Versatility in stabilization of crystalline inclusion complexes of a bulky diol host by various closely related acidic and ester guests

Ingeborg Csöregh, Shinya Hirano, Shinji Toyota, P. Bombicz, Fumio Toda

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

In order to stabilize carboxylic acid and ester molecules in a monomeric state for spectroscopic investigation, solid inclusion formation experiments have been carried out with the 2,2′-bis(hydroxydiphenylmethyl)-1,1′- biphenyl host molecule (1) and various carboxylic acid and ester compounds (27 different species). The IR spectra of the included guest molecules have been registered, and single crystals of five selected complexes (1a-e), containing formic acid (1a), acetic acid (1b), propionic acid (1c), butanoic acid (1d), and ethyl acetate (1e) as guest component, respectively, have been studied by X-ray diffraction. The IR spectroscopic investigations yielded some unexpected νC=O absorption frequencies for two of the guest molecules, namely acetic and propionic acids, but not for the other, closely related guest acid or ester molecules in this study. The X-ray diffraction analyses showed the diol host 1 molecule to assemble into similar hexamer associates in all studied crystals, with various acid/ester guests and some water molecules being included in uniform cyclic cavities inside the hexa-host units. Hence, the five solid inclusion compounds have analogous crystal shapes, unit cell dimensions and crystallographic symmetries, and their host frameworks exhibit a high degree of isostructurality. In spite of the pronounced similarities, the X-ray structural study also indicated remarkable differences in the way the various guest molecules stabilize the respective crystal structures, thus giving a possible explanation for the observed IR absorption anomalies.

Original languageEnglish
Pages (from-to)60-69
Number of pages10
JournalCrystEngComm
Volume6
DOIs
Publication statusPublished - Mar 3 2004

Fingerprint

versatility
esters
Esters
Stabilization
stabilization
inclusions
Crystalline materials
Molecules
molecules
propionic acid
Propionic acid
formic acid
Carboxylic Acids
Carboxylic acids
acetic acid
Acetic acid
carboxylic acids
Acetic Acid
acids
X ray diffraction

ASJC Scopus subject areas

  • Condensed Matter Physics

Cite this

Versatility in stabilization of crystalline inclusion complexes of a bulky diol host by various closely related acidic and ester guests. / Csöregh, Ingeborg; Hirano, Shinya; Toyota, Shinji; Bombicz, P.; Toda, Fumio.

In: CrystEngComm, Vol. 6, 03.03.2004, p. 60-69.

Research output: Contribution to journalArticle

@article{77c311263d1c4a819b8614404e02a82f,
title = "Versatility in stabilization of crystalline inclusion complexes of a bulky diol host by various closely related acidic and ester guests",
abstract = "In order to stabilize carboxylic acid and ester molecules in a monomeric state for spectroscopic investigation, solid inclusion formation experiments have been carried out with the 2,2′-bis(hydroxydiphenylmethyl)-1,1′- biphenyl host molecule (1) and various carboxylic acid and ester compounds (27 different species). The IR spectra of the included guest molecules have been registered, and single crystals of five selected complexes (1a-e), containing formic acid (1a), acetic acid (1b), propionic acid (1c), butanoic acid (1d), and ethyl acetate (1e) as guest component, respectively, have been studied by X-ray diffraction. The IR spectroscopic investigations yielded some unexpected νC=O absorption frequencies for two of the guest molecules, namely acetic and propionic acids, but not for the other, closely related guest acid or ester molecules in this study. The X-ray diffraction analyses showed the diol host 1 molecule to assemble into similar hexamer associates in all studied crystals, with various acid/ester guests and some water molecules being included in uniform cyclic cavities inside the hexa-host units. Hence, the five solid inclusion compounds have analogous crystal shapes, unit cell dimensions and crystallographic symmetries, and their host frameworks exhibit a high degree of isostructurality. In spite of the pronounced similarities, the X-ray structural study also indicated remarkable differences in the way the various guest molecules stabilize the respective crystal structures, thus giving a possible explanation for the observed IR absorption anomalies.",
author = "Ingeborg Cs{\"o}regh and Shinya Hirano and Shinji Toyota and P. Bombicz and Fumio Toda",
year = "2004",
month = "3",
day = "3",
doi = "10.1039/b316094g",
language = "English",
volume = "6",
pages = "60--69",
journal = "CrystEngComm",
issn = "1466-8033",
publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Versatility in stabilization of crystalline inclusion complexes of a bulky diol host by various closely related acidic and ester guests

AU - Csöregh, Ingeborg

AU - Hirano, Shinya

AU - Toyota, Shinji

AU - Bombicz, P.

AU - Toda, Fumio

PY - 2004/3/3

Y1 - 2004/3/3

N2 - In order to stabilize carboxylic acid and ester molecules in a monomeric state for spectroscopic investigation, solid inclusion formation experiments have been carried out with the 2,2′-bis(hydroxydiphenylmethyl)-1,1′- biphenyl host molecule (1) and various carboxylic acid and ester compounds (27 different species). The IR spectra of the included guest molecules have been registered, and single crystals of five selected complexes (1a-e), containing formic acid (1a), acetic acid (1b), propionic acid (1c), butanoic acid (1d), and ethyl acetate (1e) as guest component, respectively, have been studied by X-ray diffraction. The IR spectroscopic investigations yielded some unexpected νC=O absorption frequencies for two of the guest molecules, namely acetic and propionic acids, but not for the other, closely related guest acid or ester molecules in this study. The X-ray diffraction analyses showed the diol host 1 molecule to assemble into similar hexamer associates in all studied crystals, with various acid/ester guests and some water molecules being included in uniform cyclic cavities inside the hexa-host units. Hence, the five solid inclusion compounds have analogous crystal shapes, unit cell dimensions and crystallographic symmetries, and their host frameworks exhibit a high degree of isostructurality. In spite of the pronounced similarities, the X-ray structural study also indicated remarkable differences in the way the various guest molecules stabilize the respective crystal structures, thus giving a possible explanation for the observed IR absorption anomalies.

AB - In order to stabilize carboxylic acid and ester molecules in a monomeric state for spectroscopic investigation, solid inclusion formation experiments have been carried out with the 2,2′-bis(hydroxydiphenylmethyl)-1,1′- biphenyl host molecule (1) and various carboxylic acid and ester compounds (27 different species). The IR spectra of the included guest molecules have been registered, and single crystals of five selected complexes (1a-e), containing formic acid (1a), acetic acid (1b), propionic acid (1c), butanoic acid (1d), and ethyl acetate (1e) as guest component, respectively, have been studied by X-ray diffraction. The IR spectroscopic investigations yielded some unexpected νC=O absorption frequencies for two of the guest molecules, namely acetic and propionic acids, but not for the other, closely related guest acid or ester molecules in this study. The X-ray diffraction analyses showed the diol host 1 molecule to assemble into similar hexamer associates in all studied crystals, with various acid/ester guests and some water molecules being included in uniform cyclic cavities inside the hexa-host units. Hence, the five solid inclusion compounds have analogous crystal shapes, unit cell dimensions and crystallographic symmetries, and their host frameworks exhibit a high degree of isostructurality. In spite of the pronounced similarities, the X-ray structural study also indicated remarkable differences in the way the various guest molecules stabilize the respective crystal structures, thus giving a possible explanation for the observed IR absorption anomalies.

UR - http://www.scopus.com/inward/record.url?scp=16244395131&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=16244395131&partnerID=8YFLogxK

U2 - 10.1039/b316094g

DO - 10.1039/b316094g

M3 - Article

VL - 6

SP - 60

EP - 69

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

ER -