Molecular Structure and Conformations of <i>para</i>-Methylbenzene Sulfonamide and <i>ortho</i>-Methylbenzene Sulfonamide:  Gas Electron Diffraction and Quantum Chemical Calculations Study

Petrov, V. M.; Girichev, G. V.; Oberhammer, Heinz; Петрова, В. Н.; Giricheva, N. I.; Bardina, and Anna V.; Иванов, С. Н.

doi:10.1021/jp710532z

Cited by 24 publications

(29 citation statements)

References 13 publications

(22 reference statements)

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“…Importantly, if we consider the position of the sulphur bound oxygen atoms with respect to the piperazine nitrogen substituents, family I and IV present the anti and the fully eclipsed conformations, respectively ( Figure 3B). Thus, in agreement with previously reported results on benzosulfonamide derivatives [35][36][37] the two most favoured families of conformers are I and IV, with family I (i.e., anti conformation of the oxygen atoms with respect to the piperazine nitrogen substituents) representing the GM family, as found in the crystal structure of N,N-dimethyltoluene-p-sulfonamide [38].…”

Section: Computational Studies and Sar Analysissupporting

confidence: 92%

“…This is particularly important for sulphonamide derivatives which present electron withdrawing substituent on the sulphur atom, since it has been previously demonstrated that, in this case, the different conformers can be considered as rather rigid molecules due to a high barrier of internal rotation around the S-N bond [35], and that this effect is enhanced in the presence of an ortho-substituted phenyl ring with respect to unsubstituted or para-substituted ones [37].…”

Section: Computational Studies and Sar Analysismentioning

confidence: 99%

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Synthesis, Anticancer Activity and Computational SAR Analysis of Acylsulfonylpiperazines Derivatives

Benfodda¹,

Fritz²,

Henriquet³

et al. 2017

Med chem

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A series of 1-acyl-4-sulfonylpiperazine derivatives has been prepared. The antiproliferative effect of these compounds was evaluated in vitro against human prostate cancer cell line C4-2, several among them exhibited interesting growth inhibitory against this particular cell line. Finally, a molecular modeling study was employed to analyze the structure/activity relationships (SAR) of these novel compounds..

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Section: Computational Studies and Sar Analysissupporting

confidence: 92%

Section: Computational Studies and Sar Analysismentioning

confidence: 99%

Synthesis, Anticancer Activity and Computational SAR Analysis of Acylsulfonylpiperazines Derivatives

Benfodda¹,

Fritz²,

Henriquet³

et al. 2017

Med chem

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“…According to this study, the saturated vapor over solid benzene sulfonamide at a temperature of 150(5) C consists predominantly of a conformer with the SAN bond perpendicular to the benzene ring and the NH 2 group eclipsing the SO 2 entity. Calculations also show that the sterically unfavorable orientation of the NH 2 group is stabilized by intramolecular hydrogen bonds between O and H atoms of the sulfonamide group [49].…”

Section: Introductionmentioning

confidence: 95%

Theoretical studies of some sulphonamides as corrosion inhibitors for mild steel in acidic medium

Ebenso

Arslan

Kandemi̇rlı

et al. 2010

Int J of Quantum Chemistry

148

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Density functional theory (DFT) at the B3LYP/6-31G (d,p) and BP86/ CEP-31G* basis set levels and ab initio calculations using the RHF/6-31G (d,p) methods were performed on four sulfonamides (namely sulfaacetamide (SAM), sulfapyridine (SPY), sulfamerazine (SMR), and sulfathiazole (STI)) used as corrosion inhibitors for mild steel in acidic medium to determine the relationship between molecular structure and their inhibition efficiencies (%IE). The order of inhibition efficiency obtained was SMR > SPY > STI > SAM which corresponded with the order of most of the calculated quantum chemical parameters namely E HOMO (highest occupied molecular orbital energy), E LUMO (lowest unoccupied molecular orbital energy), the energy gap (DE), the Mulliken charges on the C, O, N, S atoms, hardness (g), softness (S), polarizability (a), dipole moment (l), total energy change (DE T ), electrophilicity (x), electron affinity (A), ionization potential (I), the absolute electronegativity (v), and the fraction of electrons transferred (DN). Quantitative structure activity relationship (QSAR) approach has been used and a correlation of the composite index of some of the quantum chemical parameters was performed to characterize the inhibition performance of the sulfonamides studied. The results showed that the %IE of the sulfonamides was closely related to some of the quantum chemical parameters but with varying degrees/order. The calculated %IE of the sulfonamides studied was found to be close to their experimental corrosion inhibition efficiencies. The experimental data obtained fits the Langmuir adsorption isotherm. The negative sign of the E HOMO values and other thermodynamic parameters obtained indicates that the data obtained supports physical adsorption mechanism.

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“…The crystal structures of BSA [4], ortho-MBSA (or 2-MBSA) [5], and para-MBSA (or 4-MBSA) [6] were studied by X-ray diffraction (XRD). Earlier, we reported the results of gas-phase electron diffraction (GED) study on the molecular structures of free molecules mentioned above [7,8].…”

Section: Introductionmentioning

confidence: 99%

“…BSA [7] and 4-MBSA [8] have two conformers each: the S-N bond is oriented orthogonally with respect to the benzene ring while the N-H and S=O bonds of the SO 2 NH 2 groups either eclipse each other (eclipsed conformers) or are in staggered positions (staggered conformers). Unfortunately, the GED method did not allow to reliably determine a quantitative ratio between the conformers in case of 4-MBSA because of low scattering power of the hydrogen atom in the NH 2 group.…”

Section: Introductionmentioning

confidence: 99%

Conformational properties of ortho-nitrobenzenesulfonamide in gas and crystalline phases. Intra- and intermolecular hydrogen bond

et al. 2011

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A combined gas-phase electron diffraction and quantum chemical (B3LYP/6-311?G**, B3LYP/cc-pvtz, MP2/ cc-pvtz) study of molecular structure of 2-nitrobenzenesulfonamide (2-NBSA) was carried out. Quantum chemical calculations showed that 2-NBSA has four conformers, two of which are stabilized by intramolecular hydrogen bond. The latter (with the S-N bond in a close to orthogonal position around the phenyl ring and differing from each other by staggered or eclipsed positions of the N-H and S=O bonds in the SO 2 NH 2 group) presented in a saturated vapor over 2-NBSA at T = 433 (3) K in commensurable amounts. Experimental internuclear distances (Ǻ ) for the staggered conformer are (Å ): r h1 (C-H) av. = 1.071(9), r h1 (C-C) av. = 1.390(4), r h1 (C-S) = 1.789(8), r h1 (S=O) av. = 1.427(6), r h1 (S-N) = 1.644(6), r h1 (N-O) av. = 1.221(4), r h1 (C 0 -N) = 1.487(8), r h1 (N-H) av. = 1.014. Calculations at B3LYP/ccpvtz level were performed to determine the structure and the energies of the transition states between conformers. It was shown that the conformer structures of free molecule differ from those of a molecule stabilized by intermolecular hydrogen bonds in a crystal. Influence of a substituent X (X = -CH 3 , -NO 2 ) on conformational features of the orthosubstituted benzenesulfonamide was established.

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Molecular Structure and Conformations of para-Methylbenzene Sulfonamide and ortho-Methylbenzene Sulfonamide: Gas Electron Diffraction and Quantum Chemical Calculations Study

Cited by 24 publications

References 13 publications

Synthesis, Anticancer Activity and Computational SAR Analysis of Acylsulfonylpiperazines Derivatives

Synthesis, Anticancer Activity and Computational SAR Analysis of Acylsulfonylpiperazines Derivatives

Theoretical studies of some sulphonamides as corrosion inhibitors for mild steel in acidic medium

Conformational properties of ortho-nitrobenzenesulfonamide in gas and crystalline phases. Intra- and intermolecular hydrogen bond

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