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Titolo:
Nitronate anion recognition and modulation of ambident reactivity by hydrogen-bonding receptors
Autore:
Linton, BR; Goodman, MS; Hamilton, AD;
Indirizzi:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA Univ Pittsburgh Pittsburgh PA USA 15260 pt Chem, Pittsburgh, PA 15260 USA
Titolo Testata:
CHEMISTRY-A EUROPEAN JOURNAL
fascicolo: 13, volume: 6, anno: 2000,
pagine: 2449 - 2455
SICI:
0947-6539(20000703)6:13<2449:NARAMO>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
MOLECULAR RECOGNITION; CARBOXYLATE; DEPROTONATION; NITROALKANES;
Keywords:
ambident nucleophiles; anions; hydrogen bonds; molecular recognition; receptors;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
26
Recensione:
Indirizzi per estratti:
Indirizzo: Linton, BR Yale Univ, Sterling Chem Lab, Box 208107, New Haven, CT 06520 USA Yale Univ Box 208107 New Haven CT USA 06520 Haven, CT 06520 USA
Citazione:
B.R. Linton et al., "Nitronate anion recognition and modulation of ambident reactivity by hydrogen-bonding receptors", CHEM-EUR J, 6(13), 2000, pp. 2449-2455

Abstract

Nitronate anions were shown to form complexes in DMSO with hydrogen-bonding receptors such as 1,3-dimethylthiourea 1 (K-a = 120 M-1) and bicyclic guanidinium 2 (K-a = 3200 M-1). A ditopic bis-thiourea exhibited increased association with substrates, that contained either two nitronates (K-a = 7000 M-1) or a combination of nitronate and carboxylate (K-a = 7200 M-1). Complexation of nitronate resulted in a change in the ambident reactivity during alkylation with p-nitrobenzyl bromide. The predominant reaction pathway wasshifted from oxygen alkylation to carbon alkylation as receptor binding strength increased. Kinetic analysis indicated an overall inhibition of nitronate reactivity, and this suggests that greater suppression of the oxygen pathway allows carbon alkylation to predominate.

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Documento generato il 25/11/20 alle ore 17:34:28