The missing link in the homologous series of lactams: the X-ray structure of valerolactam

Weck, Christian and Nauha, Elisa and Gruber, Tobias (2018) The missing link in the homologous series of lactams: the X-ray structure of valerolactam. Crys. Growth Des., 18 (12). pp. 7248-7253. ISSN 1528-7483

Full content URL: https://pubs.acs.org/doi/abs/10.1021/acs.cgd.8b014...

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The missing link in the homologous series of lactams: the X-ray structure of valerolactam
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Abstract

Lactams are an important class of heterocyclic compounds and are widely used for industrial and pharmaceutical purposes. Even decades after initial lactam syntheses, research on their physical and chemical properties is still rewarding. It delivers valuable information on the reactivity of lactams and their conformational behavior. For the small and medium-sized parent lactams the X-ray structures have been well known, except for the ‘missing link’ the 6-membered valerolactam. An X-ray structure of valerolactam is described here for the first time stimulating a comparative discussion of the homologous lactam series. The experimental solid state conformation of valerolactam differs significantly from the calculated and energy-minimized ones reported in the literature. The amide bond length in valerolactam is more or less equal to other lactams. A comparison with the structure of cyclohexene revealed striking similarities arising from the partial C-N double bond in valerolactam caused by amide resonance.

Keywords:Lactam, Valerolactam, Lactam antibiotic, X-ray diffraction, Molecular structure
Subjects:F Physical Sciences > F151 Pharmaceutical Chemistry
F Physical Sciences > F131 Crystallography
F Physical Sciences > F150 Medicinal Chemistry
F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Pharmacy
ID Code:34223
Deposited On:07 Jan 2019 12:03

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