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

doi:10.1016/S0040-4039(00)74795-2

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

Producción científica: Article › revisión exhaustiva

37 Citas (Scopus)

Resumen

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.

Idioma original	English
Páginas (desde-hasta)	3825-3828
Número de páginas	4
Publicación	Tetrahedron Letters
Volumen	33
N.º	27
DOI	https://doi.org/10.1016/S0040-4039(00)74795-2
Estado	Published - jun 1992

Nota bibliográfica

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.

Financiación

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.

Financiadores
National Institutes of Health (NIH)

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)74795-2

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@article{84f41dfd7699411e91e90d67d5808f64,

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

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.",

author = "Toshio Takahashi and Akira Uchiyama and Kaoru Yamada and Lynn, \{Bert C.\} and Gokel, \{George W.\}",

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.\textasciitilde{}), 1 \textasciitilde{},LLof a 50m\textasciitilde{} 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.",

year = "1992",

month = jun,

doi = "10.1016/S0040-4039(00)74795-2",

language = "English",

volume = "33",

pages = "3825--3828",

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TY - JOUR

T1 - Estimation of cation binding properties in crown and lariat ether complexes using fast atom bombardment mass spectrometry

AU - Takahashi, Toshio

AU - Uchiyama, Akira

AU - Yamada, Kaoru

AU - Lynn, Bert C.

AU - Gokel, George W.

N1 - 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.

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0026750656

UR - https://www.scopus.com/pages/publications/0026750656#tab=citedBy

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DO - 10.1016/S0040-4039(00)74795-2

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AN - SCOPUS:0026750656

SN - 0040-4039

VL - 33

SP - 3825

EP - 3828

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

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

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Nota bibliográfica

Financiación

ASJC Scopus subject areas

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