M. Danish, M.A. Raza, H. Rani et al.
Journal of Molecular Structure 1241 (2021) 130608
R
O
HO
O
S
O
NaHCO3
-HCl
R
Cl
+
S
N
O
H2N
COOH
O
H
R = -N-CO-CH3; 1, R = Br; 2, R = -CH3; 3, R = H; 4
Scheme 1. Synthesis of sulfonamides
2. Methods and materials
thine groups respectively. Uiso(H) was set to 1.5 times the Ueq(C)
for methyl carbon atoms while it was set to 1.2Ueq(C) for methy-
˚
2.1. Chemicals and solvents
lene and methine carbon atoms. The N-H = 0.68(7)-0.84(6) A, hy-
drogen atoms were located with difference fourier map and re-
˚
The chemicals and reagents used in this research work were
purchased from Alfa-Aesar and Sigma. Solvents such as THF, DMSO,
methanol, ammonia and ethanol were used of analytical grade and
purchased from Merck chemicals. UV/VIS spectrophotometer (UV-
2300) of Shimadzu while FTIR of Perkin-Elmer was used for bio-
logical studies and characterization of the synthesized compounds
respectively.
fined with Uiso (H) = 1.2 Ueq(N). The O-H = 0.89(7) A, hydrogen
atoms were also located with difference fourier map and refined
with Uiso (H) = 1.5 Ueq(O). The cif has been submitted [1] to the
CCDC and the assigned CCDC number is 1861457 for compound 1.
The data can be obtained free of cost from the office of the CCDC
is at 12 Union Road, Cambridge CB2 1EZ.
2.4. Antioxidant activity
2.2. Synthesis of sulfonamides (1-4)
Antioxidant potential of the synthesized sulfonamides was
The targeted sulfonamides were synthesized according to re-
ported method of Danish et al., (2015) with some modifications
[10]. Phenylalanine (1.0 mmol) and sulfonyl chlorides (1.0 mmol)
were added to 30 mL distilled water. The mixture was heated at
35°C and pH was maintained at 9 with help of 1.0 M sodium bi-
carbonate. The reaction was monitored on TLC and after comple-
tion of the reaction, 5.0 mL of 1.0 M HCl was added, resulting in
precipitate formation (Scheme 1). The product was washed with
excess of distilled water and dried in oven at low temperature.
checked according to the method of Shahwar et al., (2012) using
Table 2
Fundamental IR vibrations of sulfonamide and metal complexes
υNH(str)
υM-O
(cm−1
)
Code
(cm−1
)
υCOO (cm−1
)
)
υS=O (cm−1
)
Asym
sym
asym
sym
1
2
3
4
3270
3284
3283
3335
1625
1602
1668
1688
1413
1462
1427
1433
212
208
241
255
1345
1332
1329
1354
1187
1175
1149
1178
-
-
-
-
2.3. Crystallography
The compound was synthesized and crystallized to understand
the geometrical arrangements of atoms in the molecule in its re-
spective unit cell. Sample material was observed under the micro-
scope to find the best suitable single crystal for data collection. The
selected sample was glued over a glass fiber tip absorbed in a wax
supported by a hollow copper rod with magnetic base. This holder
was mounted on Agilent SuperNova (Dual source) Agilent Tech-
nologies Diffractometer, equipped with graphite-monochromatic
Cu/Mo Kα radiation for data collection. The data collection was
accomplished using CrysAlisPro software at 296 K under the Mo
Kα radiation [12]. The structure solution was performed using
SHELXS–97 [13] and refined by full–matrix least–squares methods
on F2 using SHELXL–97 [13], in-built with WinGX [14]. All non–
hydrogen atoms were refined anisotropically by full–matrix least
squares methods [13]. Figures were drawn using PLATON [14] and
ORTEP-3 [15]. All the C-H hydrogen atoms were positioned geo-
Table 3
Crystal data and structure refinement of compound 1
Identification code
16117
17H18N2O5S
Empirical formula
Formula weight
Temperature/K
Crystal system
Space group
C
362.39
296.15
monoclinic
P21
˚
a/A
5.1258(7)
20.257(2)
8.4164(11)
90
˚
b/A
˚
c/A
α/°
β/°
γ /°
102.272(14)
90
3
˚
Volume/A
853.93(19)
2
Z
ρ
calcmg/mm3
1.409
μ/mm-1
0.220
˚
metrically and treated as riding atoms where C–H = 0.93 A and
F(000)
Crystal size/mm3
380.0
Uiso(H) = 1.2 Ueq(C) for aromatic carbon atoms. The C-H bond dis-
0.28 × 0.24 × 0.19
6.382 to 58.626°
˚
˚
˚
tance are 0.96A, 0.97A and 0.98A for methyl, methylene and me-
2θ range for data collection
Index ranges
-7 ≤ h ≤ 6, -25 ≤ k ≤ 27, -5 ≤ l ≤ 11
3937
Table 1
Reflections collected
Independent reflections
Data/restraints/parameters
Goodness-of-fit on F2
Final R indexes [I>=2σ (I)]
Final R indexes [all data]
Physical characteristics of synthesized compounds
3203[R(int) = 0.0334]
3203/1/238
Product code
Color
Solubility
Melting point (°C)
1.063
R1 = 0.0586, wR2 = 0.1467
R1 = 0.0704, wR2 = 0.1583
0.39/-0.42
1
2
3
4
Off white
Ethanol
Ethanol
Ethanol
Ethanol
213
146
170
135
White
−3
˚
Shiny off white
Shiny off white
Largest diff. peak/hole / e A
Flack parameter
-0.05(16)
2