The Dipole Moment of Sulfanilamide and Related Compounds<sup>1,2</sup>

Kumler, W. D.; Halverstadt, I. F.

doi:10.1021/ja01853a044

Cited by 30 publications

(7 citation statements)

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“…Table 11 presents the dipole moments computed in the gas phase and different solvents (H 2 O, DMSO, CH 3 CN, MEOH, CHCl 3 , CCl 4 , C 6 H 12 ) at the different level of theories (HF, B3LYP and MP2) and basis sets using PCM and SMD solvation models. All the calculated dipole moments in the gas phase are larger than the experimental value [31], however, the dipole moment at B3LYP/6-31G(d,p) is close to the experimental value. The difference between experimental dipole moments and those calculated at B3LYP with different basis sets vary from 0.13 to 0.19 Debye, whereas for HF it ranges from 0.29 to the 0.51 Debye.…”

Section: Solvation Free Energy and Dipole Momentsupporting

confidence: 58%

Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Halim

Shaw

Poirier

2010

Journal of Molecular Structure: THEOCHEM

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Section: Solvation Free Energy and Dipole Momentsupporting

confidence: 58%

Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Halim

Shaw

Poirier

2010

Journal of Molecular Structure: THEOCHEM

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“…The melting temperature determined in this work shows great consistency with the literature . However, it is slightly lower than the value reported in ref . The fusion enthalpy measured in this work is a little bigger than that in ref .…”

Section: Results and Discussionsupporting

confidence: 86%

Solubility Determination, Modeling, and Thermodynamic Dissolution Properties of Benzenesulfonamide in 16 Neat Solvents from 273.15 to 324.45 K

Li¹,

Lei³

2019

J. Chem. Eng. Data

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Benzenesulfonamide (BSA) is known as an important chemical material and intermediate in chemical industry. Information concerning solid–liquid equilibrium of BSA in different solvents is essential for the development of its separation and reaction process. In this work, the equilibrium solubility of BSA in 16 neat solvents, namely, methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-pentanol, isopentanol, acetone, ethyl acetate, acetonitrile, cyclohexanone, cyclopentanone, methyl acetate, ethyl formate, and dichloromethane was determined by a static gravimetric method within the temperature range of 273.15–324.45 K under atmospheric pressure. The solubility of BSA increases with the rising temperature in all selected solvents. The obtained solubility was mathematically represented by using the Apelblat model, λh equation, nonrandom two-liquid (NRTL) equation, and the Wilson equation in order to correlate the experimental data with the adjustable parameters. The dissolution properties of BSA, including Gibbs energy (Δdis G), molar enthalpy (Δdis H), and molar entropy (Δdis S) were determined according to the Wilson model and the solubility data. Positive values of the dissolution enthalpy and entropy illustrated that the dissolution processes of BSA in these solvents are endothermic and entropy-driven.

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“…The calculated geometric parameters for both HF and B3LYP methods* are practically the same, with deviations among them that are of the order of 1.7% for bond lengths, 0.66% for bond angles, and 1.21% for the dihedral ones. We studied two selected dihedral angles to corroborate the Kumler–Halverstad 10 and Kumler–Strait 11 proposal that the planarity of the amino group to the benzene ring is related to the bacteriostatic activity of the molecule. For the dihedral angles N4‐C7‐C5‐C6 and N4‐C7‐C8‐C9, a value of 180° is evidence of planarity and our results illustrated that all of the studied molecules present values for dihedral angles that are close to 180°.…”

Section: Resultsmentioning

confidence: 95%

“…From a spectroscopic point of view, Kumler and Halverstad 10 and Kumler and Strait 11 studied sulfonamides and proposed a theory in which the amino group is coplanar to the benzene ring (as a result of the resonance of the amino free electron pair to the ring), proposing the planarity as the fundamental factor for the bacteriostatic activity. Later, Kumler and Daniels 12 hypothesized that another factor in the bacteriostatic activity of SNA‐type compounds is the negative charge of the SO 2 group.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical and structural properties of bacteriostatic sulfonamides: Theoretical study

Soriano-Correa

Esquivel

Sagar

2003

Int J of Quantum Chemistry

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ABSTRACT:A theoretical study at the Hartree-Fock and density functional theory levels is performed on sulfonamide-type bacteriostatic compounds with the aim to provide an insight into their structure-activity relationship. The basicity of the p-amino group is analyzed by means of the proton affinities and the protonation energies, showing that molecules presenting bacteriostatic activity are less basic, i.e., they are characterized by larger protonation energies and smaller proton affinities. The acidity of the amide group is analyzed through the deprotonation energy. The results reveal that the more acidic molecules present a larger bacteriostatic activity. This result is also confirmed from a study of bond orders. A bond order analysis of the amide group suggests that the electron attracting group in these molecules is responsible for the increase in acidity. The charge of the SO 2 group is also shown to be affected by the presence of the electron attracting group and consequently related to the acidity of the molecules. A geometric analysis shows that structures in which the amino group is more coplanar with respect to the benzenic ring possess larger bacteriostatic activity. A conformational analysis of these molecules illustrates that active molecules have relatively larger torsion energy barriers.

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The Dipole Moment of Sulfanilamide and Related Compounds^1,2

Cited by 30 publications

References 0 publications

Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Solubility Determination, Modeling, and Thermodynamic Dissolution Properties of Benzenesulfonamide in 16 Neat Solvents from 273.15 to 324.45 K

Physicochemical and structural properties of bacteriostatic sulfonamides: Theoretical study

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The Dipole Moment of Sulfanilamide and Related Compounds1,2

Cited by 30 publications

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Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Medium effect on the equilibrium geometries, vibrational frequencies and solvation energies of sulfanilamide

Solubility Determination, Modeling, and Thermodynamic Dissolution Properties of Benzenesulfonamide in 16 Neat Solvents from 273.15 to 324.45 K

Physicochemical and structural properties of bacteriostatic sulfonamides: Theoretical study

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The Dipole Moment of Sulfanilamide and Related Compounds^1,2