Molecules 2017, 22, 974
11 of 22
powder (CH2Cl2). IR (KBr, cm−1
(C–N), 1228 (C–O), 809, 736, 647 (C–Se), 589. H-NMR (300 MHz, DMSO-d6):
)
ν
3394 (NH), 3250 (br OH), 1640 (C=O), 1603, 1541 (CONH), 1288
1
δ 2.25 (s, 6H, CH3), 6.66
(dd, J = 8.2 Hz, J = 1.2 Hz, 2H, Ar-H), 6.76 (d, J = 1.2 Hz, 2H, Ar-H), 7.39 (ddd, J = 7.2 Hz, J = 7.0 Hz,
J = 1.0 Hz, 2H, Ph-H), 7.43 (d, J = 8.2 Hz, 2H, Ar-H), 7.44 (ddd, J = 7.8 Hz, J = 7.0 Hz, J = 1.6 Hz, 2H,
Ph-H), 7.77 (dd, J = 7.8 Hz, J = 1.0 Hz, 2H, Ph-H), 8.00 (dd, J = 7.2 Hz, J = 1.6 Hz, 2H, Ph-H), 9.60 (s, 2H,
OH), 9.72 (s, 2H, NH). 13C-NMR (75 MHz, DMSO-d6):
CH), 122.5 (2 C), 125.0 (2 CH), 126.3 (2 CH), 128.4 (2
132.2 (2 C), 133.0 (2 C), 135.7 (2 C), 149.9 (2
δ
20.7 (2
×
CH3), 116.4 (2
×
CH), 119.5 (2
×
×
×
×
×
CH), 130.0 (2 CH), 131.9 (2
×
×
CH),
×
×
×
×
C), 166.1 (2
×
C=O). HRMS (TOF MS ESI): m/z
for C28H24N2O4Se2 + Na+ calculated: 634.9959; found: 634.9949. Anal. Calcd. for C28H24N2O4Se2
(610.42): C, 55.09; H, 3.96; N, 4.59. Found: C, 55.18; H, 3.82; N, 4.52.
Bis[2-(2-hydroxy-5-methylphenylcarbamoyl)]phenyl Diselenide 4e. The general procedure starting from
2-hydroxy-5-methylaniline (129 mg, 1.05 mmol) and benzyl chloride
3 (240 mg, 0.55 mmol) at
RT was employed, with a 96-h reaction time ◦to obtain 4e. Yield: (285 mg, 89% calculated on
2-hydroxy-5-methylaniline); m.p.: 191.5–194.5 C; as a beige powder (CH2Cl2). IR (KBr, cm−1
) ν
3409 (NH), 3235 (br OH), 1640 (C=O), 1599, 1547 (CONH), 1504, 1279 (C–N), 1236 (C–O), 1200, 1027,
1
809, 740, 619 (C–Se), 452. H-NMR (300 MHz, DMSO-d6):
δ 2.25 (s, 6H, CH3), 6.83 (d, J = 8.2 Hz, 2H,
Ar-H), 6.89 (dd, J = 8.2 Hz, J = 1.7 Hz, 2H, Ar-H), 7.39 (ddd, J = 7.5 Hz, J = 7.1 Hz, J = 1.0 Hz, 2H,
Ph-H), 7.46 (d, J = 1.7 Hz, 2H, Ar-H), 7.47 (ddd, J = 7.8 Hz, J = 7.1 Hz, J = 1.4 Hz, 2H, Ph-H), 7.78 (dd,
J = 7.8 Hz, J = 1.0 Hz, 2H, Ph-H), 8.00 (dd, J = 7.5 Hz, J = 1.4 Hz, 2H, Ph-H), 9.49 (s, 2H, NH), 9.71 (s, 2H,
OH). 13C-NMR (75 MHz, DMSO-d6):
δ
20.2 (2
CH), 127.5 (2 C), 128.4 (2
C), 166.1 (2 C=O). HRMS (TOF MS ESI): m/z for C28H24N2O4Se2 +
×
CH3), 115.7 (2
×
CH), 124.8 (2
×
C), 125.2 (2
×
CH),
126.4 (2
×
CH), 126.5 (2
×
×
×
CH), 130.1 (2
×
CH), 132.0 (2
×
CH), 132.2
(2 C), 133.0 (2
×
×
C), 147.5 (2
×
×
Na+ calculated: 632.9967; found: 632.9987. Anal. Calcd. for C28H24N2O4Se2 (610.42): C, 55.09; H, 3.96;
N, 4.59. Found: C, 55.01; H, 3.88; N, 4.64.
Bis[2-(2-hydroxy-6-methylphenylcarbamoyl)]phenyl Diselenide 4f. The general procedure starting from
2-hydroxy-6-methylaniline (129 mg, 1.05 mmol) at RT was employed, with a 168-h reaction time to
obtain 4f. Yield: (282 mg, 88% calculated−o1n 2-hydroxy-6-methylaniline used); m.p.: 264–267 ◦C; as a
pale beige powder (CH2Cl2). IR (KBr, cm
1472, 1294 (C–N), 1191 (C–O), 1026, 781, 737, 549 (C–Se). H-NMR (300 MHz, DMSO-d6):
)
ν
3360 (NH), 3251 (OH), 1622 (C=O), 1592, 1515 (CONH),
1
δ 2.19 (s,
6H, CH3), 6.74 (d, J = 7.7 Hz, 2H, Ar-H), 6.78 (d, J = 8.2 Hz, 2H, Ar-H), 7.05 (dd, J = 8.2 Hz, J = 7.7 Hz,
2H, Ar-H), 7.39 (dd, J = 7.6 Hz, J = 6.0 Hz, 2H, Ph-H), 7.45 (dd, J = 6.8 Hz, J = 6.0 Hz, 2H, Ph-H), 7.77
(d, J = 7.6 Hz, 2H, Ph-H), 8.09 (d, J = 6.8 Hz, 2H, Ph-H), 9.39 (s, 2H, NH), 9.78 (s, 2H, OH). 13C-NMR
(75 MHz, DMSO-d6):
127.3 (2 CH), 128.5 (2
(2 C), 153.3 (2 C), 166.5 (2
632.9967; found: 632.9971. Anal. Calcd. for C28H24N2O4Se2 (610.42): C, 55.09; H, 3.96; N, 4.59. Found:
C, 55.16; H, 4.09; N, 4.45.
δ
17.9 (2
CH), 129.9 (2
C=O). HRMS (TOF MS ESI): m/z for C28H24N2O4Se2 + Na+ calculated:
×
CH3), 113.5 (2
×
CH), 120.4 (2
×
CH), 123.4 (2
×
C), 126.1 (2
×
CH),
×
×
×
CH), 131.7 (2
×
CH), 132.4 (2
×
C), 133.0 (2
×
C), 136.8
×
×
×
Bis[2-(2-hydroxy-4-chlorophenylcarbamoyl)]phenyl Diselenide 4g. The general procedure starting from
2-hydroxy-4-chloroaniline (151 mg, 1.05 mmol) at RT was employed, with a 96-h reaction time to obtain
◦
4g. Yield: (202 mg, 59% calculated on 2-hydroxy-4-chloroaniline used); m.p.: 230–234 C; as a brownish
gray powder (CH2Cl2). IR (KBr, cm−1
)
ν
3398 (NH), 3176 (br OH), 1639 (C=O), 1532 (CONH), 1414,
1342, 1265 (C–N), 1226 (C–O), 911, 734, 648, 590 (C–Se), 452. H-NMR (300 MHz, DMSO-d6):
1
δ 6.92 (dd,
J = 8.5 Hz, J = 2.2 Hz, 2H, Ar-H), 6.98 (d, J = 2.2 Hz, 2H, Ar-H), 7.40 (dd, J = 7.2 Hz, J = 7.0 Hz, 2H,
Ph-H), 7.46 (ddd, J = 7.9 Hz, J = 7.0 Hz, J = 1.2 Hz, 2H, Ph-H), 7.63 (d, J = 8.5 Hz, 2H, Ar-H), 7.76 (d,
J = 7.9 Hz, 2H, Ph-H), 8.02 (dd, J = 7.2 Hz, J = 1.2 Hz, 2H, Ph-H), 9.86 (s, 2H, NH), 10.37 (s, 2H, OH).
13C-NMR (75 MHz, DMSO-d6): δ 115.5 (2 × CH), 118.7 (2 × CH), 124.3 (2 × C), 126.4 (2 × CH), 126.6
(2
×
CH), 128.6 (2
×
CH), 129.6 (2
×
×
C), 130.0 (2
×
CH), 132.1 (2
×
CH), 132.3 (2
×
C), 132.7 (2
×
C),
151.3 (2
×
C), 166.2 (2
C=O). HRMS (TOF MS ESI): m/z for C26H18Cl2N2O4Se2 + Na+ calculated: