Nitration and photonitration of naphthalene in aqueous systems
The nitration of naphthalene was studied in aqueous solution to gain insight into the processes leading to the nitration of aromatic compounds in atmospheric hydrometeors. Reactants used were nitric acid, nitrogen dioxide and peroxynitrous acid in the dark, nitrate, and nitrite/nitrous acid under il...
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ftunivtorino:oai:iris.unito.it:2318/1095 2023-11-05T03:36:08+01:00 Nitration and photonitration of naphthalene in aqueous systems VIONE, Davide Vittorio MAURINO, Valter MINERO, Claudio PELIZZETTI, Ezio VIONE D MAURINO V MINERO C PELIZZETTI E 2005 http://hdl.handle.net/2318/1095 https://doi.org/10.1021/es048855p eng eng info:eu-repo/semantics/altIdentifier/pmid/15773483 info:eu-repo/semantics/altIdentifier/wos/WOS:000227001700025 volume:39 (4) firstpage:1101 lastpage:1110 journal:ENVIRONMENTAL SCIENCE & TECHNOLOGY http://hdl.handle.net/2318/1095 doi:10.1021/es048855p info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-13844269160 info:eu-repo/semantics/closedAccess info:eu-repo/semantics/article 2005 ftunivtorino https://doi.org/10.1021/es048855p 2023-10-10T22:16:18Z The nitration of naphthalene was studied in aqueous solution to gain insight into the processes leading to the nitration of aromatic compounds in atmospheric hydrometeors. Reactants used were nitric acid, nitrogen dioxide and peroxynitrous acid in the dark, nitrate, and nitrite/nitrous acid under illumination. Naphthalene nitration can lead to two possible isomers, 1- and 2-nitronaphthalene. The former nitrocompound preferentially forms upon electrophilic processes and in the presence of nitrogen dioxide. Electrophilic nitration of naphthalene takes place in the presence of concentrated nitric acid, but nitration with nitric acid and oxidants (charge-transfer nitration) occurs under much milder conditions than with nitric acid alone. Charge-transfer nitration may have some environmental significance in particular cases, e.g. in acidic aerosols in the presence of HNO3 and oxidants. Nitrogen dioxide is thought to have a role in PAH nitration in the Antarctic particulate matter. In previous papers we have found that nitration induced by peroxynitrous acid, HOONO, can follow two pathways, the former electrophilic (leading for instance to the formation of nitrophenols from phenol) and the latter probably involving HOONO itself (accounting for the formation of nitrobenzene from benzene). In the case of naphthalene and HOONO the electrophilic pathway mainly leads to 1-nitronaphthalene, while the other one preferentially yields 2-nitronaphthalene. The nitration of naphthalene in the presence of nitrite/nitrous acid under irradiation leads to both nitroisomers in similar ratios, and the process is not inhibited by hydroxyl scavengers. This excludes nitrogen dioxide as reactive species for nitration and marks a difference with phenol photonitration and a similarity with the behavior of benzene under comparable conditions. Nitrite photochemistry (and nitrite-induced photonitration as well) is expected to be relevant in fog and cloudwater in polluted areas. An important difference with the gas-phase nitration is that the ... Article in Journal/Newspaper Antarc* Antarctic Università degli studi di Torino: AperTo (Archivio Istituzionale ad Accesso Aperto) Environmental Science & Technology 39 4 1101 1110 |
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Università degli studi di Torino: AperTo (Archivio Istituzionale ad Accesso Aperto) |
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ftunivtorino |
language |
English |
description |
The nitration of naphthalene was studied in aqueous solution to gain insight into the processes leading to the nitration of aromatic compounds in atmospheric hydrometeors. Reactants used were nitric acid, nitrogen dioxide and peroxynitrous acid in the dark, nitrate, and nitrite/nitrous acid under illumination. Naphthalene nitration can lead to two possible isomers, 1- and 2-nitronaphthalene. The former nitrocompound preferentially forms upon electrophilic processes and in the presence of nitrogen dioxide. Electrophilic nitration of naphthalene takes place in the presence of concentrated nitric acid, but nitration with nitric acid and oxidants (charge-transfer nitration) occurs under much milder conditions than with nitric acid alone. Charge-transfer nitration may have some environmental significance in particular cases, e.g. in acidic aerosols in the presence of HNO3 and oxidants. Nitrogen dioxide is thought to have a role in PAH nitration in the Antarctic particulate matter. In previous papers we have found that nitration induced by peroxynitrous acid, HOONO, can follow two pathways, the former electrophilic (leading for instance to the formation of nitrophenols from phenol) and the latter probably involving HOONO itself (accounting for the formation of nitrobenzene from benzene). In the case of naphthalene and HOONO the electrophilic pathway mainly leads to 1-nitronaphthalene, while the other one preferentially yields 2-nitronaphthalene. The nitration of naphthalene in the presence of nitrite/nitrous acid under irradiation leads to both nitroisomers in similar ratios, and the process is not inhibited by hydroxyl scavengers. This excludes nitrogen dioxide as reactive species for nitration and marks a difference with phenol photonitration and a similarity with the behavior of benzene under comparable conditions. Nitrite photochemistry (and nitrite-induced photonitration as well) is expected to be relevant in fog and cloudwater in polluted areas. An important difference with the gas-phase nitration is that the ... |
author2 |
VIONE D MAURINO V MINERO C PELIZZETTI E |
format |
Article in Journal/Newspaper |
author |
VIONE, Davide Vittorio MAURINO, Valter MINERO, Claudio PELIZZETTI, Ezio |
spellingShingle |
VIONE, Davide Vittorio MAURINO, Valter MINERO, Claudio PELIZZETTI, Ezio Nitration and photonitration of naphthalene in aqueous systems |
author_facet |
VIONE, Davide Vittorio MAURINO, Valter MINERO, Claudio PELIZZETTI, Ezio |
author_sort |
VIONE, Davide Vittorio |
title |
Nitration and photonitration of naphthalene in aqueous systems |
title_short |
Nitration and photonitration of naphthalene in aqueous systems |
title_full |
Nitration and photonitration of naphthalene in aqueous systems |
title_fullStr |
Nitration and photonitration of naphthalene in aqueous systems |
title_full_unstemmed |
Nitration and photonitration of naphthalene in aqueous systems |
title_sort |
nitration and photonitration of naphthalene in aqueous systems |
publishDate |
2005 |
url |
http://hdl.handle.net/2318/1095 https://doi.org/10.1021/es048855p |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
info:eu-repo/semantics/altIdentifier/pmid/15773483 info:eu-repo/semantics/altIdentifier/wos/WOS:000227001700025 volume:39 (4) firstpage:1101 lastpage:1110 journal:ENVIRONMENTAL SCIENCE & TECHNOLOGY http://hdl.handle.net/2318/1095 doi:10.1021/es048855p info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-13844269160 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1021/es048855p |
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Environmental Science & Technology |
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39 |
container_issue |
4 |
container_start_page |
1101 |
op_container_end_page |
1110 |
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