Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory
This study presents a comprehensive exploration of the structure–reactivity relationship of (<i>E</i>)-3-bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy)furan-2(5H)-one. The study embarked on an in-depth investigation i...
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MDPI AG
2023-08-01
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| Series: | Crystals |
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| author | Ahmed H. Bakheit Mohamed W. Attwa Adnan A. Kadi Hamad M. Alkahtani |
| author_facet | Ahmed H. Bakheit Mohamed W. Attwa Adnan A. Kadi Hamad M. Alkahtani |
| author_sort | Ahmed H. Bakheit |
| collection | DOAJ |
| description | This study presents a comprehensive exploration of the structure–reactivity relationship of (<i>E</i>)-3-bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy)furan-2(5H)-one. The study embarked on an in-depth investigation into the solid-state crystal structure of this organic compound, employing computational Density Functional Theory (DFT) and related methodologies, which have not extensively been used in the examination of such compounds. A single-crystal X-ray diffraction (SCXRD) analysis was initially performed, supplemented by a Hirshfeld surfaces analysis. This latter approach was instrumental in visualizing and quantifying intermolecular interactions within the crystal structures, offering a detailed representation of the molecule’s shape and properties within its crystalline environment. The concept of energy framework calculations was utilized to understand the varied types of energies contributing to the supramolecular architecture of the molecules within the crystal. The Conceptual DFT (CDFT) was applied to predict global reactivity descriptors and local nucleophilic/electrophilic Parr functions, providing a deeper understanding of the compound’s chemical reactivity properties. The aromatic character and π–π stacking ability were also evaluated with the help of LOLIPOP and ring aromaticity measures. This comprehensive approach not only provides a detailed description of the structure and properties of the investigated compound but also offers valuable insights into the design and development of new materials involving 1,2,4-triazole systems. |
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| language | English |
| last_indexed | 2024-03-10T22:54:22Z |
| publishDate | 2023-08-01 |
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| spelling | doaj.art-96df7b1a4730419e8174c10a2ddde1f92023-11-19T10:08:59ZengMDPI AGCrystals2073-43522023-08-01139131310.3390/cryst13091313Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional TheoryAhmed H. Bakheit0Mohamed W. Attwa1Adnan A. Kadi2Hamad M. Alkahtani3Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi ArabiaThis study presents a comprehensive exploration of the structure–reactivity relationship of (<i>E</i>)-3-bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy)furan-2(5H)-one. The study embarked on an in-depth investigation into the solid-state crystal structure of this organic compound, employing computational Density Functional Theory (DFT) and related methodologies, which have not extensively been used in the examination of such compounds. A single-crystal X-ray diffraction (SCXRD) analysis was initially performed, supplemented by a Hirshfeld surfaces analysis. This latter approach was instrumental in visualizing and quantifying intermolecular interactions within the crystal structures, offering a detailed representation of the molecule’s shape and properties within its crystalline environment. The concept of energy framework calculations was utilized to understand the varied types of energies contributing to the supramolecular architecture of the molecules within the crystal. The Conceptual DFT (CDFT) was applied to predict global reactivity descriptors and local nucleophilic/electrophilic Parr functions, providing a deeper understanding of the compound’s chemical reactivity properties. The aromatic character and π–π stacking ability were also evaluated with the help of LOLIPOP and ring aromaticity measures. This comprehensive approach not only provides a detailed description of the structure and properties of the investigated compound but also offers valuable insights into the design and development of new materials involving 1,2,4-triazole systems.https://www.mdpi.com/2073-4352/13/9/13131,2,4-triazole derivativesdensity functional theory (DFT)Hirshfeld surface analysisglobal reactivity descriptorslocal Parr functionsaromatic character |
| spellingShingle | Ahmed H. Bakheit Mohamed W. Attwa Adnan A. Kadi Hamad M. Alkahtani Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory Crystals 1,2,4-triazole derivatives density functional theory (DFT) Hirshfeld surface analysis global reactivity descriptors local Parr functions aromatic character |
| title | Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory |
| title_full | Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory |
| title_fullStr | Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory |
| title_full_unstemmed | Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory |
| title_short | Structural Analysis and Reactivity Insights of (<i>E</i>)-Bromo-4-((4-((1-(4-chlorophenyl)ethylidene)amino)-5-phenyl-4H-1,2,4-triazol-3-yl)thio)-5-((2-isopropylcyclohexyl)oxy) Furan-2(5H)-one: A Combined Approach Using Single-Crystal X-ray Diffraction, Hirshfeld Surface Analysis, and Conceptual Density Functional Theory |
| title_sort | structural analysis and reactivity insights of i e i bromo 4 4 1 4 chlorophenyl ethylidene amino 5 phenyl 4h 1 2 4 triazol 3 yl thio 5 2 isopropylcyclohexyl oxy furan 2 5h one a combined approach using single crystal x ray diffraction hirshfeld surface analysis and conceptual density functional theory |
| topic | 1,2,4-triazole derivatives density functional theory (DFT) Hirshfeld surface analysis global reactivity descriptors local Parr functions aromatic character |
| url | https://www.mdpi.com/2073-4352/13/9/1313 |
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