Convenient and mild synthesis and characterisation of some new schiff bases

Article abstract of DOI:10.4314/bcse.v27i1.16

Some new Schiff bases were synthesized by the condensation between 2-hydroxy-1- naphthaldehyde and various diamines in 2:1 molar ratio. These pure products were prepared in methanol solution under mild reaction conditions to afford good to high yields. Th

Full text of DOI:10.4314/bcse.v27i1.16

Bull. Chem. Soc. Ethiop. 2013, 27(1), 143-149.
Printed in Ethiopia
DOI: http://dx.doi.org/10.4314/bcse.v27i1.16
ISSN 1011-3924
 2013 Chemical Society of Ethiopia
SHORT COMMUNICATION
CONVENIENT AND MILD SYNTHESIS AND CHARACTERISATION OF
SOME NEW SCHIFF BASES
Hossein Naeimi* and Zahra Sadat Nazifi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan,
Kashan, 87317, Iran
(Received May 23, 2012; revised November 8, 2012)
ABSTRACT. Some new Schiff bases were synthesized by the condensation between 2-hydroxy-1-
naphthaldehyde and various diamines in 2:1 molar ratio. These pure products were prepared in methanol solution
under mild reaction conditions to afford good to high yields. The structures of the products have been
characterized by several techniques using elemental analysis (CHN), FT-IR, 1H NMR, 13C NMR and mass
spectra.
KEY WORDS: Schiff base, 2-Hydroxy-1-naphthaldehyde, Diamine, Condensation, Synthesis
INTRODUCTION
Schiff bases are reagents, which are becoming increasingly important in the pharmaceutical, dye
and plastic industries as well as for liquid-crystal technology and mechanistic investigations of
the drugs used in pharmacology, biochemistry, physiology, food chemistry and nanotechnology
[1]. Schiff bases with donors (N, O, S, etc.) have structural similarities with natural biological
systems and imports in elucidating the mechanism of transformation reaction in biological
systems due to presence of imine (-N=CH-) group [2-10]. Schiff base complexes have been
used as drugs and they possess a wide variety of antimicrobial activity against bacteria, fungi
and certain type of tumors [11, 12]. Some drugs have increased activity when administered as
metal chelates and inhibit the growth of tumors [13, 14].
Tetradentate Schiff bases are well known to coordinate with various metal ions forming
stable compounds and some of these complexes are recognized as oxygen carriers [15]. These
compounds also find many important catalytic applications in chemistry. They are used as the
catalyst in reactions. These compounds also find many important catalytic applications, ranging
from asymmetric epoxidation [16], Lewis acid assisted organic transformations [17], solid phase
extraction of metal ions [18] to various types of polymerization [19-22] as well as their
application for the preparation of ion selective electrodes [23-27]. Recently, Ayla Balaban
Gunduzalp and co-worker have been prepared and characterized complexes of tetra dentate
Schiff base ligands [28].
In continuation of our research on the synthesis of Schiff bases and their complexes of metal
ions [29-31], we have studied the preparation of several new Schiff bases from the reaction of
2-hydroxy-1-naphthaldehyde with various diamines in methanol solution under mild conditions.
The corresponding products were identified and characterized by spectroscopic and physical
data.
__________
*Corresponding author. E-mail: naeimi@kashanu.ac.ir

144
Hossein Naeimi and Zahra sadat Nazifi
EXPERIMENTAL
Materials. Chemical were purchased from the Merck Chemical Company in high purity. All the
materials were of commercial reagent grade. The various amines and aldehydes and the solvents
used were purified by standard procedures.
Apparatus. IR spectra were obtained as KBr pellets on a Perkin–Elmer 781 spectrophotometer
1
and on an Impact 400 Nicolet FTIR spectrophotometer. H NMR spectra were recorded in
CDCl3 on a (400 MHz) Spectrometer using TMS as an internal reference. Melting points were
obtained with a Yanagimoto micro melting point apparatus are uncorrected. Mass spectra were
recorded on Micro Mass UKLTD spectra. The purity determination of the substrates and
reaction's monitoring were accomplished by TLC on silica-gel polygram SILG/UV 254 plates.
General procedure for the synthesis of Schiff base ligands. All the tetra dentate Schiff base
ligands were prepared by condensation between diamines and 2-hydroxy-1-naphthaldehyde in
methanol and purified by recrystallization from a methanol through the partial evaporation of
the more volatile dichloromethane. Schiff base ligands prepared by dissolving 2-hydroxy-1-
naphthaldehyde (0.5 g, 2.9 mmol) and diamine (0.15 g, 1.45 mmol) in methanol with stirring in
one portion. The stirring was continued to completion of the reaction. The progress of the
reaction was monitored by thin layer chromatography (TLC). After the completion of the
reaction, a colored substance was obtained. The solid product was filtered and washed with cold
MeOH. The crude product was purified by recrystallization from methanol and the pure Schiff
base was obtained in high yield after leaving for the appropriate time. The Schiff bases were
characterized by physical and spectroscopic data [15].
2,2’-[1,2-Ethanediylbis(nitrilomethylidine)]bis-(2-naphthol) (3a). Yellow solid, m.p. = 330 °C;
IR (KBr), ν/cm-1: 3200-3450 (stretch, OH, H-bonded), 1640 (stretch, C=N), 1490-1540 (C=C,
1
Ar), 1207 (stretch, C-O); H NMR (CDCl3, 400 MHz) δ (ppm): 14.09 (s, 2O-H, intramolecular
hydrogen bonding, 8.44 (s, 2CH imine), 7.75 (d, 2H, Ar), 7.31(d, 2H, Ar), 7.11 (d, 2H), 7.04 (t,
2H, Ar), 6.93 (t, 2H), 6.74 (d, 2H), 3.46 (s, 4H, 2CH2); 13C NMR (CDCl3, 100 MHz) δ (ppm):
159.24, 138.05, 136.46, 128.26, 127.76, 126.26, 125.88, 123. 32, 118.14, 106.73, 76.45, 51.98,
31.06, 28. 28.28; anal. calcd.: 77.81 (C), 5.99 (H), 7.56 (N); found: 77.83 (C), 5.67 (H), 7.37
(N).
1,1’-[1,7-Heptanediylbis(nitrilomethylidine)]bis-(2-naphthol) (3b). Yellow solid, m.p. = 172-
173 °C; IR (KBr), ν/cm-1: 3200-3500 (stretch, OH, H-bonded), 1632 (stretch, C=N), 1457-1542
1
(C=C, Ar), 1138, 1181 (stretch, C-O); H NMR (CDCl3, 400 MHz) δ (ppm): 14.35 (s, 2O-H,
intramolecular hydrogen bonding, 8.5 (s, 2CH imine), 7.6 (d, 2H, Ar), 7.49(d, 2H, Ar), 7.4 (d,
2H), 7.24 (t, 2H, Ar), 7.03 (t, 2H), 6.77 (d, 2H), 3.4 (t, 4H, 2CH2) 1-2 (m, 10H, 5CH2); 13C
NMR (CDCl3, 100 MHz) δ (ppm): 155.76, 138.35, 133.23, 128.26, 127.23, 125.44, 124.58,
121.13, 115.68, 104.49, 75.45, 51.81, 29.79, 27.08, 26.98; mass (m/z): 441 (M++1, 3), 440 (M+,
12), 281 (10), 198 (15), 143 (20), 152 (35), 184 (70), 170 (77), 115 (100).
1,1’-[1,8-Octanediylbis(nitrilomethylidine)]bis-(2-naphthol) (3c). Yellow solid, m.p. = 180-183
°C; IR (KBr), ν/cm-1: 3250-3600 (stretch, OH, H-bonded), 3049 (stretch, C-H, Aryl), 2852,
2924 (stretch, C-H, alkyl), 1634 (stretch, C=N), 1457-1542 (C=C, Ar), 1181 (stretch, C-O); 1H
NMR (CDCl3, 400 MHz) δ (ppm): 14.2 (s, 2O-H, intramolecular hydrogen bonding), 8.50 (s,
2CH imine), 1.20-1.60 (m, 4H, 2CH2), 3.50 (m, 12H, 6CH2), 7.66 (d, 2H, Ar), 7.5(d, 2H), 7.42
(d, 2H), 7.25 (t, 2H) 7.06 (m, 2H), 6.76 (d, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm): 157.58,
137.37, 133.88, 129.25, 127.95, 126.11, 125.32, 122.63, 117.69, 106.38, 76.73, 52.82, 30.58,
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28.80, 26.63; mass (m/z): 453 (M++1, 0.1), 452 (M+, 10), 295 (10), 198 (12), 143 (15), 166 (17), 184
(68), 170 (75), 115 (100).
1,1’-1,2-Phenylenediylbis(nitrilomethylidine)]bis-(2-naphthol) (3d). Orange solid, m.p. = 162-
163 °C; IR (KBr), ν/cm-1: 3373-3470 (stretch, OH, H-bonded), 3046 (stretch, C-H, aryl).1612
1
(stretch, C=N), 1487-1559 (C=C, Ar), 1169 (stretch, C-O); H NMR (CDCl3, 400 MHz) δ
(ppm): 15.45 (s, 2O-H, intramolecular hydrogen bonding), 9.39 (s, 2CH imine), 8.29 (d, 2H, J =
8) 7.73-7.61 (dd, J = 8, 4H, Ar), 7.34 (t, 2H, J = 8), 7.25 (d, 2H, Ar, J = 4), 7.15 (t, 2H, Ar, J =
4), 6.87 (t, 2H, Ar, J = 8), 6.63 (d, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm): 170.02, 153.44,
142.15, 137.56, 135.14, 132.26, 131.62, 129, 71, 128.20, 127.12, 124.29, 122.55, 119.24,
114.37; anal. calcd.: 80.36 (C), 5.30 (H), 6.69 (N); found: 80.31(C), 6.67 (H), 6.78 (N).
1,1’-1,4-Phenylenediylbis(nitrilomethylidine)]bis-(2-naphthol) (3e). Orange solid, m.p. = 189-
191 °C; IR (KBr), ν/cm-1: 3250-3500 (stretch, OH, H-bonded), 3200 (stretch, C-H, aryl), 1620
1
(stretch, C=N), 1512 (C=C, Ar), 1284 (stretch, C-O); H NMR (CDCl3, 400 MHz) δ (ppm):
15.09 (s, 2O-H, intramolecular hydrogen bonding), 9.40 (s, CH imine), 7.74 (d, 2H), 7.69, 7.54
(dd, 8H), 7.58 (t, 2H), 7.17 (t, 2H), 6.78 (d, 2 H), 6.63 (d, 2 H); 13C NMR (CDCl3, 100 MHz) δ
(ppm): 169.52, 152.36, 145,57, 136.65, 135.74, 133.20, 131.55, 129.31, 128.17, 127.80,
123.19, 122.25, 119.00, 115.82; mass (m/z): 557 (M++1,6), 556 (M+,10), 414 (10), 172 (20), 115
(23), 395 (40), 77 (70), 55 (100).
1,1’-[4,4’-Diphenylsulfonebis(nitrilomethylidine)]bis-(2-naphthol) (3f). Orange solid, m.p. =
250-253 °C; IR (KBr), ν/cm-1: 3300-3550 (stretch, OH, H-bonded), 1613 (stretch, C=N); 1496-
1
1588 (C=C, Ar), 1143 (stretch, C-O). H NMR (CDCl3, 400 MHz) δ (ppm): 15.09 (s, 2O-H,
intramolecular hydrogen bonding), 9.40 (s, CH imine), 7.74 (d, 2H), 7.69, 7.54 (dd, 8H), 7.58 (t,
2H), 7.17 (t, 2H), 6.78 (d, 2 H), 6.63 (d, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm): 174.12,
155.46, 145.57, 139.12, 138.92, 136.75, 133.44, 132.91, 131.55, 129.56, 129.14, 128.15,
127.13, 123.25, 122.46; mass (m/z): 557 (M++1,6), 556 (M+,10), 414 (10), 115 (23), 395 (40), 77
(70), 55 (100); anal. calcd.: 73.10 (C), 4.69 (H), 5.01 (N); found: 73.08(C), 4.71 (H), 5.03 (N).
1,1’-[4,4’-Diphenylmethanebis(nitrilomethylidine)]bis-(2-naphthol) (3g). Reddish yellow solid,
m.p. = 195-198 °C; IR (KBr), ν/cm-1: 3300-3500 (stretch, OH, H-bonded), 2922 (C-H, alkyl),
1623 (stretch, C=N), 1511-1544 (C=C, Ar), 1141 (stretch, C-O); 1H NMR (CDCl3, 400 MHz) δ
(ppm): 15.65 (s, 2H, O-H, intramolecular hydrogen bonding), 9.40 (s, 2CH imine), 8.24 (d, 2H),
7.69 (2H, d), 7.57 (d, 2H), 7.38, 7.19 (8H, dd), 7.13 (t, 2H), 7.06 (t, 2H), 6.78 (d, 2H), 3.61 (s,
CH2); mass (m/z): 509 (M++1, 4), 508 (M+,10), 145 (25), 103 (35), 170 (35), 76 (65), 220 (75), 262
(100); anal. calcd.: 82.96 (C), 5.17 (H), 5.53 (N); found: 82.94 (C), 5.16 (H), 5.58 (N).
1,1’-[4-Hydroxy-2,6-pyrimidinediylbis(nitrilomethylidine)]bis-(2-naphthol) (3h). Yellow solid,
m.p. = 251-253; IR (KBr), ν/cm-1: 3600-3500 (stretch, OH, H-bonded), 1614 (stretch, C=N),
1403-1486 (C=C, Ar), 1230 (stretch, C-O); 1H NMR (CDCl3, 400 MHz) δ (ppm): 11.15 (s, 2H,
O-H, intermolecular hydrogen bonding), 9.34 (s, 2CH imine), 7.90 (m, 2H), 7.7 (d, 1H), 7.45 (d,
1H), 7.41 (d, 1H), 7.17-7.39 (m, 3H), 6.60-6.20 (m, 4H). 5.20 (s, OH); mass (m/z): 437 (M++1,
5), 436 (M+, 10), 108 (16), 115 (20), 143 (35), 104 (50), 170 (55), 172 (75), 148 (100).
1,1’-[2,6-Pyrimidinediyl-4-thiolbis(nitrilomethylidine)]bis-(2-naphthol) (3i). Yellow solid, m.p.
= 276-279; IR (KBr), ν/cm-1: 3396 (stretch, OH), 1636 (stretch, (C=N), 1466 (C=C, Ar), 1203
1
(stretch, C-O), 3128 (C-H aryl); H NMR (CDCl3, 400 MHz) δ (ppm): 11.05 (s, 2H, O-H,
intermolecular hydrogen bonding), 9.22 (s, 2CH imine), 7.87 (m, 2H), 7.61 (d, 1H), 7.46 (d,
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1H), 7.37 (1H, d), 7.09-7.31 (m, 3.5H), 6.65-6.12 (m, 4H). 2.20 (s, SH); mass (m/z): 451(M++1,
4), 450 (M+, 12), 115 (15), 172 (25), 143 (35), 165 (40), 107 (47), 77 (78), 63 (90), 54 (100).
1,1’-[4-Phenyl-2,6-diyl1,3,5-triazinebis(nitrilomethylidine)]bis-(2-naphthol) (3j). Yellow solid,
o
m.p. = 164-166 C; IR (KBr), ν/cm-1: 3302 (stretch, OH), 1625 (stretch, (C=N), 1458-1541
(C=C, Ar), 1247 (stretch, C-O); 1H NMR (CDCl3, 400 MHz) δ (ppm): 13.92 (d, 2O-H,
intermolecular hydrogen bonding), 9.50 (d, 2CH imine), 8.44 (d, 2H), 8.06 (d, 2H), 7.85-7.56
(m, 6H), 7.34 (t, 2H), 6.63 (d, 2H); 13C NMR (CDCl3, 100 MHz) δ (ppm): 185, 171, 168, 163,
144, 142, 135, 133, 132, 130, 129.07, 129.8, 128, 126, 125, 120, 109; mass (m/z): 497 (M++1, 6),
496 (M+,10), 115 (20), 78 (27), 172 (30), 169 (40), 104 (50), 76 (85), 77 (100); anal. calcd.: 75.14 (C),
4.27 (H), 14.13 (N); found: 75.18 (C), 4.25 (H), 14.12 (N).
1,1’-[2,4,6-Triyl-1,3,5-triazinebis(nitrilomethylidine)]tris-(2-naphthol) (3k). Yellow solid, m.p.
= 150-153; IR (KBr), ν/cm-1: 3427 (stretch, OH), 1630 (stretch, C=N), 1403-1515 (C=C, Ar),
1247 (stretch, C-O); 1H NMR (CDCl3, 400 MHz) δ (ppm): 13.42 (s, 3O-H, intermolecular
hydrogen bonding), 9.43 (s, 3CH imine), 8.93 (d, 3H), 8.33 (d, 3H), 7.99 (d, 3H), 7.74 (t, 3H),
6.86 (d, 3H); anal. calcd.: 73.46 (C), 4.11 (H), 14.28 (N); found: 73.48 (C), 4.12 (H), 14.27 (N).
RESULTS AND DISCUSSION
The condensation reaction between 2-hydroxy-1-naphthaldehyde and various diamines in 2:1
molar ratio was obtained in high yields and short reaction times. The pure Schiff base as
corresponding products were prepared in methanol solution at room temperature under mild
reaction conditions (Scheme 1).
H
O
X
OH
N
N
rt
X
NH2
H2N
+
MeOH
OH
HO
2a - k
1
3a -k
Scheme 1
When 2 mol of 2-hydroxy-1-naphthaldehyde, 1 mol various diamines were allowed to react
at room temperature, and the corresponding products were characterized by spectroscopic and
physical data. The results of these reactions are shown in Table 1. As indicated in the table, a lot
of useful double Schiff bases were afforded in high yields and short reaction times from the one
pot reaction of 2-hydroxy-1-naphthaldehyde with various diamines. The infrared spectrum of
the Schiff base exhibited a band at 1625-1635 cm-1 assignable to ν(C=N) of ligands.
The band of OH group in the ligands, the broad signal around δ = 11.05-15.65 ppm are
assigned to the protons of the hydroxyl groups. The protons of CH=N has the same chemical
shifts in the range of δ = 9.22-9.5 ppm. The signal around δ = 6.0-6.65 ppm is assigned to the
protons of the aromatic rings (CH=CH) and signals around δ = 6.63-8.93 ppm. The signal
around δ = 155.76-185.17 ppm is assigned to the carbons of the NCHN and signals around δ =
114-171 ppm are assigned to the carbons of aromatic rings (CH=CH).
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Table 1. The obtained results related to the synthesis of Schiff bases.
Time Yield
(min) (%)a
Entry
1
Diamine
Product
3
8
95
91
90
N
N
H2N
NH2
HO
OH
(CH2)7
(CH2)7
2
3
N
N
H2N
NH2
HO
OH
(CH2)8
(CH2)8
H2N
10
N
N
NH2
HO
OH
4
45
92
N
N
H2N
NH2
HO
OH
H2N
NH2
5
6
30
90
89
75
N
N
OH
HO
SO2
N
N
H2N
SO2
NH2
HO
OH
CH2
N
N
H2N
CH2
NH2
7
8
100
72
74
HO
OH
OH
OH
N
N
80
N
N
N
H2N
N
NH2
OH
HO
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Hossein Naeimi and Zahra sadat Nazifi
SH
N
SH
N
N
9
100
77
N
N
N
H2N
NH2
OH
HO
N
N
10
90
65
N
N
N
N
N
H2N
N
NH2
OH
HO
C
C
N
N
N
H2N
N
NH2
HO
OH
N
N
N
N
11
90
50
N
C
NH2
OH
aIsolated yield.
CONCLUSION
The present work describes the synthesis of a new Schiff base ligand derived from 2-hydroxy-1-
naphthaldehyde with various diamines. These ligands might have been interesting biological
activity that would be specially designed research conducted by specialized biologists. In
conclusion, we have reported a mild, easy, clean and a very efficient method for the synthesis of
some novel Schiff bases without reflux conditions at room temperature. The products have been
obtained in high yields and short reaction times. The structure of products has been assigned by
1
physical and spectroscopic data such as; ultraviolet (UV-Vis), H NMR, 13C NMR, infrared
(IR), elemental analysis (CHN) and mass spectra.
ACKNOWLEDGEMENTS
The authors are grateful to University of Kashan for supporting this work by Grant No.
159148/11.
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