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Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies

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Abstract

Intermolecular interactions of 7-(RCONH)-[1H]-2-oxo-1,8-naphthyridines (R = Me, Et, i-Pr, t-Bu, 1-adamantyl (1-Ad), CF3, and C2F5) containing ADAD quadruple hydrogen bonding motif were studied by liquid and solid state NMR, ESI-MS, IR, and DFT calculations. 1H NMR was used to determine the dimerization constants of i-Pr and 1-Ad congeners in CDCl3. 13C and 15N cross-polarization (CP) magic angle spinning (MAS) NMR data suggest that compounds possess similar solid state structures. Further, mass spectral data reveal that in gas phase both Me and 1-Ad derivatives form also multimers due to lack of competitive solvent interactions. The structures of the gas phase multimers depend on the size of the alkyl group. These results are in agreement with quantum chemical calculations. Geometry optimization and 1H NMR spectra show that in dimers that carry bulky alkyl groups (t-Bu and 1-Ad) certain hydrogen bonds are weaker than in Me, Et, and i-Pr derivatives while strong electron acceptors, CF3 and C2F5, deshields hydrogen bonded protons but creates significant electronic F/O repulsion yielding lowering of the energy of interaction. The influence of steric effect on dimerization of quadruply hydrogen bonded dimers was correlated with the Taft E s values.

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Acknowledgments

The authors gratefully acknowledge financial support from the Academy of Finland (Elina S. project no. 119616 and Elina K. no. 127941) and the Polish Ministry of Science and Higher Education (B.O. grant no. N N204 174138). The authors are very much indebted to the Academic Computer Centre in Gdansk–TASK and CYFRONET in Cracow for providing computer time and programs.

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Authors and Affiliations

  1. Faculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Seminaryjna 3, 85-326, PL, Bydgoszcz, Poland

    Borys Ośmiałowski

  2. Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014, Jyväskylä, Finland

    Erkki Kolehmainen, Babita Behera, Reijo Kauppinen & Elina Sievänen

  3. Department of Chemistry, University of Eastern Finland, P.O. Box 111, FI-80101, Joensuu, Finland

    Elina Kalenius

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  1. Borys Ośmiałowski
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  2. Erkki Kolehmainen
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Correspondence to Borys Ośmiałowski.

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11224_2011_9808_MOESM1_ESM.doc

The file contains NMR spectra, coordinates of optimized structures, IR spectra, MS spectra, NMR and MS processing parameters and dilution experiment curves. (DOC 9907 kb)

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Ośmiałowski, B., Kolehmainen, E., Kalenius, E. et al. Intermolecular steric hindrance in 7-acylamino-[1H]-2-oxo-1,8-naphthyridines: NMR, ESI-MS, IR, and DFT calculation studies. Struct Chem 22, 1143–1151 (2011). https://doi.org/10.1007/s11224-011-9808-x

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