A Kerr effect study of conformations of 1,8-disubsituted naphtalenes as solutes

Bulgarevich, S. B.; Иванова, Н. А.; Movshovich, D. Ya.; Mannschreck, Albrecht; Kiessl, L.; Zinner, H.; Kiefl, C.

doi:10.1016/0022-2860(92)80117-z

Cited by 5 publications

(2 citation statements)

References 18 publications

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“…Chemical analysis data were obtained from Mr Stephen Boyer, London Metropolitan University. Ester 4 and amides 5 and 6 were prepared by peri-lithiation of 1-dimethylaminonaphthalene and treatment with methyl chloroformate, N,N-dimethylcarbamoyl chloride or N,N-diisopropylcarbamoyl chloride [26,27]. 2-benzoyloxy-1,1-dimethyl-1,2-dihydrobenzo[cd] 1,1-dimethyl-1,2-dihydro-2-(2′,2′-dimethyl Slow evaporation of the NMR sample led to the growth of a large crystal of 8-dimethylammonio-naphthalene-1-carboxylic acid triflate, 23.triflate, m.p.…”

Section: Experimental Generalmentioning

confidence: 99%

Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a “through space” amide

Wannebroucq

Jarmyn

Pitak

et al. 2016

Pure and Applied Chemistry

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Abstract8-Dimethylaminonaphthalene-1-carbaldehyde reacts readily at 0°C with benzoyl or pivaloyl chloride by O-acylation and formation of a N–C bond (1.566(2)–1.568(3) Å) between the peri-substituents to give a salt. The reaction is promoted by electron donation from the dimethylamino group to the carbonyl group, akin to the properties of an amide. In contrast, the corresponding methyl ester and N,N-diisopropylamide react with acid in ether by protonation of the dimethylamino group and formation of a hydrogen bond to the carbonyl group, while under similar conditions the N,N-dimethylamide undergoes ready hydrolysis to the acid. The structures of products are determined by X-ray crystallography, and from the latter hydrolysis crystals containing zwitterionic 1-dimethylammonium-naphthalene-8-carboxylate and the corresponding O-protonated cation along with dimethylammonium and triflate ions were obtained.

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Section: Experimental Generalmentioning

confidence: 99%

Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a “through space” amide

Wannebroucq

Jarmyn

Pitak

et al. 2016

Pure and Applied Chemistry

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“…13 Barriers to interconversion of naphthalenes bearing meta-substituted phenyl 14, 15 or pyridyl [16][17][18] rings at the 1-and 8-positions are much lower, and these compounds do not exist as atropisomeric diastereoisomers. The conformation 19,20 and racemisation 21 of enantiomeric atropisomers of 8-substituted-1-naphthamides and their thioamide derivatives 22 have been described by Mannschreck and Kiefl, but there are no reported examples of diastereoisomeric non-biaryl atropisomers based on a 1,8disubstituted naphthalene system.…”

Section: Introductionmentioning

confidence: 99%

Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

Clayden

Westlund

Frampton

2000

J. Chem. Soc., Perkin Trans. 1

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ChemInform Abstract: A Kerr Effect Study of Conformations of 1,8‐Disubstituted Naphthalenes as Solutes.

et al. 1992

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A Kerr Effect Study of Conformations of 1,8-Disubstituted Naphthalenes as Solutes. -The molar Kerr constants and dipole moments for the substituted naphthalenes (I), (II) and (III) are studied in dioxane solution at 298 K. -(BULGAREVICH, S. B.; IVANOVA, N. A.; MOVSHOVICH, D. YA.; MANNSCHRECK, A.; KIESSL, L.; ZINNER, H.; KIEFL, C.; J. Mol. Struct. 265 (1992) 3-4, 417-428; Inst. Phys. Org. Chem., Rostov Univ., 344711 Rostov-on-Don, USSR; EN)

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A Kerr effect study of conformations of 1,8-disubsituted naphtalenes as solutes

Cited by 5 publications

References 18 publications

Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a “through space” amide

Reactions and interactions between peri-groups in 1-dimethylamino-naphthalene salts: an example of a “through space” amide

Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

ChemInform Abstract: A Kerr Effect Study of Conformations of 1,8‐Disubstituted Naphthalenes as Solutes.

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