Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione
Само за регистроване кориснике
2024
Аутори
Lazić, AnitaRadovanović, Lidija
Rogan, Jelena
Valentić, Nataša
Đorđević, Ivana
Trišović, Nemanja
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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 acc...eptors, 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.
Кључне речи:
Crystal structure / Global reactivity descriptors / Intermolecular interactions / Quantum chemical calculations / SpirohydantoinИзвор:
Journal of Molecular Structure, 08-2024, 1310, 138234-Издавач:
- Elsevier B.V.
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200135 (Универзитет у Београду, Технолошко-металуршки факултет) (RS-MESTD-inst-2020-200135)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200287 (Иновациони центар Технолошко-металуршког факултета у Београду доо) (RS-MESTD-inst-2020-200287)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
Колекције
Институција/група
Inovacioni centarTY - JOUR AU - Lazić, Anita AU - Radovanović, Lidija AU - Rogan, Jelena AU - Valentić, Nataša AU - Đorđević, Ivana AU - Trišović, Nemanja PY - 2024-08 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/7435 AB - 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. PB - Elsevier B.V. T2 - Journal of Molecular Structure T1 - Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione SP - 138234 VL - 1310 DO - 10.1016/j.molstruc.2024.138234 ER -
@article{ author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Valentić, Nataša and Đorđević, Ivana and Trišović, Nemanja", year = "2024-08", 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.", publisher = "Elsevier B.V.", journal = "Journal of Molecular Structure", title = "Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione", pages = "138234", volume = "1310", doi = "10.1016/j.molstruc.2024.138234" }
Lazić, A., Radovanović, L., Rogan, J., Valentić, N., Đorđević, I.,& Trišović, N.. (2024-08). Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione. in Journal of Molecular Structure Elsevier B.V.., 1310, 138234. https://doi.org/10.1016/j.molstruc.2024.138234
Lazić A, Radovanović L, Rogan J, Valentić N, Đorđević I, Trišović N. Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione. in Journal of Molecular Structure. 2024;1310:138234. doi:10.1016/j.molstruc.2024.138234 .
Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Valentić, Nataša, Đorđević, Ivana, Trišović, Nemanja, "Crystallographic and theoretical analysis of a spirohydantoin derivative: 3-(4‑tert-butylbenzoyl)-1,3-diazaspiro[4.5]decane-2,4‑dione" in Journal of Molecular Structure, 1310 (2024-08):138234, https://doi.org/10.1016/j.molstruc.2024.138234 . .