Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives
Parallel, off-set π[C(=O)N(H)N=C] …π(phenyl) interactions are observed in the crystal of (2-thienyl)CH2CON(H)-N=C(H)Ph, along with more conventional non-covalent interactions. All notable interactions have been analysed by the calculated Hirshfeld surfaces, NCI plots and QTAIM analysis. The π[C(=O...
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Royal Society of Chemistry
2022
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| Online Access: | http://eprints.sunway.edu.my/1956/ http://eprints.sunway.edu.my/1956/1/Tiekink%20crystengcomm%202022%2024%20962_acc.pdf |
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| author | Tan, Sang Loon * Cardoso, Laura N. F. Souza, Marcus V. N. de Wardell, Solange M. S. V. Wardell, James L. Tiekink, Edward R. T. * |
| author_facet | Tan, Sang Loon * Cardoso, Laura N. F. Souza, Marcus V. N. de Wardell, Solange M. S. V. Wardell, James L. Tiekink, Edward R. T. * |
| author_sort | Tan, Sang Loon * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | Parallel, off-set π[C(=O)N(H)N=C] …π(phenyl) interactions are observed in the crystal of (2-thienyl)CH2CON(H)-N=C(H)Ph, along with more conventional non-covalent interactions. All notable interactions have been analysed by the calculated Hirshfeld surfaces, NCI plots and
QTAIM analysis. The π[C(=O)N(H)N=C]…π(phenyl) interactions, whereby the N(H) atom lies over the ring centroid and with the N and C atoms on either side of the N(H) atom closely
overlay 1,3-carbon atoms of the phenyl ring, are shown to be attractive. Theory suggests the energy of association provided the π[C(=O)N(H)N=C]…π(phenyl) interaction to the molecular packing to be about 15 kJ/mol, a value similar to that provided by similarly orientated benzene 2 and pyridine rings. A survey of the literature of related structures suggests comparable interactions occur in approximately 5-6% of crystals where they can potentially occur. |
| first_indexed | 2025-11-14T21:19:03Z |
| format | Article |
| id | sunway-1956 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:19:03Z |
| publishDate | 2022 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-19562022-03-08T07:26:46Z http://eprints.sunway.edu.my/1956/ Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives Tan, Sang Loon * Cardoso, Laura N. F. Souza, Marcus V. N. de Wardell, Solange M. S. V. Wardell, James L. Tiekink, Edward R. T. * QD Chemistry Parallel, off-set π[C(=O)N(H)N=C] …π(phenyl) interactions are observed in the crystal of (2-thienyl)CH2CON(H)-N=C(H)Ph, along with more conventional non-covalent interactions. All notable interactions have been analysed by the calculated Hirshfeld surfaces, NCI plots and QTAIM analysis. The π[C(=O)N(H)N=C]…π(phenyl) interactions, whereby the N(H) atom lies over the ring centroid and with the N and C atoms on either side of the N(H) atom closely overlay 1,3-carbon atoms of the phenyl ring, are shown to be attractive. Theory suggests the energy of association provided the π[C(=O)N(H)N=C]…π(phenyl) interaction to the molecular packing to be about 15 kJ/mol, a value similar to that provided by similarly orientated benzene 2 and pyridine rings. A survey of the literature of related structures suggests comparable interactions occur in approximately 5-6% of crystals where they can potentially occur. Royal Society of Chemistry 2022 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1956/1/Tiekink%20crystengcomm%202022%2024%20962_acc.pdf Tan, Sang Loon * and Cardoso, Laura N. F. and Souza, Marcus V. N. de and Wardell, Solange M. S. V. and Wardell, James L. and Tiekink, Edward R. T. * (2022) Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives. CrystEngComm, 24 (5). pp. 962-974. ISSN 1466-8033 http://doi.org/10.1039/d1ce01492g doi:10.1039/d1ce01492g |
| spellingShingle | QD Chemistry Tan, Sang Loon * Cardoso, Laura N. F. Souza, Marcus V. N. de Wardell, Solange M. S. V. Wardell, James L. Tiekink, Edward R. T. * Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title | Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title_full | Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title_fullStr | Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title_full_unstemmed | Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title_short | Experimental and computational evidence for stabilising parallel, offset π[C(=O)N(H)N=C]⋯π(phenyl) interactions in acetohydrazide derivatives |
| title_sort | experimental and computational evidence for stabilising parallel, offset π[c(=o)n(h)n=c]⋯π(phenyl) interactions in acetohydrazide derivatives |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1956/ http://eprints.sunway.edu.my/1956/ http://eprints.sunway.edu.my/1956/ http://eprints.sunway.edu.my/1956/1/Tiekink%20crystengcomm%202022%2024%20962_acc.pdf |