Synthesis, structural exploration, Hirshfeld surface analysis and computational study of two novel organosulfur compounds derived from mercaptoacetic acid

Basit Öğe Kaydı
dc.contributor.authorOsmanova, Sabiya
dc.contributor.authorAshfaq, Muhammad
dc.contributor.authorKareem, Rebaz Obaid
dc.contributor.authorTahir, Muhammad Nawaz
dc.contributor.authorAzeez, Yousif Hussein
dc.contributor.authorOmer, Rebaz Anwar
dc.contributor.authorSahin, Onur
dc.date.accessioned2026-04-25T14:19:58Z
dc.date.available2026-04-25T14:19:58Z
dc.date.issued2026
dc.departmentSinop Üniversitesi
dc.description.abstractThe reaction of 2-aminopyridine with mercaptoacetic acid was carried out in a benzene solution at a molar ratio of the initial components of 1:1. The thiylated reaction of p-bromoacetophenone with mercaptoacetic acid was carried out in a benzene solution, with a molar ratio of the initial components of 1:4. As a result, new compounds were obtained: 2-aminopyridin-1-ium-2,2 '-disulfanediyldiacetate (ASA) and 1,1-bis-(carboxymethylthio)-1-p-bromophenylethane (BSA). The structure of the newly synthesized compounds was confirmed by using single crystal XRD technique. The structure of ASA is a salt in which there exist two cations and one dianion in the asymmetric unit. The cations and dianions are interlinked by N-H & sdot;& sdot;& sdot;O and C-H & sdot;& sdot;& sdot;O bonding and further stabilization of the crystal packing is due to weak pi & sdot;& sdot;& sdot;pi and C-O & sdot;& sdot;& sdot;pi interactions. In second compound BSA, molecules are interlinked in the form of dimers through O-H & sdot;& sdot;& sdot;O bonding to complete two R22(8) loops and consecutive dimers are connected by C-H & sdot;& sdot;& sdot;Br bonding. Hirshfeld surface analysis is carried out for the exploration of the molecular interactions in terms of interatomic contacts. The theoretical investigation of two related organic compounds, ASA and BSA, using density functional theory (DFT) and related computational tools to evaluate their structural, electronic, and intermolecular interaction properties. Optimized geometries, frontier molecular orbitals (HOMO-LUMO), electrostatic potential (ESP) maps, and dipole moments were obtained using the B3LYP/6-311+G(d,p) level of theory. The analysis of electron localization function (ELF), reduced density gradient (RDG), and topological parameters (via QTAIM) provided insights into electron density distribution, hydrogen bonding, and interaction strengths within the molecules. Hirshfeld surface analysis was performed using Crystal Explorer to explore intermolecular interactions and visualize contact contributions in the crystal state. The findings suggest that ASA, with its higher dipole moment, lower energy gap, and stronger electrophilic nature, exhibits superior potential as a corrosion inhibitor compared to BSA.
dc.identifier.doi10.1016/j.molstruc.2025.144775
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.orcid0000-0002-3774-6071
dc.identifier.orcid0000-0001-6273-1309
dc.identifier.orcid0000-0003-3765-3235
dc.identifier.orcid0000-0002-6815-9806
dc.identifier.orcid0000-0001-9857-9505
dc.identifier.orcid0000-0001-6663-8777
dc.identifier.orcid0000-0003-4438-4117
dc.identifier.scopus2-s2.0-105022311896
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2025.144775
dc.identifier.urihttps://hdl.handle.net/11486/8295
dc.identifier.volume1353
dc.identifier.wosWOS:001628855200004
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260420
dc.subjectMercaptoacetic acid
dc.subjectP-bromoacetophenone
dc.subject2-aminopyridine
dc.subjectCrystal structure
dc.subjectHirshfeld surface analysis
dc.subjectDFT
dc.titleSynthesis, structural exploration, Hirshfeld surface analysis and computational study of two novel organosulfur compounds derived from mercaptoacetic acid
dc.typeArticle

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu