Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex
Abstract
A dicopper complex featuring a symmetrically bridging nitrile ligand and supported by a binucleating naphthyridine-based ligand, [Cu2(μ-η1:η1-MeCN)DPFN](NTf2)2, was treated with phosphaalkynes (RC$$\equiv$$P, isoelectronic analogues of nitriles) to yield dicopper complexes that exhibit phosphaalkynes in rare μ-η2:η2 binding coordination modes. X-ray crystallography revealed that these unusual “tilted” structures exist in two isomeric forms (R “up” vs. R “sideways”), depending on the steric profile of the phosphaalkyne's alkyl group (R = Me, Ad, or tBu). Only one isomer is observed in both solution and the solid state for R = Me (sideways) and tBu (up). With intermediate steric bulk (R = Ad), the energy difference between the two geometries is small enough that both are observed in solution, and NMR spectroscopy and computations indicate that the solid-state structure corresponds to the minor isomer observed in solution. Meanwhile, treatment of [Cu2(μ-η1:η1-MeCN)DPFN](NTf2)2 with 2-butyne affords [Cu2(μ-η2:η2-(MeC$$\equiv$$CMe))DPFN](NTf2)2: its similar ligand geometry demonstrates that the tilted μ-η2:η2 binding mode is not limited to phosphaalkynes but reflects a more general trend, which can be rationalized via an NBO analysis showing maximization of π-backbonding.
- Authors:
-
[1];
[1];
[3];
[1]
- Department of Chemistry, University of California, Berkeley, Berkeley, USA, Chemical Sciences Division
- Department of Chemistry, University of California, Berkeley, Berkeley, USA
- Institut für Anorganische Chemie, Universität Regensburg, 93040 Regensburg, Germany
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Institutes of Health (NIH); Alexander von Humboldt Foundation; National Science Foundation (NSF)
- OSTI Identifier:
- 1581662
- Alternate Identifier(s):
- OSTI ID: 1615295
- Grant/Contract Number:
- AC02-05CH11231; S10-RR027172; S10OD023532; DGE 1106400; SRR023679A; 1S10RR016634-01; GM68933
- Resource Type:
- Published Article
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Name: Chemical Science Journal Volume: 11 Journal Issue: 6; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Nicolay, Amélie, Ziegler, Micah S., Small, David W., Grünbauer, Rebecca, Scheer, Manfred, and Tilley, T. Don. Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex. United Kingdom: N. p., 2019.
Web. doi:10.1039/C9SC05835D.
Nicolay, Amélie, Ziegler, Micah S., Small, David W., Grünbauer, Rebecca, Scheer, Manfred, & Tilley, T. Don. Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex. United Kingdom. doi:10.1039/C9SC05835D.
Nicolay, Amélie, Ziegler, Micah S., Small, David W., Grünbauer, Rebecca, Scheer, Manfred, and Tilley, T. Don. Thu .
"Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex". United Kingdom. doi:10.1039/C9SC05835D.
@article{osti_1581662,
title = {Isomerism and dynamic behavior of bridging phosphaalkynes bound to a dicopper complex},
author = {Nicolay, Amélie and Ziegler, Micah S. and Small, David W. and Grünbauer, Rebecca and Scheer, Manfred and Tilley, T. Don},
abstractNote = {A dicopper complex featuring a symmetrically bridging nitrile ligand and supported by a binucleating naphthyridine-based ligand, [Cu2(μ-η1:η1-MeCN)DPFN](NTf2)2, was treated with phosphaalkynes (RC$\equiv$P, isoelectronic analogues of nitriles) to yield dicopper complexes that exhibit phosphaalkynes in rare μ-η2:η2 binding coordination modes. X-ray crystallography revealed that these unusual “tilted” structures exist in two isomeric forms (R “up” vs. R “sideways”), depending on the steric profile of the phosphaalkyne's alkyl group (R = Me, Ad, or tBu). Only one isomer is observed in both solution and the solid state for R = Me (sideways) and tBu (up). With intermediate steric bulk (R = Ad), the energy difference between the two geometries is small enough that both are observed in solution, and NMR spectroscopy and computations indicate that the solid-state structure corresponds to the minor isomer observed in solution. Meanwhile, treatment of [Cu2(μ-η1:η1-MeCN)DPFN](NTf2)2 with 2-butyne affords [Cu2(μ-η2:η2-(MeC$\equiv$CMe))DPFN](NTf2)2: its similar ligand geometry demonstrates that the tilted μ-η2:η2 binding mode is not limited to phosphaalkynes but reflects a more general trend, which can be rationalized via an NBO analysis showing maximization of π-backbonding.},
doi = {10.1039/C9SC05835D},
journal = {Chemical Science},
number = 6,
volume = 11,
place = {United Kingdom},
year = {2019},
month = {12}
}
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DOI: 10.1039/C9SC05835D
DOI: 10.1039/C9SC05835D
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