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Molecules 2017, 22(11), 2003;

19F‐NMR Diastereotopic Signals in Two N-CHF2 Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole

Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain
Instituto de Química Médica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain
Dedicated to our friend V. A. Ostrovskii of the St. Petersburg State Institute of Technology, Russia, on the occasion of his 70th birthday.
Authors to whom correspondence should be addressed.
Received: 2 November 2017 / Revised: 14 November 2017 / Accepted: 16 November 2017 / Published: 17 November 2017
(This article belongs to the Special Issue Pyrazole Derivatives)
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In this paper, we report the anisochrony of the fluorine atoms of a CHF2 group when linked to a pyrazole ring. The pyrazole is part of (4S,7R)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole also known as (4S,7R)-campho[2,3-c]pyrazole, which has two stereogenic centers. Gauge-Independent Atomic Orbital (GIAO)/Becke, 3-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,f) calculated 19F chemical shifts of the minimum energy conformations satisfactorily agree with the experimental data. The energy differences between minima need to consider solvent effects (continuum model) to be satisfactorily reproduced. View Full-Text
Keywords: 19F‐NMR; diastereotopic; anisochrony; pyrazoles; indazoles; GIAO; B3LYP; PCM 19F‐NMR; diastereotopic; anisochrony; pyrazoles; indazoles; GIAO; B3LYP; PCM

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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García-Pérez, D.; López, C.; Claramunt, R.M.; Alkorta, I.; Elguero, J. 19F‐NMR Diastereotopic Signals in Two N-CHF2 Derivatives of (4S,7R)-7,8,8-Trimethyl-4,5,6,7-tetrahydro-4,7-methano-2H-indazole. Molecules 2017, 22, 2003.

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