Synthesis, spectroscopic characterization and antibacterial activity of some chlorosulphoxide ruthenium(II) and ruthenium(III) complexes of 4-(benzylideneamino)-1,2-dimethyl-2-phenyl-1,2-dihydropyrazole-3-one, schiff base

Article abstract of DOI:10.4067/S0717-97072010000200003

In present work we report the synthesis of five complexes of three different formulations, viz. [cis-RuCl₂(SBANTP)₂]; [trans-RuCl₂SBANTP)₂]; and [RuCl₄(SBANTP)-] [X]⁺; where [X]⁺

Full text of DOI:10.4067/S0717-97072010000200003

J. Chil. Chem. Soc., 55, Nº 2 (2010)
e-mail : ccrl_2004@rediffmail.com
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
1
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
Table 1. Bond length of the 3D structure for complex 1.
Optimal
Bond length
S. No.
Atoms
C(1)-C(2)
Bond length
1
2
3
4
5
6
7
8
9
.
.
.
.
.
.
.
.
.
1.418
1.419
1.123
1.420
1.123
1.419
1.123
1.415
1.123
1.419
1.123
1.574
1.577
1.510
1.416
1.400
1.408
1.549
1.600
1.535
1.434
1.122
1.122
1.122
1.120
1.122
1.123
1.626
1.956
1.319
1.121
1.678
1.680
1.368
1.125
1.462
1.121
1.676
1.108
1.319
1.119
1.121
1.924
0.649
0.650
1.446
1.441
1.096
1.445
1.096
1.445
1.097
1.445
1.096
1.443
-
C(1)-C(6)
-
C(1)-H(81)
C(2)-C(3)
-
-
C(2)-H(79)
C(3)-C(4)
-
-
C(3)-H(78)
C(4)-C(5)
-
-
C(4)-H(77)
C(5)-C(6)
-
1
0.
1.
-
1
C(5)-H(80)
C(6)-N(7)
-
1
1
1
1
1
1
1
1
2
2
2
2
2
2
2
2
2
2
3
3
3
3
3
3
3
3
3
3
4
4
4
4
4
4
4
4
4
4
5
5
5
5
5
5
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
-
N(7)-C(8)
-
N(7)-N(11)
C(8)-C(9)
-
-
C(8)-O(29)
C(9)-C(10)
C(9)-N(20)
C(10)-N(11)
C(10)-C(16)
N(11)-C(12)
C(12)-H(13)
C(12)-H(14)
C(12)-H(15)
C(16)-H(17)
C(16)-H(18)
C(16)-H(19)
N(20)-C(21)
N(20)-Ru(58)
C(21)-C(23)
C(21)-H(22)
C(23)-C(24)
C(23)-C(28)
C(24)-C(25)
C(24)-H(76)
C(25)-C(26)
C(25)-H(74)
C(26)-C(27)
C(26)-H(65)
C(27)-C(28)
C(27)-H(64)
C(28)-H(75)
O(29)-Ru(58)
O(29)-Lp(82)
O(29)-Lp(83)
C(30)-C(31)
C(30)-C(35)
C(30)-H(70)
C(31)-C(32)
C(31)-H(68)
C(32)-C(33)
C(32)-H(67)
C(33)-C(34)
C(33)-H(66)
C(34)-C(35)
-
-
-
-
-
-
-
-
-
-
-
-
-
2.088
-
-
-
-
-
-
-
-
-
-
-
-
-
2.022
-
-
-
-
-
-
-
-
-
-
-
-
1
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
5
5
5
5
6
6
6
6
6
6
6
6
6
6
7
7
7
7
7
7
7
7
7
7
8
8
8
8
8
8
8
8
8
8
9
9
9
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
C(34)-H(69)
C(35)-N(36)
N(36)-C(37)
N(36)-N(40)
C(37)-C(38)
C(37)-O(57)
C(38)-C(39)
C(38)-N(61)
C(39)-N(40)
C(39)-C(45)
N(40)-C(41)
C(41)-H(42)
C(41)-H(43)
C(41)-H(44)
C(45)-H(46)
C(45)-H(47)
C(45)-H(48)
C(49)-C(51)
C(49)-N(61)
C(49)-H(50)
C(51)-C(52)
C(51)-C(56)
C(52)-C(53)
C(52)-H(73)
C(53)-C(54)
C(53)-H(71)
C(54)-C(55)
C(54)-H(63)
C(55)-C(56)
C(55)-H(62)
C(56)-H(72)
O(57)-Ru(58)
O(57-Lp(84)
O(57)-Lp(85)
Ru(58)-Cl(59)
Ru(58)-Cl(60)
Ru(58)-N(61)
1.097
1.561
1.567
1.507
1.448
1.379
1.465
1.507
1.609
1.515
1.434
1.122
1.122
1.122
1.122
1.120
1.122
1.309
1.630
1.122
1.674
1.692
1.442
1.100
1.451
1.097
1.684
1.100
1.314
1.114
1.116
1.924
0.650
0.648
2.267
2.261
1.961
-
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
C(5)-C(6)-N(7)
116.808
122.261
129.446
105.390
107.805
129.696
121.262
113.996
110.566
135.164
106.641
128.539
124.675
105.733
125.627
127.372
111.217
108.895
109.814
108.828
108.993
109.059
110.715
109.249
110.239
108.973
108.466
109.169
121.072
109.296
128.960
123.005
118.606
118.201
123.243
122.131
114.354
119.423
118.859
121.444
121.247
121.608
117.134
120.595
119.281
119.685
121.124
118.035
120.808
117.971
120.338
121.656
110.347
109.354
108.942
109.658
109.793
108.719
120
120
-
-
C(6)-N(7)-C(8)
-
C(6)-N(7)-N(11)
-
C(8)-N(7)-N(11)
-
-
N(7)-C(8)-C(9)
109
-
-
N(7)-C(8)-O(29)
-
C(9)-C(8)-O(29)
120
120
120
-
-
C(8)-C(9)-C(10)
-
C(8)-C(9)-N(20)
-
C(10)-C(9)-N(20)
C(9)-C(10)-N(11)
C(9)-C(10)-C(16)
N(11)-C(10)-C(16)
N(7)-N(11)-C(10)
N(7)-N(11)-C(12)
C(10)-N(11)-C(12)
N(11)-C(12)-H(13)
N(11)-C(12)-H(14)
N(11)-C(12)-H(15)
H(13)-C(12)-H(14)
H(13)-C(12)-H(15)
H(14)-C(12)-H(15)
C(10)-C(16)-H(17)
C(10)-C(16)-H(18)
C(10)-C(16)-H(19)
H(17)-C(16)-H(18)
H(17)-C(16)-H(19)
H(18)-C(16)-H(19)
C(9)-N(20)-C(21)
C(9)-N(20)-Ru(58)
C(21)-N(20)-Ru(58)
N(20)-C(21)-C(23)
N(20)-C(21)-H(22)
H(22)-C(21)-C(23)
C(21)-C(23)-C(24)
C(21)-C(23)-C(28)
C(24)-C(23)-C(28)
C(23)-C(24)-C(25)
C(23)-C(24)-H(76)
C(25)-C(24)-H(76)
C(24)-C(25)-C(26)
C(24)-C(25)-H(74)
C(26)-C(25)-H(74)
C(25)-C(26)-C(27)
C(25)-C(26)-H(65)
C(27)-C(26)-H(65)
C(26)-C(27)-C(28)
C(26)-C(27)-H(64)
C(28)-C(27)-H(64)
C(23)-C(28)-C(27)
C(23)-C(28)-H(75)
C(27)-C(28)-H(75)
C(8)-O(29)-Ru(58)
C(8)-O(29)-Lp(82)
C(8)-O(29)-Lp(83)
Ru(58)-O(29)-Lp(82)
Ru(58)-O(29)-Lp(83)
Lp(82)-O(29)-Lp(83)
-
-
-
-
-
-
-
-
-
-
-
-
-
109
109
109
109
109
109
109
109
109
109
109
109
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
-
-
-
2.242
2.242
2.088
5
5
5.
6.
Table 2. Bond angle for the 3D structure of complex 1.
Optimal
Bond Angle
S. No.
Atoms
Bond Angle
57.
5
5
6
6
6
6
6
6
6
6
6
6
7
7
7
7
7
7
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
1
2
3
4
5
6
7
8
9
.
.
.
.
.
.
.
.
.
C(2)-C(1)-C(6)
C(2)-C(1)-H(81)
C(6)-C(1)-H(81)
C(1)-C(2)-C(3)
C(1)-C(2)-H(79)
C(3)-C(2)-H(79)
C(2)-C(3)-C(4)
C(2)-C(3)-H(78)
C(4)-C(3)-H(78)
C(3)-C(4)-C(5)
C(3)-C(4)-H(77)
C(5)-C(4)-H(77)
C(4)-C(5)-C(6)
C(4)-C(5)-H(80)
C(6)-C(5)-H(80)
C(1)-C(6)-C(5)
C(1)-C(6)-N(7)
119.472
120.270
120.254
120.184
120.008
119.805
120.174
120.084
119.741
119.725
120.428
119.845
120.117
120.296
119.579
120.323
122.785
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
120
1
0.
1.
1
1
1
1
1
1
1
2.
3.
4.
5.
6.
7.
-
-
-
-
-
1
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
7
7
7
7
8
8
8
8
8
8
8
8
8
8
9
9
9
9
9
9
9
9
9
9
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
0.
1.
2.
3.
4.
5.
6.
7.
8.
9.
C(31)-C(30)-C(35)
C(31)-C(30)-H(70)
C(35)-C(30)-H(70)
C(30)-C(31)-C(32)
C(30)-C(31)-H(68)
C(32)-C(31)-H(68)
C(31)-C(32)-C(33)
C(31)-C(32)-H(67)
C(33)-C(32)-H(67)
C(32)-C(33)-C(34)
C(32)-C(33)-H(66)
C(34)-C(33)-H(66)
C(33)-C(34)-C(35)
C(33)-C(34)-H(69)
C(35)-C(34)-H(69)
C(30)-C(35)-C(34)
C(30)-C(35)-N(36)
C(34)-C(35)-N(36)
C(35)-N(36)-C(37)
C(35)-N(36)-N(40)
C(37)-N(36)-N(40)
N(36)-C(37)-C(38)
N(36)-C(37)-O(57)
C(38)-C(37)-O(57)
C(37)-C(38)-C(39)
C(37)-C(38)-N(61)
C(39)-C(38)-N(61)
C(38)-C(39)-N(40)
C(38)-C(39)-C(45)
N(40)-C(39)-C(45)
N(36)-N(40)-C(39)
N(36)-N(40)-C(41)
C(39)-N(40)-C(41)
N(40)-C(41)-H(42)
N(40)-C(41)-H(43)
N(40)-C(41)-H(44)
H(42)-C(41)-H(43)
H(42)-C(41)-H(44)
H(43)-C(41)-H(44)
C(39)-C(45)-H(46)
C(39)-C(45)-H(47)
C(39)-C(45)-H(48)
H(46)-C(45)-H(47)
H(46)-C(45)-H(48)
H(47)-C(45)-H(48)
C(51)-C(49)-N(61)
H(50)-C(49)-C(51)
H(50)-C(49)-N(61)
C(49)-C(51)-C(52)
C(49)-C(51)-C(56)
C(52)-C(51)-C(56)
C(51)-C(52)-C(53)
C(51)-C(52)-H(73)
C(53)-C(52)-H(73)
C(52)-C(53)-C(54)
C(52)-C(53)-H(71)
C(54)-C(53)-H(71)
C(53)-C(54)-C(55)
119.654
120.106
120.230
120.100
119.975
119.918
120.059
120.049
119.890
119.802
120.188
120.005
119.989
119.843
120.152
120.394
120.578
118.817
123.008
130.527
106.419
109.549
130.901
118.604
110.589
111.621
137.060
107.333
126.364
125.638
106.037
125.072
125.220
108.805
110.127
111.056
109.030
108.689
109.094
109.344
111.241
109.310
108.610
109.308
109.001
121.345
119.640
118.980
121.792
122.259
115.774
118.805
121.232
119.454
120.794
119.724
119.472
121.827
120
120
-
134.
135.
136.
137.
138.
139.
140.
141.
142.
143.
144.
145.
146.
147.
148.
149.
150.
151.
152.
153.
154.
155.
156.
157.
158.
159.
160.
161.
162.
163.
164.
165.
C(53)-C(54)-H(63)
C(55)-C(54)-H(63)
C(54)-C(55)-C(56)
C(54)-C(55)-H(62)
C(56)-C(55)-H(62)
C(51)-C(56)-C(55)
C(51)-C(56)-H(72)
C(55)-C(56)-H(72)
C(37)-O(57)-Ru(58)
C(37)-O(57)-Lp(84)
C(37)-O(57)-Lp(85)
Ru(58)-O(57)-Lp(84)
Ru(58)-O(57)-Lp(85)
Lp(84)-O(57)-Lp(85)
N(20)-Ru(58)-O(29)
N(20)-Ru(58)-O(57)
N(20)-Ru(58)-Cl(59)
N(20)-Ru(58)-Cl(60)
N(20)-Ru(58)-N(61)
O(29)-Ru(58)-O(57)
O(29)-Ru(58)-Cl(59)
O(29)-Ru(58)-Cl(60)
O(29)-Ru(58)-N(61)
O(57)-Ru(58)-Cl(59)
O(57)-Ru(58)-Cl(60)
O(57)-Ru(58)-N(61)
Cl(59)-Ru(58)-Cl(60)
Cl(59)-Ru(58)-N(61)
Cl(60)-Ru(58)-N(61)
C(38)-N(61)-C(49)
C(38)-N(61)-Ru(58)
C(49)-N(61)-Ru(58)
118.235
119.826
121.484
117.416
121.087
118.710
119.558
121.723
111.394
108.009
108.830
109.451
110.141
108.957
88.295
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
90
-
-
174.777
101.371
89.774
-
90
90
90
90
90
180
90
90
90
90
90
180
90
-
-
-
90.119
-
95.675
-
84.181
-
175.386
85.176
-
-
82.452
100.
101.
102.
103.
104.
105.
106.
107.
108.
109.
110.
-
86.511
-
86.843
-
92.096
-
164.066
99.022
-
-
120.992
109.010
123.173
-
-
-
-
-
Except few case optimal values, which are more favorable of both bond
length and bond angles are given along with the actual ones. The actual bond
length/bond angles given in Table 1 and 2 are calculated values as a result of
energy optimization in Chem 3D Ultra, while the optimal bond length/optimal
bond angles are most favorable (standard) bond length/bond angles established
by builder unit of Chem 3D. The missing of some values of standard bond
length/bond angles may be due to limitations of software. In most of the
case actual bond length and angles are closed to optimal values and thus the
proposed structure of the compound is acceptable.
Antibacterial Activity
Antibacterial activity of compound A (A = SBANTP) and complex 1,
, 3, 4 and 5 alongwith their precursors 1a-5a and 1b-2b have been tested
on Escherichia coli, MTCC 1304, a gram negative bacteria at different
concentration.
Mullar Hinton Agar (MHA) plates were prepared at 50µl suspension
of Escherichia coli, containing approximately 10 CFU (Colony Forming
Unit) were applied to the plate by spread plate technique. The wells made
on the plate were filled with 50µl of sample solution of 0.03% concentration.
Chloramphenicol solution of 0.03% was used for comparison. Now, these
plates were incubated at 37+1 C for 24-48h in a refrigerated incubator shaker.
The result shows (Table 3) that very little inhibition zone was observed around
the control compound A. However all complexes show more inhibition than
-
-
1
11.
12.
13.
14.
15.
16.
17.
18.
19.
-
1
-
1
-
1
-
1
-
1
-
1
-
2
1
-
1
-
1
1
1
1
1
1
1
1
1
1
1
1
1
1
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
-
5
-
32
-
-
o
-
-
3
3, 34
-
their precursor, probably due to increased lipophilicity in the complexes.
The complex 3, 4 and 5 were found most active than all other complexes at
.03% concentration but at the same concentration these complexes were less
-
0
-
active than chloramphenicol, the antibiotic used for comparison.
-
-
CONCLUSION
-
Therefore, it can be concluded that the reaction of cis-RuCl (SO) /
trans-RuCl (SO) with SBANTP ligand in 1:2 molar ratio replaced all the
sulphoxides. We obtained same product, whether it is dmso/tmso from different
2
4
-
2
4
-
1
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J. Chil. Chem. Soc., 55, Nº 2 (2010)
1
65