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Multinuclear NMR spectra and GIAO/DFT calculations of N-benzylazoles and N-benzylbenzazoles

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Abstract

The 1H, 13C, and 15N chemical shifts of almost the whole series of N-benzyl azoles and benzazoles, with the exception of the unknown 1-benzyl-1H-pentazole (10) and the very unstable 2-benzyl-2H-isoindole (12), have been measured. In addition, the X-ray crystal structure of 1-benzyl-1H-indazole (14) was solved (monoclinic, space group P21/n), its geometry being very close to that used for the calculations. The absolute chemical shieldings were calculated at the gauge-independent atomic orbital (GIAO)/Becke, 3-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,p) level and then transformed with very robust empirical equations into chemical shifts of the three nuclei showing an excellent agreement with the 313 experimental values.

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Funding

This work was carried out with financial support from the Spanish Ministerio de Ciencia, Innovación y Universidades (Projects PGC2018-094644-B-C2 and RTI2018-097416-B-C21) and Dirección General de Investigación e Innovación de la Comunidad de Madrid (PS2018/EMT-4329 AIRTEC-CM). Thanks are also given to the CTI (CSIC) for their continued computational support.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, A-1090, Vienna, Austria

    Wolfgang Holzer, Laura Castoldi & Viktoriya Kyselova

  2. Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Paseo Senda del Rey, 9, E-28040, Madrid, Spain

    Dionisia Sanz & Rosa M. Claramunt

  3. Departamento de Química Inorgánica, Facultad de Ciencias Químicas, UCM, Ciudad Universitaria s/n, E-28040, Madrid, Spain

    M. Carmen Torralba

  4. Instituto de Química Médica, Centro de Química Orgánica “Manuel Lora-Tamayo”, CSIC, Juan de la Cierva, 3, E-28006, Madrid, Spain

    Ibon Alkorta & José Elguero

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  1. Wolfgang Holzer
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  2. Laura Castoldi
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  3. Viktoriya Kyselova
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  4. Dionisia Sanz
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  5. Rosa M. Claramunt
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Correspondence to Rosa M. Claramunt or Ibon Alkorta.

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Holzer, W., Castoldi, L., Kyselova, V. et al. Multinuclear NMR spectra and GIAO/DFT calculations of N-benzylazoles and N-benzylbenzazoles. Struct Chem 30, 1729–1735 (2019). https://doi.org/10.1007/s11224-019-01310-3

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  • DOI: https://doi.org/10.1007/s11224-019-01310-3

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