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Related Experiment Video

Updated: Jul 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Proton sponge phosphines: electrospray-active ligands.

Nicola J Farrer¹, Robert McDonald, J Scott McIndoe

¹Department of Chemistry, The University of Cambridge, Lensfield Road, Cambridge, UKCB2 1EW.

Dalton Transactions (Cambridge, England : 2003)

|October 4, 2006

Summary

A novel proton sponge phosphine ligand enhances electrospray ionization mass spectrometry (ESI-MS) analysis. This ligand efficiently forms protonated molecules ([M + H]+) for sensitive detection of metal complexes.

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Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

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Last Updated: Jul 19, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

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Published on: November 22, 2016

Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers

Published on: May 12, 2023

Area of Science:

Organometallic Chemistry
Analytical Chemistry
Mass Spectrometry

Background:

Electrospray ionization mass spectrometry (ESI-MS) is a powerful analytical technique.
Analysis of neutral metal complexes by ESI-MS can be challenging.
Proton sponges are strong Lewis bases capable of stabilizing cations.

Purpose of the Study:

To develop a novel phosphine ligand incorporating a proton sponge moiety.
To investigate the utility of this ligand for enhancing ESI-MS analysis of neutral complexes.
To characterize the ligand and its metal complexes.

Main Methods:

Synthesis of 1,8-bis(dimethylamino)naphthyldiphenylphosphine (3) and bis{1,8-bis(dimethylamino)naphthyl}phenylphosphine (4).
Complexation of ligand 3 with metal carbonyl precursors (Fe, Mn, W).
Structural characterization of ligand and complex compounds using X-ray crystallography and ESI-MS.

Main Results:

Ligand 3 demonstrated high efficiency and selectivity in forming exclusively [M + H]+ ions.
Near 100% ionization efficiency was achieved for ligand 3 in the presence of H+.
Structurally characterized compounds include ligands 3, 4, a salt 3.HBr.EtOH, and an iron complex 5c.

Conclusions:

Attachment of a proton sponge to a phosphine ligand significantly improves ESI-MS detectability of neutral complexes.
The developed ligand enables sensitive detection of metal complexes at very low concentrations.
This strategy offers a valuable tool for the analysis of organometallic compounds.