Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline)
The title compounds 4,4′-methylenebis(2,6-diethylaniline) (C21H30N2, 1) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) (C21H28Cl2N2, 2) are of significant interest as curing agents for a wide range of resins and as building blocks for sterically demanding compounds in the synthesis of ligands fo...
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International Union of Crystallography
2025-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025000234 |
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| author | Daniil E. Smirnov Oleg S. Morozov Ekaterina S. Afanasyeva Viktor V. Avdeev |
| author_facet | Daniil E. Smirnov Oleg S. Morozov Ekaterina S. Afanasyeva Viktor V. Avdeev |
| author_sort | Daniil E. Smirnov |
| collection | DOAJ |
| description | The title compounds 4,4′-methylenebis(2,6-diethylaniline) (C21H30N2, 1) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) (C21H28Cl2N2, 2) are of significant interest as curing agents for a wide range of resins and as building blocks for sterically demanding compounds in the synthesis of ligands for catalysis. This paper describes their synthesis and the preparation of single crystals, with their structures determined through single-crystal X-ray analysis. The presence of the chlorine substituent slightly affects the twist angle between the two aromatic components. The molecules of compound 1 form a network structure through intermolecular N—H...N bonds and C—H...π interactions, while in the crystal structure of compound 2, the molecules are assembled solely through N—H...π interactions. Consequently, despite their chemical similarity, it is the precise structural data that enables us to explain their differing reactivity and opens up the possibility of evaluating steric properties for the development of new materials and ligands. |
| format | Article |
| id | doaj-art-eb1973637d30456081ea0c5e49d20db1 |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-eb1973637d30456081ea0c5e49d20db12025-02-06T07:27:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-02-0181214815210.1107/S2056989025000234ny2009Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline)Daniil E. Smirnov0Oleg S. Morozov1Ekaterina S. Afanasyeva2Viktor V. Avdeev3Department of Chemical Technology and New Materials, Faculty of Chemistry, Lomonosov Moscow State University, GSP-1, 1-3, Leninskiye Gory, Moscow, 119991, Russian FederationDepartment of Chemical Technology and New Materials, Faculty of Chemistry, Lomonosov Moscow State University, GSP-1, 1-3, Leninskiye Gory, Moscow, 119991, Russian FederationDepartment of Chemical Technology and New Materials, Faculty of Chemistry, Lomonosov Moscow State University, GSP-1, 1-3, Leninskiye Gory, Moscow, 119991, Russian FederationDepartment of Chemical Technology and New Materials, Faculty of Chemistry, Lomonosov Moscow State University, GSP-1, 1-3, Leninskiye Gory, Moscow, 119991, Russian FederationThe title compounds 4,4′-methylenebis(2,6-diethylaniline) (C21H30N2, 1) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) (C21H28Cl2N2, 2) are of significant interest as curing agents for a wide range of resins and as building blocks for sterically demanding compounds in the synthesis of ligands for catalysis. This paper describes their synthesis and the preparation of single crystals, with their structures determined through single-crystal X-ray analysis. The presence of the chlorine substituent slightly affects the twist angle between the two aromatic components. The molecules of compound 1 form a network structure through intermolecular N—H...N bonds and C—H...π interactions, while in the crystal structure of compound 2, the molecules are assembled solely through N—H...π interactions. Consequently, despite their chemical similarity, it is the precise structural data that enables us to explain their differing reactivity and opens up the possibility of evaluating steric properties for the development of new materials and ligands.https://journals.iucr.org/paper?S2056989025000234crystal structuremethylenedianilinehydrogen bondingsynthesisdisorder |
| spellingShingle | Daniil E. Smirnov Oleg S. Morozov Ekaterina S. Afanasyeva Viktor V. Avdeev Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) Acta Crystallographica Section E: Crystallographic Communications crystal structure methylenedianiline hydrogen bonding synthesis disorder |
| title | Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) |
| title_full | Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) |
| title_fullStr | Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) |
| title_full_unstemmed | Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) |
| title_short | Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) |
| title_sort | synthesis and crystal structures of 4 4 methylenebis 2 6 diethylaniline and 4 4 methylenebis 3 chloro 2 6 diethylaniline |
| topic | crystal structure methylenedianiline hydrogen bonding synthesis disorder |
| url | https://journals.iucr.org/paper?S2056989025000234 |
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