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Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione
dc.creator | Lazić, Anita | |
dc.creator | Radovanović, Lidija | |
dc.creator | Rogan, Jelena | |
dc.creator | Valentić, Nataša | |
dc.creator | Đorđević, Ivana | |
dc.creator | Trišović, Nemanja | |
dc.date.accessioned | 2024-04-19T12:28:25Z | |
dc.date.available | 2024-04-19T12:28:25Z | |
dc.date.issued | 2024-08 | |
dc.identifier.issn | 0022-2860 | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7435 | |
dc.description.abstract | Providing structural information on drug-like compounds is a significant step in efforts to develop innovative drugs with balanced solubility, cell permeability and target binding. In this paper, a new cyclohexane-5-spirohydantoin tethered with a 4‑tert-butylbenzoyl group was synthesized and its crystal structure was determined using the single crystal X-ray diffraction. The Hirshfeld surface analysis was used to gain a preliminary insight into the proportion and nature of the intermolecular interactions in the crystal structure, while their quantitative description is further presented in terms of a systematic analysis of dimeric motifs representing different recognition modes. A combination of N–H∙∙∙O and C(sp3)–H∙∙∙O hydrogen bonds, C(sp3)–H∙∙∙π, lone-pair∙∙∙π and π∙∙∙π stacking interactions links the molecules into a bilayer having two carbonyl O atoms exposed to the exterior. Further stacking of the bilayers occurs through C(sp3)–H∙∙∙O hydrogen bonds involving these O atoms as acceptors, C(sp3)–H∙∙∙π and π∙∙∙π stacking interactions between the phenyl groups. The molecular electrostatic potential surface map reveals that the carbonyl O atoms of the hydantoin ring and the phenyl ring are electrophilic centers, while the N1–H1 group is a nucleophilic center. The calculated HOMO and LUMO energies were used to semiquantitatively estimate the global reactivity descriptors suggesting the soft nature of the molecule. | |
dc.publisher | Elsevier B.V. | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200135/RS// | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200287/RS// | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS// | en |
dc.rights | restrictedAccess | |
dc.source | Journal of Molecular Structure | en |
dc.subject | Crystal structure | |
dc.subject | Global reactivity descriptors | |
dc.subject | Intermolecular interactions | |
dc.subject | Quantum chemical calculations | |
dc.subject | Spirohydantoin | |
dc.title | Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione | en |
dc.type | article | en |
dc.rights.license | ARR | en |
dc.citation.spage | 138234 | |
dc.citation.volume | 1310 | |
dc.identifier.doi | 10.1016/j.molstruc.2024.138234 | |
dc.identifier.scopus | 2-s2.0-85190070291 | |
dc.type.version | publishedVersion |