19350-55-1

Basic information

• Product Name: 1-(4-chlorobenzyl)-1,4-dihydronicotinamide
• Synonyms: 1-(4-chlorobenzyl)-1,4-dihydronicotinamide
• CAS NO: 19350-55-1
• Molecular Weight: 248.712
• Mol File: 19350-55-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(4-chlorobenzyl)-1,4-dihydronicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorobenzyl)-1,4-dihydronicotinamide(19350-55-1)
• EPA Substance Registry System: 1-(4-chlorobenzyl)-1,4-dihydronicotinamide(19350-55-1)

Safety Data

• Hazardous Substances Data: 19350-55-1(Hazardous Substances Data)

Upstream product

• 622-95-7 4-chlorobenzyl bromide 
• 98-92-0 nicotinamide 
• 6951-52-6 1-(p-Chlor-benzyl)-3-carbamoyl-pyridiniumchlorid 

Downstream Products

• 4217-54-3 9,10-dihydro-10-methylacridine 
• 105762-87-6 3-Carbamoyl-1-(4-chloro-benzyl)-pyridinium; perchlorate 
• 697-91-6 2,6-dichloro-p-benzoquinone radical anion 
• 695-99-8 2-Chloro-[1,4]benzoquinone 
• 488-48-2 p-bromanil radical anion 
• 615-93-0 2,5-dichloro-1,4-benzoquinone radical anion 

Relevant articles and documents

Negative kinetic temperature effect on the hydride transfer from NADH analogue BNAH to the radical cation of N-benzylphenothiazine in acetonitrile

The reaction rates of 1-(p-substituted benzyl)-1,4-dihydronicotinamide (G-BNAH) with N-benzylphenothiazine radical cation (PTZ?+) in acetonitrile were determined. The results show that the reaction rates (k obs) decreased from 2.80 × 107 to 2.16 × 107 M-1 s-1 for G = H as the reaction temperature increased from 298 to 318 K. The activation enthalpies of the reactions were estimated according to Eyring equation to give negative values (-3.4 to -2.9 kcal/mol). Investigation of the reaction intermediate shows that the charge-transfer complex (CT-complex) between G-BNAH and PTZ ?+ was formed in front of the hydride transfer from G-BNAH to PTZ?+. The formation enthalpy of the CT-complex was estimated by using the Benesi-Hildebrand equation to give the values from -6.4 to -6.0 kcal/mol when the substituent G in G-BNAH changes from CH3O to Br. Detailed thermodynamic analyses on each elementary step in the possible reaction pathways suggest that the hydride transfer from G-BNAH to PTZ?+ occurs by a concerted hydride transfer via a CT-complex. The effective charge distribution on the pyridine ring in G-BNAH at the various stages-the reactant G-BNAH, the charge-transfer complex, the transition-state, and the product G-BNA+-was estimated by using the method of Hammett-type linear free energy analysis, and the results show that the pyridine ring carries relative effective positive charges of 0.35 in the CT-complex and 0.45 in the transition state, respectively, which indicates that the concerted hydride transfer from G-BNAH to PTZ?+ was practically performed by the initial charge (-0.35) transfer from G-BNAH to PTZ?+ and then followed by the transfer of hydrogen atom with partial negative charge (-0.65). It is evident that the present work would be helpful in understanding the nature of the negative temperature effect, especially on the reaction of NADH coenzyme with the drug phenothiazine in vivo.