Synthesis of carbazonyloxy-based chalcones

Article abstract of DOI:10.1007/s11164-012-0668-9

A series of 12 1-{4-[3-(9H-carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl} -3-(substituted aryl)-propenone were synthesized using 4-(oxiran-2-ylmethoxy)- 9H-carbazole and p-amino acetophenone as starting materials. Synthesis of chalcone was by base catalyst. They were characterized using FTIR, ¹H NMR, ¹³C NMR, and spectroscopy analysis.

Full text of DOI:10.1007/s11164-012-0668-9

Res Chem Intermed (2013) 39:1089–1100
DOI 10.1007/s11164-012-0668-9
Synthesis of carbazonyloxy-based chalcones
•
M. H. Malani B. Z. Dholakiya
Received: 5 May 2012 / Accepted: 28 May 2012 / Published online: 29 June 2012
Ó Springer Science+Business Media B.V. 2012
Abstract A series of 12 1-{4-[3-(9H-carbazol-4-yloxy)-2-hydroxy-propylamino]-
phenyl}-3-(substituted aryl)-propenone were synthesized using 4-(oxiran-2-yl-
methoxy)-9H-carbazole and p-amino acetophenone as starting materials. Synthesis
1
of chalcone was by base catalyst. They were characterized using FTIR, H NMR,
13C NMR, and spectroscopy analysis.
Keywords Epoxide Á Nucleophile Á Chalcone
Introduction
Due to the intrinsic reactivity of the epoxide ring, epoxides are valuable
intermediates in the production of high added-value chemicals like pharmaceuticals
[2]. Epoxides are attractive for further derivatization because they readily react with
halides, carbon, nitrogen, oxygen, or sulfur nucleophiles [3]. Epoxides are widely
used as building blocks in organic chemistry. They can be prepared efficiently, and
their ability to undergo ring-opening reactions with different nucleophiles contrib-
utes to their synthetic value. In particular, nucleophilic openings, mediated by
hetero- or carbonucleophiles, of the homochiral three-membered heterocycles,
easily accessible via chemoenzymatic synthesis, are of great importance in the
preparation of naturally occurring molecules [4, 10]. b-Amino alcohols are versatile
intermediates in the synthesis of a wide range of biologically active natural and
synthetic products, unnatural aminoacids, b-blockers in pharmaceuticals, and
M. H. Malani Á B. Z. Dholakiya (&)
Department of Applied Chemistry, S. V. National Institute of Technology,
Ichhanath, Surat 395007, Gujarat, India
e-mail: bzd.svnit@gmail.com
M. H. Malani
e-mail: maheshmalani.svnit@gmail.com
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M. H. Malani, B. Z. Dholakiya
insecticides. The ring opening of epoxides by amines is an important route for the
preparation of b-amino alcohols. The classical approach for the synthesis of
b-amino alcohols involves the ring opening of epoxides using excess amounts of
amine as nucleophile at elevated temperatures [8]. Chalcone passes conjugated
double bonds and a completely delocalized p electron system, and both benzene
molecules passing such a system have relatively low redox potentials and have a
greater probability of undergoing electron transfer reactions [1]. A number of
chalcones (i.e. 1,3-diaryl-2-propen-1-ones) have demonstrated cytotoxic and
anticancer properties, because of their preferential reactivity towards cellular thiols
in contrast to amino and hydroxyl groups found in nucleic acids [6]. Compounds
with electron releasing groups such as methoxy and hydroxyl showed better
antibacterial activity than others not having such groups. Compounds having
pharmacophores, such as chloro, dichloro and fluoro groups, have exhibited more
anti-fungal activity on all three fungi than the others. Chalcone derivatives with
these substituents show greater antimicrobial activity [7].
Experimental
Materials and instrumentation
All reagents were of analytical reagent grade and were used without further
purification. Solvents employed were purified by standard procedure before use.
4-(oxiran-2-ylmethoxy)-9H-carbazole was prepared as per reported process [5] and
p-amino acetophenone was purchased from Aldrich, The melting points were
determined in open capillary on Veego (Model: VMP-D) electronic apparatus and
are uncorrected. The reactions were monitored and Rf value were determined using
analytical thin layer chromatography (TLC) with Merck Silica gel 60 and F-254 pre
coated plates (0.25 mm thickness). Spots on the TLC plates were visualized using
ultraviolet light (254 nm). FTIR spectra (4,000–400 cm-1) recorded on a Shimadzu
8400-S spectrophotometer using KBr disk. 1H and 13C NMR spectra were recorded
on Bruker 400 MHz model spectrometer using DMSO and TMS as internal
reference (chemical shifts in d ppm).
Synthesis of 1-(4-{[3-(9H-carbazol-4-yloxy)-2-
hydroxypropyl]amino}phenyl)ethanone
A mixture of 4-(oxiran-2-ylmethoxy)-9H-carbazole (1.0 g, 4.17 mmol), 4-amino
acetophenone (0.56 g, 4.17 mmol), potassium carbonate (1.15 g, 8.35 mmol) and
10 ml acetonitrile as a solvent was taken in round bottom flaks. Reaction mass was
heated at 58–62 °C with constant stirring for 8.0 h (Scheme 1). Reaction was
monitored by using TLC. After completion of the reaction, the mass was cooled to
25–30 °C, filtered for removal of salt, and the filtrate was evaporated to dryness
under reduced pressure to get the crude compound. Recrystallization was carried out
in acetone as solvent to get the pure compound (1.4 g, 90 % yield). The obtained
compound was a light cream colored powder having a melting point of 51–53 °C.
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Synthesis of carbazonyloxy-based chalcones
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Scheme 1 Synthesis of compounds 4a–l
Preparation of chalcone from 1-(4-{[3-(9H-carbazol-4-yloxy)-2-
hydroxypropyl]amino}phenyl) ethanone 4a–l
The target compounds were prepared as shown in Scheme 1 using Claisen–Schmidt
condensation of 1-(4-{[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl]amino}phenyl)
ethanone and various aldehydes (Scheme 1). Reaction was carried out under basic
condition in alcoholic solution at 55–60 °C for 12 h. The final compound was
isolated from water at 6–7 pH. Isolated compounds were recrystallized in ethanol.
Synthesized compounds were characterized by various spectroscopic techniques.
Derivatives and physical parameters are shown in Table 1.
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-methoxy-
phenyl)-propenone 4a
Yield 77 %; mp 152–153 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 4.3 d ppm (3H, s,
–OCH3), 6.18 d ppm (1H, t, –NH aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH),
7.29 d ppm (1H, dd, –NH-p-Ar–C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7
d ppm (12H, m, Ar–H), 7.87 d ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR
(400 MHz, DMSO) 49, 58, 67, 73, 78, 100, 110, 118, 121, 123, 125, 128, 128.7,
129, 130, 134.6, 138, 140, 142.5, 157, 189 d ppm; FTIR (KBr) tmax cm-1: 3,030
(C=C), 1,713 (C=O), 1,342 (C–N of Ar), 812 (p-disubstituted Ar), 3,310 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(2-hydroxy-
phenyl)-propenone 4b
Yield 58 %; mp 102–103 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
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M. H. Malani, B. Z. Dholakiya
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Synthesis of carbazonyloxy-based chalcones
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M. H. Malani, B. Z. Dholakiya
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Synthesis of carbazonyloxy-based chalcones
1095
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O), 9.0 d ppm (1H, s, –OH); 13C NMR (400 MHz,
DMSO) 59, 68, 73, 78, 100, 110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6,
138, 141, 142.5, 156, 188 d ppm; FTIR (KBr) tmax cm-1: 3,045 (C=C),
1,692 (C=O), 1,334 (C–N of Ar), 818 (p-disubstituted Ar), 3,365 (N–H), 3,235
(–OH).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-phenyl-
propenone 4c
1
Yield 82 %; mp 93–95 °C; H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (12H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6, 138, 141, 142.5, 156, 188 d
ppm; FTIR (KBr) tmax cm-1: 2,990 (C=C), 1,653 (C=O), 1,338 (C–N of Ar), 819
(p-disubstituted Ar), 3,223 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(2-chloro-
phenyl)-propenone 4d
Yield 62 %; mp 163–165 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6, 138, 141, 142.5, 156, 188 d
ppm; FTIR (KBr) tmax cm-1: 2,928 (C=C), 1,670 (C=O), 1,348 (C–N of Ar), 823
(p-disubstituted Ar), 3,338 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-chloro-
phenyl)-propenone 4e
Yield 74 %; mp 184–188 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
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M. H. Malani, B. Z. Dholakiya
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6, 138, 141, 142.5, 156, 188 d
ppm; FTIR (KBr) tmax cm-1: 2,965 (C=C), 1,640 (C=O), 1,339 (C–N of Ar), 833
(p-disubstituted Ar), 3,240 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(3-nitro-
phenyl)-propenone 4f
Yield 84 %; mp 190–193 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6, 138, 141, 142.5, 156, 188 d
ppm; FTIR (KBr) tmax cm-1: 2,985 (C=C), 1,705 (C=O), 1,355 (C–N of Ar), 836
(p-disubstituted Ar), 3,380 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-methoxy-3-
nitro-phenyl)-propenone 4g
Yield 86 %; mp 170–173 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 4.3 d ppm (3H, s,
–OCH3), 6.18 d ppm (1H, t, –NH aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH),
7.29 d ppm (1H, dd, –NH-p-Ar–C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7
d ppm (10H, m, Ar–H), 7.87 d ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR
(400 MHz, DMSO) 48, 59, 68, 72, 78, 100, 110, 118, 121, 124, 125, 128, 128.3,
129, 130.2, 134.6, 138, 141, 142, 155, 187 d ppm; FTIR (KBr) tmax cm-1: 2,928
(C=C), 1,720 (C=O), 1,322 (C–N of Ar), 816 (p-disubstituted Ar), 3,315 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-methyl-
phenyl)-propenone 4h
Yield 88 %; mp 168–171 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 3.8 d ppm (3H, s, –CH3) 4.1 d ppm (2H, d, Ar–O–CH2),
6.18 d ppm (1H, t, –NH aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm
(1H, dd, –NH-p-Ar–C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H,
m, Ar–H), 7.87 d ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 41,
57, 68, 73, 78, 100, 110, 118, 121, 124, 125, 126, 128.7, 129, 130.2, 134, 138, 141,
142.5, 154, 190 d ppm; FTIR (KBr) tmax cm-1: 2,917 (C=C), 1,647 (C=O), 1,331
(C–N of Ar), 819 (p-disubstituted Ar), 3,300 (N–H).
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Synthesis of carbazonyloxy-based chalcones
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1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-naphthalen-1-
yl-propenone 4i
Yield 82 %; mp 184–187 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (13H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 127, 128, 128.5, 129, 130.2, 131, 133,134.6, 138, 141,
142.5, 156, 188 d ppm; FTIR (KBr) tmax cm-1: 2,933 (C=C), 1,680 (C=O), 1,314
(C–N of Ar), 838 (p-disubstituted Ar), 3,420 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-hydroxy-
phenyl)-propenone 4j
Yield 75 %; mp 150–151 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O), 9.1 d ppm (1H, s, –OH); 13C NMR (400 MHz,
DMSO) 59, 68, 73, 78, 100, 110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6,
138, 141, 142.5, 156, 188 d ppm; FTIR (KBr) tmax cm-1: 2,980 (C=C), 1,695
(C=O), 1,319 (C–N of Ar), 830 (p-disubstituted Ar), 3,365 (N–H), 3,258 (–OH).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(3,4 dimethoxy-
phenyl)-propenone 4k
Yield 65 %; mp 153–155 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 4.3 d ppm (3H, s,
–OCH3), 4.5 d ppm (3H, s, –OCH3), 6.18 d ppm (1H, t, –NH aliphatic), 6.8 d ppm
(2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–C=O), 8.23 d ppm (1H, s,
NH– carbazole), 6.6–7.7 d ppm (10H, m, Ar–H), 7.87 d ppm (1H, dd, –NH-p-Ar–
C=O); 13C NMR (400 MHz, DMSO) 48, 51, 57, 69, 72, 80, 101, 111, 118, 122, 124,
125, 128, 128.7, 129, 130, 134.6, 138.1, 141, 142.5, 156.1, 188.2 d ppm; FTIR
(KBr) tmax cm-1: 3,000 (C=C), 1,670 (C=O), 1,336 (C–N of Ar), 822 (p-
disubstituted Ar), 3,378 (N–H).
1-{4-[3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-phenyl}-3-(4-nitro-
phenyl)-propenone 4l
Yield 79 %; mp 146–148 °C; 1H NMR (400 MHz, DMSO), 2.5 d ppm (1H, s, –OH
aliphatic), 3.34 d ppm (1H, d, –CH=CH), 3.3 d ppm (1H, d, –CH=CH), 3.5 d ppm
(1H, m, –CH2CHOHCH2), 4.1 d ppm (2H, d, Ar–O–CH2), 6.18 d ppm (1H, t, –NH
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M. H. Malani, B. Z. Dholakiya
aliphatic), 6.8 d ppm (2H, t, –CHOHCH2NH), 7.29 d ppm (1H, dd, –NH-p-Ar–
C=O), 8.23 d ppm (1H, s, NH– carbazole), 6.6–7.7 d ppm (11H, m, Ar–H), 7.87 d
ppm (1H, dd, –NH-p-Ar–C=O); 13C NMR (400 MHz, DMSO) 59, 68, 73, 78, 100,
110, 118, 121, 124, 125, 128, 128.7, 129, 130.2, 134.6, 138, 141, 142.5, 156, 188 d
ppm; FTIR (KBr) tmax cm-1: 2,978 (C=C), 1,705 (C=O), 1,343 (C–N of Ar), 828
(p-disubstituted Ar), 3,348 (N–H).
Results and discussion
The important infrared spectral bands and their tentative assignments for carbazonyl
compounds and their chalcones were recorded as KBr disks and are presented in
1
Fig. 1. H NMR data of compound 4c revealed a peak at 8.23 d ppm for –NH
carbazole (Fig. 2). The 1H NMR data of compounds 4c revealed signals between 6.6
and 7.7 d ppm for aromatic protons (Fig. 2). The 13C NMR data of compound 4c
relevant peak at 128, 129, 130, 141 d ppm, for aromatic carbon and at 188 d ppm for
carbonyl carbon (Fig. 3). The IR spectra of compounds 4c revealed characteristic
bands between 3,020 and 3,090 cm-1 confirming the presence of (C=C) groups. IR
spectrum of the compounds showed characteristic bands between 1,640 and
1,720 cm-1 confirming the presence of C=O groups of carbazonyl compounds. IR
spectrum of the compound 4f, g and l showed a characteristic band around at
1,400 cm-1 confirming the presence of –NO2 group [9].
Fig. 1 FTIR spectra of 4c compound
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Synthesis of carbazonyloxy-based chalcones
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Fig. 2 1H NMR spectra of 4c compound
Fig. 3 13C NMR of 4c compound
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M. H. Malani, B. Z. Dholakiya
Conclusion
The present investigation revealed carbazonyloxy b-hydroxy amine-based chal-
cones as potential intermediates for development of new antibacterial drugs. In
future, carbazonyloxy b-hydroxy amine-based chalcones will be used for the further
development of new chemical entities.
Acknowledgments We are very grateful to the Department of Applied Chemistry, SVNIT, Surat for
providing laboratory facilities and Mr. Avtar Singh SAIF Punjab University for spectral analysis. We are
also grateful to the Centre of Excellence, Vapi, Gujarat, India, for providing us necessary analytical
facilities.
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