Aniline Benzene Rings Research Articles

Investigation into the ring-substituted polyanilines and their application for the detection and adsorption of sulfur dioxide

It has been demonstrated in this study that the substituents on the monomer aniline benzene ring are able to introduce the significant differences to the resulting polyaniline tm)s collective properties. We systematically evaluated the structural perturbation effects of two substituents (methyl and methoxy) of aniline monomer through the electrochemical method. Our results showed that the methoxy group induces the less structural perturbation than the methyl counterpart, because of its partial double bond restriction. The morphologies are different for the polyaniline and the ring-substituted polyanilines, in which substituted polyanilines feature the larger porosities with the addition of these side groups. The influential effects of the methoxy side group have been further illustrated and amplified by its superior sensing performance towards the environmentally-significant sulfur dioxide gas, evaluated through the construction of the quartz crystal microbalance (QCM)-based gas sensor with these polyaniline materials. The as-constructed gas sensor tm)s sensitivity, selectivity and stability in terms of its SO2 responses have been evaluated in details. The methoxy-substituted polyaniline was tested to show the unique gas sensing properties for the sulfur dioxide at the low concentrations (50•250ppm) and function as the adsorbing material at the high concentrations (500•1250ppm). Thus it can be used both as sensing material as well as a novel filter and/or storage reservoir for the removal of sulfur dioxide pollutant from the environments.

N-(2,3-Dimethylphenyl)-2-nitrobenzenesulfonamide

There are two independent mol­ecules in the asymmetric unit of the title compound, C14H14N2O4S. The N—H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The mol­ecules are twisted at the S—N bonds with torsion angles of −60.4 (3) and 58.8 (3)° in the two mol­ecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both mol­ecules are involved in an intra­molecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link like mol­ecules into inversion dimers.

4-Chloro-N-(2,3-dimethylphenyl)benzamide

In the title compound, C15H14ClNO, the ortho- and meta-methyl substituents in the aniline ring are anti to the N—H bond. The dihedral angle between the benzoyl and aniline benzene rings is 95.0 (1)°. N—H⋯O hydrogen bonds and C—H⋯π inter­actions link the mol­ecules in the crystal structure.

4-Chloro-N-(3,5-dichlorophenyl)-2-methylbenzenesulfonamide

In the title compound, C13H10Cl3NO2S, torsion angle of the C—SO2—NH—C group in the mol­ecule is −58.57 (26)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.2 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Zinc triflate-catalyzed intermolecular hydroamination of vinylarenes and anilines: scopes and limitations

Intermolecular hydroamination of vinylarenes and anilines was studied using zinc triflate as catalyst. NMR experiments supported a Lewis acid activation of the CC double bond. Electronic/steric effect study indicated that Lewis acidity of the catalyst as well as the coordination property of the amine were the governing factors for successful hydroamination of the substrates. More nucleophilic amine would bind more tightly to the central metal, leading to an unproductive coordination. Approach of bulky amine to CC bond would be hindered, and an alternative electrophilic substitution on benzene ring of the amine would become the major reaction. Electrophilic substitution would become predominant when strong electron-donating group is presented on aniline benzene ring.

4-Chloro-N-(3,4-dimethylphenyl)-2-methylbenzenesulfonamide

In the title compound, C15H16ClNO2S, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is syn with respect to the meta-methyl group in the aniline benzene ring and the ortho-methyl group in the sulfonyl benzene ring. The C—SO2—NH—C torsion angle is −49.72 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 71.6 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

2-Chloro-N-(4-methylphenyl)benzamide

In the title compound, C14H12ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond. The benzoyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains running along the c-axis direction.

4-Chloro-N-(3,4-dichlorophenyl)-2-methylbenzenesulfonamide

In the title compound, C13H10Cl3NO2S, the N—C bond in the C—SO2—NH—C segment forms trans and gauche torsion angles with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is anti to the meta-Cl atom in the anilino benzene ring and nearly syn with respect to the ortho-methyl group in the sulfonyl benzene ring. The C—SO2—NH—C torsion angle is −49.4 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 54.6 (1)°. In the crystal, mol­ecules are linked into chains along the c-axis direction by inter­molecular N—H⋯O hydrogen bonds.

2,4-Dichloro-N-(2,3-dichlorophenyl)benzenesulfonamide

In the title compound, C12H7Cl4NO2S, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is syn with respect to the ortho-Cl atoms in the aniline and sulfonyl benzene rings. The C—SO2—NH—C torsion angle is −51.98 (18)°. The sulfonyl and aniline benzene rings are tilted by 67.7 (1)° relative to each other. An intra­molecular N—H⋯Cl hydrogen bond occurs.

4-Chloro-N-(2,6-dimethylphenyl)-2-methylbenzenesulfonamide

In the title compound, C15H16ClNO2S, the C—SO2—NH—C torsion angle is −61.15 (16)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 38.8 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

4-Chloro-N-(2,5-dimethylphenyl)-2-methylbenzenesulfonamide

The asymmetric unit of the title compound, C15H16ClNO2S, contains three independent moleules. The conformation of the N—H bonds are anti to the ortho-methyl groups of the sulfonyl benzene rings in all the mol­ecules. The sulfonyl and the aniline benzene rings are tilted relative to each other by 43.0 (2), 37.0 (2) and by 46.0 (1)° in the three mol­ecules. In the crystal, inter­molecular N—H⋯O hydrogen bonds link each of the mol­ecules into centrosymmetric dimers.

2,4-Dichloro-N-(3,5-dimethylphenyl)benzenesulfonamide

In the crystal of the title compound, C14H13Cl2NO2S, the N—H bond in the C—SO2—NH—C segment is syn to one of the meta-methyl groups in the aniline benzene ring and anti to the other. Further, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to the S=O bonds. The C—SO2—NH—C torsion angle is 54.9 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds. There are also weak C—H⋯O hydrogen bonds between these dimers.

2,4-Dichloro-N-(2,4-dimethylphenyl)benzenesulfonamide

In the title compound, C14H13Cl2NO2S, the C—SO2—NH—C torsion angle is −71.4 (4)°. The sulfonyl and aniline benzene rings are tilted relative to one another by 44.6 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

2,4-Dichloro-N-(3,4-dimethyl-phen-yl)benzene-sulfonamide.

In the title compound, C14H13Cl2NO2S, the C—SO2—NH—C torsion angle is −60.84 (18). The sulfonyl and the aniline benzene rings are tilted relative to each other by 66.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

2,4-Dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide

In the crystal of the title compound, C14H13Cl2NO2S, the N—H bond in the C—SO2—NH—C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The mol­ecule is bent at the S atom with a C—SO2—NH—C torsion angle of −100.48 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains.

4-Chloro-N-(2,3-dimethylphenyl)-2-methylbenzenesulfonamide

The asymmetric unit of the title compound, C15H16ClNO2S, contains two independent moleules. The conformation of the N—H bonds are anti to the ortho-methyl groups in the sulfonyl benzene rings of both the mol­ecules, while the N—H bonds are anti to the ortho- and meta-methyl groups in the aniline ring of one of the mol­ecules and syn in the other. Furthermore, the torsion angles of the C—SO2—NH—C segments in the two mol­ecules of are −66.8 (3) and 70.3 (3)°. The sulfonyl and the aniline benzene rings are oriented at angles of 44.1 (1) and 39.7 (1)° in the two mol­ecules. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into dimers.

4-Chloro-N-(3-methylphenyl)benzenesulfonamide

In the crystal of the title compound, C13H12ClNO2S, the N—H bond is anti to the meta-methyl group in the aniline ring. The C—SO2—NH—C torsion angle is −57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

N-(2,6-Dichlorophenyl)-4-methylbenzenesulfonamide

In the title compound, C13H11Cl2NO2S, the mol­ecule is bent at the S atom with a C—SO2—NH—C torsion angle of −90.4 (2)°. The sulfonyl benzene and the aniline benzene rings are tilted relative to each other by 51.7 (1)°. In the crystal, mol­ecules are linked by N— H⋯O inter­actions into chains with graph-set notation C(4) along [100].

N-(2,4-Dichlorophenyl)-2,4-dimethylbenzenesulfonamide

In the title compound, C14H13Cl2NO2S, the mol­ecule is bent at the S atom with an C—SO2—NH—C torsion angle of −69.9 (2)°. The dihedral angle between the sulfonyl and aniline benzene rings is 44.0 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O hydrogen bonds. An intra­molecular N—H⋯Cl hydrogen bond is also observed.

N-(2-Chlorophenyl)-2,4-dimethylbenzenesulfonamide

In the title compound, C14H14ClNO2S, the conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. The mol­ecule is bent at the S atom with a C—SO2—NH—C torsion angle of −54.9 (2)°. The sulfonyl and aniline benzene rings are rotated relative to each other by 75.7 (1)°. An intra­molecular N—H⋯Cl hydrogen bond is present. In the crystal, inter­molecular N—H⋯O hydrogen-bonding inter­actions are observed and the mol­ecules are packed into chains parallel to the b axis.