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Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations
A series of water-soluble metal formazanates, [Al 2 (OH) 2 (H 2 O) 8 ](HL) 2 ( 1 ), [{Fe(H 2 O) 4 }(HL)(H 2 L)]·2H 2 O ( 2 ) and [Cu(en) 2 (H 2 O) 2 ][CuL(H 2 O) 2 ] 2 ( 3 ), were synthesized by the reaction of sodium 2-(2-(( E )-cyano(( E )-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzene...
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| Published in: | New journal of chemistry 2022-03, Vol.46 (11), p.52-511 |
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| Main Authors: | , , , , |
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| cites | cdi_FETCH-LOGICAL-c211t-249300f8cc441233c8ad2ed21b5ed3851da12e6c63905858b9b2c436270d81513 |
| container_end_page | 511 |
| container_issue | 11 |
| container_start_page | 52 |
| container_title | New journal of chemistry |
| container_volume | 46 |
| creator | Gurbanov, Atash V Andrade, Marta A Martins, Luísa M. D. R. S Mahmudov, Kamran T Pombeiro, Armando J. L |
| description | A series of water-soluble metal formazanates, [Al
2
(OH)
2
(H
2
O)
8
](HL)
2
(
1
), [{Fe(H
2
O)
4
}(HL)(H
2
L)]·2H
2
O (
2
) and [Cu(en)
2
(H
2
O)
2
][CuL(H
2
O)
2
]
2
(
3
), were synthesized by the reaction of sodium 2-(2-((
E
)-cyano((
E
)-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzenesulfonate (
Na
2
HL
) with Al(NO
3
)
3
·9H
2
O, FeCl
3
·6H
2
O and Cu(NO
3
)
2
·3H
2
O (in the presence of ethylenediamine) in methanol, respectively. The formazan pro-ligand
Na
2
HL
and its complexes
1-3
were characterized by ESI-MS,
1
H/
13
C NMR (for
Na
2
HL
), IR spectroscopy, elemental and X-ray diffraction analyses (for
1-3
). According to the X-ray analysis, the formazanate behaves as an anion or displays a mono- or bidentate coordination mode, for the Al, Fe or Cu centre, respectively. All complexes were tested as catalysts for the peroxidative (with H
2
O
2
) oxidation of cyclohexane and cyclohexanol to the coresponding organic products at room temperature. The complexes
2
and
3
are active homogeneous catalysts for the microwave-assisted peroxidative oxidation with aqueous H
2
O
2
of cyclohexane (to cyclohexanol and cyclohexanone) and cyclohexanol to cyclohexanone.
The synthesis, structure and catalytic performance of water-soluble Al(
iii
), Fe(
iii
) and Cu(
ii
) formazanates in the oxidation of cyclohexane and cyclohexanol to the coresponding organic products are reported. |
| doi_str_mv | 10.1039/d1nj06211e |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2640943340</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2640943340</sourcerecordid><originalsourceid>FETCH-LOGICAL-c211t-249300f8cc441233c8ad2ed21b5ed3851da12e6c63905858b9b2c436270d81513</originalsourceid><addsrcrecordid>eNpF0N9LwzAQB_AgCs7pi-9CwJdNVs0ladb6NubmD4a-KD6WNE1ZZ5bMpEXnX29dRZ_u4D7ccV-EToFcAmHpVQF2RQQF0HuoB0ykUUoF7Lc9cB6RmItDdBTCihCAsYAe-niVtfZRcKbJjcYTMxiO8FwPhljaAk-btimdX8svaVsYrnHY2nqpQxVGONS-UXXj9WiH5WZjKiXrytmAK4uleZNWdyOj3NIZ7D6rogPH6KCUJuiT39pHL_PZ8_QuWjzd3k8ni0i1T9QR5SkjpEyU4hwoYyqRBdUFhTzWBUtiKCRQLZRgKYmTOMnTnCrOBB2TIoEYWB-dd3s33r03OtTZyjXeticzKjhJOWOctOqiU8q7ELwus42v1tJvMyDZT7DZDTw-7IKdtfiswz6oP_cfPPsGw61zaA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2640943340</pqid></control><display><type>article</type><title>Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations</title><source>Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)</source><creator>Gurbanov, Atash V ; Andrade, Marta A ; Martins, Luísa M. D. R. S ; Mahmudov, Kamran T ; Pombeiro, Armando J. L</creator><creatorcontrib>Gurbanov, Atash V ; Andrade, Marta A ; Martins, Luísa M. D. R. S ; Mahmudov, Kamran T ; Pombeiro, Armando J. L</creatorcontrib><description>A series of water-soluble metal formazanates, [Al
2
(OH)
2
(H
2
O)
8
](HL)
2
(
1
), [{Fe(H
2
O)
4
}(HL)(H
2
L)]·2H
2
O (
2
) and [Cu(en)
2
(H
2
O)
2
][CuL(H
2
O)
2
]
2
(
3
), were synthesized by the reaction of sodium 2-(2-((
E
)-cyano((
E
)-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzenesulfonate (
Na
2
HL
) with Al(NO
3
)
3
·9H
2
O, FeCl
3
·6H
2
O and Cu(NO
3
)
2
·3H
2
O (in the presence of ethylenediamine) in methanol, respectively. The formazan pro-ligand
Na
2
HL
and its complexes
1-3
were characterized by ESI-MS,
1
H/
13
C NMR (for
Na
2
HL
), IR spectroscopy, elemental and X-ray diffraction analyses (for
1-3
). According to the X-ray analysis, the formazanate behaves as an anion or displays a mono- or bidentate coordination mode, for the Al, Fe or Cu centre, respectively. All complexes were tested as catalysts for the peroxidative (with H
2
O
2
) oxidation of cyclohexane and cyclohexanol to the coresponding organic products at room temperature. The complexes
2
and
3
are active homogeneous catalysts for the microwave-assisted peroxidative oxidation with aqueous H
2
O
2
of cyclohexane (to cyclohexanol and cyclohexanone) and cyclohexanol to cyclohexanone.
The synthesis, structure and catalytic performance of water-soluble Al(
iii
), Fe(
iii
) and Cu(
ii
) formazanates in the oxidation of cyclohexane and cyclohexanol to the coresponding organic products are reported.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj06211e</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkanes ; Aluminum ; Catalysts ; Chemical synthesis ; Coordination compounds ; Copper ; Cyclohexane ; Cyclohexanone ; Ethylenediamine ; Ferric chloride ; Hydrogen peroxide ; Infrared spectroscopy ; Iron ; NMR ; Nuclear magnetic resonance ; Oxidation ; Room temperature ; Water chemistry ; X ray analysis</subject><ispartof>New journal of chemistry, 2022-03, Vol.46 (11), p.52-511</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c211t-249300f8cc441233c8ad2ed21b5ed3851da12e6c63905858b9b2c436270d81513</citedby><cites>FETCH-LOGICAL-c211t-249300f8cc441233c8ad2ed21b5ed3851da12e6c63905858b9b2c436270d81513</cites><orcidid>0000-0001-8323-888X ; 0000-0002-7603-5192 ; 0000-0002-5403-9352 ; 0000-0003-0743-6520 ; 0000-0003-1415-8012</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Gurbanov, Atash V</creatorcontrib><creatorcontrib>Andrade, Marta A</creatorcontrib><creatorcontrib>Martins, Luísa M. D. R. S</creatorcontrib><creatorcontrib>Mahmudov, Kamran T</creatorcontrib><creatorcontrib>Pombeiro, Armando J. L</creatorcontrib><title>Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations</title><title>New journal of chemistry</title><description>A series of water-soluble metal formazanates, [Al
2
(OH)
2
(H
2
O)
8
](HL)
2
(
1
), [{Fe(H
2
O)
4
}(HL)(H
2
L)]·2H
2
O (
2
) and [Cu(en)
2
(H
2
O)
2
][CuL(H
2
O)
2
]
2
(
3
), were synthesized by the reaction of sodium 2-(2-((
E
)-cyano((
E
)-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzenesulfonate (
Na
2
HL
) with Al(NO
3
)
3
·9H
2
O, FeCl
3
·6H
2
O and Cu(NO
3
)
2
·3H
2
O (in the presence of ethylenediamine) in methanol, respectively. The formazan pro-ligand
Na
2
HL
and its complexes
1-3
were characterized by ESI-MS,
1
H/
13
C NMR (for
Na
2
HL
), IR spectroscopy, elemental and X-ray diffraction analyses (for
1-3
). According to the X-ray analysis, the formazanate behaves as an anion or displays a mono- or bidentate coordination mode, for the Al, Fe or Cu centre, respectively. All complexes were tested as catalysts for the peroxidative (with H
2
O
2
) oxidation of cyclohexane and cyclohexanol to the coresponding organic products at room temperature. The complexes
2
and
3
are active homogeneous catalysts for the microwave-assisted peroxidative oxidation with aqueous H
2
O
2
of cyclohexane (to cyclohexanol and cyclohexanone) and cyclohexanol to cyclohexanone.
The synthesis, structure and catalytic performance of water-soluble Al(
iii
), Fe(
iii
) and Cu(
ii
) formazanates in the oxidation of cyclohexane and cyclohexanol to the coresponding organic products are reported.</description><subject>Alkanes</subject><subject>Aluminum</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Coordination compounds</subject><subject>Copper</subject><subject>Cyclohexane</subject><subject>Cyclohexanone</subject><subject>Ethylenediamine</subject><subject>Ferric chloride</subject><subject>Hydrogen peroxide</subject><subject>Infrared spectroscopy</subject><subject>Iron</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxidation</subject><subject>Room temperature</subject><subject>Water chemistry</subject><subject>X ray analysis</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpF0N9LwzAQB_AgCs7pi-9CwJdNVs0ladb6NubmD4a-KD6WNE1ZZ5bMpEXnX29dRZ_u4D7ccV-EToFcAmHpVQF2RQQF0HuoB0ykUUoF7Lc9cB6RmItDdBTCihCAsYAe-niVtfZRcKbJjcYTMxiO8FwPhljaAk-btimdX8svaVsYrnHY2nqpQxVGONS-UXXj9WiH5WZjKiXrytmAK4uleZNWdyOj3NIZ7D6rogPH6KCUJuiT39pHL_PZ8_QuWjzd3k8ni0i1T9QR5SkjpEyU4hwoYyqRBdUFhTzWBUtiKCRQLZRgKYmTOMnTnCrOBB2TIoEYWB-dd3s33r03OtTZyjXeticzKjhJOWOctOqiU8q7ELwus42v1tJvMyDZT7DZDTw-7IKdtfiswz6oP_cfPPsGw61zaA</recordid><startdate>20220314</startdate><enddate>20220314</enddate><creator>Gurbanov, Atash V</creator><creator>Andrade, Marta A</creator><creator>Martins, Luísa M. D. R. S</creator><creator>Mahmudov, Kamran T</creator><creator>Pombeiro, Armando J. L</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-8323-888X</orcidid><orcidid>https://orcid.org/0000-0002-7603-5192</orcidid><orcidid>https://orcid.org/0000-0002-5403-9352</orcidid><orcidid>https://orcid.org/0000-0003-0743-6520</orcidid><orcidid>https://orcid.org/0000-0003-1415-8012</orcidid></search><sort><creationdate>20220314</creationdate><title>Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations</title><author>Gurbanov, Atash V ; Andrade, Marta A ; Martins, Luísa M. D. R. S ; Mahmudov, Kamran T ; Pombeiro, Armando J. L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c211t-249300f8cc441233c8ad2ed21b5ed3851da12e6c63905858b9b2c436270d81513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkanes</topic><topic>Aluminum</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Coordination compounds</topic><topic>Copper</topic><topic>Cyclohexane</topic><topic>Cyclohexanone</topic><topic>Ethylenediamine</topic><topic>Ferric chloride</topic><topic>Hydrogen peroxide</topic><topic>Infrared spectroscopy</topic><topic>Iron</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidation</topic><topic>Room temperature</topic><topic>Water chemistry</topic><topic>X ray analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gurbanov, Atash V</creatorcontrib><creatorcontrib>Andrade, Marta A</creatorcontrib><creatorcontrib>Martins, Luísa M. D. R. S</creatorcontrib><creatorcontrib>Mahmudov, Kamran T</creatorcontrib><creatorcontrib>Pombeiro, Armando J. L</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gurbanov, Atash V</au><au>Andrade, Marta A</au><au>Martins, Luísa M. D. R. S</au><au>Mahmudov, Kamran T</au><au>Pombeiro, Armando J. L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations</atitle><jtitle>New journal of chemistry</jtitle><date>2022-03-14</date><risdate>2022</risdate><volume>46</volume><issue>11</issue><spage>52</spage><epage>511</epage><pages>52-511</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A series of water-soluble metal formazanates, [Al
2
(OH)
2
(H
2
O)
8
](HL)
2
(
1
), [{Fe(H
2
O)
4
}(HL)(H
2
L)]·2H
2
O (
2
) and [Cu(en)
2
(H
2
O)
2
][CuL(H
2
O)
2
]
2
(
3
), were synthesized by the reaction of sodium 2-(2-((
E
)-cyano((
E
)-(2-sulfonatophenyl)diazenyl)methylene)hydrazineyl) benzenesulfonate (
Na
2
HL
) with Al(NO
3
)
3
·9H
2
O, FeCl
3
·6H
2
O and Cu(NO
3
)
2
·3H
2
O (in the presence of ethylenediamine) in methanol, respectively. The formazan pro-ligand
Na
2
HL
and its complexes
1-3
were characterized by ESI-MS,
1
H/
13
C NMR (for
Na
2
HL
), IR spectroscopy, elemental and X-ray diffraction analyses (for
1-3
). According to the X-ray analysis, the formazanate behaves as an anion or displays a mono- or bidentate coordination mode, for the Al, Fe or Cu centre, respectively. All complexes were tested as catalysts for the peroxidative (with H
2
O
2
) oxidation of cyclohexane and cyclohexanol to the coresponding organic products at room temperature. The complexes
2
and
3
are active homogeneous catalysts for the microwave-assisted peroxidative oxidation with aqueous H
2
O
2
of cyclohexane (to cyclohexanol and cyclohexanone) and cyclohexanol to cyclohexanone.
The synthesis, structure and catalytic performance of water-soluble Al(
iii
), Fe(
iii
) and Cu(
ii
) formazanates in the oxidation of cyclohexane and cyclohexanol to the coresponding organic products are reported.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj06211e</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0001-8323-888X</orcidid><orcidid>https://orcid.org/0000-0002-7603-5192</orcidid><orcidid>https://orcid.org/0000-0002-5403-9352</orcidid><orcidid>https://orcid.org/0000-0003-0743-6520</orcidid><orcidid>https://orcid.org/0000-0003-1415-8012</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2022-03, Vol.46 (11), p.52-511 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_proquest_journals_2640943340 |
| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Alkanes Aluminum Catalysts Chemical synthesis Coordination compounds Copper Cyclohexane Cyclohexanone Ethylenediamine Ferric chloride Hydrogen peroxide Infrared spectroscopy Iron NMR Nuclear magnetic resonance Oxidation Room temperature Water chemistry X ray analysis |
| title | Water-soluble Al(), Fe() and Cu() formazanates: synthesis, structure, and applications in alkane and alcohol oxidations |
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