Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

Article abstract of DOI:10.1016/j.saa.2013.03.023

A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3- (substituted phenyl)-2-propen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chalcones were characterized by their physical constants and spectral data. The group frequencies of infrared ν(cm^-1) of CO s-cis and s-trans, CH in-plane and out of plane, CHCH out of plane, CC out of plane modes, NMR chemical shifts δ(ppm) of H_α, H_β, CO, C_α and C_β of these chalcones were correlated with Hammett substituent constants, F and R parameters using single and multi-regression analyses. From the results of statistical analyses, the effects of substituents on the group frequencies are explained. Antibacterial, antifungal and insect antifeedant activities of these chalcones have been studied.

Full text of DOI:10.1016/j.saa.2013.03.023

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
Contents lists available at SciVerse ScienceDirect
Spectrochimica Acta Part A: Molecular and
Biomolecular Spectroscopy
journal homepage: www.elsevier.com/locate/saa
Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity,
antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl
chalcones
a
b
M. Subramanian a, , G. Vanangamudi , G. Thirunarayanan
⇑
a PG & Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram 608 102, India
b Department of Chemistry, Annamalai University, Annamalainagar 608 002, India
h i g h l i g h t s
g r a p h i c a l a b s t r a c t
ꢀ
Some 2,5-dimethyl-3-furyl chalcones
been synthesized using
hydroxyapatite catalyzed aldol
condensation.
Better yields of the chalcones (more
than 80%) obtained.
These chalcones were characterized
by their analytical and spectroscopic
data.
O
O
O
CH3
H
Hydroxyapatite
H2O, MW
X
X
CH3
CH3
H3C
H3C
ꢀ
ꢀ
O
O
ꢀ
ꢀ
Antimicrobial activities of these
chalcones have been studied.
Easy-workup synthesis involving
shorter reaction time was adopted.
a r t i c l e i n f o
a b s t r a c t
Article history:
A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3-(substituted phenyl)-2-pro-
pen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-
2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chal-
cones were characterized by their physical constants and spectral data. The group frequencies of infrared
Received 23 November 2012
Received in revised form 14 February 2013
Accepted 3 March 2013
Available online 14 March 2013
m
(cmꢁ1) of CO s-cis and s-trans, CH in-plane and out of plane, CH@CH out of plane, ˜C@C— out of plane
modes, NMR chemical shifts d(ppm) of H , Hb, CO, C and Cb of these chalcones were correlated with
a
a
Keywords:
2,5-Dimethyl-3-furyl chalcones
Hydrotalcite
Microwave irradiation
IR and NMR spectra
Hammett correlation
Antimicrobial and insect antifeedant
activities
Hammett substituent constants, F and R parameters using single and multi-regression analyses. From
the results of statistical analyses, the effects of substituents on the group frequencies are explained. Anti-
bacterial, antifungal and insect antifeedant activities of these chalcones have been studied.
Ó 2013 Elsevier B.V. All rights reserved.
Introduction
major role for the geometrical isomeric conformers namely E or Z
type. Among these kinds of the enones the E conformers are more
The enones containing both the ends with aryl–aryl or aryl–alkyl
groups are known as chalcones or , b-unsaturated ketones. The car-
bonyl and vinyl parts are important for their structural conformers
stable than Z. The infrared spectroscopic data of carbonyl absorption
is important for prediction of s-cis or s-trans conformers of enones.
Nuclear magnetic resonance spectroscopy provides the information
about the number of protons present in the molecules and their cat-
egories either E- or Z in the above molecules. These categories of pro-
tons can be identified in the organic molecules, based on their
coupling constants. These enones have been synthesized by many
solvent assisted or solvent-free methods. Now-a-days the solvent-
a
namelys-cisor s-trans. The vinylprotonsare importantand they play
⇑
Corresponding author. Tel.: +91 4144 230754.
E-mail address: drmsgacplcmcdm@gmail.com (M. Subramanian).
1386-1425/$ - see front matter Ó 2013 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.saa.2013.03.023

M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
117
free synthetic methods are important for environmental remedia-
tion by reducing the pollution from hazardous chemical usage for
saving our planet. Numerous green solvent free synthetic methodol-
ogies have been used for synthesis of carbonyl compounds such as
enols, enones, chalcones, acid chlorides, acyl bromides and their es-
ters. Similarly many catalysts were employed for synthesis of above
said compounds such as silica–sulphuric acid [1–3], anhydrous zinc
chloride [4], clay [5], ground chemistry catalysts-grinding the reac-
tants with sodium hydroxide [6], aqueous alkali in lower tempera-
ture [7], solid sulphonic acid from aqueous alkali in lower
temperature [7], solid sulphonic acid from bamboo [8], barium
hydroxide [9] anhydrous sodium bicarbonate [10], microwave as-
sisted synthesis [11], Fly-ash:water [12], Fly-ash:H2SO4 [13], thionyl
chloride [14], NaOH–CTABr [15], ZnAAl Hydrotalcite adhere ionic li-
quid [16], silica sol–gel [17], natural phosphate modified with so-
dium nitrate [18], highly ordered mesoporous AlSBA-15ASO3H
hybrid material [19], KOH [20], Iodine–Alumina [21], hydroxyapa-
tite [22], and sulfated titania [23]. The quantitative structure-activ-
ity relationshipand quantitativeproperty relationship of the organic
substrates have been studied from the spectral data associated with
their molecular equilibration [24]. The Hammett correlation of spec-
tral data of organic compounds are useful for the prediction of their
structure, stereo-chemical and physicochemical properties [25,26].
The vibrational stretches of carbonyl groups gave two molecular
conformers in unsaturated ketones such as s-cis and s-trans isomers.
Thes-cis carbonylgroup stretchesarehigher thanthose ofthe s-trans
carbonyl group. Based on this the structure of molecular equilibra-
tion can be predicted in geometrical isomers, keto–enol tautomer’s
in unsaturated carbonyl compounds [27], alkenes, alkynes, styrenes,
nitro-styrenes and naphthacyl ketones and their esters [28]. If the
molecules possess any substituent in the aromatic ring, correspond-
ing absorption frequencies in IR and the chemical shift in NMR vary
from ketone to ketone depending upon the type of substituents
whether they are electron donating or electron withdrawing in nat-
ure. From these data the effect of substituents can be studied on the
particular functional group of the molecule by means of regression
analyses [29]. Further these data are employed for the study of tran-
sition state reaction mechanism [30], structure activity of biological
potentials [31], normal coordinate analysis [32], theoretical study of
long range interactions in the beta sheet structures of oligo peptides
[33], enone–dienol tautomerism [34], density functional theory
[35], rotational barriers in selenomides [36]and gas phase reactivity
of alkyl sulphides [37]. The out of plane and in-plane deformation
frequencies in fingerprint region are also used for QSAR and QPR
study [38]. Generally chalcones possess various multipronged activ-
ities [39] such as anticancer, antimicrobial [40], antioxidant [41],
antiviral[42], anti-aids [43], insect antifeedant [15], antimalarial
[44], anti-plasmodial [45] agrochemicals and drugs [46]. These
potentialsarealsoappliedforthestudyofstructureactivityrelation-
ships [47,48]. From the literature survey it is observed that there is
no report on the microwave assisted synthesis, effect of substitu-
ents-QSAR or QPR study and antimicrobial activities with 2,5-di-
methyl-3-furyl chalcones in the past. Therefore the authors have
taken efforts to synthesize some substituted styryl 2,5-dimethyl-
3-furyl ketones, to studied the correlation analysis with their IR
and NMR spectroscopic data and evaluated their antimicrobial
activities.
point apparatus and are uncorrected. Infrared spectra (KBr, 4000–
400 cmꢁ1) have been recorded on AVATAR-300 Fourier transform
spectrophotometer. The NMR spectra of chalcones were recorded
in INSTRUM AV300 NMR spectrometer operating at 300 MHz for
1H and 75.46 MHz for 13C spectra in DMSO solvent using TMS as
internal standard. Electron impact (EI) (70 eV) and chemical ioni-
zation mode FAB+ mass spectra were recorded with a JEOL
JMS600H spectrometer.
Synthesis of substituted styryl 2,5-methyl-3-furyl ketones [22]
An appropriate equimolar quantity of 3-acetyl-2,5-methyl-fur-
on (2.5 mmol), various substituted benzaldehydes (2.5 mmol) in
methanol (10 mL) and 1 g hydroxyapatitie was added and the mix-
ture was stirred at room temperature for 5 min. Methanol was
evaporated to give a homogeneous solid. About 5 mL of water
was added to this solid and the mixture was irradiated by micro-
wave for the appropriate time (Scheme 1). After completion of
reaction, dichloromethane (20 mL) was added, followed by simple
filtration. The solution was concentrated and to purified by re-crys-
tallization. The synthesized chalcones are characterized by their
physical constants, IR, 1H and 13C NMR and Mass spectral data.
Analytical and Mass spectral data are presented in Table 1.
Results and discussion
Infrared spectral study
In the present study, the synthesized substituted styryl 2,5-di-
methyl-3-furyl ketones exist as s-cis and s-trans conformers. These
conformers are confirmed by the carbonyl group doublets obtained
in the range of 1600–1700 cmꢁ1. They are shown in Fig. 1 and the
corresponding carbonyl frequencies (cmꢁ1) of the conformers are
presented in Table 2. The s-cis conformers absorb at higher vibra-
tional frequencies than s-trans conformers. Generally carbonyl
doublets obtained at lower absorption frequencies for the electron
donating substituents in the chalcones whereas the electron with-
drawing substituents doublets at higher frequencies in both the
conformers. In this present study also, the same trend was ob-
served. These frequencies were correlated with various Hammett
sigma constants and Swain–Lupton’s parameters [52] by single
and multi linear regression analysis. While seeking Hammett cor-
relation involving group frequencies, the form of the Hammett
equation employed is
m
¼
q
r
þ
mo
ð1Þ
where mo is the frequency for the parent member of the series.
The results of single parameter statistical analyses of carbonyl
frequencies with substituent constants are presented in Table 3.
From Table 3, no correlation is observed for
with Hammett sigma and F and R parameters. A satisfactory corre-
lation is observed for CO s-trans stretches with Hammett sigma
mC@O s-cis stretches
m
and F and R parameters except for some substituents like H, 4-F,
3-OH, 3-OCH3, 4-OCH3, and 4-CH3. When these substituents are in-
cluded in the regression they reduce the correlation considerably.
The polar effects of the substituents are not capable of predicting
the reactivity on the carbonyl frequencies of all ketones as per
the conjugative structure shown in Fig. 2. All correlations gave a
Experimental
negative
substituent is found to be higher in s-trans than in s-cis conformers.
The ratio of qcis qtrans is less than 1. This shows that the transmis-
q values and the degree of transmittance of the effect of
Materials and methods
/
sion of substituent effects on carbonyl group of s-trans conformers
All chemicals used were purchased from Sigma–Aldrich and E-
Merck chemical companies. Melting points of all chalcones have
been determined in open glass capillaries on Mettler FP51 melting
are more sensitive than s-cis conformers.
The assigned in-plane and out of plane deformation modes of
CHip, CHop, CH@CHop and C@Cop (cmꢁ1) of 2,5-dimethyl-3-furyl

118
M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
O
O
O
CH3
2
1
β
H
3
Hydroxyapatite
H2O, MW
X
X
CH3
H3C
CH3
H3C
4
6
O
O
5
X= H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
Scheme 1. Synthesis of substituted styryl 2,5-dimethyl-3-furyl ketones.
Table 1
Analytical and mass spectral data of substituted styryl 2,5-dimethyl-3-furyl ketones.
Entry
M.F.
F.W.
Yield (%)
M.P. (°C)
Mass (m/z)
1
2
3
4
5
6
7
8
9
C
C
C
C
C
C
C
C
C
C
C
15H18O2
230
308
264
264
248
246
246
260
260
275
275
88
83
86
85
82
80
81
86
86
84
84
125–126 (125)[49]
56–57
82–83
95–96 (95)[50]
88–89
130–131
72–73 (74)[51]
136–137
62–63
132–133
165–166
230[M+], 215, 201, 153, 131, 127, 113, 103, 99, 85, 77, 71, 29, 15
308[M+], 310[M+2], 294, 293, 229, 208, 180, 154, 153, 127, 113, 99, 85, 78,15
264[M+], 266[M+2], 249, 235, 229, 165, 153, 136, 111, 71
15H17BrO2
15H17ClO2
15H17ClO2
15H17FO2
15H18O3
15H18O3
15H20O3
15H20O3
15H17 N O4
15H17 N O4
264[M+], 266[M+2], 249, 235, 229, 165, 153, 137, 136, 127,111, 99, 71, 34, 29, 15
248[M+], 250[M+2], 229, 233, 219, 153, 149, 127, 121, 113, 99, 95, 18, 15
246[M+], 229, 231, 153, 147, 127, 121, 113, 99, 15
246[M+], 229, 231, 217, 153, 147, 127, 121, 119, 113, 99, 93, 71, 55, 53, 17, 15
260[M+], 245, 231, 229, 133, 127, 91,71, 55, 29, 15
260[M+], 245, 231, 229, 161, 133, 127, 107, 99, 91,71, 55, 31, 29, 15
275[M+], 260, 246, 229, 222, 148, 127, 71, 27, 15
10
11
275[M+], 260, 246, 229, 246, 222, 176, 153, 148, 127, 99, 77, 71, 55, 45, 27, 15
H3C
O
O
X
X
CH3
H3C
O
H3C
O
s-cis
s-trans
Fig. 1. The s-cis and s-trans conformers of 2,5-dimethyl-3-furyl chalcone.
Table 2
Infrared spectral data
m
(cmꢁ1) of COs-cis and s-trans stretches, CHip and op, CH@CHop and ˜C@C—op modes of substituted styryl 2,5-dimethyl-3-furyl ketones.
Entry
Substituent
COs-cis
COs-trans
CHop
CHip
CH@CHop
˜C@C—
op
1
2
3
4
5
6
7
8
9
H
4-Br
2-Cl
4-Cl
1655.08
1664.38
1659.77
1660.25
1661.04
1652.70
1678.23
1646.42
1655.39
1641.61
1655.35
1599.26
1597.90
1616.44
1615.73
1593.42
1619.14
1643.84
1592.12
1590.49
1578.78
1594.34
1176.15
1181.29
1179.08
1179.67
1159.22
1177.61
1163.17
1123.29
1176.64
1123.29
1113.56
767.12
733.35
759.95
736.04
720.70
782.48
780.11
770.69
715.66
738.91
727.23
1019.76
1070.38
1016.66
1012.70
1096.09
1079.52
1020.48
1020.61
1015.71
1020.82
1016.74
595.88
619.18
676.32
652.35
608.13
680.85
648.00
613.70
554.15
661.15
674.60
4-F
3-OH
4-OH
3-OCH3
4-OCH3
3-NO2
4-NO2
10
11
ketones are presented in Table 2. The larger value of deformation
mode frequency for the system is due to the low mobility of elec-
tron between the ˜C@C— and the ACH@CHA frame work. All the
deformation modes of substituted styryl 2,5-dimethyl-3-furyl ke-
tones are correlated with different substituent constants accord-
ing to Thirunaraynan et al. [1,4b,14,24,27–29,39,45,48] and
Shorter [53]. The results of statistical analysis are given in
Table 3.
lation is found to decrease when these substituents are included in
the regression analysis. The field effects of the substituents failed
in the correlation. This is due to the reason stated earlier and also
due to the change of the vinyl CH@CH into CAC.
The correlation of CHop modes of these ketones with Hammett
substituent constants, F and R parameters is found satisfactory
along with negative
q values except for H, 4-F and 4-OCH3 substit-
uents. The degree of transmission of substituent effects on these vi-
nyl protons CHop modes is higher than that of CHip and the ratio of
CHip/CHop is less than one.
The observed CH@CH and ˜C@C— out of plane frequencies in the
present study are given in Table 2. All the deformation CH@CH and
From the Table 3, the CHip modes of these ketones with Ham-
mett substituent constants
correlated satisfactorily along with negative
4-Br, 2-Cl, 4-Cl, 3-OCH3, 3-NO2 and 4-NO2 substituents. The corre-
r
,
r+
,
rR and R parameters have been
q
values except for

M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
119
Table 3
Results of statistical analysis of infrared
Hammett rR constants and F and R parameters.
m
(cmꢁ1) COs-cis and COs-trans, CHip and op, CH@CHop and ˜C@C—op modes of substituted styryl 2,5-dimethyl-3-furyl ketones with
r, , rI,
r+
Frequency
COs-cis
Constants
r
I
q
s
n
Correlated derivatives
r
0.853
0.843
0.738
0.811
0.681
0.822
1659.47
1657.61
1653.79
1659.43
1658.58
1655.36
ꢁ14.309
ꢁ7.676
ꢁ15.890
ꢁ5.498
ꢁ3.139
ꢁ5.228
8.51
8.79
9.28
10.0
10.05
9.82
11
11
11
11
11
11
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
COs-trans
r
0.905
0.569
0.929
0.941
0.903
0.904
1607.99
1604.49
1614.13
1559.72
1614.73
1596.17
ꢁ27.638
ꢁ17.059
ꢁ26.639
ꢁ31.990
ꢁ26.569
ꢁ20.628
16.20
15.81
18.41
17.53
18.32
17.00
10
10
8
8
10
7
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-OH, 3-NO2, 4-NO2
r+
rI
rR
F
R
CHip
r
0.906
0.905
0.942
0.904
0.804
0.935
1166.60
1160.38
1181.01
1149.46
1183.08
1151.06
ꢁ47.416
ꢁ24.116
ꢁ55.643
ꢁ45.003
ꢁ57.471
ꢁ22.521
21.23
22.97
25.12
25.37
24.61
25.90
8
11
9
8
11
7
H, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 4-OCH3
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
CHop
r
0.934
0.928
0.958
0.921
0.958
0.943
751.96
748.85
796.22
743.49
776.29
739.10
ꢁ23.455
ꢁ11.214
ꢁ70.920
ꢁ22.234
ꢁ7.576
24.05
24.50
920.84
25.01
20.78
23.11
9
9
9
9
10
9
H, 4-Br, 2-Cl, 4-Cl, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 3-OH, 4-OH, 3-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
ꢁ21.216
CH@CHop
r
0.913
0.919
0.812
0.866
0.810
0.851
1037.11
1035.81
1028.04
1024.91
1016.76
1021.45
ꢁ11.559
ꢁ9.699
18.915
31.94
31.63
31.99
29.99
30.64
27.65
8
8
11
11
11
11
H, 2-Cl, 4-Cl, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 2-Cl, 4-Cl, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
ꢁ47.708
45.159
R
ꢁ37.90
C@Cop
r
0.905
0.903
0.747
0.833
0.834
0.803
626.34
634.09
579.99
647.42
603.73
636.19
56.230
20.042
94.938
56.763
65.913
53.423
36.53
40.18
37.19
39.78
39.59
42.16
8
9
11
11
11
11
H, 4-Br, 4-Cl, 4-F,3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
r = Correlation co-efficient;
q = slope; I = intercept; s = standard deviation; n = number of substituents.
constants and F and R parameters. While seeking the multi-
regression analysis, satisfactory correlations are obtained for
these stretches with Swain–Lupton and F and R parameters
[52]. The correlated multi regression equations are given in the
following equations:
O
CH3
H3C
O
O
m
COs-cis ðcmꢁ1Þ ¼ 1652:98ðꢂ8:787Þ þ 1:776ðꢂ0:168ÞrI
ꢁ 16:455ðꢂ0:147ÞrR
CH3
Fig. 2. Resonance conjugative structure.
ðR ¼ 0:939; n ¼ 11; P > 90%Þ
ð2Þ
ð3Þ
ð4Þ
ð5Þ
˜C@C— out of plane modes of substituted styryl 2,5-dimethyl-3-fur-
yl ketones are correlated with different substituent constants
[1,3,4–6,22,24,25]. The results of statistical analysis are shown in
Table 3. Uniformly the deformation modes of CH@CHop and C@Cop
of substituted styryl 2,5-dimethyl-3-furyl ketones have been corre-
m
m
m
COs-cis ðcmꢁ1Þ ¼ 1655:78ðꢂ8:455Þ ꢁ 0:928ðꢂ0:160ÞF
ꢁ 5:125ðꢂ0:813ÞR
ðR ¼ 0:922; n ¼ 11; P > 90%Þ
lated satisfactorily with Hammett
r and r
+ constants except for 4-
Br, 2-Cl, 4-F, 3-OH and 4-OH substituents. The correlation is found
to decrease when these substituents are included in the regression
analysis. The remaining sigma constants and F and R parameters
failed in the correlations. This is due to the inductive, resonance
and field effects of the substituents that are not capable of trans-
mitting to the vinyl protons and carbons. The CH@CHop modes pro-
COs-trans ðcmꢁ1Þ ¼ 1603:40ðꢂ16:393Þ ꢁ 14:534ðꢂ3:145ÞrI
ꢁ 27:379ðꢂ2:661ÞrR
ðR ¼ 0:943; n ¼ 11; P > 90%Þ
COs-trans ðcmꢁ1Þ ¼ 1604:59ðꢂ14:228Þ ꢁ 18:553ðꢂ2:703ÞF
ꢁ 27:379ðꢂ1:369ÞR
duce negative
q values with some of the sigma constants and
positive values in the case of C@Cop modes.
q
Some of the single parameter correlations fail with the infra-
red COs-cis, CHip, CHop, CH@CHop and C@Cop with Hammett sigma
ðR ¼ 0:951; n ¼ 11; P > 95%Þ

120
M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
The assigned 1H NMR chemical shifts (ppm) of dH and dHb of
substituted styryl 2,5-dimethyl-3-furyl ketones are presented in
Table 3. These chemical shifts are correlated with Hammett substi-
tuent constants and F and R parameters. The results of statistical
analyses of these chemical shifts (ppm) are shown in Table 5. From
m
m
m
m
m
m
CHip ðcmꢁ1Þ ¼ 1168:55ðꢂ22:775Þ ꢁ 41:459ðꢂ4:370ÞrI
a
ꢁ 31:783ðꢂ3:705ÞrR
ðR ¼ 0:949; n ¼ 11; P > 90%Þ
ð6Þ
ð7Þ
CHip ðcmꢁ1Þ ¼ 1173:81ðꢂ20:258Þ ꢁ 50:158ðꢂ3:849ÞF
ꢁ 16:970ðꢂ1:946ÞR
the Table 5, Hammett
r
and rR constants are satisfactorily corre-
val-
lated with H chemical shifts. All correlations give positive
q
a
ues. This shows that the normal substituent effects operate in all
ketones. The polar, inductive field and resonance effects failed in
correlation. This is due to the incapability of substituents for pre-
dicting the reactivity through the substituent effects on the vinyl
ðR ¼ 0:952; n ¼ 11; P > 95%Þ
CHop ðcmꢁ1Þ ¼ 776:11ðꢂ19:743Þ ꢁ 71:077ðꢂ37:885ÞrI
þ 0:354ðꢂ0:032ÞrR
H
a
proton chemical shifts and is associated with the conjugative
structure shown in Fig. 2 The Hb chemical shifts of these ketones
failed in correlation with Hammett sigma constants and F and R
parameters. During the correlation all Hammett constants and F
ðR ¼ 0:958; n ¼ 11; P > 95%Þ
ð8Þ
and R parameters gave negative
q values. This shows that the nor-
CHopðcmꢁ1Þ ¼ 766:1014ðꢂ16:542Þ ꢁ 59:540ðꢂ3:434ÞF
ꢁ 18:626ðꢂ1:564ÞR
mal substituent effects reversed in all ketones.
Some of the single parameter correlations failed with the 1H
NMR of dH and dHb chemical shifts with Hammett sigma con-
a
ðR ¼ 0:966; n ¼ 11; P > 95%Þ
ð9Þ
stants and F and R parameters. While seeking the multi regression
analysis of these frequencies, satisfactory correlations obtained
with Swain–Lupton and F and R parameters [52]. The correlated
multi regression equations are the following equations:
CH ¼ CHop ðcmꢁ1Þ ¼ 998:16ðꢂ20:867Þ ꢁ 64:593ðꢂ39:070ÞrI
ꢁ 45:0494ðꢂ10:910ÞrR
dHaðppmÞ ¼ 7:239ðꢂ0:211Þ þ 0:795ðꢂ0:040ÞrI
þ 0:152ðꢂ0:034ÞrR
ðR ¼ 0:967; n ¼ 11; P > 95%Þ
ð10Þ
CH ¼ CHop ðcmꢁ1
Þ
ðR ¼ 0:938; n ¼ 12; P > 90%Þ
ð15Þ
ð16Þ
ð17Þ
ð18Þ
¼ 1035:11ðꢂ30:61Þ þ 65:917ðꢂ30:213ÞF
þ 25:172ðꢂ0:561ÞR
ðR ¼ 0:981; n ¼ 11; P > 95%Þ
dHaðppmÞ ¼ 7:341ðꢂ0:212Þ þ 0:551ðꢂ0:040ÞF
þ 0:363ðꢂ0:020ÞR
ð11Þ
ðR ¼ 0:966; n ¼ 12; P > 95%Þ
m
C ¼ Cop ðcmꢁ1
Þ
dHbðppmÞ ¼ 8:948ðꢂ0:676Þ ꢁ ꢁ1:008ðꢂ0:129ÞrI
þ 1:242ðꢂ0:110ÞrR
¼ 610:12ðꢂ34:582Þ þ 81:262ðꢂ6:636ÞrI
þ 30:934ðꢂ5:623ÞrR
ðR ¼ 0:950; n ¼ 11; P > 95%Þ
ðR ¼ 0:938; n ¼ 12; P > 90%Þ
ð12Þ
ð13Þ
dHbðppmÞ ¼ 8:804ðꢂ0:628Þ ꢁ 0:751ðꢂ0:011ÞF
þ 0:575ðꢂ0:060ÞR
m
C ¼ Cop ðcmꢁ1
Þ
¼ 605:51ðꢂ34:061Þ þ 67:668ðꢂ6:672ÞF
ꢁ 4:066ðꢂ3:272ÞR
ðR ¼ 0:934; n ¼ 11; P > 90%Þ
ðR ¼ 0:934; n ¼ 12; P > 90%Þ
13C NMR spectral study
1H Spectral study
The assigned carbonyl carbon chemical shifts (ppm) of dCO, dC
a
and dCb of substituted styryl 2,5-dimethyl-3-furyl ketones are pre-
sented in Table 4 and these chemical shifts are correlated with
Hammett sigma constants and F and R parameters. The results of
statistical analysis are shown in Table 5. From the Table 5, the car-
bonyl carbon chemical shifts correlated satisfactorily with Ham-
The 1H NMR spectra of 11 2,5-dimethyl-3-furyl chalcones under
investigation were recorded in deuterated dimethyl sulphoxide
employing tetramethylsilane (TMS) as internal standard. The sig-
nals of the ethylenic protons are assigned. They are calculated as
AB or AA0 or BB0 systems respectively [24,27–29,54,55]. The chem-
mett
r,
r+
,
rR constants and
R
parameter. All correlations
showed positive
q
values except for
r
and
r
+ constants. This shows
ical shifts of H are at higher field than those of Hb in this series of
a
that the normal substituent effects operate in all ketones.
ketones. The ethylenic protons give an AB pattern and the b-proton
doublet in most cases is well separated from the signals of the aro-
matic protons. The assigned chemical shifts of the ethylenic pro-
tons are presented in Table 4.
In nuclear magnetic resonance spectra, the proton chemical
shifts d(ppm) depends on the electronic environment of the nuclei
concerned. These shifts can be correlated with reactivity parame-
ters. Thus the Hammett equation may be used in the form as below
The assigned chemical shifts(ppm) of C and Cb vinyl carbons in
a
substituted styryl 2,5-dimethyl-3-furyl ketones were correlated
with Hammett sigma constants and F and R parameters. The C
a
chemical shifts poorly correlated with Hammett
r,
r+ constants
and R parameter, showing positive values. This shows that the
q
normal substituent effects operate in all ketones. The inductive,
resonance and field effects of the substituents failed in correlation.
The resonanace parameters produced negative
chemical shifts(ppm) of substituted styryl 2,5-dimethyl-3-furyl ke-
q values. The Cb
Logd ¼ Logd0 þ
qr
ð14Þ
where d0 is the chemical shift in the corresponding parent
tones failed in correlation with Hammett sigma constants and F
compound.
and R parameters producing positive q values. This is due to the

M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
121
Table 4
The 1H chemical shifts(ppm)of dH , dHb, 13C chemical shifts of dCO, dC , dCb and ring carbons of substituted styryl 2,5-dimethyl-3-furyl ketones.
a
a
Entry
X
H
a
(1H, d)
Hb (1H, d)
Ring protons
X
CO
C
Cb
C1
C2
C3
C4
C5
a
1
2
3
4
5
6
7
8
9
H
4-Br
2-Cl
4-Cl
7.342
7.209
7.550
8.070
7.291
7.210
7.391
7.152
7.058
7.792
7.729
7.752
7.733
7.621
8.853
7.860
7.709
7.761
7.680
7.690
8.935
8.249
7.403–7.761 (6H, m)
7.325–7.302 (5H, m)
7.568–7.613 (5H, m)
7.868–8.842 (5H, m)
7.311–7.840 (5H, m)
7.267–7.613 (5H, m)
7.429–7.725 (5H, m)
7.568–7.613 (5H, m)
7.287–7.634 (5H, m)
7.795–8.865 (5H, m)
7.568–8.264 (5H, m)
–
–
–
–
–
–
–
185.55
177.17
185.74
185.49
185.69
186.66
186.31
183.25
155.84
187.23
184.87
122.32
120.02
122.18
124.52
123.86
124.11
121.17
121.96
121.77
124.89
122.11
141.26
143.12
140.42
141.14
141.42
143.40
137.93
140.68
142.40
143.68
141.14
126.98
133.07
133.28
133.89
130.19
136.12
127.95
136.65
127.50
136.21
145.14
128.64
126.00
130.84
129.10
129.23
117.77
127.32
111.36
126.57
122.08
127.78
128.75
120.39
129.07
128.05
115.86
158.51
116.23
165.67
114.18
148.35
121.22
128.00
122.57
129.50
136.04
162.18
115.62
157.63
114.23
161.27
120.68
148.31
128.75
130.39
126.93
128.05
115.86
130.07
116.23
130.02
114.18
129.81
121.22
4-F
3-OH
4-OH
3-OCH3
4-OCH3
3-NO2
4-NO2
2.450 (3H, s)
2.433 (3H, s)
–
–
10
11
0
0
0
0
0
0
Entry
X
C6
X
C2
C3
C4
C5
C6
C7
1
2
3
4
5
6
7
8
9
H
4-Br
2-Cl
4-Cl
128.64
126.00
127.61
129.10
129.30
120.13
127.32
119.57
126.57
132.64
127.78
–
–
–
–
–
–
–
158.13
158.43
158.02
158.04
158.00
158.50
157.12
158.62
156.72
157.09
158.74
125.25
105.14
109.48
110.72
105.53
105.57
105.66
107.36
106.75
105.57
109.23
105.35
152.67
152.34
153.71
150.04
150.08
150.59
149.68
150.97
157.45
153.48
150.38
14.36
14.19
15.85
14.43
14.46
14.56
14.69
14.03
14.30
14.06
15.53
7.68
7.82
7.49
7.67
8.00
7.96
8.31
8.09
7.37
7.52
8.32
127.08
129.07
124.97
126.72
124.12
125.65
124.03
127.50
126.58
128.74
4-F
3-OH
4-OH
3-OCH3
4-OCH3
3-NO2
4-NO2
55.61
55.23
–
10
11
–
Table 5
Results of statistical analysis of 1H chemical shifts(ppm)of dH , dHb protons, 13C chemical shifts of dCO, dC and dCb carbons of of substituted styryl 2,5-dimethyl-3-furyl ketones
a
a
with Hammett
r
,
r+
,
rI
,
rR constants and F and R parameters.
Function
Constants
r
q
I
s
n
Correlated derivatives
dH
a
r
0.964
0.846
0.864
0.957
0.847
0.856
0.566
0.255
1.021
0.765
7.349
7.425
7.038
7.604
7.143
7.592
0.25
0.28
0.25
0.27
0.29
0.27
9
H, 4-Br, 2-Cl, 4-F, 3-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
11
11
10
11
11
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2,4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
ꢁ0.708
R
0.424
dHb
r
0.804
0.816
0.812
0.828
0.814
0.801
ꢁ0.100
ꢁ0.199
ꢁ0.458
0.922
8.297
8.297
8.460
8.484
8.488
8.315
0.77
0.76
0.76
0.74
0.76
0.75
11
11
11
11
11
11
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
ꢁ0.502
R
ꢁ4.715
dCO
r
0.934
0.941
0.839
0.921
0.838
0.906
ꢁ11.149
ꢁ6.171
18.254
8.233
16.956
1.339
180.46
181.90
175.06
183.97
175.16
182.66
8.61
8.79
8.84
9.21
8.88
9.62
10
11
11
10
11
11
4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH33-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 4-OCH3, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
dC
a
r
0.940
0.817
0.863
0.705
0.836
0.810
1.741
0.447
4.871
0.337
4.598
ꢁ0.395
122.36
122.61
120.38
122.72
120.73
122.49
1.46
1.57
1.23
1.59
1.26
1.59
10
11
11
11
11
11
H, 4-Br, 2-Cl, 4-Cl, 4-F, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
R
dCb
r
0.831
0.803
0.802
0.834
0.806
0.811
1.429
0.406
141.29
141.49
141.58
142.11
141.71
141.67
1.63
1.70
1.72
1.58
1.71
1.71
11
11
11
11
11
11
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
H, 4-Br, 2-Cl, 4-Cl, 4-F, 3-OH, 4-OH, 3-OCH3, 4-OCH3, 3-NO2, 4-NO2
r+
rI
rR
F
ꢁ0.199
2.747
ꢁ0.481
0.441
R
r = Correlation co-efficient;
q = slope; I = intercept; s = standard deviation; n = number of substituents.
reason stated earlier and it is associated with the conjugated struc-
ture shown in Fig. 2.
Swain–Lupton and F and R parameters [52]. The correlated multi
regression equations are in the following equations:
Single parameter correlations failed with the 13C NMR of dC
a
dCO ðppmÞ ¼ 185:173ðꢂ8:358Þ þ 17:005ðꢂ1:604ÞrI
þ 2:827ðꢂ1:360ÞrR
and dCb chemical shifts(ppm) with Hammett sigma constants and
F and R parameters. While seeking the multi-regression analysis
of these frequencies, a satisfactory correlation obtained with
ðR ¼ 0:940; n ¼ 12; P > 90%Þ
ð19Þ

122
M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
dCO ðppmÞ ¼ 184:85ðꢂ7:645Þ þ 17:202ðꢂ1:452ÞF
ꢁ 0:564ðꢂ0:073ÞR
ðR ¼ 0:939; n ¼ 12; P > 90%Þ
ð20Þ
dCa ðppmÞ ¼ 120:20ðꢂ1:128Þ þ 5:473ðꢂ2:014ÞrI
ꢁ 1:362ðꢂ0:184ÞrR
Plate 2
Plate 4
Plate 1
Plate 3
ðR ¼ 0:966; n ¼ 12; P > 95%Þ
ð21Þ
ð22Þ
ð23Þ
ð24Þ
dCa ðppmÞ ¼ 120:215ðꢂ1:024Þ þ 5:008ðꢂ1:909ÞF
ꢁ 0:949ðꢂ0:096Þ
ðR ¼ 0:968; n ¼ 12; P > 95%Þ
dCbðppmÞ ¼ 142:87ðꢂ1:467Þ ꢁ 1:645ðꢂ0:028ÞrI
þ 3:270ðꢂ0:238ÞrR
ðR ¼ 0:943; n ¼ 12; P > 90%Þ
dCb ðppmÞ ¼ 141:99ðꢂ1:461Þ ꢁ 0:705ðꢂ0:097ÞF
þ 0:520ðꢂ0:014ÞR
Plate 6
Plate 8
Plate 5
Plate 7
ðR ¼ 0:914; n ¼ 12; P > 90%Þ
Microbial activities
Chalcones possess a wide range of multipronged and biological
activities [15,39–46]. These multipronged activities present in dif-
ferent chalcones are examined against respective microbes-bacte-
ria, fungi, and insect antifeedants.
Antibacterial sensitivity assay
Antibacterial sensitivity assay was performed using Kirby–Bau-
er [56] disc diffusion technique. In each Petri plate about 0.5 mL of
the test bacterial sample was spread uniformly over the solidified
Mueller Hinton agar using sterile glass spreader. Then the discs
with 5 mm diameter made up of Whatman No. 1 filter paper,
impregnated with the solution of the compound were placed on
the medium using sterile forceps. The plates were incubated for
24 h at 37 °C by keeping the plates upside down to prevent the col-
lection of water droplets over the medium. After 24 h, the plates
were visually examined and the diameter values of the zone of
inhibition were measured. Triplicate results were recorded by
repeating the same procedure.
Plate 10
Plate 12
Plate 9
Plate 11
The antibacterial screening effect of synthesized chalcones is
shown in Fig. 3. (Plates 1–12). The zone of inhibition of these chal-
cones against standards were presented in Table TS1 (See supple-
mentary data) and the clustered column chart is shown in
Fig. FS1 (See supplementary data). From the chart, it is inferred
that the chalcones with AOH substituent at 3rd position showed
excellent activity against all microorganisms except for S. aureus.
This series showed excellent activity against P. aeruginosa.
Fig. 3. Antibacterial activities of substituted styryl 3, 5-dimethyl-3-furyl ketones-
petri dishes.
were measured. Triplicate results were recorded by repeating the
same procedure.
The antifungal activities of substituted chalcones synthesized in
the present study are shown in Fig. FS2 (See supplementary data)
for plates 1–6 and the zone of inhibition values of the effect are given
in Table TS2 (See supplementary data). Analysis of the clustered col-
umn chart, shown in Fig. FS3 (See supplementary data) indicated
that the fluoro substituted chalcones have very good activity on all
the three fungal species. The substituents like 4-Cl, 4-F, 3-OCH3
and 4-NO2 substituents showed greater antifungal effect on M.
spp. The fluoro substituted chalcone showed excellent activity on
T. viride species.
Antifungal sensitivity assay
Antifungal sensitivity assay was performed using Kirby–Bauer
[56] disc diffusion technique. PDA medium was prepared and ster-
ilized as above. It was poured (ear bearing heating condition) in the
Petri-plate which was already filled with 1 mL of the fungal spe-
cies. The plate was rotated clockwise and counter clock-wise for
uniform spreading of the species. The discs were impregnated with
the test solution. The test solution was prepared by dissolving
15 mg of the chalcone in 1 mL of DMSO solvent. The medium
was allowed to solidify and kept for 24 h. Then the plates were
visually examined and the diameter values of zone of inhibition
Insect antifeedant activity
The multipronged activities present in different chalcones are
intended to examine their insect antifeedant activities against cas-
tor semilooper. The larvae of Achoea janata L. were reared as de-

M. Subramanian et al. / Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 110 (2013) 116–123
123
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instar larvae were selected for testing because the larvae at this
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Some substituted styryl 2,5-dimethyl-3-furyl ketones have
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of infrared and nuclear magnetic resonance spectroscopic data
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these chalcones had studied using Bauer–Kirby method.
Acknowledgement
The authors thank to The Head, Instrumentation Laboratory,
Department of Chemistry, Madurai Kamaraj University, Madurai
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Appendix A. Supplementary material
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.saa.2013.03.023.
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