Versatility of the 1,1′-binaphthyl-2,2′-dicarboxylic acid host in solid-state inclusion: Crystal and molecular structures of the dimethylformamide (1:2), dimethyl sulphoxide (1:1), and bromobenzene (1:1) clathrates

Ingeborg Csöregh, Agneta Sjögren, Mátyás Czugler, Miklós Cserzö, Edwin Weber

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Abstract

The clathrate structures of the host 1,1′-binaphthyl-2,2′- dicarboxylic acid (1) with dimethylformamide, (2), dimethyl sulphoxide, (3), and bromobenzene, (4) as guest molecules have been studied. X-Ray structure analyses show that the capacity for inclusion is primarily dependent on the proton donor-acceptor (co-ordinating) ability of the host. Nevertheless, the structures are very different. In (2) [crystal data: a = 14.916(13), b = 9.882(10), c = 17.128(13) Å, p = 90.45(7)°, space group P2 1/c, Z = 4,Rf = 0.066 for 2 550 observations] the guest molecules can act both as proton donor and acceptor in hydrogen bonding with the host, in (3) [a = 12.912(5), 6 = 17.979(15), c = 9.702(7) Å, β = 110.79(7)°, P21/n, Z = 4, Rf = 0.080 for 1 932 reflexions] the guest molecule acts as proton acceptor only, and in (4) [a = 9.955(2), b = 10.426(3), c = 12.005(3) Å, α = 77.34(2), β = 93.02(2), γ = 104.59(2)°, P1, Z = 2, Rf = 0.074 for 1 555 observations] a 'true' clathrate structure is established, with bromobenzene being incorporated in a hydrogen-bonded host matrix of (1). The decrease in co-ordinating bond strength between host and guest is also manifested in the gradual increase of disorder observed for these guest species. Conclusions concerning the clathrate formation selectivity of (1) are derived from the structural observations.

Original languageEnglish
Pages (from-to)507-513
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number4
DOIs
Publication statusPublished - 1986

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Dimethylformamide
Dicarboxylic Acids
Dimethyl Sulfoxide
Molecular structure
Protons
Crystal structure
Molecules
Hydrogen
Hydrogen bonds
X rays
Crystals
bromobenzene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

@article{40621396ac3142daa5bfacca8499e937,
title = "Versatility of the 1,1′-binaphthyl-2,2′-dicarboxylic acid host in solid-state inclusion: Crystal and molecular structures of the dimethylformamide (1:2), dimethyl sulphoxide (1:1), and bromobenzene (1:1) clathrates",
abstract = "The clathrate structures of the host 1,1′-binaphthyl-2,2′- dicarboxylic acid (1) with dimethylformamide, (2), dimethyl sulphoxide, (3), and bromobenzene, (4) as guest molecules have been studied. X-Ray structure analyses show that the capacity for inclusion is primarily dependent on the proton donor-acceptor (co-ordinating) ability of the host. Nevertheless, the structures are very different. In (2) [crystal data: a = 14.916(13), b = 9.882(10), c = 17.128(13) {\AA}, p = 90.45(7)°, space group P2 1/c, Z = 4,Rf = 0.066 for 2 550 observations] the guest molecules can act both as proton donor and acceptor in hydrogen bonding with the host, in (3) [a = 12.912(5), 6 = 17.979(15), c = 9.702(7) {\AA}, β = 110.79(7)°, P21/n, Z = 4, Rf = 0.080 for 1 932 reflexions] the guest molecule acts as proton acceptor only, and in (4) [a = 9.955(2), b = 10.426(3), c = 12.005(3) {\AA}, α = 77.34(2), β = 93.02(2), γ = 104.59(2)°, P1, Z = 2, Rf = 0.074 for 1 555 observations] a 'true' clathrate structure is established, with bromobenzene being incorporated in a hydrogen-bonded host matrix of (1). The decrease in co-ordinating bond strength between host and guest is also manifested in the gradual increase of disorder observed for these guest species. Conclusions concerning the clathrate formation selectivity of (1) are derived from the structural observations.",
author = "Ingeborg Cs{\"o}regh and Agneta Sj{\"o}gren and M{\'a}ty{\'a}s Czugler and Mikl{\'o}s Cserz{\"o} and Edwin Weber",
year = "1986",
doi = "10.1039/P29860000507",
language = "English",
pages = "507--513",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Royal Society of Chemistry",
number = "4",

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TY - JOUR

T1 - Versatility of the 1,1′-binaphthyl-2,2′-dicarboxylic acid host in solid-state inclusion

T2 - Crystal and molecular structures of the dimethylformamide (1:2), dimethyl sulphoxide (1:1), and bromobenzene (1:1) clathrates

AU - Csöregh, Ingeborg

AU - Sjögren, Agneta

AU - Czugler, Mátyás

AU - Cserzö, Miklós

AU - Weber, Edwin

PY - 1986

Y1 - 1986

N2 - The clathrate structures of the host 1,1′-binaphthyl-2,2′- dicarboxylic acid (1) with dimethylformamide, (2), dimethyl sulphoxide, (3), and bromobenzene, (4) as guest molecules have been studied. X-Ray structure analyses show that the capacity for inclusion is primarily dependent on the proton donor-acceptor (co-ordinating) ability of the host. Nevertheless, the structures are very different. In (2) [crystal data: a = 14.916(13), b = 9.882(10), c = 17.128(13) Å, p = 90.45(7)°, space group P2 1/c, Z = 4,Rf = 0.066 for 2 550 observations] the guest molecules can act both as proton donor and acceptor in hydrogen bonding with the host, in (3) [a = 12.912(5), 6 = 17.979(15), c = 9.702(7) Å, β = 110.79(7)°, P21/n, Z = 4, Rf = 0.080 for 1 932 reflexions] the guest molecule acts as proton acceptor only, and in (4) [a = 9.955(2), b = 10.426(3), c = 12.005(3) Å, α = 77.34(2), β = 93.02(2), γ = 104.59(2)°, P1, Z = 2, Rf = 0.074 for 1 555 observations] a 'true' clathrate structure is established, with bromobenzene being incorporated in a hydrogen-bonded host matrix of (1). The decrease in co-ordinating bond strength between host and guest is also manifested in the gradual increase of disorder observed for these guest species. Conclusions concerning the clathrate formation selectivity of (1) are derived from the structural observations.

AB - The clathrate structures of the host 1,1′-binaphthyl-2,2′- dicarboxylic acid (1) with dimethylformamide, (2), dimethyl sulphoxide, (3), and bromobenzene, (4) as guest molecules have been studied. X-Ray structure analyses show that the capacity for inclusion is primarily dependent on the proton donor-acceptor (co-ordinating) ability of the host. Nevertheless, the structures are very different. In (2) [crystal data: a = 14.916(13), b = 9.882(10), c = 17.128(13) Å, p = 90.45(7)°, space group P2 1/c, Z = 4,Rf = 0.066 for 2 550 observations] the guest molecules can act both as proton donor and acceptor in hydrogen bonding with the host, in (3) [a = 12.912(5), 6 = 17.979(15), c = 9.702(7) Å, β = 110.79(7)°, P21/n, Z = 4, Rf = 0.080 for 1 932 reflexions] the guest molecule acts as proton acceptor only, and in (4) [a = 9.955(2), b = 10.426(3), c = 12.005(3) Å, α = 77.34(2), β = 93.02(2), γ = 104.59(2)°, P1, Z = 2, Rf = 0.074 for 1 555 observations] a 'true' clathrate structure is established, with bromobenzene being incorporated in a hydrogen-bonded host matrix of (1). The decrease in co-ordinating bond strength between host and guest is also manifested in the gradual increase of disorder observed for these guest species. Conclusions concerning the clathrate formation selectivity of (1) are derived from the structural observations.

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