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Three decades of unveiling the complex chemistry of C-nitroso species with computational chemistry

Organic Chemistry Frontiers 2022年第1期9卷 223-264页

作者： Pauline Bianchi jean-christophe m.monbaliu Center for Integrated Technology and Organic Synthesis MolSys Research UnitUniversity of LiègeB-4000 Liège(Sart Tilman)Belgium

C-Nitroso species are characterized by a unique nitrogen–oxygen combination located next to a carbon backbone,which confers them a unique ambiphilic and high reactivity towards nucleophilic,electrophilic but also radical *** this ambivalence can be seen as a strong asset for developing versatile synthetic aminohydroxylation and/or hydroxylamination processes mainly through nitroso Diels–Alder,nitroso ene,and nitrosoaldol reactions,it also contributes to complex optimization and rationalization arising from the many competitive pathways,that is,the occurrence of regioisomers and stereoisomers,as well as dimerization and tautomerization *** reactivity profiles are usually seen by synthetic organic chemists as major hurdles to overcome,despite the armada of analytical and purification methods available to them,and hence to achieve selective and exploitable developments of such *** rise of computational chemistry and resources has certainly changed their perspectives,since it provides a very different angle to gather insights on intrinsic properties,reactivity,and *** silico chemistry also provides a robust alternative to time and resource-consuming synthetic work and can therefore contribute to alleviate wasteful preparations by guiding the chemist toward the best combination of reagents to achieve high selectivity and *** synergistic combination of synthetic organic chemistry and computational chemistry,within the specific context of the complex chemistry of C-nitroso species,is discussed in this *** review aims at giving an overview of the molecular and chemical properties obtained through computational chemistry as an enabling support for the rationalization and optimization of reactions relying on ambiphilic C-nitroso species over the 3 last *** provides clear,concise,and illustrated guidelines for the synthetic chemist in search of inspiration through computations.

关键词： chemistry reactivity isomers

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A multifaceted approach towards understanding the peculiar behavior of(α)-hydroxyiminophosphonates

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Organic Chemistry Frontiers 2022年第1期9卷 173-182页

作者： Thomas Toupy christopher Kune Kristof Van Hecke Loïc Quinton jean-christophe m.monbaliu Center for Integrated Technology and Organic Synthesis MolSys Research UnitUniversity of LiègeB-4000 Liège(Sart Tilman)Belgium mass Spectrometry Laboratory MolSys Research UnitUniversity of LiègeB-4000 Liège(Sart Tilman)Belgium XStruct Department of ChemistryGhent UniversityKrijgslaan 281-S3B-9000 GhentBelgium

The peculiar isomer-selective reduction of(α)-hydroxyiminophosphonates(oxime isomers)into(α)-hydroxyaminophosphonate(hydroxylamine)derivatives is presented.A library of 16(α)-hydroxyiminophosphonates is prepared and studied via a unique multifaceted approach involving the interplay of NmR,XRD,mS,Im-mS and computational chemistry *** combination of NmR,XRD and HPLC enables the seamless separation,identification and quantification of the oxime isomers(E/Z).Tandem mS(mS/mS)enables the determination of the fragmentation patterns for both *** energy breakdown curves highlight the order of apparition of the fragments as well as their related energy of fragmentation,demonstrating that the strength of the C–P bond in the Z isomers is much weaker than in the E *** chemistry demonstrates that favorable protonation site is isomer-dependent with the phosphonate moiety being the favorable protonation site for the E isomers,while protonation occurs preferentially on the amino moiety for Z isomers regardless of the phosphite *** combination of these various methods led an unprecedented level of characterization of oxime isomers,providing a better uderstanding of the isomer-dependent behavior of(α)-hydroxyiminophosphonates.

关键词： isomers phosphonate moiety

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应用阻塞球囊和基于导管的支架植入物样灌注装置行经皮离体肝脏灌注:猪模型实验性研究

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国际医学放射学杂志 2010年第6期 591-591页

作者： G.maleux D.monbaliu C.Verslype C.Casteleyn m.Van De Velde P.Cornillie 刘竞艳 Department of Radiology University Hospitals LeuvenHerestraat 493000LeuvenBelgium

目的评价在猪模型上进行的新型经皮离体肝脏灌注(PILP)系统的可行性及安全性。方法 PILP导管的放置已经过6只荷兰长白猪的测试,包括门静脉和肝动脉阻塞球囊、沙漏状腔静脉支架植入物。在门静脉远端与右侧股静脉

关键词：肝脏介入操作导管定向操作动物实验离体肝脏灌注

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