Supplementary Information
Synthesis, characterization and application of poly (N, N'-dibromo-Nethylnaphthyl-2, 7-disulfonamide) as an efficient catalyst for the synthesis of
2-arylbenzimidazole and 2-aryl-1-arylmethyl-1 H-1, 3-benzimidazole
derivatives
Vida Saleh 1,*, Ardeshir Khazaei 1,*, Hamid Abizadeh 1, Shahnaz Saednia
1
2
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan
6517838683, Iran
2
Young Researchers & Elites Club, Toyserkan Branch, Islamic Azad university, Toyserkan, Iran.
*Corresponding authors (email: Khazaei_1326@yahoo.com, Vida.saleh@yahoo.com)
Table of Contents
Page
Figure S1. IR spectrum of naphthalene-2, 7-disufonyl chloride (nujol) ………………..
S4
Figure S2. 1H NMR (90 MHz, CDCl3) spectrum of naphthalene-2, 7-disufonyl chloride
S4
Figure S3. IR spectrum of poly (N-ethylnaphthyl-2, 7-disulfonamide) (KBr) …………
S5
Figure S4. 1H NMR (400 MHz, DMSO-d6) spectrum of poly (N-ethylnaphthyl-2, 7disulfonamide) ……………………………………………………………………………. S5
Figure S5. 13C NMR (100.6 MHz, DMSO-d6) spectrum of poly (N- ethylnaphthyl-2, 7disulfonamide) ……………………………………………………………………………. S6
Figure S6. Gel permeation chromatography (GPC) diagram for poly (N-ethylnaphthyl2, 7-disulfonamide) ……………………………………………………………………….
S6
Figure S7. IR spectrum of PBNS (KBr) …………………………………………………. S7
Figure S8. 1H NMR (400 MHz, DMSO-d6) spectrum of PBNS ………………………… S7
Figure S9. 13C NMR (100.6 MHz, DMSO-d6) spectrum of PBNS ……………………… S8
Figure S10. TGA/DTG thermogram of poly (N-ethylnaphthyl-2, 7-disulfonamide) ……. S8
Figure S11. TGA/DTG thermogram of PBNS …………………………………………... S9
Figure S12. IR spectrum of 2-phenyl-1 H-benzoimidazole(KBr) ………………………
S9
Figure S13. 1H NMR (90 MHz, CDCl3) spectrum of 2-phenyl-1 H-benzoimidazole…..
S10
Figure S14. IR spectrum of [4-(1 H-Benzoimidazol-2-yl)-phenyl]-dimethyl-amine
(KBr) ……………………………………………………………………………………...
S10
Figure S15. 1H NMR (90 MHz, CDCl3) spectrum of [4-(1H-Benzoimidazol-2-yl)phenyl]-dimethyl-amine …………………………………………………………………..
S11
Figure S16. IR spectrum of 2-(1 H-Benzoimidazol-2-yl)-phenol (KBr) ………………...
S11
Figure S17. 1H NMR (90 MHz, CDCl3) spectrum of 2-(1 H-Benzoimidazol-2-yl)phenol ……………………………………………………………………………………..
S12
Figure S18. IR spectrum of 2-p-Tolyl-1 H-benzoimidazole (KBr) ……………………… S12
Figure S19. 1H NMR (90 MHz, CDCl3) spectrum of 2-p-Tolyl-1 H-benzoimidazole …..
S13
Figure S20. IR spectrum of 2-(2-methoxy-phenyl)-1 H-benzoimidazole (KBr) ………...
S13
Figure S21. 1H NMR (90 MHz, CDCl3) spectrum of 2-(2-methoxy-phenyl)-1 Hbenzoimidazole …………………………………………………………………………...
S14
Figure S22. IR spectrum of 2-(3-nitro-phenyl)-1 H-benzoimidazole (KBr) …………….. S14
Table of Contents
1
Figure S23.
Page
H NMR (90 MHz, CDCl3) spectrum of 2-(3-nitro-phenyl)-1 H-
benzoimidazole …………………………………………………………………………...
1
Figure S24.
S15
H NMR (90 MHz, CDCl3) spectrum of 2-(4-chloro-phenyl)-1 H-
benzoimidazole …………………………………………………………………………...
S15
Figure S25. IR spectrum of 2-furan-2-yl-1 H-benzoimidazole (KBr) ..………………...
S16
Figure S26. 1H NMR (90 MHz, CDCl3) spectrum of 2-furan-2-yl-1 H-benzoimidazole
S16
Figure S27. IR spectrum of 1-benzyl-2-phenyl-1 H-benzoimidazole (KBr) ……….….
S17
1
Figure S28.
H NMR (90 MHz, CDCl3) spectrum of 1-benzyl-2-phenyl-1 H-
benzoimidazole …………………………………………………………………………...
S17
Figure S29. IR spectrum of 1-(4-nitro-benzyl)-2-(4-nitro-phenyl)-1 H-benzoimidazole
(KBr) ……………………………………………………………………………………...
S18
Figure S30. 1H NMR (90 MHz, CDCl3) spectrum of 1-(4-nitro-benzyl)-2-(4-nitrophenyl)-1 H-benzoimidazole ………………………………………………………..……. S18
Figure S31. IR spectrum of 1-(3-nitro-benzyl)-2-(3-nitro-phenyl)-1 H-benzoimidazole
(KBr) ……………………………………………………………………………………...
S19
Figure S32. 1H NMR (90 MHz, CDCl3) spectrum of 1-(3-nitro-benzyl)-2-(3-nitrophenyl)-1 H-benzoimidazole ……………………………...……………………………… S19
Figure
S33.
IR
spectrum
of
1-(4-chloro-benzyl)-2-(4-chloro-phenyl)-1
H-
benzoimidazole (KBr) …………………………………………………………………….
S20
Figure S34. 1H NMR (90 MHz, CDCl3) spectrum of 1-(4-chloro-benzyl)-2-(4-chlorophenyl)-1 H-benzoimidazole ……………………………………………………………... S20
Figure
S35.
IR
spectrum
of
1-(4-cyano-benzyl)-2-(4-cyano-phenyl)-1
H-
benzoimidazole (KBr) …………………………………………………………………….
S21
Figure S36. 1H NMR (90 MHz, CDCl3) spectrum of 1-(4-cyano-benzyl)-2-(4-cyanophenyl)-1 H-benzoimidazole ...…………………………………………………………… S21
Figure S37. IR spectrum of 1-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-1 Hbenzoimidazole (KBr) …………………………………………………………………….
Figure S38.
13
S22
C NMR spectrum (90 MHz, CDCl3) of 1-(4-methoxy-benzyl)-2-(4-
methoxy-phenyl)-1 H-benzoimidazole …………………………………………………...
S22
ClO2S
SO2Cl
Figure S1.IR spectrum of naphthalene-2, 7-disufonyl chloride
ClO2S
SO2Cl
Figure S2.1H NMR spectrum (90 MHz,CDCl3) of naphthalene-2, 7-disufonyl chloride.
S4
O
O
S
N
H O
S
N
O H
n
Figure S3.IR spectrum of poly (N-ethylnaphthyl-2, 7-disulfonamide) (KBr).
O
O
S
N
H O
S
N
O H
n
Figure S4.1H NMR(400 MHz,DMSO-d6) spectrum ofpoly (N-ethylnaphthyl-2, 7disulfonamide).
S5
O
O
S
N
H O
S
N
O H
n
Figure S5.13C NMR(100.6 MHz,DMSO-d6) spectrum ofpoly (N-ethylnaphthyl-2, 7disulfonamide).
Figure S6.Gel permeation chromatography (GPC) diagram for poly (N-ethylnaphthyl-2, 7disulfonamide).
S6
O
O
S
S
O
O
N
N
Br
n
Br
Figure S7. IR spectrum of PBNS (KBr).
O
O
S
S
O
O
N
N
Br
Figure S8. 1H NMR(400 MHz, DMSO-d6) spectrum ofPBNS.
S7
Br
n
O
O
S
S
O
O
N
Br
N
n
Br
Figure S9.13C NMR(100.6 MHz, DMSO-d6) spectrum ofPBNS.
O
O
S
N
H O
S
N
O H
Figure S10. TGA/DTG thermogram ofpoly (N-ethylnaphthyl-2, 7-disulfonamide).
S8
n
O
O
S
S
O
O
N
N
Br
n
Br
Figure S11. TGA/DTG thermogram of PBNS.
N
N
H
Figure S12. IR spectrum of 2-phenyl-1H-benzoimidazole (KBr).
S9
N
N
H
Figure S13.1H NMR(90 MHz, CDCl3) spectrum of2-phenyl-1H-benzoimidazole.
N
N(CH3)2
N
H
Figure S14.IR spectrum of [4-(1 H-Benzoimidazol-2-yl)-phenyl]-dimethyl-amine (KBr).
S10
N
N(CH3)2
N
H
Figure S15.1H NMR(90 MHz, CDCl3)spectrum of [4-(1H-Benzoimidazol-2-yl)-phenyl]dimethyl-amine.
N
N
H
HO
Figure S16.IR spectrum of 2-(1 H-Benzoimidazol-2-yl)-phenol (KBr).
S11
N
N
H
HO
Figure S17.1H NMR(90 MHz, CDCl3)spectrumof 2-(1H-Benzoimidazol-2-yl)-phenol.
N
CH3
N
H
Figure S18.IR spectrum of 2-p-Tolyl-1H-benzoimidazole (KBr).
S12
N
CH3
N
H
Figure S19.1H NMR(90 MHz, CDCl3)spectrumof 2-p-Tolyl-1H-benzoimidazole.
N
N
H
H 3C O
Figure S20.IR spectrum of 2-(2-methoxy-phenyl)-1H-benzoimidazole (KBr).
S13
N
N
H
H3CO
Figure S21.1H NMR(90 MHz, CDCl3)spectrumof 2-(2-methoxy-phenyl)-1 H-benzoimidazole.
N
N
H
NO2
Figure S22.IR spectrum of 2-(3-nitro-phenyl)-1H-benzoimidazole (KBr).
S14
N
N
H
NO2
Figure S23.1H NMR (90 MHz, CDCl3)spectrum of 2-(3-nitro-phenyl)-1H-benzoimidazole.
N
Cl
N
H
Figure S24.1H NMR(90 MHz, CDCl3)spectrum of 2-(4-chloro-phenyl)-1H-benzoimidazole.
S15
N
N
H
O
Figure S25.IR spectrum of 2-furan-2-yl-1H-benzoimidazole (KBr).
N
N
H
O
Figure S26.1H NMR(90 MHz, CDCl3)spectrum of 2-furan-2-yl-1H-benzoimidazole.
S16
N
N
Figure S27.IR spectrum of 1-benzyl-2-phenyl-1H-benzoimidazole (KBr).
N
N
Figure S28.1H NMR(90 MHz, CDCl3)spectrum of 1-benzyl-2-phenyl-1H-benzoimidazole.
S17
NO2
N
NO2
N
Figure S29.IR spectrum of 1-(4-nitro-benzyl)-2-(4-nitro-phenyl)-1H-benzoimidazole (KBr).
NO 2
N
N O2
N
Figure S30.1H NMR(90 MHz, CDCl3)spectrum of 1-(4-nitro-benzyl)-2-(4-nitro-phenyl)-1Hbenzoimidazole.
S18
N O2
N
N
NO2
Figure S31.IR spectrum of 1-(3-nitro-benzyl)-2-(3-nitro-phenyl)-1H-benzoimidazole (KBr).
NO2
N
N
NO2
Figure S32.1H NMR(90 MHz, CDCl3)spectrum of 1-(3-nitro-benzyl)-2-(3-nitro-phenyl)-1Hbenzoimidazole.
S19
Cl
N
Cl
N
Figure S33.IR spectrum of 1-(4-chloro-benzyl)-2-(4-chloro-phenyl)-1H-benzoimidazole (KBr).
Cl
N
Cl
N
Figure S34.1H NMR(90 MHz, CDCl3)spectrumof 1-(4-chloro-benzyl)-2-(4-chloro-phenyl)-1Hbenzoimidazole.
S20
CN
N
CN
N
Figure S35.IR spectrum of 1-(4-cyano-benzyl)-2-(4-cyano-phenyl)-1H-benzoimidazole (KBr).
CN
N
CN
N
Figure S36.1H NMR(90 MHz, CDCl3)spectrum of 1-(4-cyano-benzyl)-2-(4-cyano-phenyl)-1Hbenzoimidazole.
S21
OC H3
N
OC H 3
N
Figure S37.IR spectrum of 1-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-1H-benzoimidazole
(KBr).
OC H 3
N
OC H3
N
Figure S38.13C NMRspectrum (90 MHz, CDCl3) of 1-(4-methoxy-benzyl)-2-(4-methoxyphenyl)-1H-benzoimidazole.
S22