Theoretical analysis of tautomerization of succinimide and analogous compounds: insights from DFT approach View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2018-01-15

AUTHORS

Subhendu Sarkar, Tamalika Ash, Tanay Debnath, Abhijit K. Das

ABSTRACT

Tautomerizations of biologically and medicinally important heterocyclic compound, 2,5-pyrrolidinedione, commonly known as succinimide and two of its analogous compounds, 2,4-pyrrolidinedione and 3,4-pyrrolidinedione have been investigated at the density functional theory (DFT)/M06-2X level in aqueous medium, implementing polarizable continuum model (PCM). We have extended our investigation of tautomerism to the sulfur analogues of the aforementioned compounds also, i.e., 2,5-pyrrolidinedithione, 2,4-pyrrolidinedithione, and 3,4-pyrrolidinedithione. Tautomerism observed in these compounds are mainly keto-enol, thio-thiol and amine-imine, but we have detected two new kind of tautomerization shown by some of the abovementioned compounds, named as keto-epoxy (for the oxygen analogue) and thio-thioepoxy (for the sulfur analogue) which have not yet been reported in the literature. Relative energies (Er) and activation energies (Ea) have been calculated for all the tautomers and tautomerization processes. The potential energy surfaces (PESs) have been constructed using the M06-2X energy values. It has been observed that the energy difference found in the tautomers of sulfur analogues is relatively lower than that of the corresponding oxygen analogues, so does the activation energy barrier. As one-electron redox properties play an important role in biological systems, we have also explored the effect of conformational changes on the overall redox properties of the said compounds by calculating the adiabatic and vertical ionization potentials (AIPs and VIPs, respectively) and adiabatic electron affinities (AEAs). More... »

PAGES

881-896

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11224-018-1075-7

DOI

http://dx.doi.org/10.1007/s11224-018-1075-7

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1100399560


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"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India", 
          "id": "http://www.grid.ac/institutes/grid.417929.0", 
          "name": [
            "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Sarkar", 
        "givenName": "Subhendu", 
        "id": "sg:person.010455461123.77", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010455461123.77"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India", 
          "id": "http://www.grid.ac/institutes/grid.417929.0", 
          "name": [
            "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Ash", 
        "givenName": "Tamalika", 
        "id": "sg:person.01230005433.50", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01230005433.50"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India", 
          "id": "http://www.grid.ac/institutes/grid.417929.0", 
          "name": [
            "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Debnath", 
        "givenName": "Tanay", 
        "id": "sg:person.013616574672.33", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013616574672.33"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India", 
          "id": "http://www.grid.ac/institutes/grid.417929.0", 
          "name": [
            "Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Das", 
        "givenName": "Abhijit K.", 
        "id": "sg:person.01011272142.88", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01011272142.88"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/s00214-007-0310-x", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1024437999", 
          "https://doi.org/10.1007/s00214-007-0310-x"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s12039-007-0077-6", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1004738996", 
          "https://doi.org/10.1007/s12039-007-0077-6"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s11224-012-0153-5", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1028943622", 
          "https://doi.org/10.1007/s11224-012-0153-5"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s00894-008-0374-0", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1041301563", 
          "https://doi.org/10.1007/s00894-008-0374-0"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s11224-014-0402-x", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1017536512", 
          "https://doi.org/10.1007/s11224-014-0402-x"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf00481046", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1034491459", 
          "https://doi.org/10.1007/bf00481046"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/s11224-014-0511-6", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1021614959", 
          "https://doi.org/10.1007/s11224-014-0511-6"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "2018-01-15", 
    "datePublishedReg": "2018-01-15", 
    "description": "Tautomerizations of biologically and medicinally important heterocyclic compound, 2,5-pyrrolidinedione, commonly known as succinimide and two of its analogous compounds, 2,4-pyrrolidinedione and 3,4-pyrrolidinedione have been investigated at the density functional theory (DFT)/M06-2X level in aqueous medium, implementing polarizable continuum model (PCM). We have extended our investigation of tautomerism to the sulfur analogues of the aforementioned compounds also, i.e., 2,5-pyrrolidinedithione, 2,4-pyrrolidinedithione, and 3,4-pyrrolidinedithione. Tautomerism observed in these compounds are mainly keto-enol, thio-thiol and amine-imine, but we have detected two new kind of tautomerization shown by some of the abovementioned compounds, named as keto-epoxy (for the oxygen analogue) and thio-thioepoxy (for the sulfur analogue) which have not yet been reported in the literature. Relative energies (Er) and activation energies (Ea) have been calculated for all the tautomers and tautomerization processes. The potential energy surfaces (PESs) have been constructed using the M06-2X energy values. It has been observed that the energy difference found in the tautomers of sulfur analogues is relatively lower than that of the corresponding oxygen analogues, so does the activation energy barrier. As one-electron redox properties play an important role in biological systems, we have also explored the effect of conformational changes on the overall redox properties of the said compounds by calculating the adiabatic and vertical ionization potentials (AIPs and VIPs, respectively) and adiabatic electron affinities (AEAs).", 
    "genre": "article", 
    "id": "sg:pub.10.1007/s11224-018-1075-7", 
    "inLanguage": "en", 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1046791", 
        "issn": [
          "1040-0400", 
          "1572-9001"
        ], 
        "name": "Structural Chemistry", 
        "publisher": "Springer Nature", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "3", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "29"
      }
    ], 
    "keywords": [
      "polarizable continuum model", 
      "potential energy surface", 
      "redox properties", 
      "density functional theory", 
      "one-electron redox properties", 
      "analogous compounds", 
      "sulfur analogues", 
      "adiabatic electron affinity", 
      "important heterocyclic compounds", 
      "overall redox properties", 
      "keto-enol", 
      "corresponding oxygen analogues", 
      "investigation of tautomerism", 
      "activation energy barrier", 
      "aqueous media", 
      "heterocyclic compounds", 
      "tautomerization process", 
      "vertical ionization potentials", 
      "abovementioned compounds", 
      "energy surface", 
      "DFT approach", 
      "aforementioned compounds", 
      "energy barrier", 
      "electron affinity", 
      "functional theory", 
      "oxygen analogs", 
      "tautomerization", 
      "relative energies", 
      "ionization potential", 
      "compounds", 
      "energy difference", 
      "tautomerism", 
      "tautomers", 
      "activation energy", 
      "succinimide", 
      "biological systems", 
      "energy values", 
      "continuum model", 
      "conformational changes", 
      "M06", 
      "properties", 
      "analogues", 
      "energy", 
      "new kind", 
      "surface", 
      "Biologically", 
      "affinity", 
      "potential", 
      "medium", 
      "important role", 
      "investigation", 
      "process", 
      "barriers", 
      "insights", 
      "kind", 
      "theoretical analysis", 
      "values", 
      "effect", 
      "analysis", 
      "system", 
      "changes", 
      "approach", 
      "theory", 
      "role", 
      "levels", 
      "differences", 
      "model", 
      "literature", 
      "Tautomerizations of biologically", 
      "thio-thiol", 
      "keto-epoxy", 
      "thio-thioepoxy"
    ], 
    "name": "Theoretical analysis of tautomerization of succinimide and analogous compounds: insights from DFT approach", 
    "pagination": "881-896", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1100399560"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/s11224-018-1075-7"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/s11224-018-1075-7", 
      "https://app.dimensions.ai/details/publication/pub.1100399560"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2021-12-01T19:41", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20211201/entities/gbq_results/article/article_779.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1007/s11224-018-1075-7"
  }
]
 

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/s11224-018-1075-7'

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/s11224-018-1075-7'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/s11224-018-1075-7'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/s11224-018-1075-7'


 

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

179 TRIPLES      22 PREDICATES      104 URIs      89 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/s11224-018-1075-7 schema:about anzsrc-for:03
2 anzsrc-for:0302
3 schema:author N7dad1d94853a4dcba722c0b9defd43ca
4 schema:citation sg:pub.10.1007/bf00481046
5 sg:pub.10.1007/s00214-007-0310-x
6 sg:pub.10.1007/s00894-008-0374-0
7 sg:pub.10.1007/s11224-012-0153-5
8 sg:pub.10.1007/s11224-014-0402-x
9 sg:pub.10.1007/s11224-014-0511-6
10 sg:pub.10.1007/s12039-007-0077-6
11 schema:datePublished 2018-01-15
12 schema:datePublishedReg 2018-01-15
13 schema:description Tautomerizations of biologically and medicinally important heterocyclic compound, 2,5-pyrrolidinedione, commonly known as succinimide and two of its analogous compounds, 2,4-pyrrolidinedione and 3,4-pyrrolidinedione have been investigated at the density functional theory (DFT)/M06-2X level in aqueous medium, implementing polarizable continuum model (PCM). We have extended our investigation of tautomerism to the sulfur analogues of the aforementioned compounds also, i.e., 2,5-pyrrolidinedithione, 2,4-pyrrolidinedithione, and 3,4-pyrrolidinedithione. Tautomerism observed in these compounds are mainly keto-enol, thio-thiol and amine-imine, but we have detected two new kind of tautomerization shown by some of the abovementioned compounds, named as keto-epoxy (for the oxygen analogue) and thio-thioepoxy (for the sulfur analogue) which have not yet been reported in the literature. Relative energies (Er) and activation energies (Ea) have been calculated for all the tautomers and tautomerization processes. The potential energy surfaces (PESs) have been constructed using the M06-2X energy values. It has been observed that the energy difference found in the tautomers of sulfur analogues is relatively lower than that of the corresponding oxygen analogues, so does the activation energy barrier. As one-electron redox properties play an important role in biological systems, we have also explored the effect of conformational changes on the overall redox properties of the said compounds by calculating the adiabatic and vertical ionization potentials (AIPs and VIPs, respectively) and adiabatic electron affinities (AEAs).
14 schema:genre article
15 schema:inLanguage en
16 schema:isAccessibleForFree false
17 schema:isPartOf N33463ba15760430587069b6ce21dfa79
18 N5dbd63b42b994d21829442dc5aa74827
19 sg:journal.1046791
20 schema:keywords Biologically
21 DFT approach
22 M06
23 Tautomerizations of biologically
24 abovementioned compounds
25 activation energy
26 activation energy barrier
27 adiabatic electron affinity
28 affinity
29 aforementioned compounds
30 analogous compounds
31 analogues
32 analysis
33 approach
34 aqueous media
35 barriers
36 biological systems
37 changes
38 compounds
39 conformational changes
40 continuum model
41 corresponding oxygen analogues
42 density functional theory
43 differences
44 effect
45 electron affinity
46 energy
47 energy barrier
48 energy difference
49 energy surface
50 energy values
51 functional theory
52 heterocyclic compounds
53 important heterocyclic compounds
54 important role
55 insights
56 investigation
57 investigation of tautomerism
58 ionization potential
59 keto-enol
60 keto-epoxy
61 kind
62 levels
63 literature
64 medium
65 model
66 new kind
67 one-electron redox properties
68 overall redox properties
69 oxygen analogs
70 polarizable continuum model
71 potential
72 potential energy surface
73 process
74 properties
75 redox properties
76 relative energies
77 role
78 succinimide
79 sulfur analogues
80 surface
81 system
82 tautomerism
83 tautomerization
84 tautomerization process
85 tautomers
86 theoretical analysis
87 theory
88 thio-thioepoxy
89 thio-thiol
90 values
91 vertical ionization potentials
92 schema:name Theoretical analysis of tautomerization of succinimide and analogous compounds: insights from DFT approach
93 schema:pagination 881-896
94 schema:productId N6953812aab674c74ae79b23d06a1f29e
95 Nd0702b5e504f4c768a77b43cc4fd01b2
96 schema:sameAs https://app.dimensions.ai/details/publication/pub.1100399560
97 https://doi.org/10.1007/s11224-018-1075-7
98 schema:sdDatePublished 2021-12-01T19:41
99 schema:sdLicense https://scigraph.springernature.com/explorer/license/
100 schema:sdPublisher Ncf59786d8e924f7b8359f5763ad7d8d6
101 schema:url https://doi.org/10.1007/s11224-018-1075-7
102 sgo:license sg:explorer/license/
103 sgo:sdDataset articles
104 rdf:type schema:ScholarlyArticle
105 N33463ba15760430587069b6ce21dfa79 schema:volumeNumber 29
106 rdf:type schema:PublicationVolume
107 N37008e746d3643dba5df1019df3730a2 rdf:first sg:person.01011272142.88
108 rdf:rest rdf:nil
109 N5dbd63b42b994d21829442dc5aa74827 schema:issueNumber 3
110 rdf:type schema:PublicationIssue
111 N6953812aab674c74ae79b23d06a1f29e schema:name dimensions_id
112 schema:value pub.1100399560
113 rdf:type schema:PropertyValue
114 N7dad1d94853a4dcba722c0b9defd43ca rdf:first sg:person.010455461123.77
115 rdf:rest N8bc60cdd4ec044d88e310ef498a9480a
116 N8bc60cdd4ec044d88e310ef498a9480a rdf:first sg:person.01230005433.50
117 rdf:rest Nd80ab8f732a44cf2b5bb3f38a84064ed
118 Ncf59786d8e924f7b8359f5763ad7d8d6 schema:name Springer Nature - SN SciGraph project
119 rdf:type schema:Organization
120 Nd0702b5e504f4c768a77b43cc4fd01b2 schema:name doi
121 schema:value 10.1007/s11224-018-1075-7
122 rdf:type schema:PropertyValue
123 Nd80ab8f732a44cf2b5bb3f38a84064ed rdf:first sg:person.013616574672.33
124 rdf:rest N37008e746d3643dba5df1019df3730a2
125 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
126 schema:name Chemical Sciences
127 rdf:type schema:DefinedTerm
128 anzsrc-for:0302 schema:inDefinedTermSet anzsrc-for:
129 schema:name Inorganic Chemistry
130 rdf:type schema:DefinedTerm
131 sg:journal.1046791 schema:issn 1040-0400
132 1572-9001
133 schema:name Structural Chemistry
134 schema:publisher Springer Nature
135 rdf:type schema:Periodical
136 sg:person.01011272142.88 schema:affiliation grid-institutes:grid.417929.0
137 schema:familyName Das
138 schema:givenName Abhijit K.
139 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01011272142.88
140 rdf:type schema:Person
141 sg:person.010455461123.77 schema:affiliation grid-institutes:grid.417929.0
142 schema:familyName Sarkar
143 schema:givenName Subhendu
144 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010455461123.77
145 rdf:type schema:Person
146 sg:person.01230005433.50 schema:affiliation grid-institutes:grid.417929.0
147 schema:familyName Ash
148 schema:givenName Tamalika
149 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.01230005433.50
150 rdf:type schema:Person
151 sg:person.013616574672.33 schema:affiliation grid-institutes:grid.417929.0
152 schema:familyName Debnath
153 schema:givenName Tanay
154 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.013616574672.33
155 rdf:type schema:Person
156 sg:pub.10.1007/bf00481046 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034491459
157 https://doi.org/10.1007/bf00481046
158 rdf:type schema:CreativeWork
159 sg:pub.10.1007/s00214-007-0310-x schema:sameAs https://app.dimensions.ai/details/publication/pub.1024437999
160 https://doi.org/10.1007/s00214-007-0310-x
161 rdf:type schema:CreativeWork
162 sg:pub.10.1007/s00894-008-0374-0 schema:sameAs https://app.dimensions.ai/details/publication/pub.1041301563
163 https://doi.org/10.1007/s00894-008-0374-0
164 rdf:type schema:CreativeWork
165 sg:pub.10.1007/s11224-012-0153-5 schema:sameAs https://app.dimensions.ai/details/publication/pub.1028943622
166 https://doi.org/10.1007/s11224-012-0153-5
167 rdf:type schema:CreativeWork
168 sg:pub.10.1007/s11224-014-0402-x schema:sameAs https://app.dimensions.ai/details/publication/pub.1017536512
169 https://doi.org/10.1007/s11224-014-0402-x
170 rdf:type schema:CreativeWork
171 sg:pub.10.1007/s11224-014-0511-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1021614959
172 https://doi.org/10.1007/s11224-014-0511-6
173 rdf:type schema:CreativeWork
174 sg:pub.10.1007/s12039-007-0077-6 schema:sameAs https://app.dimensions.ai/details/publication/pub.1004738996
175 https://doi.org/10.1007/s12039-007-0077-6
176 rdf:type schema:CreativeWork
177 grid-institutes:grid.417929.0 schema:alternateName Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India
178 schema:name Department of Spectroscopy, Indian Association for the Cultivation of Science, Jadavpur, 700032, Kolkata, India
179 rdf:type schema:Organization
 




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


...