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

ABSTRACT: In this paper, we report the anisochrony of the fluorine atoms of a CHF? 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.

SUBMITTER: Garcia-Perez D 

PROVIDER: S-EPMC6150283 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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<sup>19</sup>F-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.

García-Pérez Diana D   López Concepción C   Claramunt Rosa M RM   Alkorta Ibon I   Elguero José J  

Molecules (Basel, Switzerland) 20171117 11

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 (4<i>S</i>,7<i>R</i>)-7,8,8-trimethyl-4,5,6,7-tetrahydro-4,7-methano-2<i>H</i>-indazole also known as (4<i>S</i>,7<i>R</i>)-campho[2,3-<i>c</i>]pyrazole, which has two stereogenic centers. Gauge-Independent Atomic Orbital (GIAO)/Becke, 3-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,f) calculated <sup>19</sup>F chemical shifts of the minimum energy conformations sa  ...[more]

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