70083-49-7

Basic information

• Product Name: Quinolinium, 3-cyano-1-(phenylmethyl)-, bromide
• CAS NO: 70083-49-7
• Molecular Formula: C17H13N2.Br
• Molecular Weight: 325.208
• Mol File: 70083-49-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Quinolinium, 3-cyano-1-(phenylmethyl)-, bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Quinolinium, 3-cyano-1-(phenylmethyl)-, bromide(70083-49-7)
• EPA Substance Registry System: Quinolinium, 3-cyano-1-(phenylmethyl)-, bromide(70083-49-7)

Safety Data

• Hazardous Substances Data: 70083-49-7(Hazardous Substances Data)

Upstream product

• 34846-64-5 3-cyanoquinoline 
• 100-39-0 benzyl bromide 
• 73184-18-6 1-benzyl-3-cyano-1,4-dihydroquinoline 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 

Downstream Products

• 85289-84-5 1-benzyl-3-cyanoquinolinium perchlorate 
• 73184-18-6 1-benzyl-3-cyano-1,4-dihydroquinoline 
• 87861-99-2 5-(4-Trifluoromethyl-benzyl)-phenanthridinium; bromide 
• 85749-95-7 1-Benzyl-1,2-dihydro-quinoline-3-carbonitrile 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 
• 13076-43-2 3-(aminocarbonyl)-1-benzylpyridinium bromide 

Relevant articles and documents

Intramolecular kinetic isotope effect in hydride transfer from dihydroacridine to a quinolinium ion. Rejection of a proposed two-step mechanism with a kinetically significant intermediate

The intramolecular kinetic isotope effect (KIE) for hydride transfer from 10-methyl-9,10-dihydroacridine to 1-benzyl-3-cyanoquinolinium ion has been found to be 5-6 by both 1H NMR and mass spectrometry. This KIE is consistent with other hydride transfers. It is inconsistent with the high intermolecular KIEs derived by fitting to a two-step mechanism with a kinetically significant intermediate complex, and it is inconsistent with the strong temperature dependence of those KIEs. We therefore reject the two-step mechanism for this reaction, and we suggest that other cases proposed to follow this mechanism are in error.

Marcus Theory of Hydride Transfer from an Anionic reduced Deazaflavin to NAD+ Analogues

Eighteen rate constants, kij for hydride transfer from the conjugate base of 1,5-dihydro-3,10-dimethyl-5-diazaisoalloxazine to a variety of pyridinium, quinolinium, phenanthridinium, and acridinium ions have been determined. (All the oxidizing agents can be regarded as analogues of NAD+.) The kij values span 7 powers of 10 and the corresponding equilibrium constants, Kij, span more than 13 powers of 10.For reactions with ΔG0 near zero, the kij values are close to those given by modified Marcus theory (ref 10).However, with more negative ΔG0 values, the observed kij increase more strogly than the calculated values.Agreement can be produced by making the standard free energy of precursor complex formation, symbolized WT +- here, to indicate that it applies to reactants of opposite charge, a linear function of ΔG0, and treating the slope and interrcept of the linear relation as adjustable parameters.The best fit is obtained with WT+-(in kJ*mol-1)=-9.4+0.11ΔG0.An avarage discrepancy between calculated and observed ln kij values of 0.5 is achieved, which is a good as the overall fit achieved for hydride transfer from neutral NADH analogues to NAD+ analogues (ref 10).The form and the parameterization of Wf are shown to be a physically reasonable approximation for reactions with ΔG00.These results strengthen the conclusion (ref 10) that a wide range of hydride transfer rates can be quantitavely understood without introducing high-energy metastable intermediates (radicals and radical ions).