Low-temperature study of the molecular and crystal structures of 2-(2′-tosylamino-5′-nitrophenyl)-4H-3,1-benzoxazin-4-one, an organic luminophore View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2001-03

AUTHORS

A. N. Utenyshev, O. S. Filipenko, B. M. Bolotin, V. I. Ponomarev

ABSTRACT

The crystal structure of 2-(2′-tosylamino-5′-nitrophenyl)-4H-3,1-benzoxazin-4-one (I) is studied by X-ray diffraction at 100 K (C21H15N3O6S, a = 20.899(2) Å, b = 10.948(1) Å, c = 8.260(1) Å, V = 1889.3(1) Å3, Z = 4, and space group Pbn21). The compound exhibits an anomalous Stokes shift. Upon cooling, the oxazineaminophenyl fragment of compound I acquires a quinoid structure and the linear parameters of the intramolecular N-H⋯N hydrogen bond increase (the distance between the heterocyclic nitrogen atom and the hydrogen atom of the tosylamino group becomes 1.92 Å). The complete optimization of the geometry of molecules in compound I and unsubstituted 2-(2′-tosylaminophenyl)-4H-3,1-benzoxazin-4-one in the ground singlet electronic state is performed by the semiempirical method with the MOPAC program. It is shown that the oxygen atoms in the sulfo group of molecule I are nonequivalent, because one of them is involved in the intermolecular C-H⋯O hydrogen bond. More... »

PAGES

225-229

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/1.1358398

DOI

http://dx.doi.org/10.1134/1.1358398

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1004865287


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/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0302", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Inorganic Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0306", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Physical Chemistry (incl. Structural)", 
        "type": "DefinedTerm"
      }, 
      {
        "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"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia", 
          "id": "http://www.grid.ac/institutes/grid.418949.9", 
          "name": [
            "Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Utenyshev", 
        "givenName": "A. N.", 
        "id": "sg:person.015236213545.72", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015236213545.72"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia", 
          "id": "http://www.grid.ac/institutes/grid.418949.9", 
          "name": [
            "Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Filipenko", 
        "givenName": "O. S.", 
        "id": "sg:person.013100520031.61", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013100520031.61"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "IREA State Research Institute of Chemical Reagents and Special-Purity Substances, Bogorodskii val 3, 107076, Moscow, Russia", 
          "id": "http://www.grid.ac/institutes/None", 
          "name": [
            "IREA State Research Institute of Chemical Reagents and Special-Purity Substances, Bogorodskii val 3, 107076, Moscow, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Bolotin", 
        "givenName": "B. M.", 
        "id": "sg:person.012440374506.23", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012440374506.23"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Institute of Structural Macrokinetics and Problems of Materials Technology, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia", 
          "id": "http://www.grid.ac/institutes/grid.4886.2", 
          "name": [
            "Institute of Structural Macrokinetics and Problems of Materials Technology, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ponomarev", 
        "givenName": "V. I.", 
        "id": "sg:person.010535710631.46", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010535710631.46"
        ], 
        "type": "Person"
      }
    ], 
    "datePublished": "2001-03", 
    "datePublishedReg": "2001-03-01", 
    "description": "The crystal structure of 2-(2\u2032-tosylamino-5\u2032-nitrophenyl)-4H-3,1-benzoxazin-4-one (I) is studied by X-ray diffraction at 100 K (C21H15N3O6S, a = 20.899(2) \u00c5, b = 10.948(1) \u00c5, c = 8.260(1) \u00c5, V = 1889.3(1) \u00c53, Z = 4, and space group Pbn21). The compound exhibits an anomalous Stokes shift. Upon cooling, the oxazineaminophenyl fragment of compound I acquires a quinoid structure and the linear parameters of the intramolecular N-H\u22efN hydrogen bond increase (the distance between the heterocyclic nitrogen atom and the hydrogen atom of the tosylamino group becomes 1.92 \u00c5). The complete optimization of the geometry of molecules in compound I and unsubstituted 2-(2\u2032-tosylaminophenyl)-4H-3,1-benzoxazin-4-one in the ground singlet electronic state is performed by the semiempirical method with the MOPAC program. It is shown that the oxygen atoms in the sulfo group of molecule I are nonequivalent, because one of them is involved in the intermolecular C-H\u22efO hydrogen bond.", 
    "genre": "article", 
    "id": "sg:pub.10.1134/1.1358398", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1295066", 
        "issn": [
          "1063-7745", 
          "1562-689X"
        ], 
        "name": "Crystallography Reports", 
        "publisher": "Pleiades Publishing", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "2", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "46"
      }
    ], 
    "keywords": [
      "benzoxazin-4", 
      "compound I", 
      "crystal structure", 
      "hydrogen bond increases", 
      "geometry of molecules", 
      "anomalous Stokes shift", 
      "X-ray diffraction", 
      "organic luminophores", 
      "quinoid structure", 
      "sulfo groups", 
      "hydrogen bonds", 
      "linear parameter", 
      "MOPAC program", 
      "oxygen atoms", 
      "bond increases", 
      "Stokes shift", 
      "low-temperature studies", 
      "semiempirical methods", 
      "molecule I", 
      "electronic states", 
      "complete optimization", 
      "luminophores", 
      "structure", 
      "bonds", 
      "diffraction", 
      "compounds", 
      "molecules", 
      "atoms", 
      "optimization", 
      "geometry", 
      "parameters", 
      "fragments", 
      "shift", 
      "state", 
      "method", 
      "group", 
      "increase", 
      "ground", 
      "cooling", 
      "study", 
      "program"
    ], 
    "name": "Low-temperature study of the molecular and crystal structures of 2-(2\u2032-tosylamino-5\u2032-nitrophenyl)-4H-3,1-benzoxazin-4-one, an organic luminophore", 
    "pagination": "225-229", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1004865287"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1134/1.1358398"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1134/1.1358398", 
      "https://app.dimensions.ai/details/publication/pub.1004865287"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2022-11-24T20:50", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20221124/entities/gbq_results/article/article_341.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1134/1.1358398"
  }
]
 

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.10.1134/1.1358398'

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

curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1134/1.1358398'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1134/1.1358398'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1134/1.1358398'


 

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

133 TRIPLES      20 PREDICATES      68 URIs      58 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1134/1.1358398 schema:about anzsrc-for:03
2 anzsrc-for:0302
3 anzsrc-for:0306
4 anzsrc-for:0307
5 schema:author Nb54ee67ba1404856af03d7ac21b881f0
6 schema:datePublished 2001-03
7 schema:datePublishedReg 2001-03-01
8 schema:description The crystal structure of 2-(2′-tosylamino-5′-nitrophenyl)-4H-3,1-benzoxazin-4-one (I) is studied by X-ray diffraction at 100 K (C21H15N3O6S, a = 20.899(2) Å, b = 10.948(1) Å, c = 8.260(1) Å, V = 1889.3(1) Å3, Z = 4, and space group Pbn21). The compound exhibits an anomalous Stokes shift. Upon cooling, the oxazineaminophenyl fragment of compound I acquires a quinoid structure and the linear parameters of the intramolecular N-H⋯N hydrogen bond increase (the distance between the heterocyclic nitrogen atom and the hydrogen atom of the tosylamino group becomes 1.92 Å). The complete optimization of the geometry of molecules in compound I and unsubstituted 2-(2′-tosylaminophenyl)-4H-3,1-benzoxazin-4-one in the ground singlet electronic state is performed by the semiempirical method with the MOPAC program. It is shown that the oxygen atoms in the sulfo group of molecule I are nonequivalent, because one of them is involved in the intermolecular C-H⋯O hydrogen bond.
9 schema:genre article
10 schema:isAccessibleForFree false
11 schema:isPartOf N32302cdaf963464c99b18789c5e52e8b
12 N94ca6d7689014d5d99bcef05cb9f4f6c
13 sg:journal.1295066
14 schema:keywords MOPAC program
15 Stokes shift
16 X-ray diffraction
17 anomalous Stokes shift
18 atoms
19 benzoxazin-4
20 bond increases
21 bonds
22 complete optimization
23 compound I
24 compounds
25 cooling
26 crystal structure
27 diffraction
28 electronic states
29 fragments
30 geometry
31 geometry of molecules
32 ground
33 group
34 hydrogen bond increases
35 hydrogen bonds
36 increase
37 linear parameter
38 low-temperature studies
39 luminophores
40 method
41 molecule I
42 molecules
43 optimization
44 organic luminophores
45 oxygen atoms
46 parameters
47 program
48 quinoid structure
49 semiempirical methods
50 shift
51 state
52 structure
53 study
54 sulfo groups
55 schema:name Low-temperature study of the molecular and crystal structures of 2-(2′-tosylamino-5′-nitrophenyl)-4H-3,1-benzoxazin-4-one, an organic luminophore
56 schema:pagination 225-229
57 schema:productId Ncd71fddb8bfe4cb990aadc39e81da380
58 Ne8cdd31052b049a7ab0f6834c1945db0
59 schema:sameAs https://app.dimensions.ai/details/publication/pub.1004865287
60 https://doi.org/10.1134/1.1358398
61 schema:sdDatePublished 2022-11-24T20:50
62 schema:sdLicense https://scigraph.springernature.com/explorer/license/
63 schema:sdPublisher N2d9f56a6375d48d8ad13be003d81d988
64 schema:url https://doi.org/10.1134/1.1358398
65 sgo:license sg:explorer/license/
66 sgo:sdDataset articles
67 rdf:type schema:ScholarlyArticle
68 N218cdbb6b82e450f91919d5e10ec524f rdf:first sg:person.010535710631.46
69 rdf:rest rdf:nil
70 N2d9f56a6375d48d8ad13be003d81d988 schema:name Springer Nature - SN SciGraph project
71 rdf:type schema:Organization
72 N32302cdaf963464c99b18789c5e52e8b schema:volumeNumber 46
73 rdf:type schema:PublicationVolume
74 N94ca6d7689014d5d99bcef05cb9f4f6c schema:issueNumber 2
75 rdf:type schema:PublicationIssue
76 Nb17ab9523d22414fbc14ae6c13995b6f rdf:first sg:person.013100520031.61
77 rdf:rest Nee7c556ba6b74c319740f859921268aa
78 Nb54ee67ba1404856af03d7ac21b881f0 rdf:first sg:person.015236213545.72
79 rdf:rest Nb17ab9523d22414fbc14ae6c13995b6f
80 Ncd71fddb8bfe4cb990aadc39e81da380 schema:name dimensions_id
81 schema:value pub.1004865287
82 rdf:type schema:PropertyValue
83 Ne8cdd31052b049a7ab0f6834c1945db0 schema:name doi
84 schema:value 10.1134/1.1358398
85 rdf:type schema:PropertyValue
86 Nee7c556ba6b74c319740f859921268aa rdf:first sg:person.012440374506.23
87 rdf:rest N218cdbb6b82e450f91919d5e10ec524f
88 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
89 schema:name Chemical Sciences
90 rdf:type schema:DefinedTerm
91 anzsrc-for:0302 schema:inDefinedTermSet anzsrc-for:
92 schema:name Inorganic Chemistry
93 rdf:type schema:DefinedTerm
94 anzsrc-for:0306 schema:inDefinedTermSet anzsrc-for:
95 schema:name Physical Chemistry (incl. Structural)
96 rdf:type schema:DefinedTerm
97 anzsrc-for:0307 schema:inDefinedTermSet anzsrc-for:
98 schema:name Theoretical and Computational Chemistry
99 rdf:type schema:DefinedTerm
100 sg:journal.1295066 schema:issn 1063-7745
101 1562-689X
102 schema:name Crystallography Reports
103 schema:publisher Pleiades Publishing
104 rdf:type schema:Periodical
105 sg:person.010535710631.46 schema:affiliation grid-institutes:grid.4886.2
106 schema:familyName Ponomarev
107 schema:givenName V. I.
108 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010535710631.46
109 rdf:type schema:Person
110 sg:person.012440374506.23 schema:affiliation grid-institutes:None
111 schema:familyName Bolotin
112 schema:givenName B. M.
113 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012440374506.23
114 rdf:type schema:Person
115 sg:person.013100520031.61 schema:affiliation grid-institutes:grid.418949.9
116 schema:familyName Filipenko
117 schema:givenName O. S.
118 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013100520031.61
119 rdf:type schema:Person
120 sg:person.015236213545.72 schema:affiliation grid-institutes:grid.418949.9
121 schema:familyName Utenyshev
122 schema:givenName A. N.
123 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.015236213545.72
124 rdf:type schema:Person
125 grid-institutes:None schema:alternateName IREA State Research Institute of Chemical Reagents and Special-Purity Substances, Bogorodskii val 3, 107076, Moscow, Russia
126 schema:name IREA State Research Institute of Chemical Reagents and Special-Purity Substances, Bogorodskii val 3, 107076, Moscow, Russia
127 rdf:type schema:Organization
128 grid-institutes:grid.418949.9 schema:alternateName Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia
129 schema:name Institute for Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia
130 rdf:type schema:Organization
131 grid-institutes:grid.4886.2 schema:alternateName Institute of Structural Macrokinetics and Problems of Materials Technology, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia
132 schema:name Institute of Structural Macrokinetics and Problems of Materials Technology, Russian Academy of Sciences, 142432, Chernogolovka, Moscow oblast, Russia
133 rdf:type schema:Organization
 




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


...