Charles Christopher Kanakam

Synthesis, structural, spectroscopic studies, NBO analysis, NLO and HOMO–LUMO of 4-methyl-N-(3-nitrophenyl)benzene sulfonamide with experimental and theoretical approaches

The sulfonamide compound, 4-methyl-N-(3-nitrophenyl)benzene sulfonamide (abbreviated as 4M3NPBS) has been synthesized and characterized by FTIR, FT-Raman NMR, single crystal X-ray diffraction and thermal analysis. Density functional (DFT) calculations have been carried out for the title compound by performing DFT level of theory using B3LYP/6-31G(d,p) basis set. The calculated results show that the predicted geometry can well reproduce the structural parameters. Predicted vibrational frequencies have been assigned and compared with the experimental IR spectra and they support each other. The UV-Vis spectrum of the compound was recorded. The theoretical electronic absorption spectra have been calculated by using CIS, TD-DFT, ZINDO methods. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. The first order hyperpolarizability (β0) of 4M3NPBS was calculated using B3LYP/6-31G(d,p) method on the basis of finite-field approach. In addition, frontier molecular orbitals and molecular electrostatic potential were carried out by using density functional theory (DFT/B3LYP) 6-31G(d,p) basis set. The calculated HOMO and LUMO energies show that charge transfer occur in the molecule. The thermal stability of the title compound was determined with the aid of thermo gravimetric analysis (TGA) and differential thermal analysis (DTA).

Synthesis, X-ray structural, characterization, NBO and HOMO-LUMO analysis using DFT study of 4-methyl-N-(naphthalene-1-yl)benzene sulfonamide.

The sulfonamide compound, 4-methyl-N-(naphthalene-1-yl)benzene sulfonamide (abbreviated as 4MNBS) was synthesized from the reaction of 4-methyl benzene sulfonyl chloride with 1-naphthyl amine. The 4MNBS was characterized by FTIR, (1)H NMR, (13)C NMR, single crystal X-ray diffraction (XRD) and thermal analysis. By using the Density Functional Theory (DFT) method with 6-31G(d,p) basis set, the molecular geometry and vibrational frequencies were calculated and compared with the experimental data. The title compound crystallizes in the triclinic system of space group p-1 with a=10.3873(7)Å, b=10.4090(7)Å, c=15.7084(10)Å; α=75.735(3)°; ß=70.737(3)°; γ=68.120(3)° and z=4. Stability of the molecule arising from hyper conjugative interactions, charge delocalization has been analyzed using natural bond orbital (NBO) analysis. In addition, atomic charges, frontier molecular orbitals and molecular electrostatic potential were computed by using Density Functional Theory (DFT/B3LYP) 6-31G(d,p) basis set. The calculated HOMO and LUMO energies show that charge transfer occurs in the molecule.

2,4-Dinitro-1-naphthyl 4-toluene­sulfonate

In the title compound, C17H12N2O7S, the dihedral angle between the benzene ring and the naphthyl plane is 26.34 (6)°. The nitro groups make dihedral angles of 40.09 (4) and 37.05 (3)° with the naphthyl plane. In the crystal structure, weak intra- and intermolecular C—H⋯O interactions are observed.

2-Meth-oxy-4-methyl-phenyl 4-toluene-sulfonate.

In the title molecule, C15H16O4S, the interplanar angle between the two aromatic rings is 45.07 (7)°. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

3-Benzyl­idene-6-methoxy­chroman-4-one

In the title compound, C17H14O3, the dihedral angle between the phenyl ring and the benzene ring of the chromanone moiety is 67.78 (3)°. The six-membered heterocyclic ring of the chromanone moiety adopts a half-chair conformation. The structure is stabilized by weak intermolecular C—H⋯O interactions that link the molecules into inversion dimers.

6-Formyl-2-meth-oxy-3-nitro-phenyl 4-toluene-sulfonate.

In the title compound, C15H13NO7S, the interplanar angle between the two aromatic rings is 26.04 (3)°. The crystal structure is stabilized by C—H⋯O interactions.

2-(5,7-Dimeth-oxy-4-oxo-4H-chromen-2-yl)phenyl 4-toluene-sulfonate.

In the crystal structure of the title compound, C24H20O7S, the chromone system makes a dihedral angle of 37.32 (7)° with the adjacent benzene ring. The chromone ring system and the tolyl ring are almost parallel, with a dihedral angle of 4.56 (9)°. The tolyl ring is twisted at an angle of 41.75 (6)° with respect to the benzene ring. Weak intra- and intermolecular C—H⋯O interactions are observed.

8-Meth-oxy-3-(4-methyl-benzyl-idene)-6-(prop-1-en-yl)chroman-4-one.

In the title compound, C21H20O3, the tolyl ring makes a dihedral angle of 31.11 (6)° with the benzene ring of the chromanone unit. The pyrone ring adopts a half-chair conformation. The molecular structure is stabilized by a weak intramolecular C—H⋯O interaction and the crystal packing is stabilized by weak intermolecular C—H⋯O interactions and a C—H⋯π interaction.