M. Nasr-Esfahani et al. / C. R. Chimie xxx (2016) 1e9
3
Scheme 2. Syntheses of 1-amidoalkyl-2-naphthols and 1-(a-aminoalkyl)-2-naphthols.
amine for amidoalkyl naphthols and aminoalkyl naphthol,
respectively), and ASA NPs (0.1 mmol) were mixed thor-
oughly. The flask was heated at 80 ꢀC with concomitant
stirring. The reaction was monitored by thin-layer chro-
matography (n-hexaneeEtOAc, 3:1). After completion of
the reaction, hot ethanol (5 mL) was added and the ob-
tained mixture was filtered and then washed with ethanol
to separate the pure catalyst. The solvent was then evap-
orated and the crude products were recrystallized in
ethanol to give pure products. The recovered catalyst was
dried and reused for subsequent runs. The following is the
physical and spectral data of new compounds.
1517, 1473,1394,1349,1222,1187, 1172,1110, 1058, 993, 925,
838, 811; 1H NMR (400 MHz, DMSO-d6)
(ppm): 6.28 (s, 2H,
d
NH2), 7.22 (d, 1H, J ¼ 8.0 Hz, CH), 7.30 (t,1H, J ¼ 7.8 Hz, ArH),
7.41 (d, 1H, J ¼ 9.2 Hz, ArH), 7.46e7.55 (m, 4H, ArH), 7.62 (s,
1H, ArH), 7.84 (d, 1H, J ¼ 8.4 Hz, ArH), 7.98 (d, 1H, J ¼ 8.0 Hz,
ArH), 8.04 (d, 1H, J ¼ 9.2 Hz, ArH), 8.94 (d, 1H, J ¼ 2.8 Hz,
NH), 9.43 (s, 1H, OH); 13C NMR (125 MHz, DMSO-d6)
d(ppm): 53.40, 113.77, 117.37, 122.48, 123.52, 125.72, 126.34,
128.04, 129.18, 129.25, 130.40, 130.90, 131.03, 131.45, 131.81,
145.82, 148.03, 149.56.
2.2.4. 1-[(4-Methoxyphenyl)(morpholino)methyl]naphthalen-
2-ol (4c)
2.2.1. N-[5-Bromo-2-hydroxyphenyl)(2-hydroxynaphthalen-1-
yl)methyl]acetamide (3g)
Mp: 131e133 ꢀC, Rf ¼ 0.56 (n-hexaneeethyl acetate,
1:1); IR (KBr, cmꢁ1): 3448, 2958, 2923, 2854, 2823, 1621,
1598, 1581, 1509, 1461, 1448, 1413, 1398, 1361, 1313, 1278,
1255, 1240, 1178, 1118, 1093, 1072, 1031, 998, 948, 877, 835,
Mp: 220e221 ꢀC, Rf ¼ 0.5 (n-hexaneeethyl acetate, 2:1);
IR (KBr, cmꢁ1): 3501, 3424, 3160, 2977, 1654, 1519, 1440,
1415, 1367, 1328, 1270, 1170, 821, 811; 1H NMR (400 MHz,
821, 767, 746; 1H NMR (400 MHz, CDCl3)
d(ppm): 2.40 (bt,
DMSO-d6)
d
(ppm): 1.93 (s, 3H, CH3), 6.68 (d, 1H, J ¼ 8.8 Hz,
4H, J ¼ 4.8 Hz, NCH2), 3.62 (bs, 4H, OCH2), 3.68 (s, 3H,
OCH3), 5.33 (s,1H, CH), 6.87 (d, 2H, J ¼ 8.8 Hz, ArH), 7.11 (dd,
2H, J1 ¼8.8 Hz, J2 ¼ 2.0 Hz, ArH), 7.26 (t, 1H, J ¼ 7.4 Hz, ArH),
7.41 (dd, 1H, J1 ¼ 8.4 Hz, J2 ¼ 6.8 Hz, ArH), 7.54 (d, 2H,
J ¼ 8.4 Hz, ArH), 7.73 (d, 1H, J ¼ 8.8 Hz, ArH), 7.77 (d, 1H,
J ¼ 8.0 Hz, ArH), 8.03 (br s, 1H, OH); 13C NMR (125 MHz,
CH), 7.14e7.21 (m, 3H, ArH), 7.28 (t,1H, J ¼ 7.4 Hz, ArH), 7.45
(t, 1H, J ¼ 7.6 Hz, ArH), 7.61 (s, 1H, NH), 7.72 (d, 1H,
J ¼ 8.8 Hz, ArH), 7.78 (d, 1H, J ¼ 8.0 Hz, ArH), 8.21 (d, 1H,
J ¼ 8.8 Hz, ArH), 8.46 (d, 1H, J ¼ 8.8, ArH), 9.74 (br s,1H, OH),
9.93 (br s, 1H, OH); 13C NMR (125 MHz, DMSO-d6)
d(ppm):
23.09, 56.58, 110.10, 117.40, 118.98, 119.16, 122.77, 123.73,
126.50,128.62,128.79,129.39,130.40,131.69,131.83,133.12,
153.77, 154.36, 169.16.
DMSO-d6) d(ppm): 52.44, 55.44, 66.62, 69.81,114.57,116.42,
119.88, 122.03, 123.00, 126.93, 128.79, 129.09, 129.64,
131.62, 132.50, 154.55, 154.87, 159.24.
2.2.2. N-[(3-Ethoxy-4-hydroxyphenyl)(2-hydroxynaphtalene-
1-yl)methyl]benzamide (3l)
3. Results and discussion
Mp: 225e228 ꢀC; Rf ¼ 0.41 (n-hexaneeethyl acetate,
3:1); IR (KBr, cmꢁ1): 3399, 3150, 2981, 1621, 1598, 1575,
1509,1477,1434,1384,1348,1280,1232,1124, 813, 788, 777,
3.1. Characterization of ASA NPs
Some techniques such as IR spectroscopy, thermal
gravimetric analysis (TGA), powder XRD, EDAX spectros-
copy, and TEM were used to characterize ASA NPs.
750; 1H NMR (400 MHz, CDCl3)
d(ppm): 1.25 (t, 3H,
J ¼ 7.0 Hz, CH3), 3.91 (q, 2H, J ¼ 6.9 Hz, CH2), 6.65e6.70 (m,
2H, ArH), 6.95 (s, 1H, CH), 7.21 (d, 1H, J ¼ 7.2 Hz, ArH), 7.26
(d, 1H, J ¼ 8.8 Hz, ArH), 7.32 (t, 1H, J ¼ 7.4 Hz, ArH),
7.46e7.51 (m, 3H, ArH), 7.53e7.57 (m, 1H, ArH), 7.78e7.86
(m, 4H, ArH), 8.10 (d, 1H, J ¼ 8.4 Hz, ArH), 8.83 (s, 1H, NH),
9.04 (br s, 1H, J ¼ 8.4 Hz, OH), 10.35 (br s, 1H, OH); 13C NMR
Some important changes in the structure of molecular
species were confirmed by FTIR spectroscopy. In the IR
spectra of anhydrous sodium aluminate (Fig. 1a) the bands
at 3550e3238 and 1671 cmꢁ1 are attributed to the vibra-
tional bending mode of eOH group of physically adsorbed
water. The intensity of broad band at 1452 cmꢁ1 corre-
sponding to the carbonate increased after exposing to the
air [28]. The band at 825 cmꢁ1 is corresponded to the for-
mation of OeO triangular species bonds, and the band at
460 cmꢁ1 is attributed to OeNaeO bonds [28]. The bands
located at 644, 615, 580, and 534 cmꢁ1 have been associ-
ated with the vibrations of AleO bond [29].
(125 MHz, DMSO-d6) d(ppm): 15.19, 49.74, 64.43, 111.03,
113.40, 115.71, 119.05, 119.21, 119.90, 123.13, 123.32, 127.09,
127.55, 128.84, 129.00, 129.05, 129.61, 131.84, 132.74, 133.16,
134.96, 134.99, 146.30, 146.88, 153.47, 165.98.
2.2.3. [(3-Bromophenyl)(2-hydroxynaphtalene-1-yl)methyl]
urea (3q)
Mp: 228e232 ꢀC, Rf ¼ 0.31(n-hexaneeethyl acetate,
The broad peaks at 3419e2545 and 1673 cmꢁ1 in the IR
spectrum of aluminatesulfonic acid (Fig. 1b) are attributed
3:2); IR (KBr, cmꢁ1): 3440, 3262, 2923, 1749, 1708, 1633,
Please cite this article in press as: M. Nasr-Esfahani, et al., Aluminatesulfonic acid: Novel and recyclable nanocatalyst for efficient
j.crci.2016.02.003