Corrigendum: Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial-F Preference(Chem. Eur. J., 2020, 26, 10.1002/chem.202001355)

Zackaria Nairoukh, Felix Strieth-Kalthoff, Klaus Bergander, Frank Glorius

Research output: Contribution to journalComment/debate

1 Scopus citations

Abstract

The authors became aware that the values of free enthalpy differences (ΔG) and dipole moments (μ) of some compounds (1A, 3A, 4A, 5C, 9A, 11A, 12A, 13, 14, 15) given in the main manuscript were reported incorrectly. Although the mentioned values are presented correctly in the Supporting Information, the corrected Schemes (Scheme 2 and 3) and Tables (Table 1 and 2) are shown below to avoid any future confusion. This correction does not alter in any way the analysis and conclusions drawn in the article. The authors apologize for this error and for any inconvenience caused. Scheme (Figure presented.) The conformational preferences of 3-fluoropiperidine (1) and 3,5-difluoropiperidine (2) and their TFA-(A), HCl-(B), and NH-(C)-analogues. The free enthalpy differences between the equatorial conformer to the axial conformer (ΔG) are presented as follows: ΔG Solvent (ΔG Gas Phase). The ΔG values for TFA-, and for both HCl-, and NH-analogues are given in chloroform and water, respectively. All values are given in kcal mol−1. Experimentally, all analogues of 1 and 2 showed high axial preference. In NH-analogues 1C and 2C, we were unable to determine the orientation of the N−H bond because of a fast H/D exchange in solution. [a] Both computational analysis and experimental observation were carried out in toluene. Scheme (Figure presented.) The conformational preferences of cis-3-fluoro-4-methylpiperidine (3) and its TFA-(A), HCl-(B), and NH-(C)- analogues. All values are given in kcal mol−1. The experimental observation is based on 3J(19F,1H) values. See the Supporting Information for more details. Table Conformational behavior of all-cis-(multi)fluorinated piperidines.[a] (Table presented.) [a] The conformational preferences of fluorinated piperidine (1–12) and its R=TFA-(A), HCl-(B), and NH-(C)-analogues. The ΔG values for TFA- and for both HCl-, and NH-analogues are given in chloroform and water, respectively. All values are given in kcal mol−1. [b] This compound was measured in toluene. Table The conformational preferences of 3,5-difluoropiperidine derivatives.[a] (Table presented.) [a] All values are given in kcal mol−1. The experimental observation is based on 3J(19F,1H) values. See the Supporting Information for more details.

Original languageAmerican English
Pages (from-to)14018-14019
Number of pages2
JournalChemistry - A European Journal
Volume26
Issue number61
DOIs
StatePublished - 2 Nov 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH GmbH

Fingerprint

Dive into the research topics of 'Corrigendum: Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial-F Preference(Chem. Eur. J., 2020, 26, 10.1002/chem.202001355)'. Together they form a unique fingerprint.

Cite this