N)azomethine), 1561 (m,
CH2), 3.56 (br, s, 2H, GlcN residue), 3.39–3.29 (q, 6H, 3 ꢂ CH2 of sh, amide II), 1373 (m, sh, amide III), 1280 (m, sh, n(Ar–O)), 1067
CH2CH3), 3.15–2.94 (q, 6H, 3 ꢂ CH2 of CH2CH3), 2.76 (t, J ¼ 8.2 (m, sh, n(C–O–C)str), 836 (s, sh, n(PF )). 1H NMR (600 MHz, 1%
ꢁ
6
ꢀ
Hz, 4H, GlcN and GlcNHAc residue), 2.43–2.34 (br, m, 3H, CH3, CD3COOD/D2O)60 d (ppm): 10.37 (s, 1H, ꢂOH), 10.28 (s, 1H,
C
NHAc), 2.12–2.01 (t, JHH ¼ 7.00 Hz, 9H, 3 ꢂ CH2CH3), 1.88–1.76 OH), 9.08 (d, J ¼ 10.8 Hz, 2H, 2 ꢂ H–C]N), 8.26 (br, s, 1H, NH
(t, JHH ¼ 7.02 Hz, 9H, 3 ꢂ CH2CH3). 13C NMR (151 MHz, 1% of GlcNHAc residue), 8.13 (d, J ¼ 2.2 Hz, 1H, Ar-H), 7.98 (d, J ¼
ꢀC
CD3COOD/D2O)60
d (ppm): 177.21, 164.30, 159.57, 138.23, 8.7 Hz, 1H, Ar-H), 7.85–7.77 (m, 3H, 3 ꢂ Ar-H), 7.47 (d, J ¼ 8.7
135.13, 133.42, 126.51, 124.22, 122.73, 119.08, 107.34, 100.21, Hz, 1H, Ar-H), 5.75 (s, 4H, 2 ꢂ CH2 of CH2Ar), 5.26 (d, J ¼ 7.3 Hz,
83.89, 77.61, 76.55, 72.36, 66.19, 61.28, 56.91, 53.65, 50.48, 1H, GlcN residue), 4.28–4.23 (m, 6H, GlcN and GlcNAc residue),
36.97, 31.99, 29.78, 23.66, 17.89.
4.21 (br, s, 2H, GlcNAc residue), 3.90 (t, J ¼ 7.2 Hz, 4H, GlcN and
5-(2-Methoxypyridinium chloride)-salicylidene chitosan GlcNAc residue), 3.63 (br, s, 2H, GlcN residue), 3.41 (q, 6H, 3 ꢂ
(ILCSB3). Pale yellow powder, yield (1.58 g, 98.7%). FTIR (KBr, CH2 of CH2CH3), 3.17 (q, 6H, 3 ꢂ CH2 of CH2CH3), 2.76 (t, J ¼
cmꢁ1): 3436 (vs, br, n(O–H+NH )), 3158 (m, br, n(N–H)), 1656 (s, sh, 8.2 Hz, 4H, GlcN and GlcNHAc residue), 2.40–2.34 (br, m, 3H,
2
n(C]O)acetyl), 1640 (vs, sh, n(C]N)azomethine), 1524 (m, sh, amide CH3, NHAc), 2.03–1.92 (t, JHH ¼ 6.99, 7.01 Hz, 9H, 3 ꢂ CH2CH3),
II), 1373 (m, sh, amide III), 1286 (m, sh, n(Ar–O)), 1159 (s, sh, 2.03–1.92 (t, JHH ¼ 7.15 Hz, 9H, 3 ꢂ CH2CH3). 13C NMR (151
ꢀ
n(H–C]C+H–C]N)bend, Py), 1070 (m, sh, n(C–O–C)str), 897 (m, sh, MHz, 1% CD3COOD/D2O)60 d (ppm): 179.89, 166.93, 159.87,
C
n(C–O–C), b-glycosidic linkage), 769, 657 (m, sh, Py+). 1H NMR 139.36, 135.55, 134.27, 128.86, 125.74, 122.69, 120.83, 107.25,
ꢀ
(600 MHz, 1% CD3COOD/D2O)60 d (ppm): 10.35 (s, 1H, OH), 100.99, 83.77, 77.23, 76.18, 72.07, 66.66, 61.50, 56.20, 53.31,
C
10.27 (s, 1H, OH), 8.99 (dd, J ¼ 18.4, 7.4 Hz, 2H, 2 ꢂ H–C]N), 51.63, 36.79, 32.06, 30.13, 24.89, 18.92.
8.24 (d, J ¼ 7.5 Hz, 1H, Py), 8.15 (d, J ¼ 7.3 Hz, 1H, NH of
5-(2-Methoxypyridinium hexauorophosphate)-salicylidene
GlcNHAc residue), 8.00 (d, J ¼ 8.7 Hz, 1H, Py), 7.81 (dd, J ¼ 26.5, chitosan (ILCSB6). Yellowish white powder, yield (1.85 g,
7.5 Hz, 4H, Py + Ar), 7.59 (t, J ¼ 7.7 Hz, 1H, Ar), 7.48 (d, J ¼ 8.7 98.9%). FTIR (KBr, cmꢁ1): 3438 (vs, br, n(O–H+NH )), 3161 (m, br,
2
Hz, 1H, Ar), 5.98 (s, 4H, 2 ꢂ CH2 of CH2Ar), 5.25 (d, J ¼ 7.7 Hz, n(N–H)), 1655 (s, sh, n(C]O)acetyl), 1637 (vs, sh, n(C]N)azomethine),
1H, GlcN residue), 4.48 (s, 6H, 2 ꢂ CH3 of MeOPy), 4.27 (br, s, 1530 (m, sh, amide II), 1371 (m, sh, amide III), 1284 (m, sh,
2H, GlcN and GlcNHAc residue), 4.15–4.00 (br, m, 4H, GlcN and n(Ar–O)), 1160 (s, sh, n(H–C]C+H–C]N)bend, Py), 1070 (m, sh,
GlcNHAc residue), 3.83 (t, J ¼ 7.2 Hz, 2H, GlcN residue), 3.56 n(C–O–C)str), 898 (m, sh, n(C–O–C), b-glycosidic linkage), 840 (s, sh,
+
1
ꢁ
(br, s, 2H, GlcN residue), 3.27–3.14 (br, m, 4H, GlcN and n(PF )). 769, 655 (m, sh, Py ). H NMR (600 MHz, 1% CD3COOD/
6
ꢀ
GlcNHAc residue), 2.76 (t, J ¼ 8.1 Hz, 2H, GlcNHAc residue), D2O)60 C d (ppm): 10.36 (s, 1H, OH), 10.27 (s, 1H, OH), 9.03 (d,
2.40 (dd, J ¼ 15.6, 8.6 Hz, 3H, NHAc). 13C NMR (151 MHz, 1% J ¼ 7.4 Hz, 2H, 2 ꢂ H–C]N), 8.24 (d, J ¼ 7.5 Hz, 1H, Py), 8.14 (d,
ꢀC
CD3COOD/D2O)60
d (ppm): 177.10, 172.20, 166.91, 163.00, J ¼ 7.2 Hz, 1H, NH of GlcNHAc residue), 7.98 (d, J ¼ 8.7 Hz, 1H,
156.50, 145.76, 140.02, 137.85, 134.09, 125.86, 122.05, 118.99, Py), 7.80 (d, J ¼ 7.5 Hz, 4H, Py + Ar), 7.55 (t, J ¼ 7.6 Hz, 1H, Ar),
114.19, 113.77, 91.88, 81.51, 73.45, 71.10, 68.34, 62.06, 58.38, 7.41 (d, J ¼ 8.1 Hz, 1H, Ar), 5.88 (s, 4H, 2 ꢂ CH2 of CH2Ar), 5.23
56.41, 53.48, 50.71, 42.36, 31.21, 17.54, 13.93.
5-(1-Methylimidazol-3-ium
(d, J ¼ 7.7 Hz, 1H, GlcN residue), 4.45 (s, 6H, 2 ꢂ CH3 of
hexauorophosphate)-salicyli- MeOPy), 4.27 (br, s, 2H, GlcN and GlcNHAc residue), 4.17–4.03
dene chitosan (ILCSB4). Yellow powder, yield (1.81 g, 98.9%). (br, m, 4H, GlcN and GlcNHAc residue), 3.82 (t, J ¼ 7.0 Hz, 2H,
FTIR (KBr, cmꢁ1): 3431 (vs, br, n(O–H+NH )), 3145 (m, br, n(N–H)), GlcN residue), 3.54 (br, s, 2H, GlcNHAc residue), 3.18–3.00 (br,
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20904 | RSC Adv., 2016, 6, 20901–20915
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