Synthesis and characterization of some α-naphthyl selenium/tellurium derivatives: X-ray crystal structure of benzyl-1-naphthyl selenide and diphenylmethyl-1-naphthyl selenide

Bhasin, K. K.; Singh, Neelam; Dhiman, Rishu; Ram, Ganga; Shivani, .; Mehta, S.K.; Butcher, Ray J.

doi:10.1016/j.jorganchem.2005.09.033

Cited by 6 publications

(3 citation statements)

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“…Starting substrates, dipyridyl/dinaphthyl/bis(diphenylmethyl) diselenide (1-6) were prepared using the reported procedure [41][42][43][44][45][46]. Commercially available reagents such as ethyl 2-chloroethanoate 7a, ethyl 3-chloropropanoate 7b and ethyl 4-chlorobutanoate 7c were used as such without further purification.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Bhalla

Nagpal

Kumar

et al. 2009

Journal of Organometallic Chemistry

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Section: Resultsmentioning

confidence: 99%

“…In addition, successful attempts have also been made towards the design, synthesis and structural studies of symmetrical and unsymmetrical organochalcogens in our laboratory [41][42][43][44][45][46].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Bhalla

Nagpal

Kumar

et al. 2009

Journal of Organometallic Chemistry

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“…Registry no. : 1-(methylthio)naphthalene [10075-72-6]; bis-(1-naphthyl)sulfide [607-53-4]; 1-naphthyl phenyl sulfide [7570-98-1]; methyl 1-naphthyl selenide [20613-85-8]; bis(1-naphthyl)selenide [227010-30-2].…”

Section: Methodsmentioning

confidence: 99%

Combined Experimental and Theoretical Studies on the Radical Nucleophile Addition Reaction for Sulfide- and Selenide-Centered Anions

et al. 2019

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The reactivity of sulfur- and selenium-centered nucleophiles toward 1-naphthyl radicals was studied in dimethylsulfoxide. The photostimulated reaction of sulfide anions, –SC(NH)C6H5 (1), –SC(NH)NH2 (2), and –SC(NH)CH3 (3), renders, after the addition of MeI, methyl 1-naphthylsulfide as a main product together with bis(1-naphthyl) sulfide and naphthalene under irradiation. Concordantly, the reaction of selenide anions, –SeC(NH)C6H5 (4), –SeC(NH)NH2 (5), and –SeCN (6), produces methyl 1-naphthyl selenide, bis(1-naphthyl) selenide, and naphthalene in the presence of potassium tert-butoxide anion (entrainment conditions). Absolute rate constants for the coupling of ions 1–6 to 1-naphthyl radicals were determined; as a general trend, the selenide-centered nucleophiles enhance in 2 times the reactivity of their sulfide analogues. From the mechanistic study, it is proposed that the unstable radical anion produced by the addition of the nucleophile to 1-naphthyl radical affords, after fragmentation, 1-naphthylsulfide/selenide anion. In addition, experimental results are discussed in terms of density functional theory calculations. There is a generally good agreement between the experimental and the calculated reactivities, the spin density being the main parameter to describe the difference found among the anions under study. Moreover, the calculations predict that anion –SeC(NH)CH3 (7) would be a good candidate for the synthesis of selenide derivatives.

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NMR of Organoselenium and Organotellurium Compounds

Panda

Singh

2012

Patai's Chemistry of Functional Groups

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This chapter gives a systematic account of and surveys the available data on 77 Se and 125 Te NMR spectra of organochalcogen compounds such as chacogenols, mono and dichalcogenides, chalcogenolates, tetra and hexa substituted chalcogen compounds, chalcogenyl halides, chalcogen‐containing heterocycles and macrocycles, chalcogen‐oxygen/nitrogen compounds, etc. The review is based on the literature from 1985 to 2011 and includes 780 references. The 77 Se/ 125 Te NMR spectra of organochalcogen compounds reveal expansive chemical shifts (δ Se /δ Te ) leading to sharp sensitivity of these nuclei (Se/Te) to their environment such as solvent, temperature, molecular geometry, ligand backbone, oxidation state, chelate ring size, steric strain, etc. This is well illustrated by the advantageous use of this spectroscopy in the successful determination of the solution state structure of several organochalcogen compounds. It is noted that the 125 Te and 77 Se chemical shifts of a large number of structurally similar organotellurium and selenium compounds show linear relationship.

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Synthesis and characterization of some α-naphthyl selenium/tellurium derivatives: X-ray crystal structure of benzyl-1-naphthyl selenide and diphenylmethyl-1-naphthyl selenide

Cited by 6 publications

References 36 publications

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Combined Experimental and Theoretical Studies on the Radical Nucleophile Addition Reaction for Sulfide- and Selenide-Centered Anions

NMR of Organoselenium and Organotellurium Compounds

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