Comparison of gas-phase proton and ammonium ion affinities of crown ethers and related acyclic analogs

Liou, Chien Chung; Brodbelt, Jennifer S.

doi:10.1021/ja00043a021

Cited by 73 publications

(33 citation statements)

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“…Several recent studies utilizing tandem quadrupole and quadrupolar ion trap mass spectrometry have investigated various crown and acyclic ethers as model host compounds and have described extensively the interactions of these factors in gas phase polyether/ammonium ion com- plexes. [25][26][27] These researchers consistently report effective hydrogen-bonding between ammonium ions and the polyether host oxygens as comprising the predominant binding interactions in the complexes investigated. Polyether molecules offering numerous sites for complexation of ammonium ions by multiple hydrogen-bonding interactions indicated the formation of strongly bound, internally excited complexes that offered high energy barriers to decomposition, thus resulting in the observed skeletal covalent bond cleavages.…”

Section: Resultsmentioning

confidence: 70%

Electrospray ionization mass spectrometry with in-source collision-induced dissociation of monensin factors and related metabolites

Kiehl

Julian

Kennington

1998

Rapid Commun. Mass Spectrom.

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Monensins are a series of polyether ionophore antibiotic factors produced by Streptomyces cinnamonensis. Three monensin factors and four metabolites of monensin A isolated from cattle feces were investigated by electrospray ionization mass spectrometry (ESI-MS). In-source collision-induced dissociation (CID) of the alkali metal and ammonium molecular ion adducts of monensin produce strikingly different mass spectra, with the alkali metal complexes exhibiting little dissociation and the ammoniated forms characterized by extensive fragmentation of the polyether skeletal structure with the production of several structurally diagnostic ions. The observed fragmentation of ammoniated monensin primarily involves opening of the cyclic ether rings and consecutive H 2 O losses. The propensity of ammoniated monensin derivatives toward skeletal fragmentation may involve the complexation of the thermally labile NH 4 ion through multiple hydrogen-bonding interactions with the polyether complexing oxygens resulting in decreased stability of the resultant complex. Comparison of the in-source CID spectra associated with the structurally similar compounds evaluated provides for the proposal of a general scheme for the fragmentation of ammoniated monensins and related compounds, the consistency of which indicates the usefulness of ESI-MS with insource CID in ionophore structure elucidation. # 1998 John Wiley & Sons, Ltd. Received 8 May 1998; Accepted 20 May 1998 Monensin is a polyether monocarboxylic acid ionophore and refers to a group of factors comprising an antibiotic complex first isolated from Streptomyces cinnamonensis.

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Section: Resultsmentioning

confidence: 70%

Electrospray ionization mass spectrometry with in-source collision-induced dissociation of monensin factors and related metabolites

Kiehl

Julian

Kennington

1998

Rapid Commun. Mass Spectrom.

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“…Due to multiple hydrogen bonding, relative ammonium ion affinities are much larger for the larger crown ethers than their proton affinities (Meot-Ner (Mautner), 1983;Liou & Brodbelt, 1992a, Wu & Brodbelt, 1993. Within the series of crowns, the binding energy of NH 4 þ ranks in the order of 12-crown-4 < 15-crown-5 < 18-crown-6 < 21-crown-7.…”

Section: A Ammonium Ion Affinitiesmentioning

confidence: 99%

Molecular recognition and supramolecular chemistry in the gas phase

Schalley

2001

Mass Spectrometry Reviews

289

178

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Supramolecular chemistry, in particular, the fields of molecular recognition and self-assembly, profit much from the development of soft ionization techniques and advanced methods for mass analysis and gas-phase chemistry. Vice versa, weakly bonded architectures and host-guest complexes represent a veritable challenge for the mass spectrometrist, leading to further development of methods and techniques. This review describes the state-of-the-art in this field, and includes topics such as the effects of solvation on meta binding to crown ethers, chiral discrimination of guests by chiral hosts, the elucidation of the secondary structure of self assembled complexes, and the mechanistic pathways of self assembly or the fragmentations of supramolecular complexes in the gas phase.

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“…Accurate experimental values of such fundamental quantities such as gas phase metal ion-ether bond dissociation enthalpies would provide an ideal component to theoretical predictions. Unfortunately, very few experimental studies conducted over past several decades were attempted to measure this quantity [18][19][20][21]. Although, extensive computational works [22][23][24][25][26][27][28][29][30][31][32][33][34][35] were done on conformational structures of crown ethers and their interaction with various metal ions either in gas phase or in solution, they were limited to the discrete type of interaction, i.e., interaction of single crown ether with a series of metal ions.…”

Section: Introductionmentioning

confidence: 99%

Preferential interaction of charged alkali metal ions (guest) within a narrow cavity of cyclic crown ethers (neutral host): A quantum chemical investigation

Boda²,

Ali³

2010

Journal of Molecular Structure: THEOCHEM

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Comparison of gas-phase proton and ammonium ion affinities of crown ethers and related acyclic analogs

Cited by 73 publications

References 0 publications

Electrospray ionization mass spectrometry with in-source collision-induced dissociation of monensin factors and related metabolites

Electrospray ionization mass spectrometry with in-source collision-induced dissociation of monensin factors and related metabolites

Molecular recognition and supramolecular chemistry in the gas phase

Preferential interaction of charged alkali metal ions (guest) within a narrow cavity of cyclic crown ethers (neutral host): A quantum chemical investigation

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