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Orio M Jarjayes O Baptiste B Philouze C Duboc C Mathias JL Benisvy L Thomas F 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(17):5416-5429
Two di-tert-butylphenols incorporating an N-methylbenzimidazole moiety in the ortho or para position have been synthesised ((Me)OH and (pMe)OH, respectively). Their X-ray structures evidence a hydrogen bond between the phenolic proton and the iminic nitrogen atom, whose nature is intra- and intermolecular, respectively. The present studies demonstrate that (Me)OH is readily oxidised by an intramolecular PET mechanism to form the hydrogen-bonded phenoxyl-N-methylbenzimidazolium system ((Me)OH)(.+) , whereas oxidation of (pMe)OH occurs by intermolecular PET, affording the neutral phenoxyl benzimidazole ((pMe)O)(.) system. The deprotonations of (Me)OH and (pMe)OH yield the corresponding phenolate species ((Me)O)(-) and ((pMe)O)(-), respectively, whilst that of the previously reported (H)OH (analogous to (Me)OH but lacking the N-methyl group) produces an unprecedented hydrogen-bonded phenol benzimidazolate species, as evidenced by its X-ray structure. The latter is believed to be in equilibrium in solution with its tautomeric phenolate form, as suggested by NMR, electrochemistry and DFT studies. The one-electron oxidations of the anions occur by a simple ET process affording phenoxyl radical species, whose electronic structure has been studied by HF-EPR spectroscopy and DFT calculations. In particular, analysis of the g(1) tensor shows the order 2.0079>2.0072>2.0069>2.0067 for ((Me)O)(.), ((H)O)(.), ((Me)OH)(.+) and ((H)OH)(.+), respectively. ((Me)O)(.) exhibits the largest g(1) tensor (2.0079), consistent with the absence of intramolecular hydrogen bond. The g(1) tensor of ((H)O)(.) is intermediate between those of ((Me)OH)(.+) and ((Me)O)(.) (g(1)=2.0072), indicating that the phenoxyl oxygen is hydrogen-bonded with a neutral benzimidazole partner. 相似文献
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Jenny-Lee Panayides Helen Panagiotopoulos Manuel A. Fernandes Charles B. de Koning 《Tetrahedron》2007,63(22):4737-4747
A number of protected 7-isopropoxy-8-methoxy-1,2,3,6-tetrahydro-2-benzazocines were synthesized from 2-allyl-3-isopropoxy-4-methoxybenzaldehyde using ring-closing metathesis as the key step. In addition, two 9-isopropoxy-8-methoxy-3,6-dihydro-2-benzazocines were synthesized from 5-isopropoxy-4-methoxy-2-[(1E)-3-phenyl-2-propenyl]benzaldehyde, which in turn was obtained from the thermal Claisen-Cope rearrangement of 4-methoxy-3-{[(2E)-3-phenyl-2-propenyl]oxy}benzaldehyde. Finally, five of the 2-benzazocine compounds were tested for anti-cancer activity. 相似文献
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Jess S. Boronico Alexandros Panayides 《Journal of Applied Mathematics and Decision Sciences》2001,5(3):133-150
This paper focuses on a service provider who, faced with competition, must determine the optimal price and level of service quality to provide in order to maximize profits. Service quality and price are assumed to impact jointly on demand for services. Both demand and service quality impact on the cost of providing service. While a considerable literature exists on the impact of service quality on demand or cost, less work has focused on the explicit impact of service quality jointly on both demand for and the cost of providing services. A service quality constraint is appended to the formulation in order to guarantee that a declared service standard is met. Conditions are developed which characterize optimal solutions, together with comparative statics. Illustrative results are presented based on empirical data obtained from a supermarket study. 相似文献
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