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Characterization of hydrogen-bonded aggregates in chloroform by electrospray ionization mass spectrometry

Journal Article · · Journal of Organic Chemistry
DOI:https://doi.org/10.1021/jo951345g· OSTI ID:501786
; ;  [1]
  1. Pacific Northwest Labs., Richland, WA (United States); and others

The authors report the measurement of molecular weights of seven noncovalent aggregates based on the cyanuric acid-melamine (CA{center_dot}M) lattice, obtained from negative ion spectra using electrospray ionization mass spectrometry (ESI-MS). These results are important for three reasons. First, past assignments of the structures of these noncovalent assemblies has been based on inferences from a range of indirect techniques: H and {sup 13}C NMR spectroscopies, titration experiments, gel permeation chromatrography (GPC), and vapor phase osmometry (VPO). A more accurate determination of mass than that provided by GPC and VPO offers additional support for the assigned stoichiometries and structures. Second, the ability to obtain mass spectra of noncovalent aggregates that are of limited stability, those that form only in aprotic, nonpolar organic solvents, provides a further demonstration of the value of ESI-MS as a technique with which to study molecular recognition and self-assembly in nonaqueous solutions. Third, the use of Ph{sub 4}PCl as an organic-soluble, charge carrier is undocumented. These results also suggest that thermal dissociation experiments may be useful in determining the relative stabilities of noncovalent assemblies. 3 figs., 3 tabs.

OSTI ID:
501786
Journal Information:
Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 6 Vol. 61; ISSN 0022-3263; ISSN JOCEAH
Country of Publication:
United States
Language:
English

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