Solid-state binding of dimethyl sulphoxide involving carboxylic host molecules. X-ray crystal structures of four inclusion species View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1990-04

AUTHORS

Ingeborg Csöregh, Mátyás Czugler, Anne Ertan, Edwin Weber, Jochen Ahrendt

ABSTRACT

The crystal structures of four dimethyl sulphoxide (DMSO) inclusion compounds with different carboxylic acid hosts,1–4, have been studied by single crystal X-ray analysis. Crystals of thetrans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid inclusion compound (1a), [1 · DMSO (1: 1)] show monoclinic (P21/n) symmetry with the unit cell dimensionsa = 11.522(4),b = 18.658(2),c = 8.709(1) Å and β = 98.92(2)°. The clathrate of the 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (2a), [2 · DMSO (1: 2)] is triclinic (PĪ) with the cell dimensionsa = 15.043(7),b =9.657(4),c = 8.118(7) Å, α = 101.81(5), β = 96.05(4) and γ = 100.04(4)°. Triclinic (PĪ) symmetry is shown also by the inclusion compound of 9,10-dihydro-9,10-ethanoanthracene-11-monocarboxylic acid (3a) [3 · DMSO (1:1)] with the cell dimensionsa=6.3132(1),b=7.9846(2),c=17.5314(4) Å, α = 96.46(2), β = 87.08(2) and γ = 106.02(2)°. The 9,9′-bianthryl-2-monocarboxylic acid clathrate (4a) [4 · DMSO (1:1)] is monoclinic (P21/n) and the cell dimensions area = 19.625(18),b = 8.817(1),c = 14.076(8) Å and β = 97.92(6)°. In all these structures, the hosts show the same basic recognition pattern for the DMSO guest, involving a strong O-H ... O bond from the COON to the S=O group, and a possible C-H ... O type interaction between the carbonyl O atom of the host and a CH3 group of the guest. The crystals consist of discrete host-guest aggregates which are mainly held together by weak intermolecular interactions of the Van der Waals' type. The stoichiometries of the aggregates are, however, different. More... »

PAGES

275-287

References to SciGraph publications

  • 1983-03. A proposal for the classification and nomenclature of host-guest-type compounds in JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf01041884

    DOI

    http://dx.doi.org/10.1007/bf01041884

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1043246814


    Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
    Incoming Citations Browse incoming citations for this publication using opencitations.net

    JSON-LD is the canonical representation for SciGraph data.

    TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

    [
      {
        "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
        "about": [
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0307", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Theoretical and Computational Chemistry", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Chemical Sciences", 
            "type": "DefinedTerm"
          }
        ], 
        "author": [
          {
            "affiliation": {
              "alternateName": "Stockholm University", 
              "id": "https://www.grid.ac/institutes/grid.10548.38", 
              "name": [
                "Department of Structural Chemistry, Arrhenius Laboratory, University of Stockholm, S-10691, Stockholm, Sweden"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Cs\u00f6regh", 
            "givenName": "Ingeborg", 
            "id": "sg:person.015544624271.40", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015544624271.40"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Stockholm University", 
              "id": "https://www.grid.ac/institutes/grid.10548.38", 
              "name": [
                "Department of Structural Chemistry, Arrhenius Laboratory, University of Stockholm, S-10691, Stockholm, Sweden"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Czugler", 
            "givenName": "M\u00e1ty\u00e1s", 
            "id": "sg:person.01106253502.68", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01106253502.68"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Stockholm University", 
              "id": "https://www.grid.ac/institutes/grid.10548.38", 
              "name": [
                "Department of Structural Chemistry, Arrhenius Laboratory, University of Stockholm, S-10691, Stockholm, Sweden"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Ertan", 
            "givenName": "Anne", 
            "id": "sg:person.012165324074.55", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012165324074.55"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "University of Bonn", 
              "id": "https://www.grid.ac/institutes/grid.10388.32", 
              "name": [
                "Institut f\u00fcr Organische Chemie und Biochemie der Universit\u00e4t Bonn, Gerhard-Domagk-Strasse 1, D-5300, Bonn 1, FR-Germany"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Weber", 
            "givenName": "Edwin", 
            "id": "sg:person.01016205541.34", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01016205541.34"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "University of Bonn", 
              "id": "https://www.grid.ac/institutes/grid.10388.32", 
              "name": [
                "Institut f\u00fcr Organische Chemie und Biochemie der Universit\u00e4t Bonn, Gerhard-Domagk-Strasse 1, D-5300, Bonn 1, FR-Germany"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Ahrendt", 
            "givenName": "Jochen", 
            "id": "sg:person.014405674471.91", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014405674471.91"
            ], 
            "type": "Person"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1007/bf00658018", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1001841862", 
              "https://doi.org/10.1007/bf00658018"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf00658018", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1001841862", 
              "https://doi.org/10.1007/bf00658018"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1039/p29860000507", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1014189202"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1039/p29880001251", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1018274927"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1002/ange.19881000110", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1039934372"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1002/ange.19881000804", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1051510691"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1021/ja00323a039", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1055723397"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1021/ja00383a012", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1055728003"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1021/jo00236a033", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1055974574"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "https://doi.org/10.1021/jo00260a007", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1055975918"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "1990-04", 
        "datePublishedReg": "1990-04-01", 
        "description": "The crystal structures of four dimethyl sulphoxide (DMSO) inclusion compounds with different carboxylic acid hosts,1\u20134, have been studied by single crystal X-ray analysis. Crystals of thetrans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid inclusion compound (1a), [1 \u00b7 DMSO (1: 1)] show monoclinic (P21/n) symmetry with the unit cell dimensionsa = 11.522(4),b = 18.658(2),c = 8.709(1) \u00c5 and \u03b2 = 98.92(2)\u00b0. The clathrate of the 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (2a), [2 \u00b7 DMSO (1: 2)] is triclinic (P\u012a) with the cell dimensionsa = 15.043(7),b =9.657(4),c = 8.118(7) \u00c5, \u03b1 = 101.81(5), \u03b2 = 96.05(4) and \u03b3 = 100.04(4)\u00b0. Triclinic (P\u012a) symmetry is shown also by the inclusion compound of 9,10-dihydro-9,10-ethanoanthracene-11-monocarboxylic acid (3a) [3 \u00b7 DMSO (1:1)] with the cell dimensionsa=6.3132(1),b=7.9846(2),c=17.5314(4) \u00c5, \u03b1 = 96.46(2), \u03b2 = 87.08(2) and \u03b3 = 106.02(2)\u00b0. The 9,9\u2032-bianthryl-2-monocarboxylic acid clathrate (4a) [4 \u00b7 DMSO (1:1)] is monoclinic (P21/n) and the cell dimensions area = 19.625(18),b = 8.817(1),c = 14.076(8) \u00c5 and \u03b2 = 97.92(6)\u00b0. In all these structures, the hosts show the same basic recognition pattern for the DMSO guest, involving a strong O-H ... O bond from the COON to the S=O group, and a possible C-H ... O type interaction between the carbonyl O atom of the host and a CH3 group of the guest. The crystals consist of discrete host-guest aggregates which are mainly held together by weak intermolecular interactions of the Van der Waals' type. The stoichiometries of the aggregates are, however, different.", 
        "genre": "research_article", 
        "id": "sg:pub.10.1007/bf01041884", 
        "inLanguage": [
          "en"
        ], 
        "isAccessibleForFree": false, 
        "isPartOf": [
          {
            "id": "sg:journal.1119385", 
            "issn": [
              "1388-3127", 
              "2212-1765"
            ], 
            "name": "Journal of Inclusion Phenomena and Macrocyclic Chemistry", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "3", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "8"
          }
        ], 
        "name": "Solid-state binding of dimethyl sulphoxide involving carboxylic host molecules. X-ray crystal structures of four inclusion species", 
        "pagination": "275-287", 
        "productId": [
          {
            "name": "readcube_id", 
            "type": "PropertyValue", 
            "value": [
              "cdffdad5b490efeb6f2e48f580302d4037860b7cf1ef372be0fbb14808643fa3"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1007/bf01041884"
            ]
          }, 
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1043246814"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1007/bf01041884", 
          "https://app.dimensions.ai/details/publication/pub.1043246814"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2019-04-11T00:12", 
        "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
        "sdPublisher": {
          "name": "Springer Nature - SN SciGraph project", 
          "type": "Organization"
        }, 
        "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000001_0000000264/records_8695_00000496.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "http://link.springer.com/10.1007/BF01041884"
      }
    ]
     

    Download the RDF metadata as:  json-ld nt turtle xml License info

    HOW TO GET THIS DATA PROGRAMMATICALLY:

    JSON-LD is a popular format for linked data which is fully compatible with JSON.

    curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/bf01041884'

    N-Triples is a line-based linked data format ideal for batch operations.

    curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/bf01041884'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/bf01041884'

    RDF/XML is a standard XML format for linked data.

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/bf01041884'


     

    This table displays all metadata directly associated to this object as RDF triples.

    120 TRIPLES      21 PREDICATES      36 URIs      19 LITERALS      7 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1007/bf01041884 schema:about anzsrc-for:03
    2 anzsrc-for:0307
    3 schema:author N58989a55db31427abc96eedec046ab91
    4 schema:citation sg:pub.10.1007/bf00658018
    5 https://doi.org/10.1002/ange.19881000110
    6 https://doi.org/10.1002/ange.19881000804
    7 https://doi.org/10.1021/ja00323a039
    8 https://doi.org/10.1021/ja00383a012
    9 https://doi.org/10.1021/jo00236a033
    10 https://doi.org/10.1021/jo00260a007
    11 https://doi.org/10.1039/p29860000507
    12 https://doi.org/10.1039/p29880001251
    13 schema:datePublished 1990-04
    14 schema:datePublishedReg 1990-04-01
    15 schema:description The crystal structures of four dimethyl sulphoxide (DMSO) inclusion compounds with different carboxylic acid hosts,1–4, have been studied by single crystal X-ray analysis. Crystals of thetrans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid inclusion compound (1a), [1 · DMSO (1: 1)] show monoclinic (P21/n) symmetry with the unit cell dimensionsa = 11.522(4),b = 18.658(2),c = 8.709(1) Å and β = 98.92(2)°. The clathrate of the 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid (2a), [2 · DMSO (1: 2)] is triclinic (PĪ) with the cell dimensionsa = 15.043(7),b =9.657(4),c = 8.118(7) Å, α = 101.81(5), β = 96.05(4) and γ = 100.04(4)°. Triclinic (PĪ) symmetry is shown also by the inclusion compound of 9,10-dihydro-9,10-ethanoanthracene-11-monocarboxylic acid (3a) [3 · DMSO (1:1)] with the cell dimensionsa=6.3132(1),b=7.9846(2),c=17.5314(4) Å, α = 96.46(2), β = 87.08(2) and γ = 106.02(2)°. The 9,9′-bianthryl-2-monocarboxylic acid clathrate (4a) [4 · DMSO (1:1)] is monoclinic (P21/n) and the cell dimensions area = 19.625(18),b = 8.817(1),c = 14.076(8) Å and β = 97.92(6)°. In all these structures, the hosts show the same basic recognition pattern for the DMSO guest, involving a strong O-H ... O bond from the COON to the S=O group, and a possible C-H ... O type interaction between the carbonyl O atom of the host and a CH3 group of the guest. The crystals consist of discrete host-guest aggregates which are mainly held together by weak intermolecular interactions of the Van der Waals' type. The stoichiometries of the aggregates are, however, different.
    16 schema:genre research_article
    17 schema:inLanguage en
    18 schema:isAccessibleForFree false
    19 schema:isPartOf N03f3188ee3744fe98f26332cbeccd2e3
    20 N67cbdf2a04f442868cb1a8ede2a5c918
    21 sg:journal.1119385
    22 schema:name Solid-state binding of dimethyl sulphoxide involving carboxylic host molecules. X-ray crystal structures of four inclusion species
    23 schema:pagination 275-287
    24 schema:productId N3365bbcaa0ef48f49760fc86f9645fa1
    25 Nb1b04eadaed64a72b4aaffdb24f6040d
    26 Nb63408d312764d76a0f84e29dbaedf67
    27 schema:sameAs https://app.dimensions.ai/details/publication/pub.1043246814
    28 https://doi.org/10.1007/bf01041884
    29 schema:sdDatePublished 2019-04-11T00:12
    30 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    31 schema:sdPublisher N60efe39981c84180aae326ccd3765048
    32 schema:url http://link.springer.com/10.1007/BF01041884
    33 sgo:license sg:explorer/license/
    34 sgo:sdDataset articles
    35 rdf:type schema:ScholarlyArticle
    36 N03f3188ee3744fe98f26332cbeccd2e3 schema:issueNumber 3
    37 rdf:type schema:PublicationIssue
    38 N234b02827661422ba3901486571bdfce rdf:first sg:person.014405674471.91
    39 rdf:rest rdf:nil
    40 N3365bbcaa0ef48f49760fc86f9645fa1 schema:name doi
    41 schema:value 10.1007/bf01041884
    42 rdf:type schema:PropertyValue
    43 N58989a55db31427abc96eedec046ab91 rdf:first sg:person.015544624271.40
    44 rdf:rest Nc8e5fb2777544e22afd9b2d85a88e51d
    45 N60efe39981c84180aae326ccd3765048 schema:name Springer Nature - SN SciGraph project
    46 rdf:type schema:Organization
    47 N67cbdf2a04f442868cb1a8ede2a5c918 schema:volumeNumber 8
    48 rdf:type schema:PublicationVolume
    49 N9109ab9b40154637a58fdb86feb6668e rdf:first sg:person.01016205541.34
    50 rdf:rest N234b02827661422ba3901486571bdfce
    51 Nb1b04eadaed64a72b4aaffdb24f6040d schema:name dimensions_id
    52 schema:value pub.1043246814
    53 rdf:type schema:PropertyValue
    54 Nb63408d312764d76a0f84e29dbaedf67 schema:name readcube_id
    55 schema:value cdffdad5b490efeb6f2e48f580302d4037860b7cf1ef372be0fbb14808643fa3
    56 rdf:type schema:PropertyValue
    57 Nc8e5fb2777544e22afd9b2d85a88e51d rdf:first sg:person.01106253502.68
    58 rdf:rest Ne908a0475df74dc4a4c4e4fe1040f47f
    59 Ne908a0475df74dc4a4c4e4fe1040f47f rdf:first sg:person.012165324074.55
    60 rdf:rest N9109ab9b40154637a58fdb86feb6668e
    61 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
    62 schema:name Chemical Sciences
    63 rdf:type schema:DefinedTerm
    64 anzsrc-for:0307 schema:inDefinedTermSet anzsrc-for:
    65 schema:name Theoretical and Computational Chemistry
    66 rdf:type schema:DefinedTerm
    67 sg:journal.1119385 schema:issn 1388-3127
    68 2212-1765
    69 schema:name Journal of Inclusion Phenomena and Macrocyclic Chemistry
    70 rdf:type schema:Periodical
    71 sg:person.01016205541.34 schema:affiliation https://www.grid.ac/institutes/grid.10388.32
    72 schema:familyName Weber
    73 schema:givenName Edwin
    74 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01016205541.34
    75 rdf:type schema:Person
    76 sg:person.01106253502.68 schema:affiliation https://www.grid.ac/institutes/grid.10548.38
    77 schema:familyName Czugler
    78 schema:givenName Mátyás
    79 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01106253502.68
    80 rdf:type schema:Person
    81 sg:person.012165324074.55 schema:affiliation https://www.grid.ac/institutes/grid.10548.38
    82 schema:familyName Ertan
    83 schema:givenName Anne
    84 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012165324074.55
    85 rdf:type schema:Person
    86 sg:person.014405674471.91 schema:affiliation https://www.grid.ac/institutes/grid.10388.32
    87 schema:familyName Ahrendt
    88 schema:givenName Jochen
    89 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014405674471.91
    90 rdf:type schema:Person
    91 sg:person.015544624271.40 schema:affiliation https://www.grid.ac/institutes/grid.10548.38
    92 schema:familyName Csöregh
    93 schema:givenName Ingeborg
    94 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015544624271.40
    95 rdf:type schema:Person
    96 sg:pub.10.1007/bf00658018 schema:sameAs https://app.dimensions.ai/details/publication/pub.1001841862
    97 https://doi.org/10.1007/bf00658018
    98 rdf:type schema:CreativeWork
    99 https://doi.org/10.1002/ange.19881000110 schema:sameAs https://app.dimensions.ai/details/publication/pub.1039934372
    100 rdf:type schema:CreativeWork
    101 https://doi.org/10.1002/ange.19881000804 schema:sameAs https://app.dimensions.ai/details/publication/pub.1051510691
    102 rdf:type schema:CreativeWork
    103 https://doi.org/10.1021/ja00323a039 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055723397
    104 rdf:type schema:CreativeWork
    105 https://doi.org/10.1021/ja00383a012 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055728003
    106 rdf:type schema:CreativeWork
    107 https://doi.org/10.1021/jo00236a033 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055974574
    108 rdf:type schema:CreativeWork
    109 https://doi.org/10.1021/jo00260a007 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055975918
    110 rdf:type schema:CreativeWork
    111 https://doi.org/10.1039/p29860000507 schema:sameAs https://app.dimensions.ai/details/publication/pub.1014189202
    112 rdf:type schema:CreativeWork
    113 https://doi.org/10.1039/p29880001251 schema:sameAs https://app.dimensions.ai/details/publication/pub.1018274927
    114 rdf:type schema:CreativeWork
    115 https://www.grid.ac/institutes/grid.10388.32 schema:alternateName University of Bonn
    116 schema:name Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Strasse 1, D-5300, Bonn 1, FR-Germany
    117 rdf:type schema:Organization
    118 https://www.grid.ac/institutes/grid.10548.38 schema:alternateName Stockholm University
    119 schema:name Department of Structural Chemistry, Arrhenius Laboratory, University of Stockholm, S-10691, Stockholm, Sweden
    120 rdf:type schema:Organization
     




    Preview window. Press ESC to close (or click here)


    ...