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.

Multinuclear NMR spectra and GIAO/DFT calculations of N-benzylazoles and N-benzylbenzazoles / W. Holzer, L. Castoldi, V. Kyselova, D. Sanz, R.M. Claramunt, M.C. Torralba, I. Alkorta, J. Elguero. - In: STRUCTURAL CHEMISTRY. - ISSN 1040-0400. - 30:5(2019 Oct), pp. 1729-1735. [10.1007/s11224-019-01310-3]

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

L. Castoldi
Secondo
;
2019-10

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.
Carbon-13 NMR; GIAO calculations; N-benzylazoles; Nitrogen-15 NMR; Proton NMR; X-ray crystal structure;
Settore CHIM/06 - Chimica Organica
7-mar-2019
Article (author)
File in questo prodotto:
File Dimensione Formato  
Holzer2019_Article_MultinuclearNMRSpectraAndGIAOD.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 784.49 kB
Formato Adobe PDF
784.49 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/890747
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 10
  • ???jsp.display-item.citation.isi??? 8
social impact