Šekutor, Marina; Pinacho, Pablo; Loru, Donatella; Šumanovac, Tatjana; Schnell, Melanie (2024) Characterization of adamantyl thioethers by rotational spectroscopy. In: Kassal, Petar; Meštrović, Ernest; Namjesnik, Danijel; Šekutor, Marina; Tomišić, Vladislav; Usenik, Andrea, (eds.) Solutions in Chemistry 2024: Book of Abstracts. Zagreb, Croatian Chemical Society, p. 105 .
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Abstract
The thioether group (R–S–R´) is a common motif in the structures of bioactive molecules and is often a starting point in the formation of higher oxidation state sulfur derivatives.1 Despite a vast number of known thioether containing derivatives, a compound class incorporating the adamantyl group remains scarcely described in the literature. However, such alkyl adamantyl thioethers could have pharmaceutical applications due to a combination of properties emerging from these functional subunits. We therefore studied the fundamental properties of a prepared series of alkyl adamantyl thioethers using a combination of high-resolution rotational spectroscopy and computational tools.2 Here it should be noted that the studied 1,1' diadamantyl thioether is one of the largest molecules studied to date by high-resolution rotational spectroscopy. We also compared the obtained findings with a structurally analogous 1,1'-diadamantyl ether that we explored previously3,4 in order to assess the influence of the sulfur atom on the intermolecular cluster formation with solvents molecules, especially water (Figure 1). Investigation of such microsolvated clusters provides valuable insights into the preference of water to establish sulfur-centered hydrogen bonds with thioethers.
| Item Type: | Conference or workshop item published in conference proceedings (UNSPECIFIED) | ||||||||
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| Uncontrolled Keywords: | thioether; sulfur centered hydrogen bond; adamantyl derivatives; non-covalent interactions; rotational spectroscopy | ||||||||
| Subjects: | NATURAL SCIENCES NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Chemistry > Organic Chemistry |
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| Divisions: | Division of Organic Chemistry and Biochemistry | ||||||||
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| Depositing User: | Kristina Ciglar | ||||||||
| Date Deposited: | 07 Oct 2025 10:01 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/10042 |
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