Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6A-(ω-aminoalkylamino)-6A-deoxy-β-cyclodextrins in aqueous solution

Suzanna D. Kean; Bruce L. May; Philip Clements; Stephen F. Lincoln; Christopher J. Easton

doi:10.1039/A806488A

Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6^A-(ω-aminoalkylamino)-6^A-deoxy-β-cyclodextrins in aqueous solution

Suzanna D. Kean, Bruce L. May, Philip Clements, Stephen F. Lincoln, Christopher J. Easton

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

A potentiometric titration study of the complexion of the guests benzoic acid, 4-methylbenzoic acid and (RS)-2-phenylpropanoic acid and their conjugate bases by host 6^A-(ω-aminoalkylamino)-6 ^A-deoxy-β-cyclodextrins, where the ω-aminoalkylamino groups are -NH(CH₂)_nNH₂ (n = 2, 3, 4 and 6), is reported. Of the 64 host-guest complexes whose formation is statistically possible over the pH range 2.0-12.0 studied, 35 were detected. Their stability constants range from 140 ± 35 dm³ mol^-1 for the [βCDNH(CH₂)₂NH₃·4-methylbenzoate] complex to 1760 ± 150 dm³ mol^-1 for the [βCDNH(CH₂)₆NH ₂·(S)-2-phenylpropanoate]^- complex at 298.2 K and I = 0.10 mol dm^-3 (NaClO₄). The charge and hydrophobicity of both host and guest appear to be significant factors in the variation of host-guest complex stability. Qualitative structural information on the host-guest complexes obtained from 600 MHz ¹H NMR ROESY spectroscopy is generally consistent with the structures generated by molecular modelling.

Original language	English
Pages (from-to)	1257-1263
Number of pages	7
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	6
DOIs	https://doi.org/10.1039/A806488A
Publication status	Published - 1 Jun 1999
Externally published	Yes

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@article{e374e04d37164b2993347c3d57c76c34,

title = "Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6A-(ω-aminoalkylamino)-6A-deoxy-β-cyclodextrins in aqueous solution",

abstract = "A potentiometric titration study of the complexion of the guests benzoic acid, 4-methylbenzoic acid and (RS)-2-phenylpropanoic acid and their conjugate bases by host 6A-(ω-aminoalkylamino)-6 A-deoxy-β-cyclodextrins, where the ω-aminoalkylamino groups are -NH(CH2)nNH2 (n = 2, 3, 4 and 6), is reported. Of the 64 host-guest complexes whose formation is statistically possible over the pH range 2.0-12.0 studied, 35 were detected. Their stability constants range from 140 ± 35 dm3 mol-1 for the [βCDNH(CH2)2NH3·4-methylbenzoate] complex to 1760 ± 150 dm3 mol-1 for the [βCDNH(CH2)6NH 2·(S)-2-phenylpropanoate]- complex at 298.2 K and I = 0.10 mol dm-3 (NaClO4). The charge and hydrophobicity of both host and guest appear to be significant factors in the variation of host-guest complex stability. Qualitative structural information on the host-guest complexes obtained from 600 MHz 1H NMR ROESY spectroscopy is generally consistent with the structures generated by molecular modelling.",

author = "Kean, {Suzanna D.} and May, {Bruce L.} and Philip Clements and Lincoln, {Stephen F.} and Easton, {Christopher J.}",

year = "1999",

month = jun,

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doi = "10.1039/A806488A",

language = "English",

pages = "1257--1263",

journal = "Journal of the Chemical Society. Perkin Transactions 2",

issn = "0300-9580",

publisher = "Royal Society of Chemistry",

number = "6",

}

Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6^A-(ω-aminoalkylamino)-6^A-deoxy-β-cyclodextrins in aqueous solution. / Kean, Suzanna D.; May, Bruce L.; Clements, Philip et al.
In: Journal of the Chemical Society. Perkin Transactions 2, No. 6, 01.06.1999, p. 1257-1263.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6A-(ω-aminoalkylamino)-6A-deoxy-β-cyclodextrins in aqueous solution

AU - Kean, Suzanna D.

AU - May, Bruce L.

AU - Clements, Philip

AU - Lincoln, Stephen F.

AU - Easton, Christopher J.

PY - 1999/6/1

Y1 - 1999/6/1

N2 - A potentiometric titration study of the complexion of the guests benzoic acid, 4-methylbenzoic acid and (RS)-2-phenylpropanoic acid and their conjugate bases by host 6A-(ω-aminoalkylamino)-6 A-deoxy-β-cyclodextrins, where the ω-aminoalkylamino groups are -NH(CH2)nNH2 (n = 2, 3, 4 and 6), is reported. Of the 64 host-guest complexes whose formation is statistically possible over the pH range 2.0-12.0 studied, 35 were detected. Their stability constants range from 140 ± 35 dm3 mol-1 for the [βCDNH(CH2)2NH3·4-methylbenzoate] complex to 1760 ± 150 dm3 mol-1 for the [βCDNH(CH2)6NH 2·(S)-2-phenylpropanoate]- complex at 298.2 K and I = 0.10 mol dm-3 (NaClO4). The charge and hydrophobicity of both host and guest appear to be significant factors in the variation of host-guest complex stability. Qualitative structural information on the host-guest complexes obtained from 600 MHz 1H NMR ROESY spectroscopy is generally consistent with the structures generated by molecular modelling.

AB - A potentiometric titration study of the complexion of the guests benzoic acid, 4-methylbenzoic acid and (RS)-2-phenylpropanoic acid and their conjugate bases by host 6A-(ω-aminoalkylamino)-6 A-deoxy-β-cyclodextrins, where the ω-aminoalkylamino groups are -NH(CH2)nNH2 (n = 2, 3, 4 and 6), is reported. Of the 64 host-guest complexes whose formation is statistically possible over the pH range 2.0-12.0 studied, 35 were detected. Their stability constants range from 140 ± 35 dm3 mol-1 for the [βCDNH(CH2)2NH3·4-methylbenzoate] complex to 1760 ± 150 dm3 mol-1 for the [βCDNH(CH2)6NH 2·(S)-2-phenylpropanoate]- complex at 298.2 K and I = 0.10 mol dm-3 (NaClO4). The charge and hydrophobicity of both host and guest appear to be significant factors in the variation of host-guest complex stability. Qualitative structural information on the host-guest complexes obtained from 600 MHz 1H NMR ROESY spectroscopy is generally consistent with the structures generated by molecular modelling.

U2 - 10.1039/A806488A

DO - 10.1039/A806488A

M3 - Article

AN - SCOPUS:0000599406

SN - 0300-9580

SP - 1257

EP - 1263

JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

IS - 6

ER -

Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6A-(ω-aminoalkylamino)-6A-deoxy-β-cyclodextrins in aqueous solution

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Host-guest complexation of aromatic carboxylic acids and their conjugate bases by 6^A-(ω-aminoalkylamino)-6^A-deoxy-β-cyclodextrins in aqueous solution