The role of π–π, C–H⋯halogen, and halogen⋯π interactions in the crystal packing of 9-aminoacridinium 3-halobenzoate salts: an experimental and theoretical investigation.
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| Title: | The role of π–π, C–H⋯halogen, and halogen⋯π interactions in the crystal packing of 9-aminoacridinium 3-halobenzoate salts: an experimental and theoretical investigation. |
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| Authors: | Nowak, Patryk1 (AUTHOR), Sikorski, Artur1 (AUTHOR), Mirocki, Artur1 (AUTHOR) artur.mirocki@ug.edu.pl |
| Source: | Structural Chemistry. Jun2026, Vol. 37 Issue 3, p1191-1202. 12p. |
| Subjects: | Intermolecular interactions, Stacking interactions, Molecular self-assembly, Computational chemistry |
| Abstract: | The crystal structures of 9-aminoacridinium 3-halobenzoate salts (X = Cl, Br, I) were compared in terms of molecular packing and intermolecular interactions. All three compounds crystallize in the monoclinic P2₁/c space group, are isomorphous, and exhibit a high degree of structural similarity with closely related packing motifs. Analysis of geometric parameters confirms proton transfer from the carboxylic group of the acid to the endocyclic nitrogen atom of 9-aminoacridine, consistent with ΔpKa predictions indicating salt formation. Analysis of intermolecular interactions shows that the crystal packing is stabilized by a network of N–H⋯O and C–H⋯O hydrogen bonds, as well as π–π stacking, C–H⋯halogen, and halogen⋯π interactions. Geometric analysis of the halogen⋯π contacts indicates that these interactions can be classified as weak n–π* interactions. Energy framework calculations demonstrate that the energetic stability of the crystals increases with halogen size (I > Br > Cl), in agreement with the observed melting points, and highlight the dominant role of dispersion forces in stabilizing the supramolecular architecture across all three structures. [ABSTRACT FROM AUTHOR] |
| Copyright of Structural Chemistry is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 193807158 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: The role of π–π, C–H⋯halogen, and halogen⋯π interactions in the crystal packing of 9-aminoacridinium 3-halobenzoate salts: an experimental and theoretical investigation. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Nowak%2C+Patryk%22">Nowak, Patryk</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Sikorski%2C+Artur%22">Sikorski, Artur</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Mirocki%2C+Artur%22">Mirocki, Artur</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> artur.mirocki@ug.edu.pl</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Structural+Chemistry%22">Structural Chemistry</searchLink>. Jun2026, Vol. 37 Issue 3, p1191-1202. 12p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Intermolecular+interactions%22">Intermolecular interactions</searchLink><br /><searchLink fieldCode="DE" term="%22Stacking+interactions%22">Stacking interactions</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+self-assembly%22">Molecular self-assembly</searchLink><br /><searchLink fieldCode="DE" term="%22Computational+chemistry%22">Computational chemistry</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The crystal structures of 9-aminoacridinium 3-halobenzoate salts (X = Cl, Br, I) were compared in terms of molecular packing and intermolecular interactions. All three compounds crystallize in the monoclinic P2₁/c space group, are isomorphous, and exhibit a high degree of structural similarity with closely related packing motifs. Analysis of geometric parameters confirms proton transfer from the carboxylic group of the acid to the endocyclic nitrogen atom of 9-aminoacridine, consistent with ΔpKa predictions indicating salt formation. Analysis of intermolecular interactions shows that the crystal packing is stabilized by a network of N–H⋯O and C–H⋯O hydrogen bonds, as well as π–π stacking, C–H⋯halogen, and halogen⋯π interactions. Geometric analysis of the halogen⋯π contacts indicates that these interactions can be classified as weak n–π* interactions. Energy framework calculations demonstrate that the energetic stability of the crystals increases with halogen size (I > Br > Cl), in agreement with the observed melting points, and highlight the dominant role of dispersion forces in stabilizing the supramolecular architecture across all three structures. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Structural Chemistry is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1007/s11224-026-02758-w Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 12 StartPage: 1191 Subjects: – SubjectFull: Intermolecular interactions Type: general – SubjectFull: Stacking interactions Type: general – SubjectFull: Molecular self-assembly Type: general – SubjectFull: Computational chemistry Type: general Titles: – TitleFull: The role of π–π, C–H⋯halogen, and halogen⋯π interactions in the crystal packing of 9-aminoacridinium 3-halobenzoate salts: an experimental and theoretical investigation. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Nowak, Patryk – PersonEntity: Name: NameFull: Sikorski, Artur – PersonEntity: Name: NameFull: Mirocki, Artur IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 06 Text: Jun2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 10400400 Numbering: – Type: volume Value: 37 – Type: issue Value: 3 Titles: – TitleFull: Structural Chemistry Type: main |
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