Estimation of cation binding properties in crown and lariat ether complexes using fast atom bombardment mass spectrometry

Toshio Takahashi, Akira Uchiyama, Kaoru Yamada, Bert C. Lynn, George W. Gokel

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

The complexation behavior of crown and lariat ethers with alkali metal ions has been asessed by means of FAB-mass spectrometry and shown to correlate semi-quantitatively with findings obtained in the solution phase.

Original languageEnglish
Pages (from-to)3825-3828
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number27
DOIs
StatePublished - Jun 1992

Bibliographical note

Funding Information:
References Address correspondence to either author. We gratefully acknowledge partial support of this work by a grant [GM 36262) from the NIH. %hang. H.; Chu. I.-H.: Leming, S.; Dearden, D.V.; J. Am Chem Sot. lBB1, 113. 7415. (a) Dishong, D.M.: Diamond, C.J.: Cinoman, MI.; Gokel, G.W.: J. Am Chem Sot. 1983, 105, 566. (b) Schultz, Rk: Dishong. D.M.: Gokel, G.W.; J. Am Chem. Sot. 1982, 104, 625. (c) .Schultz, RA.: White, B.D.: Dishong. D.M.: Arnold, K.A.; Gokel. G.W.: J. Am. Chem Sot. 1986. 107, 6659. (d) Gatto, V.J.; Gokel, G.W.; J. Am Chem Sot. 1984, 106, 8241. (;I) Johnstone. RAW.; Lewis, LAS.; J. C. S. Chem Comrnun. 1984. 1268. (b) Johnstone. RkW.: Lewis. LAS.: Int. J. Mass Spxtrom 1983. 46. 451. (c) Johnstone. RA.W.: Lewis, I.A.S.; Rose, M.E.; Tetrahedron 1983, 39. 1597. Honas. G.: Boss, C.: Vegnon. M.R; Rapid Cot-nnum Mass Spcctrom 1988, 2.88. Yamada. K.: Matsutanf. S.: Uchiyama. A: Takahashi. T.: J. IncL Phenom 1991. II. 49. FAH spectra were acquired on a JEOL DX 303 by using a 6-8 KeV Xe primary beam and a r-nitrobenzyl alcohol matrix. The spectra reported herein were peak averaged over 4 scans losing a DA 5000 data system. The compounds reported in this paper were prepared as previously described.2 In a typical experiment, m-nitrobenzyl alcohol (1 y.~), 1 ~,LLof a 50m~ lariat ether solution (CHCls). and 1 PL of a 50 mM aqueous solution of metal chloride were carefully mixed on the FAD probe. Binding constants for the lariat ethers were determined potentiometrically in anhydrous methanol as previously described.2 hioue. Y. and Gokel, G.W. (Eds.), Cation Sinding by Macrocycles, Marcel Dekker, New York, 1990. Nakano. A.: Xie, 9.: Mall&n, J.V.: Echegoyen. L.: Gokel, G.W.; J. Am Chem Sot. 1990, 112, 1287. Gandour, RD.: Fronczek, F.R; Gatto, V.J.; Minganti. C.: Schultz, RA.: White, B.D.; Arnold, K.A.; Mazaocchi, D.: Miller, S.R: Gokel, G.W.: J. Am Chem Sot. 1986. 108, 4678.

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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