Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Aguilar-Castro, Liliana; Tlahuextl, Margarita; Mendoza-Huízar, Luis Humberto; Tapia-Benavides, Antonio R.; Tlahuext, Hugo

doi:10.3998/ark.5550190.0009.517

Cited by 5 publications

(6 citation statements)

References 26 publications

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“…Furthermore, it is of interest to compare the NBO energies of intramolecular hydrogen bonding and hydrogen-bonding-like interactions (we classify this way LP(O) → σ*(C–H) interactions) in our compounds with NBO energies of intramolecular hydrogen bonding for several amides considered by Aguilar-Castro et al In this work, the calculated NBO energies of intramolecular hydrogen bonding are generally within ca. 1–3 kcal/mol, and only two energies are larger, 20.02 and 9.47 kcal/mol.…”

Section: Resultsmentioning

confidence: 90%

Polymorphs of Substituted p-Toluenesulfonanilide: Synthesis, Single-Crystal Analysis, Hirshfeld Surface Exploration, and Theoretical Investigation

Riaz,

Ali,

Ashfaq

et al. 2023

ACS Omega

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Polymorphism is an exciting feature of chemical systems where a compound can exist in different crystal forms. The present investigation is focused on the two polymorphic forms, triclinic (MSBT) and monoclinic (MSBM), of ethyl 3-iodo-4-((4methylphenyl)sulfonamido)benzoate prepared from ethyl 4-amino-3-iodobenzoate. The prepared polymorphs were unambiguously confirmed by single-crystal X-ray diffraction (SC-XRD) analysis. According to the SC-XRD results, the molecular configurations of both structures are stabilized by intramolecular N−H•••I and C−H••• O bonding. The crystal packing of MSBT is different as compared to the crystal packing of MSBM because MSBT is crystallized in the triclinic crystal system with the space group P1̅ , whereas MSBM is crystallized in the monoclinic crystal system with the space group P2 1 /c. The molecules of MSBT are interlinked in the form of dimers through N−H•••O bonding to form R 2 2 (8) loops, while the MSBM molecules are connected with each other in the form of an infinite chain through C−H•••O bonding. The crystal packing of both compounds is further stabilized by off-set π•••π stacking interactions between phenyl rings, which is found stronger in MSBM as compared to in MSBT. Moreover, Hirshfeld surface exploration of the polymorphs was carried out, and the results were compared with the closely related literature structure. Accordingly, the supramolecular assembly of these polymorphs is mainly stabilized by noncovalent interactions or intermolecular interactions. Furthermore, a density functional theory (DFT) study was also carried out, which provided good support for the SC-XRD and Hirshfeld studies, suggesting the formation of both intramolecular and intermolecular interactions for both compounds.

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Section: Resultsmentioning

confidence: 90%

Polymorphs of Substituted p-Toluenesulfonanilide: Synthesis, Single-Crystal Analysis, Hirshfeld Surface Exploration, and Theoretical Investigation

Riaz,

Ali,

Ashfaq

et al. 2023

ACS Omega

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“…the hyperconjugative interaction in benzenesulfonylamine acetamide amounts up to ca. 9.5 kcal/mol, determining its conformational behavior [26]. Similarly, l O p → σ * orbital interactions are key aspects in the conformational preferences of acyl thiourea compounds [27].…”

Section: Resultsmentioning

confidence: 99%

Computational Investigations, Hirshfeld Surface Analysis, Interaction Energy Calculations, and Energy Framework Crystal Structure of Methyl 2-Amino-5-Hydroxybenzoate

et al. 2021

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The title compound with the molecular formula C 8 H 9 NO 3 is synthesized by refluxing 2-amino-5hydroxybenzoic acid in methanol. The molecular structure of the compound is determined by single crystal X-ray diffraction. Methyl 2-amino-5-hydroxybenzoate crystallizes in the orthorhombic space group P2 1 2 1 2 1 with a = 4.973(2) Å, b = 10.923(5) Å, c = 14.074(6) Å, Z = 4 and V = 764.4(6) Å 3 . DFT is used to compute HOMO-LUMO energy levels, to predict the reactivity of substituents (NH 2 and OH), and to determine the nucleophilic character of these two groups. The orientation and nature of substituents on benzene favors the formation of a stable six-membered ring via hydrogen bonding which plays a key role in the properties of the investigated compound. The natural bond orbital (NBO) population analysis demonstrates that the hyperconjugative effect between the donor lone pairs located on the carbonyl oxygen atom and the N-H group, via the lp O → σ*(N-H) 1,6-remote interaction, is responsible for the preferred conformation. The molecular electrostatic potential (MEP) surface shows the electrical neutrality in the molecule. To get an insight to the intermolecular interactions in the crystal a Hirshfeld surface analysis is also carried out.

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“…For comparison, similar lpO → σ*(N-H) interaction in acetamide derivatives, namely benzenesulfonylamin amount up to ca. 9.5 kcal/mol [39].…”

Section: Natural Bond Analysis (Nbo)mentioning

confidence: 99%

A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

et al. 2022

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Hybrid moieties of ethynylated-thiourea, Th1 and Th2 have been synthesised via the addition reaction between ethynyl derivatives and 4-tert-butylbenzoyl isothiocyanate in acetone, and were characterised by selected spectroscopic methods (i.e., 1 H and 13 C NMR, UV-visible, FT-IR) and elemental analysis. Thermogravimetric analysis indicated that Th1 and Th2 were relatively stable up to ca. 210 °C. Single-crystal X-ray diffraction was used to identify the crystal structure of Th2 in which the centre of 1-acyl thiourea moiety (-C(O)NHC(S)NH) exhibits S conformation. The Hirshfeld surface analysis has allowed visualizing the crystal packing, which is characterised by the prolonged intermolecular N-H⋯O = C and N-H⋯S = C hydrogen-bonding interactions within Th2 molecule. Electrochemical data of both compounds correspondingly exhibit irreversible redox potential processes. Besides, frontier molecular orbitals and Natural Bond Orbital population analysis were computed at the B3LYP/6-31G (d, p) level of approximation, suggesting strong delocalization of the electronic density through a conjugated π-system involving the ethynyl-phenyl and thiourea groups.

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Hydrogen bond studies in substituted N-(2-hydroxyphenyl)-2-[(4-methylbenzenesulfonyl)amino]acetamides

Cited by 5 publications

References 26 publications

Polymorphs of Substituted p-Toluenesulfonanilide: Synthesis, Single-Crystal Analysis, Hirshfeld Surface Exploration, and Theoretical Investigation

Polymorphs of Substituted p-Toluenesulfonanilide: Synthesis, Single-Crystal Analysis, Hirshfeld Surface Exploration, and Theoretical Investigation

Computational Investigations, Hirshfeld Surface Analysis, Interaction Energy Calculations, and Energy Framework Crystal Structure of Methyl 2-Amino-5-Hydroxybenzoate

A Dual Approach on Experimental, Theoretical Insight of Structural Elucidation, Hirshfeld Surface Analysis, Optical and Electrochemical Properties of Acyl Thiourea-Ethynyl Hybrid Derivatives

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