6407-10-9Relevant academic research and scientific papers
Aromatic nucleophilic substitution of hydrogen: Mechanism of reaction of 6-nitroquinoline with cyanide ions, with and without participation of methyl cyanoacetate
Halama, Ales,Kavalek, Jaromir,Machacek, Vladimir,Weidlich, Tomas
, p. 1839 - 1845 (2007/10/03)
The mechanism of nucleophilic substitution of hydrogen (SNArH) in 6-nitroquinoline 1 by action of cyanide ion in the presence or in the absence of methyl cyanoacetate in dimethyl sulfoxide has been studied by means of 1H NMR. The main reaction products and some side products have been identified and their time-concentration dependences have been determined. An experiment with 13C enriched potassium cyanide proved that the cyano group replaces hydrogen at the 5-position of the starting compound 1. The two main products obtained from the reaction mixture of 6-nitroquinoline 1 and potassium cyanide are 6-hydroxyquinoline-5-carbonitrile 11 and 6,6′-azoquinoline-5,5′-dicarbonitrile 13. On the basis of the data obtained, a mechanism has been suggested for aromatic nucleophilic substitution of hydrogen by cyanide ion in 6-nitroquinoline 1 involving a Meisenheimer adduct of 6-nitroquinoline 1 with cyanide ion and 6-nitrosoquinoline-5-carbonitrile 14 as unstable intermediates.
The contribution of secondary proton bridges to the catalytic power of the serine proteases
Bibbs, Jeffrey A.,Garoutte, Michael P.,Wang, Bing,Tittel, Paul D.,Barbara Schowen,Schowen, Richard L.
, p. 573 - 579 (2007/10/03)
The curvature of proton-inventory functions (rate constants in mixtures of protium and deuterium oxides) for hydrolysis of substrates of varying structure by trypsins from four different sources has been used as a signal of transition-state stabilization by a short, strong hydrogen bonds ("low-barrier hydrogen bonds") at the histidine-aspartate site of the catalytic triad. Previous estimates suggested contributions as large as 85 kJ mol-1 but the current findings are consistent with contributions of no more than a few kJ mol-1. WILEY-VCH Verlag GmbH, 1998.
Substituent Effects on One-Bond 15N-13C Couplings in N,N-Dimethylanilines and Nitrobenzenes. Effect of Steric Inhibition of Conjugation
Axenrod, T.,Watnick, C. M.,Wieder, M. J.,Duangthai, S.,Webb, G. A.,et. al
, p. 11 - 15 (2007/10/02)
The 1J(15N13C) values for a series of ring-substituted N,N-dimethylaniline-15N derivatives and a series of nitrobenzene-15N derivatives were measured from the 13C spectra.In the nitrobenzenes, small changes in 1J(15N13C) are attribut
