Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB)

Tatum, N.J.; Yufit, D.S.; Cobb, S.L.; Coxon, C.R.

doi:10.1016/j.jfluchem.2015.02.007

Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB)

Tatum, N.J.; Yufit, D.S.; Cobb, S.L.; Coxon, C.R.

Authors

N.J. Tatum

D.S. Yufit

Professor Steven Cobb s.l.cobb@durham.ac.uk
Professor

C.R. Coxon

Abstract

Herein we report the first X-ray crystal structure of the well-known (S)-l-ala-Ni-BPB complex (1) and compare this with the X-ray crystal structures obtained for two novel fluorinated (S)-l-ala-Ni-BPB complexes (8 and 12) that contain either an S- or R-fluorine atom on the proline ring of the BPB ligand. The preparation of complexes 8 and 12 has been enabled by the synthesis of two new fluorinated BPB ligands (7 and 11). In this work we looked to observe the structural effects that the introduction of a single fluorine atom had on the known complex 1. Arising from this, we highlight a novel fluorine–nickel interaction that on the basis of DFT calculations appears to provide additional stabilization to one of the complexes prepared ((S)-l-ala-Ni-BPB complex 8).

Citation

Tatum, N., Yufit, D., Cobb, S., & Coxon, C. (2015). Synthesis, Ni(II) Schiff base complexation and structural analysis of fluorinated analogs of the ligand (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB). Journal of Fluorine Chemistry, 173, 77-83. https://doi.org/10.1016/j.jfluchem.2015.02.007

Journal Article Type	Article
Acceptance Date	Feb 12, 2015
Publication Date	May 1, 2015
Deposit Date	May 22, 2015
Publicly Available Date	May 22, 2015
Journal	Journal of Fluorine Chemistry
Print ISSN	0022-1139
Publisher	Elsevier
Peer Reviewed	Peer Reviewed
Volume	173
Pages	77-83
DOI	https://doi.org/10.1016/j.jfluchem.2015.02.007
Keywords	Fluoro-proline, Fluorinated ligands, Gauche effect, Nickel complex, X-ray crystallography.

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© 2015 The Authors. Published by Elsevier B.V. This is an open access article under the CC BY license
(http://creativecommons.org/licenses/by/4.0/).