Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer
The homodimers of transiently chiral molecules offer physical insight into the process of molecular recognition, the preference for homo or heterochiral aggregation and the nature of the non-covalent interactions stabilizing the adducts. We report the observation of the benzyl mercaptan dimer in the...
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| Format: | Article |
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MDPI AG
2021-10-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/13/11/2022 |
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| author | Rizalina Tama Saragi Marcos Juanes Ruth Pinacho José Emiliano Rubio José A. Fernández Alberto Lesarri |
| author_facet | Rizalina Tama Saragi Marcos Juanes Ruth Pinacho José Emiliano Rubio José A. Fernández Alberto Lesarri |
| author_sort | Rizalina Tama Saragi |
| collection | DOAJ |
| description | The homodimers of transiently chiral molecules offer physical insight into the process of molecular recognition, the preference for homo or heterochiral aggregation and the nature of the non-covalent interactions stabilizing the adducts. We report the observation of the benzyl mercaptan dimer in the isolation conditions of a supersonic jet expansion, using broadband (chirped-pulse) microwave spectroscopy. A single homochiral isomer was observed for the dimer, stabilized by a cooperative sequence of S-H···S and S-H···π hydrogen bonds. The structural data, stabilization energies and energy decomposition describe these non-covalent interactions as weak and dispersion-controlled. A comparison is also provided with the benzyl alcohol dimer. |
| first_indexed | 2024-03-10T05:01:05Z |
| format | Article |
| id | doaj.art-516cd5165c6e4f1da71ca18f7c719865 |
| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-10T05:01:05Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-516cd5165c6e4f1da71ca18f7c7198652023-11-23T01:43:33ZengMDPI AGSymmetry2073-89942021-10-011311202210.3390/sym13112022Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan DimerRizalina Tama Saragi0Marcos Juanes1Ruth Pinacho2José Emiliano Rubio3José A. Fernández4Alberto Lesarri5Departamento de Química Física y Química Inorgánica, Facultad de Ciencias-I.U. CINQUIMA, Universidad de Valladolid, Paseo de Belén, 7, 47011 Valladolid, SpainDepartamento de Química Física y Química Inorgánica, Facultad de Ciencias-I.U. CINQUIMA, Universidad de Valladolid, Paseo de Belén, 7, 47011 Valladolid, SpainDepartamento de Electrónica, Escuela Técnica Superior de Ingenieros de Telecomunicación, Universidad de Valladolid, Paseo de Belén, 15, 47011 Valladolid, SpainDepartamento de Electrónica, Escuela Técnica Superior de Ingenieros de Telecomunicación, Universidad de Valladolid, Paseo de Belén, 15, 47011 Valladolid, SpainDepartamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, SpainDepartamento de Química Física y Química Inorgánica, Facultad de Ciencias-I.U. CINQUIMA, Universidad de Valladolid, Paseo de Belén, 7, 47011 Valladolid, SpainThe homodimers of transiently chiral molecules offer physical insight into the process of molecular recognition, the preference for homo or heterochiral aggregation and the nature of the non-covalent interactions stabilizing the adducts. We report the observation of the benzyl mercaptan dimer in the isolation conditions of a supersonic jet expansion, using broadband (chirped-pulse) microwave spectroscopy. A single homochiral isomer was observed for the dimer, stabilized by a cooperative sequence of S-H···S and S-H···π hydrogen bonds. The structural data, stabilization energies and energy decomposition describe these non-covalent interactions as weak and dispersion-controlled. A comparison is also provided with the benzyl alcohol dimer.https://www.mdpi.com/2073-8994/13/11/2022chiral recognitiontransient chiralitynon-covalent interactionssulfur hydrogen bondingrotational spectroscopyjet spectroscopy |
| spellingShingle | Rizalina Tama Saragi Marcos Juanes Ruth Pinacho José Emiliano Rubio José A. Fernández Alberto Lesarri Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer Symmetry chiral recognition transient chirality non-covalent interactions sulfur hydrogen bonding rotational spectroscopy jet spectroscopy |
| title | Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer |
| title_full | Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer |
| title_fullStr | Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer |
| title_full_unstemmed | Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer |
| title_short | Molecular Recognition, Transient Chirality and Sulfur Hydrogen Bonding in the Benzyl Mercaptan Dimer |
| title_sort | molecular recognition transient chirality and sulfur hydrogen bonding in the benzyl mercaptan dimer |
| topic | chiral recognition transient chirality non-covalent interactions sulfur hydrogen bonding rotational spectroscopy jet spectroscopy |
| url | https://www.mdpi.com/2073-8994/13/11/2022 |
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