The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules
The <i>in</i> forms of molecular iron maidens are known for their unique ultrashort interaction between the apical hydrogen atom or its small substituent and the surface of the benzene ring. It is generally believed that this forced ultrashort X<inline-formula><math xmlns="...
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| Format: | Article |
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MDPI AG
2023-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/5/2244 |
| _version_ | 1797614841147424768 |
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| author | Mirosław Jabłoński |
| author_facet | Mirosław Jabłoński |
| author_sort | Mirosław Jabłoński |
| collection | DOAJ |
| description | The <i>in</i> forms of molecular iron maidens are known for their unique ultrashort interaction between the apical hydrogen atom or its small substituent and the surface of the benzene ring. It is generally believed that this forced ultrashort X<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mo>⋯</mo><mi>π</mi></mrow></semantics></math></inline-formula> contact is associated with high steric hindrance, which is responsible for specific properties of iron maiden molecules. The main aim of this article is to investigate the influence of significant charge enrichment or depletion of the benzene ring on the characteristics of the ultrashort C-X<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mo>⋯</mo><mi>π</mi></mrow></semantics></math></inline-formula> contact in iron maiden molecules. For this purpose, three strongly electron-donating (-NH<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mrow></mrow><mn>2</mn></msub></semantics></math></inline-formula>) or strongly electron-withdrawing (-CN) groups were inserted into the benzene ring of <i>in</i>-[3<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msup><mrow></mrow><mrow><mn>4</mn><mo>,</mo><mn>10</mn></mrow></msup></semantics></math></inline-formula>][7]metacyclophane and its halogenated (X = F, Cl, Br) derivatives. It is shown that, despite such extremely electron-donating or electron-accepting properties, the considered iron maiden molecules surprisingly reveal quite high resistance to changes in electronic properties. |
| first_indexed | 2024-03-11T07:16:58Z |
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| id | doaj.art-caacfb3a78e04aa48937ad71a24efa5f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T07:16:58Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-caacfb3a78e04aa48937ad71a24efa5f2023-11-17T08:13:58ZengMDPI AGMolecules1420-30492023-02-01285224410.3390/molecules28052244The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden MoleculesMirosław Jabłoński0Faculty of Chemistry, Nicolaus Copernicus University in Toruń, Gagarina 7, 87-100 Toruń, PolandThe <i>in</i> forms of molecular iron maidens are known for their unique ultrashort interaction between the apical hydrogen atom or its small substituent and the surface of the benzene ring. It is generally believed that this forced ultrashort X<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mo>⋯</mo><mi>π</mi></mrow></semantics></math></inline-formula> contact is associated with high steric hindrance, which is responsible for specific properties of iron maiden molecules. The main aim of this article is to investigate the influence of significant charge enrichment or depletion of the benzene ring on the characteristics of the ultrashort C-X<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mo>⋯</mo><mi>π</mi></mrow></semantics></math></inline-formula> contact in iron maiden molecules. For this purpose, three strongly electron-donating (-NH<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msub><mrow></mrow><mn>2</mn></msub></semantics></math></inline-formula>) or strongly electron-withdrawing (-CN) groups were inserted into the benzene ring of <i>in</i>-[3<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><msup><mrow></mrow><mrow><mn>4</mn><mo>,</mo><mn>10</mn></mrow></msup></semantics></math></inline-formula>][7]metacyclophane and its halogenated (X = F, Cl, Br) derivatives. It is shown that, despite such extremely electron-donating or electron-accepting properties, the considered iron maiden molecules surprisingly reveal quite high resistance to changes in electronic properties.https://www.mdpi.com/1420-3049/28/5/2244ultrashort interactioniron maidencageendohedral complexrepulsionhindrance |
| spellingShingle | Mirosław Jabłoński The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules Molecules ultrashort interaction iron maiden cage endohedral complex repulsion hindrance |
| title | The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules |
| title_full | The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules |
| title_fullStr | The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules |
| title_full_unstemmed | The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules |
| title_short | The Ultrashort Spike–Ring Interaction in Substituted Iron Maiden Molecules |
| title_sort | ultrashort spike ring interaction in substituted iron maiden molecules |
| topic | ultrashort interaction iron maiden cage endohedral complex repulsion hindrance |
| url | https://www.mdpi.com/1420-3049/28/5/2244 |
| work_keys_str_mv | AT mirosławjabłonski theultrashortspikeringinteractioninsubstitutedironmaidenmolecules AT mirosławjabłonski ultrashortspikeringinteractioninsubstitutedironmaidenmolecules |