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Schmidt, LcAuthor

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February 8, 2025
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Reactivity of sulfur centered nucleophiles in photoinduced reactions with 1-bromonaphthalene

Publicated to: Arkivoc. 411-419 - 2003-01-01 (), DOI: 10.3998/ark.5550190.0004.a39

Authors:

Argüello, JE; Schmidt, LC; Peñéñory, AB
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Affiliations

- Author

Abstract

The reactivity of S2- (1), -SCN (2) and -SCNH(NH2) (3) in photoinduced substitution reactions with 1-bromonaphthalene (5) in DMSO was studied. The photostimulated reaction of ion 1 with 5 renders after quenching with MeI 1-(methylthio) naphthalene (16%), bis (1-naphthyl) sulfide (17.5%) and naphthalene (42%). The lack of reaction in the dark and the inhibition of the photoinduced one by the presence of di-tert-butylnitroxide (DTBN) and p-dinitrobenzene (p-DNB) are evidence of a radical chain mechanism for these substitution reactions. On the other hand, ion 2 was unreactive towards 5, both as an electron donor under photostimulation and as a nucleophile. Finally the thiourea anion (3) affords after a photoinduced reaction with 5 and quenching with MeI, 1-methylthionaphthalene (50%), bis (1-naphthyl) sulfide (22%) and naphthalene (9%). This reaction does not occur in the dark and is inhibited in the presence of DTBN. By using hydrogen abstraction from DMSO as competitive reaction, the absolute rate constants for the addition of ions 1, 3 and benzene thiolate ions (4) to 1-naphthyl radicals have been determined to be 0.5 x 10(9) M(-1)s(-1), 1.0 x 10(9) M(-1)s(-1) and 5.1 x 10(9) M(-1)s(-1) respectively.
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Keywords

Aromatic substitutionArylElectron-transferIonMechanismPhotoinduced electron transferRadicalsReactivitS(rn)1 reactionsSodium sulfideThiourea

Quality index

Bibliometric impact. Analysis of the contribution and dissemination channel

The work has been published in the journal Arkivoc, and although the journal is classified in the quartile Q4 (Agencia WoS (JCR)), its regional focus and specialization in Chemistry, Organic, give it significant recognition in a specific niche of scientific knowledge at an international level.

Independientemente del impacto esperado determinado por el canal de difusión, es importante destacar el impacto real observado de la propia aportación.

Según las diferentes agencias de indexación, el número de citas acumuladas por esta publicación hasta la fecha 2025-12-21:

  • WoS: 11
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Impact and social visibility

From the perspective of influence or social adoption, and based on metrics associated with mentions and interactions provided by agencies specializing in calculating the so-called "Alternative or Social Metrics," we can highlight as of 2025-12-21:

  • The use of this contribution in bookmarks, code forks, additions to favorite lists for recurrent reading, as well as general views, indicates that someone is using the publication as a basis for their current work. This may be a notable indicator of future more formal and academic citations. This claim is supported by the result of the "Capture" indicator, which yields a total of: 5 (PlumX).

It is essential to present evidence supporting full alignment with institutional principles and guidelines on Open Science and the Conservation and Dissemination of Intellectual Heritage. A clear example of this is:

  • The work has been submitted to a journal whose editorial policy allows open Open Access publication.
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