Crystal structures of three cyclohexane‑based γ‑spirolactams
- The title compounds, 2-azaspiro[4.5]deca-1-one, C₉H₁₅NO, (1a), cis-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1b), and trans-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1c), were synthesized from benzoic acids 2 in only 3 steps in high yields. Crystallization from n-hexane afforded single crystals, suitable for X-ray diffraction. Thus, the configurations, conformations, and interesting crystal packing effects have been determined unequivocally. The bicyclic skeleton consists of a lactam ring, attached by a spiro junction to a cyclohexane ring. The lactam ring adopts an envelope conformation and the cyclohexane ring has a chair conformation. The main difference between compound 1b and compound 1c is the position of the carbonyl group on the 2-pyrrolidine ring with respect to the methyl group on the 8-position of the cyclohexane ring, which is cis (1b) or trans (1c). A remarkable feature of all three compounds is the existence of a mirror plane within the molecule. Given that all compounds crystallize in centrosymmetric spaceThe title compounds, 2-azaspiro[4.5]deca-1-one, C₉H₁₅NO, (1a), cis-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1b), and trans-8-methyl-2-azaspiro[4.5]deca-1-one, C₁₀H₁₇NO, (1c), were synthesized from benzoic acids 2 in only 3 steps in high yields. Crystallization from n-hexane afforded single crystals, suitable for X-ray diffraction. Thus, the configurations, conformations, and interesting crystal packing effects have been determined unequivocally. The bicyclic skeleton consists of a lactam ring, attached by a spiro junction to a cyclohexane ring. The lactam ring adopts an envelope conformation and the cyclohexane ring has a chair conformation. The main difference between compound 1b and compound 1c is the position of the carbonyl group on the 2-pyrrolidine ring with respect to the methyl group on the 8-position of the cyclohexane ring, which is cis (1b) or trans (1c). A remarkable feature of all three compounds is the existence of a mirror plane within the molecule. Given that all compounds crystallize in centrosymmetric space groups, the packing always contains interesting enantiomer-like pairs. Finally, the structures are stabilized by intermolecular N–H···O hydrogen bonds.…
Verfasserangaben: | Tobias Krueger, Alexandra Kelling, Torsten LinkerORCiDGND, Uwe SchildeORCiDGND |
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URN: | urn:nbn:de:kobv:517-opus4-434911 |
DOI: | https://doi.org/10.25932/publishup-43491 |
Titel des übergeordneten Werks (Deutsch): | Postprints der Universität Potsdam Mathematisch-Naturwissenschaftliche Reihe |
Untertitel (Englisch): | determination of configurations and conformations |
Schriftenreihe (Bandnummer): | Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (738) |
Publikationstyp: | Postprint |
Sprache: | Englisch |
Datum der Erstveröffentlichung: | 18.09.1019 |
Erscheinungsjahr: | 2019 |
Veröffentlichende Institution: | Universität Potsdam |
Datum der Freischaltung: | 18.09.2019 |
Freies Schlagwort / Tag: | 2-Azaspiro[4.5]deca-1-ones; Cis- and trans-form; Configuration; Conformation; Lactams |
Ausgabe: | 738 |
Seitenanzahl: | 9 |
Quelle: | BMC Chemistry 13 (2019) 69 DOI: 10.1186/s13065-019-0586-7 |
Organisationseinheiten: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
DDC-Klassifikation: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Peer Review: | Referiert |
Publikationsweg: | Open Access |
Lizenz (Deutsch): | CC-BY - Namensnennung 4.0 International |
Externe Anmerkung: | Bibliographieeintrag der Originalveröffentlichung/Quelle |