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dc.contributor.CRUESPUniversidade Estadual de Campinaspt_BR
dc.typeArtigo de periódicopt_BR
dc.titleRegioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gelpt_BR
dc.contributor.authorRodrigues, JARpt_BR
dc.contributor.authorde Oliveira, APpt_BR
dc.contributor.authorMoran, PJSpt_BR
dc.contributor.authorCustodio, Rpt_BR
unicamp.authorUniv Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazilpt_BR
dc.subjectnitrationpt_BR
dc.subjectnitric acid and derivativespt_BR
dc.subjectphenolspt_BR
dc.subjectregioselectionpt_BR
dc.subject.wosNitrogen-dioxidept_BR
dc.subject.wosSubstitutionpt_BR
dc.subject.wosDerivativespt_BR
dc.subject.wosCatalystspt_BR
dc.subject.wosAromaticspt_BR
dc.subject.wosEsterspt_BR
dc.subject.wosAcidpt_BR
dc.description.abstractThe reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six-center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation, (C) 1999 Elsevier Science Ltd. All rights reserved.pt
dc.relation.ispartofTetrahedronpt_BR
dc.relation.ispartofabbreviationTetrahedronpt_BR
dc.publisher.cityOxfordpt_BR
dc.publisher.countryInglaterrapt_BR
dc.publisherPergamon-elsevier Science Ltdpt_BR
dc.date.issued1999pt_BR
dc.date.monthofcirculationMAY 28pt_BR
dc.identifier.citationTetrahedron. Pergamon-elsevier Science Ltd, v. 55, n. 22, n. 6733, n. 6738, 1999.pt_BR
dc.language.isoenpt_BR
dc.description.volume55pt_BR
dc.description.issuenumber22pt_BR
dc.description.firstpage6733pt_BR
dc.description.lastpage6738pt_BR
dc.rightsfechadopt_BR
dc.rights.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policypt_BR
dc.sourceWeb of Sciencept_BR
dc.identifier.issn0040-4020pt_BR
dc.identifier.wosidWOS:000080579600002pt_BR
dc.identifier.doi10.1016/S0040-4020(99)00320-8pt_BR
dc.date.available2014-12-02T16:30:26Z
dc.date.available2015-11-26T16:44:19Z-
dc.date.accessioned2014-12-02T16:30:26Z
dc.date.accessioned2015-11-26T16:44:19Z-
dc.description.provenanceMade available in DSpace on 2014-12-02T16:30:26Z (GMT). No. of bitstreams: 1 WOS000080579600002.pdf: 367337 bytes, checksum: 841145ce9502633fbcb87524414b4692 (MD5) Previous issue date: 1999en
dc.description.provenanceMade available in DSpace on 2015-11-26T16:44:19Z (GMT). No. of bitstreams: 2 WOS000080579600002.pdf: 367337 bytes, checksum: 841145ce9502633fbcb87524414b4692 (MD5) WOS000080579600002.pdf.txt: 17530 bytes, checksum: d7dd9401cfba69d8d14550432ec72f20 (MD5) Previous issue date: 1999en
dc.identifier.urihttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/80407pt_BR
dc.identifier.urihttp://www.repositorio.unicamp.br/handle/REPOSIP/80407
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/80407-
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