The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators
The structures of 2-(3-hydroxy-5-methylphenoxy)-N-(4-nitrophenyl)acetamide), B1, and 2-(3-hydroxy-5-methylphenoxy)-N-(4-(trifluoromethyl)phenyl)acetamide, B2, are crystallized in the crystal symmetry of the monoclinic structure and in the space group of P2<sub>1</sub>/c. For the differen...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/12/9/1252 |
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| author | Boontana Wannalerse Paradee Kwanmuang Piangkwan Jansukra Bussaba Pinchaipat Tanwawan Duangthongyou Panitat Hasin Apisit Songsasen Kittipong Chainok Songwut Suramitr |
| author_facet | Boontana Wannalerse Paradee Kwanmuang Piangkwan Jansukra Bussaba Pinchaipat Tanwawan Duangthongyou Panitat Hasin Apisit Songsasen Kittipong Chainok Songwut Suramitr |
| author_sort | Boontana Wannalerse |
| collection | DOAJ |
| description | The structures of 2-(3-hydroxy-5-methylphenoxy)-N-(4-nitrophenyl)acetamide), B1, and 2-(3-hydroxy-5-methylphenoxy)-N-(4-(trifluoromethyl)phenyl)acetamide, B2, are crystallized in the crystal symmetry of the monoclinic structure and in the space group of P2<sub>1</sub>/c. For the different structures of B1 and B2, B1 displays an absolute planarity conformation with torsion angles of 172.2–179.1. The two molecules of B1 are linked by a hydrogen bond of N–H…O–N–O, where a hydrogen atom of amide is bound to an oxygen atom of the nitro-substituted group. In the case of B2, the molecules are connected to each other through the hydrogen bonding interaction of C=O…H–O. DFT calculations reveal that the transition from HOMO to LUMO of B1 and B2 shows the absorption bands B1 and B2 at 314 and 240 nm, respectively. Upon the addition of an OH<sup>−</sup> ion, the absorption bands of B1 and B2 shift to a longer wavelength than the original bands of B1 and B2. According to the <sup>1</sup>H-NMR results, the NH proton of B1 and B2 disappears due to the deprotonation process. The methylene group and aromatic region move to upfield shift when adding an OH<sup>−</sup> ion. |
| first_indexed | 2024-03-10T00:19:34Z |
| format | Article |
| id | doaj.art-21b4832cf0a441f1a1d8924a7932351d |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-10T00:19:34Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-21b4832cf0a441f1a1d8924a7932351d2023-11-23T15:43:59ZengMDPI AGCrystals2073-43522022-09-01129125210.3390/cryst12091252The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> IndicatorsBoontana Wannalerse0Paradee Kwanmuang1Piangkwan Jansukra2Bussaba Pinchaipat3Tanwawan Duangthongyou4Panitat Hasin5Apisit Songsasen6Kittipong Chainok7Songwut Suramitr8Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry, Faculty of Science, Naresuan University, Phitsanulok 65000, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok 10900, ThailandThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, ThailandDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, ThailandThe structures of 2-(3-hydroxy-5-methylphenoxy)-N-(4-nitrophenyl)acetamide), B1, and 2-(3-hydroxy-5-methylphenoxy)-N-(4-(trifluoromethyl)phenyl)acetamide, B2, are crystallized in the crystal symmetry of the monoclinic structure and in the space group of P2<sub>1</sub>/c. For the different structures of B1 and B2, B1 displays an absolute planarity conformation with torsion angles of 172.2–179.1. The two molecules of B1 are linked by a hydrogen bond of N–H…O–N–O, where a hydrogen atom of amide is bound to an oxygen atom of the nitro-substituted group. In the case of B2, the molecules are connected to each other through the hydrogen bonding interaction of C=O…H–O. DFT calculations reveal that the transition from HOMO to LUMO of B1 and B2 shows the absorption bands B1 and B2 at 314 and 240 nm, respectively. Upon the addition of an OH<sup>−</sup> ion, the absorption bands of B1 and B2 shift to a longer wavelength than the original bands of B1 and B2. According to the <sup>1</sup>H-NMR results, the NH proton of B1 and B2 disappears due to the deprotonation process. The methylene group and aromatic region move to upfield shift when adding an OH<sup>−</sup> ion.https://www.mdpi.com/2073-4352/12/9/1252hydrogen bondsdeprotonation processred shift |
| spellingShingle | Boontana Wannalerse Paradee Kwanmuang Piangkwan Jansukra Bussaba Pinchaipat Tanwawan Duangthongyou Panitat Hasin Apisit Songsasen Kittipong Chainok Songwut Suramitr The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators Crystals hydrogen bonds deprotonation process red shift |
| title | The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators |
| title_full | The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators |
| title_fullStr | The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators |
| title_full_unstemmed | The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators |
| title_short | The Synthesis, Crystal Structure, DFT Calculations and Optical Properties of Orcinolic Derivatives as OH<sup>−</sup> Indicators |
| title_sort | synthesis crystal structure dft calculations and optical properties of orcinolic derivatives as oh sup sup indicators |
| topic | hydrogen bonds deprotonation process red shift |
| url | https://www.mdpi.com/2073-4352/12/9/1252 |
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