A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles
Identifieur interne : 002873 ( Istex/Corpus ); précédent : 002872; suivant : 002874A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles
Auteurs : J. Catalán ; O. M ; P. Pérez ; M. Yá EzSource :
- Tetrahedron [ 0040-4020 ] ; 1982.
Abstract
We have carried out ab initio calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.
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DOI: 10.1016/S0040-4020(01)82458-3
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Pérez</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author><author><name sortKey="Ya Ez, M" sort="Ya Ez, M" uniqKey="Ya Ez M" first="M." last="Yá Ez">M. Yá Ez</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11</idno><date when="1983" year="1983">1983</date><idno type="doi">10.1016/S0040-4020(01)82458-3</idno><idno type="url">https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">002873</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a">A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title><author><name sortKey="Catalan, J" sort="Catalan, J" uniqKey="Catalan J" first="J." last="Catalán">J. Catalán</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author><author><name sortKey="M, O" sort="M, O" uniqKey="M O" first="O." last="M">O. M</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author><author><name sortKey="Perez, P" sort="Perez, P" uniqKey="Perez P" first="P." last="Pérez">P. Pérez</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author><author><name sortKey="Ya Ez, M" sort="Ya Ez, M" uniqKey="Ya Ez M" first="M." last="Yá Ez">M. Yá Ez</name><affiliation><mods:affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="ISSN">0040-4020</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1982">1982</date><biblScope unit="volume">39</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="2851">2851</biblScope><biblScope unit="page" to="2861">2861</biblScope></imprint><idno type="ISSN">0040-4020</idno></series><idno type="istex">38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11</idno><idno type="DOI">10.1016/S0040-4020(01)82458-3</idno><idno type="PII">S0040-4020(01)82458-3</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4020</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">We have carried out ab initio calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.</div></front></TEI><istex><corpusName>elsevier</corpusName><author><json:item><name>J. Catalán</name><affiliations><json:string>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</json:string></affiliations></json:item><json:item><name>O. Mó</name><affiliations><json:string>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</json:string></affiliations></json:item><json:item><name>P. Pérez</name><affiliations><json:string>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</json:string></affiliations></json:item><json:item><name>M. Yáñez</name><affiliations><json:string>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</json:string></affiliations></json:item></author><language><json:string>eng</json:string></language><abstract>We have carried out ab initio calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.</abstract><qualityIndicators><score>8</score><pdfVersion>1.2</pdfVersion><pdfPageSize>468 x 754 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>0</keywordCount><abstractCharCount>1633</abstractCharCount><pdfWordCount>5923</pdfWordCount><pdfCharCount>38547</pdfCharCount><pdfPageCount>11</pdfPageCount><abstractWordCount>254</abstractWordCount></qualityIndicators><title>A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title><pii><json:string>S0040-4020(01)82458-3</json:string></pii><genre><json:string>research-article</json:string></genre><serie><genre></genre><language><json:string>unknown</json:string></language><title>Part 1.</title></serie><host><volume>39</volume><pii><json:string>S0040-4020(00)X0652-7</json:string></pii><pages><last>2861</last><first>2851</first></pages><issn><json:string>0040-4020</json:string></issn><issue>17</issue><genre><json:string>Journal</json:string></genre><language><json:string>unknown</json:string></language><title>Tetrahedron</title><publicationDate>1983</publicationDate></host><categories><wos><json:string>CHEMISTRY, ORGANIC</json:string></wos></categories><publicationDate>1982</publicationDate><copyrightDate>1983</copyrightDate><doi><json:string>10.1016/S0040-4020(01)82458-3</json:string></doi><id>38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11</id><fulltext><json:item><original>true</original><mimetype>application/pdf</mimetype><extension>pdf</extension><uri>https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/fulltext/pdf</uri></json:item><json:item><original>true</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/fulltext/txt</uri></json:item><json:item><original>false</original><mimetype>application/zip</mimetype><extension>zip</extension><uri>https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>ELSEVIER</p></availability><date>1983</date></publicationStmt><sourceDesc><biblStruct type="inbook"><analytic><title level="a">A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title><author><persName><forename type="first">J.</forename><surname>Catalán</surname></persName><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation></author><author><persName><forename type="first">O.</forename><surname>Mó</surname></persName><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation></author><author><persName><forename type="first">P.</forename><surname>Pérez</surname></persName><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation></author><author><persName><forename type="first">M.</forename><surname>Yáñez</surname></persName><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation></author></analytic><monogr><title level="j">Tetrahedron</title><title level="j" type="abbrev">TET</title><idno type="pISSN">0040-4020</idno><idno type="PII">S0040-4020(00)X0652-7</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1982"></date><biblScope unit="volume">39</biblScope><biblScope unit="issue">17</biblScope><biblScope unit="page" from="2851">2851</biblScope><biblScope unit="page" to="2861">2861</biblScope></imprint></monogr><idno type="istex">38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11</idno><idno type="DOI">10.1016/S0040-4020(01)82458-3</idno><idno type="PII">S0040-4020(01)82458-3</idno></biblStruct></sourceDesc></fileDesc><profileDesc><creation><date>1983</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>We have carried out ab initio calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.</p></abstract></profileDesc><revisionDesc><change when="1982-11-30">Received</change><change when="1982">Published</change></revisionDesc></teiHeader></istex:fulltextTEI></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla"><item-info><jid>TET</jid><aid>01824583</aid><ce:pii>S0040-4020(01)82458-3</ce:pii><ce:doi>10.1016/S0040-4020(01)82458-3</ce:doi><ce:copyright type="unknown" year="1983"></ce:copyright></item-info><head><ce:title>A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</ce:title><ce:author-group><ce:author><ce:given-name>J.</ce:given-name><ce:surname>Catalán</ce:surname></ce:author><ce:author><ce:given-name>O.</ce:given-name><ce:surname>Mó</ce:surname></ce:author><ce:author><ce:given-name>P.</ce:given-name><ce:surname>Pérez</ce:surname></ce:author><ce:author><ce:given-name>M.</ce:given-name><ce:surname>Yáñez</ce:surname></ce:author><ce:affiliation><ce:textfn>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</ce:textfn></ce:affiliation></ce:author-group><ce:date-received day="30" month="11" year="1982"></ce:date-received><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>We have carried out <ce:italic>ab initio</ce:italic> calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.</ce:simple-para></ce:abstract-sec></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>A theoretical study of the structure, charge distribution and gas-phase basicity of azaindoles</title></titleInfo><name type="personal"><namePart type="given">J.</namePart><namePart type="family">Catalán</namePart><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">O.</namePart><namePart type="family">Mó</namePart><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">P.</namePart><namePart type="family">Pérez</namePart><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">M.</namePart><namePart type="family">Yáñez</namePart><affiliation>Departamento de Química Física y Química Cuántica, Centro Coordinado CSIC-UAM, Facultad de Ciencias, C-XIV, Universidad Autónoma de Madrid, Cantoblanco, Madrid 34 Spain</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article"></genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1982</dateIssued><dateCaptured encoding="w3cdtf">1982-11-30</dateCaptured><copyrightDate encoding="w3cdtf">1983</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract lang="en">We have carried out ab initio calculations, using a STO-3G minimal basis set, for indazole, benzimidazole, azaindoles and their tautomeric forms. The structural changes which take place in the exchange of the imino proton are fully analized and explained in terms of hybridization effects, valence-shell electron-pairs repulsions and intramolecular non-bonded interactions. These structural changes affect substantially to the endocyclic bond angles which involved both N's. The structure and the charge distribution of the 5-membered ring of azaindoles is very little affected by the position of the aza N. The dicoordinated nitrogen atom is more negative than the tricoordinated one (with the exception of 1H-indazole). As in indoles, C3 of azaindoles is the C atom with the highest electronic density. The prototropic tautomerism in these species is accompanied by a strong migration of charge from the 6 to the 5-membered ring, which results in a considerable increase of the polarity and the basicity of the corresponding tautomeric forms. The predicted PA's are in good agreement with the experimental evidence. C5 is the most reactive C atom of indazole and benzimidazole, although in the former C3 is almost as active as C5. In azaindoles the most basic C atom is C3. Azaindoles are less reactive than indole toward electrophilic agents. Our predicted PA's for N protonation present differences much smaller than those observed in solution. We propose, as a possible explanation, an influence of the tautomeric forms which are more basic in the gas-phase, and more easy to stabilize in aqueous solution, than the normal ones.</abstract><relatedItem type="host"><titleInfo><title>Tetrahedron</title></titleInfo><titleInfo type="abbreviated"><title>TET</title></titleInfo><genre type="Journal">journal</genre><originInfo><dateIssued encoding="w3cdtf">1983</dateIssued></originInfo><identifier type="ISSN">0040-4020</identifier><identifier type="PII">S0040-4020(00)X0652-7</identifier><part><date>1983</date><detail type="volume"><number>39</number><caption>vol.</caption></detail><detail type="issue"><number>17</number><caption>no.</caption></detail><extent unit="issue pages"><start>2733</start><end>2868</end></extent><extent unit="pages"><start>2851</start><end>2861</end></extent></part></relatedItem><identifier type="istex">38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11</identifier><identifier type="DOI">10.1016/S0040-4020(01)82458-3</identifier><identifier type="PII">S0040-4020(01)82458-3</identifier><recordInfo><recordContentSource>ELSEVIER</recordContentSource></recordInfo></mods></metadata><enrichments><istex:catWosTEI uri="https://api.istex.fr/document/38BCCD87C36EFF1CB5CA0BEF061E8CBCA8737B11/enrichments/catWos"><teiHeader><profileDesc><textClass><classCode scheme="WOS">CHEMISTRY, ORGANIC</classCode></textClass></profileDesc></teiHeader></istex:catWosTEI></enrichments></istex></record>Pour manipuler ce document sous Unix (Dilib)
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