The synthesis and crystal structure of (E)-2-{[(4-methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol : Hirshfeld surface analysis, DFT calculations and anticorrosion studies
The title Schiff base compound, (E)-2-{[(4-methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol, C19H17NO2 (I), was synthesized via the reaction of 2-amino-4-methylphenol with 4-methoxynaphthalene-1-carbaldehyde. The structure of I was characterized by NMR, IR and UV-Vis spectroscopies in different solvents. The interatomic contacts in the crystal structure were explored using Hirshfeld surface analysis, which, together with the two-dimensional fingerprint plots, confirm the predominance of dispersion forces in the crystal structure. The molecule of I has a twisted conformation, with the mean plane of the naphthalene ring system being inclined to the plane of the phenol ring by 33.41 (4)°. In the crystal, molecules are linked by C-H...O hydrogen bonds to form inversion dimers. There are parallel-displaced π-π interactions present, together with C-H...π interactions, resulting in the formation of a three-dimensional structure. The anticorrosion potential of I was also investigated using density functional theory (DFT) in the gas phase and in various solvents. The compound was shown to exhibit significant anticorrosion properties for iron and copper. The molecular structure of I was determined by DFT calculations at the M062X/6-311+g(d) level of theory and compared with the crystallographically determined structure. Local and global reactivity descriptors were computed to predict the reactivity of I. Excellent agreement was observed between the calculated results and the experimental data.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:79 |
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| Enthalten in: |
Acta crystallographica. Section C, Structural chemistry - 79(2023), Pt 8 vom: 01. Aug., Seite 324-333 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yahiaoui, Ahmed Abderrahim [VerfasserIn] |
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| Links: |
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| Themen: |
Anticorrosion |
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| Anmerkungen: |
Date Revised 05.08.2023 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1107/S2053229623005867 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM360047998 |
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| 100 | 1 | |a Yahiaoui, Ahmed Abderrahim |e verfasserin |4 aut | |
| 245 | 1 | 4 | |a The synthesis and crystal structure of (E)-2-{[(4-methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol |b Hirshfeld surface analysis, DFT calculations and anticorrosion studies |
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| 500 | |a Date Revised 05.08.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a The title Schiff base compound, (E)-2-{[(4-methoxynaphthalen-1-yl)methylidene]amino}-4-methylphenol, C19H17NO2 (I), was synthesized via the reaction of 2-amino-4-methylphenol with 4-methoxynaphthalene-1-carbaldehyde. The structure of I was characterized by NMR, IR and UV-Vis spectroscopies in different solvents. The interatomic contacts in the crystal structure were explored using Hirshfeld surface analysis, which, together with the two-dimensional fingerprint plots, confirm the predominance of dispersion forces in the crystal structure. The molecule of I has a twisted conformation, with the mean plane of the naphthalene ring system being inclined to the plane of the phenol ring by 33.41 (4)°. In the crystal, molecules are linked by C-H...O hydrogen bonds to form inversion dimers. There are parallel-displaced π-π interactions present, together with C-H...π interactions, resulting in the formation of a three-dimensional structure. The anticorrosion potential of I was also investigated using density functional theory (DFT) in the gas phase and in various solvents. The compound was shown to exhibit significant anticorrosion properties for iron and copper. The molecular structure of I was determined by DFT calculations at the M062X/6-311+g(d) level of theory and compared with the crystallographically determined structure. Local and global reactivity descriptors were computed to predict the reactivity of I. Excellent agreement was observed between the calculated results and the experimental data | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a DFT calculations | |
| 650 | 4 | |a Hirshfeld surface analysis | |
| 650 | 4 | |a Schiff base | |
| 650 | 4 | |a anticorrosion | |
| 650 | 4 | |a carbaldehyde | |
| 650 | 4 | |a crystal structure | |
| 650 | 4 | |a quantum chemical calculations | |
| 700 | 1 | |a Ghichi, Nadir |e verfasserin |4 aut | |
| 700 | 1 | |a Hannachi, Douniazed |e verfasserin |4 aut | |
| 700 | 1 | |a Mezhoud, Bilel |e verfasserin |4 aut | |
| 700 | 1 | |a Djedouani, Amel |e verfasserin |4 aut | |
| 700 | 1 | |a Kraim, Khairedine |e verfasserin |4 aut | |
| 700 | 1 | |a Crochet, Aurélien |e verfasserin |4 aut | |
| 700 | 1 | |a Stoeckli-Evans, Helen |e verfasserin |4 aut | |
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