Acc

Hasson, Brian F.; Ma, Charlie; Wang, Lu; Wazer, David E.; Fisher, Brandon J.; Christodouleas, John P.; Dragun, Anthony E.; Budach, Volker; Holmes, Timothy; Troicki, Filip T.; Poli, Jaganmohan; Mell, Loren K.; Mose, Stephan; Limbergen, Erik; Saw, Cheng B.; Wong, Michael L.; Brashears, James H.; Heese, Curt; Rengan, Ramesh; Thomas, Charles R.; Reiff, Jay E.; Patel, Nisha R.; Wong, Michael L.; Grabenbauer, Gerhard G.; Jensen, Lindsay G.; Rose, Brent S.; Mundt, Arno J.; Yue, Ning J.; Rubin, Rene; Speer, Tod W.; Indelicato, Daniel J.; Sagerman, Robert H.; Komarnicky-Kocher, Lydia T.; Knowlton, Christin A.; Mackay, Michelle Kolton; Chalal, Jo Ann; Michalski, Darek; Huq, M. Saiful

doi:10.1007/978-3-540-85516-3_1002

Cited by 1 publication

(2 citation statements)

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“…Aromaticity (antiaromaticity) is a fundamental concept to account for structure and reactivity of electron delocalized cyclic compounds, intermediates and transition states. The earliest postulates applied to cyclic π-delocalized systems (Hückel Rule [19][20][21][22]) but more recently include cyclic delocalized s-systems as well [23]. Aromatic species are characterized by their thermodynamic properties of inherent stabilities [24], structures with hybrid bond lengths [25], specific reactions such as preferred substitution not encountered by acyclic or nonaromatic systems [26], and secondary magnetic fields generated by ring current effects detectable by magnetic resonance spectroscopy (NMR for example).…”

Section: Aromaticity and Antiaromaticity Of Pyrroles Azepines And Their N-oxidesmentioning

confidence: 99%

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Predicted Reversal in N-Methylazepine/N-Methyl-7-azanorcaradiene Equilibrium upon Formation of Their N-Oxides

et al. 2020

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Density functional calculations and up to five different basis sets have been applied to the exploration of the structural, enthalpy and free energy changes upon conversion of the azepine to the corresponding N-oxide. Although it is well known that azepines are typically much more stable than their 7-azanorcaradiene valence isomers, the stabilities are reversed for the corresponding N-oxides. Structural, thermochemical as well as nucleus-independent chemical shift (NICS) criteria are employed to probe the potential aromaticity, antiaromaticity and nonaromaticity of N-methylazepine, its 7-azanorcaradiene valence isomer. For the sake of comparison, analogous studies are performed on N-methylpyrrole and its N-oxide.

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Section: Aromaticity and Antiaromaticity Of Pyrroles Azepines And Their N-oxidesmentioning

confidence: 99%

“…Fenton reagent also epoxidized the parent compound (19, R = H) to form 20 (R = H) [35]. Interestingly, only the N-methyl compound (19, R = CH 3 ) formed an N-oxide (21) with m-CPBA [36]. The amide linkage in carbamazepine makes this and related azepine N-amides resistant to N-oxide formation.…”

Section: Experimental Evidence For Azepine N-oxidesmentioning

confidence: 99%